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Index pages |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 1-54
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摘要:
Index of Authors Cited Upright numerals show the page on which a reference appearslitalic characters indicate the reference number on that page. Aareskjold K. 381135. 382167 89 Afzal J. 2101124 Allen M. S. 287186 88 89 90 107 Anjaneyulu A. S. R.,161122 179 Aaron R. W. 287/151 Afzal M. 4581140 108 138 209183 86 Aarsman M. E. G. 510168 69 70 Agami C. 492166 Allen R. D. 41/85 Anjo D. M. 3851358 359 Aarts J. M. M. J. G.,4591216 Agarwal N. 5601400 Allen W. R. 5581270 Anke T. 4261104 Aasen A. J. 381128 Agarwal S. 931170 Allevi P. 492145 100.4941225 Ankel-Fuchs D. 580/131 Abboud M. M. 43/14 30 44/101 Agarwal S. K. 21 11208 Allin D. V. 160/110 Anlezark G. M. 233156 Abd El-Kawi M. 92/64 Agati G. 579165 Almqvist P. 951362 Annaev Ch. 161166 167 168 173 Abd El-Salam N. A.161/171 Agatsuma K. 1611185 Alon E. 961400 Annen K. 491116 492159 Abdel-Salam N. A. 161148 Ageta H. 15/72 73 171223 224 Al-Oriquat G.,4581140 Annesley T. 3841253 Abdilalimov O. 248130 225 Alpsten A. 92/37 Annis G. D. 144185 Abdullaev N. D. 15/35 47 48 49 Aggarwal S. G. 21 11192 400128 Alsema G. J. 5571198 Ansari A. A. 171204 50 51 52 53 159147 1611169 Agnew W. S. 5561110 Alshuth T. 3851323 328 Ansari J. A. 4941213 170 Agosta W. C. 2881173 Althaus J. R. 346116 Antipin M. Yu. 15/71 Abdullaev U. A. 22511 Agrawal P. 21 11208 Alvarado S. 1611177 Antippa A. F. 3851360 Abdusamatov A, 232112 13 Aharonowitz Y. 4931164 Alvarez F. M. 2101174 Anton D. L. 46/24] 3181132 Anton I. A. 3181128 Abe H. 4931131 Ahearn G. P. 2881159 Alvear M. 556/80 Abe S. 51 1/84 85 Ahern D.G. 233155 Alves L. M. 457167 74 Antus S. 458/164 4941217 Abe T. 951276 Ahlsten M. 558l288 Alward S. J. 144164 65 Anwar S. 5801174 Abeles R. H. 3181132. 523121 Ahmad M. U. 161139 Alworth W. L. 3181124 Anzenbacher P. 3841314 Abell C. 523153 Ahmad S. 39914 Al-Yahya M. A. 15911 Aoki H. 425141 426197 Aberhart D. J. 1791109 31711 51 Ahmad V. U. 161125 Aman P. 4591269 Aoki K. 3871544 54 318199 100. 5561135 Ahmad Y. 791108 Amann M. 178132 Aoki T. 3871533 534 535 523128 Aoyagi F. 3871512 Abid A. A. 451160 Ahmed M. 15912 27 32 Amaro J. 161146 Abiko A. 457191 Ahmed M. S. 233143 Ambade M. S. 21 11193 Aoyagi R. 3841247 Aoyagi T. 178/86 4261100 Abood L. G. 941192 Ahmed S. Z. 318/106 Ameer F. 21911.5 Aoyama Y. 5591325 328 329 333 Abouchara M. L. 92/60 Ahond A. 79/68 69 83 187127 Amenta D.S. 225153 341,343 Abraham E. P. 178192 93 94 Ahrens F. 931133 Amer M. 160/141 179/107 31712 4 7 8 13 1.5 20 Aiba C. J. 21 11225 Amico V. 3871548 Apel K. 451155 519/105 108 Ill 21 25 33 36 43 45 55 56 57 Aigner H.,55/36 Amir S. 951346 Aplin R. T. 31117 8 43 31 8/62 63 69 70 72 75 76 77 Aimi N. 17/216,78/39 41 79/76 Amit Z. 941260 Appel R. 219135 80 94 96 97 96 97 Amiya T. 187/19 Appendino G. 159174 160/76 131 Abraham R. J. 461231 238 239 Akaboshi S. 4931160 Ammanamanchi R. 187136 142 580/151 Ammann W. 161128 Applebury M. L. 3851348 351 Abrahamson E. W. 3841278 Akaki T. 381157 Ammar H. A. 233131 ApSimon J. W. 14/31 Abrahamson W. W. 3841279 Akamanchi K. G.,4941211 Ammons W. S. 951364 Aragozzini F. 346130 31 42413 4. Abramo-Bruno D.5571191 Akasu M. 92/67 Amrhein N. 3181136 319/140. 5101 4261109 Abubakirov N. K. 15/35 47 48 Akatsuka T. 457195 96 10 11 13 14 Arai K. 425114 47 49 50 51 52 53 161166 167 Akermark B. 346124 Amuro N. 579150 Arai M. 426185 168 173 Akhila A. 523130 An Y. 951315 Arai Y. 15/72 111223 Aburaki S. 42518 Akhrem A. A. 5571206 207 5581 Ananthanarayan T. P. 4931142 Araki K. 382197 Accarie C. 5581266 263 Anastasia M.,492130 45 100 4931 Araki Y.,144118 Acemoglu M. 382174 75 76 Akhtar M. 4312 13 14 30,44196 125 132 4941225 556/146. 5571 Arata Y. 931122 Achari B. 233173 98 101,45/111 160 3861415 5571 161 Aratani T. 151109 220 5581234 579144 Anastasis P. 523155 Arbin A. 931155 Acharya K. R. 159164 523182 Akita H. 383/150 3861431 433 Andersen J. M. 551/186 Achauder J.R. 14/21 Arcamone F. 381127 Achenbach H. 209159 381126 4261 4261 102 Anderson C. M. 5571172 Arcari G. 78/55 113 Akiyama S. 931167 168 Anderson J. R. 425146 Archer S. 941190 192 22514 Acheson R. M. 7814 Al-Ani H. A. M. 458/151 51 1/76 Anderson K. E. 579140 Alaniya M. D. 15/35 Anderson L.,209132 Ardisson J. 801146 Achiwa K. 209142 Arebalo R. E. 523122. 555154 55 Acito M. 22514 Alavi M. 555125 Anderson L. A. 78/29 56 5511154 Ackland M. J. 523180 Al-Bayati R. 425133 Anderson M. G. 3191168 Arend G. 2881202 Acklin W. 178166 Albersheim P. 456110 457164. 4591 Anderson 0. P. 15/111 Arfin S. M. 318198 Acs T. 801163 199 205 207 208,218 219 220 Anderson P. C. 4261140 Argade P. V. 3851325 Acuna P. 23216 221 222 223 226 249 250 253 Anderson P. M.,44/45 65 Argay G.801154 Adachi K. 144163 269 270 Anderson R. G. W. 555129 Argyle J. C. 556191 94 Adair W. L. Jr. 3871537 539 Albers-Schonberg G. 555/15 18 Anderson R. J. 2891235 Ariga N. 5591335 375 Adamovich T. B. 5571207 Alberts A. W. 555/15 18 Anderson-Prouty A. J. 4591218 Arigayo S. 524199 Adams R. P. 5241136 Albonico S. M. 39915 Andersson K. 225128 Arigoni D. 461199 210 212 215 Adamson H. 451158 5791109 110 Albrecht A. M. 3851382 Anding C. 5561137 220 178166 287194 3 191162 5561 Addadi L. 3191173 Albrecht P. 3871516 580/171 Ando H. 92/10 117. 5801130 Addae-Mensah I. 209159 Albu P. 961373 Ando K. 425142 Arimoto M. 210195 119 Addicott F. T. 381115 Alcorn M. 5571153 Ando M. 1451109 Aripov A. N. 220165 Adeboye J. O. 24/34 Aldridge D. C. 34614 Ando N.5581269 Aripova S. F. 22511 24/30 Adekenov S. M. 160/140 Aldridge G. N. 7814 Ando S. 5581269 Alisawa M. l5lllO Adeoye A. O. 78/62 Alegrio L. V. 2111233 Andrade C. H. S. 21 11224 Arison B. H. 248125 Adesanya S. A. 4581168 169 Ales D. C. 161132 Andreali C. 4581135 Arletti A. 941246 Adesomoju A. A, 80/171 233150 Aleskerova A. N. 1601139 Andreev S. 5601432 Armstrong D. G. 5571214 Adikaram N. K. B. 457150 51 62 Alexander G. J. 961382 Andrew R.,961376 Armstrong H. E. 28618 13 Adinolfi M. 14/15 15/43 Alfano R. R. 3851395 3861419 433 Andrewes A. G. 381129 34 Armstrong R. J. 3831182 Adisewojo S. S. 94/99 Alferov Yu. M. 3851375 Andrews P. J. 92/20 Arno M. 1451108 Adjaye A. E. 23217 Ali I. 791108 112 Andrews P. R. 3191170 174 175 Arnold E. 15/36 Adler A. 160197 Ah M.243117 177 Arnold G. F. 15/36 Adler J. H. 5601434 Ali R. S. 25113 Andriamialisoa R. Z. 801157 Arnotskaya N. E. 3841303 Adler M. W. 951294 Ali S. A. 44/94 Anet F. A. L. 3871546 Arnott D. M. 461206 580/188 Adlercreutz H. 209127 32 35 36 Aliau S. 556/142 5571188 Anetai M. 4581130 132 133 Arnsten A. F. T. 951334 37 Aljancic-Solaja. I. 49117 Angel C. 951307 AronofT S. 451139 176 Adlersberg M. 318//21,557/150 Allais D. P. 92/56 57 58 93/161 Angelin B. 523118 Arora G. S. 144182 83 84 Adlington R. M. 178192 93 100 232122 Angenot L. 78/22 801167 169,921 Arora V. K. 25118 31117 8 33 59 318f67 70 73 Allard M. 2881152 62 Arrhenius T. S. 144172 76 77 78 79 80 Allen A. C. 941188 235 Angst C. 461201 Arriaga-Giner F. J. 160/123 Adriaens P. 31 7/18 Allen B. E. 556197 Angus J.A. 225131 Arrigo-Reina R.,951289 Aeling J. L. 461261 Allen F. H. 286141 Angus R. H. 5591372 Arsenault G. P. 34/16 Afza N. 79/78 Allen M. 951355 Angyal S. J. 287/138 Arsenault T. 2881224 1-2 NATURAL PRODUCT REPORTS 1985 Arseniyadis S. ISjl 12 17/210 Bailey J. A. 451147 4581150 4591 Bartl K. 3191179 Beil M. E. 951351 Arunachalam T. 4931154 557/203. 198 Bartlett A. J. 425127 28 Beke D. 92/30 941216 217 218 5581233. 5591348 Bailey P. A. 3841244 Bartlett D. L. 5511152 Bekker A. R. 3831205 387/552 Arvanitis A, 2891231 Bailey P. D. 24/10 Bartlett L. 2811146 Btlanger A. 491128 Arzamastsev A. P. 3861410 Bain J. P. 286129 Bartlett P. A. 14417 Belanger F. C. 451146 147 148 Arzamastsev E. V. 931112 Baitz-Gacs E. 79/101. 801154 Bartlett P. D. 28617 18 26 149 152 173 Asada Y.391123 Bajwa B. S. 941197 Barton D. H. R. 2871140 141 4921 Belardini M. 3811507 Asahina Y. 286112 82 287198 Baker E. W. 461257 31 39 77 4931150 4941212 Belaud C. 381120. 4921110 Asakawa Y. 159113 1601144 145 Baker F. C. 457152 Asano Y. 3181134 51019 Baker H. N. 557/156 Barua A. ,B, 3821131 132 3861492 Belcher R. B. 451110 Asato A. E. 382192 101 3831158 Baker K. M. 286161. 287/118 Barua J. N. 160/106 492168 Belkin S. 43/18 Barua N. C. 159154 491111 Bel’kov M. V.,3851343 3861406 3841270 3861411,426 439 Baker P. M. 21 11237 Ashida T. 381159 Baker R. 14416 Baruah J. N. 159154. 1611164 4911 Bell A. A. 451134 11 I2 Bell D. 555131 Ashida Y. 387/551 Baker T. A. 555159 Baruah R. N. 1611164 Bell E. A. 219132 Ashimori A. 931158 160 Baker-Cohen K.F. 43/29 Barz W. 4581184 186 51 1/78 5241 Bell F. P 5571185 Ashworth D. M. 347188 Balasubramaniam S. 161188 92/64 120 Bell G. D. 555119 Askin P. 5241102 Balasubramanian V.,492140 5571 Basa S.C. 400132 Bell J. N. 4581150 Aslanian D. 3841304 217 218 Asplund R. O. 161/167 Balavoine G. 2881174 Basabe P.,15/70 Bell T. G. 220154 Basham H. G. 457161 Bellesia F. 523145 48 Assem E. M. 39915 Baldwin B. C. 5591326 Bashiardes G. 287/141 Bellido I. S. 159/4 160198 Asveld E. W. S. 144161 Baldwin E. T. 5801137 Bashir M. 79/80 108 112 132 Belloc J. 3841315 3851397 Atal C. K. 209158 2111192 243117 Baldwin G. S. 3191172 133 Beloeil J. C. 1611187 492158 400128 30 Baldwin J. E. 144134 35 118192 Basile G. 451127 Belousova L. I. 2811127 Ates N. 159130 160/120 129 93 94 100 105 248110 31717 8 Bassleer R.78/22 Belozerskaya T. A. 3861478 479 Atkinson E. R. 22514 11 16 17 20 21 26 29 30 33 Bastiaannet J. 510170 Belyaeva 0.B. 451154 579/101 Atkinson G. H. 3841290 3851319 36 47 48 57 59 318166 67 69 Basu S. 233173 Bement W. J. 519139 321 322 323 70 72 73 75 76 77 78 79 80 Bateman D. F. 451161 Benages I. A. 39915 Atsuta Y. 5581284 290 84 94 95 I01 Attah-Poku S. K. 144164 6.5 Baliah V. 181116 Bates R. B. 209170 Bender J. L. 318/115. 51016 Atta-ur-Rahman 111204 78/63 791 Baht G. A. 951365 Batirov Kh. E. 210196 Benedikt E. 519160 61 62 80 108 109 112. 132 133 134 Ball L. F. 3181130 Batschauer A. 579/105 Benei J . 78/53 54 145. 801147 Batsuren D. 92/13. 210196 39918 Benetti S. 14/71 Atton J. 451120 Balliano G. 15/60 61 5561133 Batta A.K.. 4921120 121 5581285 Benigni D. A. 1451105 Atwell L. 961422 558l302,303,304 5591363 364 296 300 Benin D. 3851358 Au K. G. 3191159 Ballini R. 491110 19 Battersby A. R. 4316 44/47 48 51 Benisek W. F. 5571223 Audouin M. 15/90 Ballschmiter K. 451180 52 56 57 59 61 63 67 69 72 Benn M.,21918 Augmor J. D. 211/183 Balogh-Nair V. 3821115 119 134 74 80 81 84 102 105. 451110 Benn M. H. 931163 391122 3831154 155. 3861425 433 441 182 189 192 461194 195 196 Aupetit B. 5581266 Balsevich J. 178/55 197 198 ZOO,201 204,205,206 Bennasar M.-L. 79/87 88 Auricchio S. 14418 4261108 Ban N. 1451122 207 208 209 211 21.5 216 221 Bennett G. N. 3191149 AuSkova M. 78/54 Ban Y. 191125 24313 248138 222 240 177/8 118143 53 2881 Bennett R. D. 15/92 3871499. 5231 Avila W.B. 210/101 65,67 Avissar Y. J. 578/10 Bandaranayake W. M. 3831226 169 579126 33 49 5801127 128 Bennett T. 951367 Avram M. J. 931101 Bandhyopadhyay R. 400130 186 187 188 189 Avrutov 1. M. 3811521 522 Bando H. 187119 Bauch H.-J. 346141 Bennett T. B. 287/151 Aweryn B. 178/58 Bandurski R. S. 510137 Baude G. 492164 Benoist J. M. 951279 280 363 Awruch J. 579164 Banerjee S. 209167 84 210197 Baudet M. 9216 Bensasson R. V.,382180 81. 3851 2811109 344 Axelson M. 209127 28 29 32 34 Banerji A. 24817 511/93 523131 Baudouin G. 187/10 Benson M.,558l305 37 Baudouy R. 1451124 Axelsson K. 951296 Banerji J. 79/77 Bauer P.E. 17/210. 4931207 Bentley K. W. 94119.5 Ayabe S. 931174 178/40 Banerji N. 14/20 15/41 Bauer R. 225112 Bentley R. 346112 3871570 Bauernfeind J. C. 38118 Benton G.A. 555144 4.5 Ayafor J. F. 15/94 Banfi L. 426190 Ayer W. A. 15/36 37 523157 Banholzer R. 225111 12 14 Baum N. A. 3861484 Bentz H. 2881198 Ayers A. R. 4591219 Banks S. W. 458/152 153 154 Baumert A. 118189 90 Benveniste P. 5561132 133 5591 Ayim J. S. K. 92/26 155 156 157 192 Baxter R. L. 461246 118157 96 309 310 311 312 314 315 360 Ayres D. C. 20915. 210/103 21 11 Bano S. 161125 311112 53 369 370 371 Bansal S. K. 5591351 376 Bayerque A. L. 3821116 Benyhe S. 941183 179 Azerad R. 3181118 122 Banthorpe D. V.,523140 5241113 Bays D. E. 287183 Benz J. 451163 164 166 168 5231 Azoulay E. 3871574 114 115 556197 Bazaes S. 556176 77 84 5801115 Azuma K. 4261103 Baraldi P. G. 144171 Bazzani C. 941246 Beppu T. 425126 Baralt O. 425162 Bazzaz M. B. 451174 5801114 Berchtold G.A. 3191159 176 178 Baranov A. G. 92/35 Beale J. M. 191143 5241127 181 510119 Baranyai M. 382185 Beale M. H. 524194 Berenbaum M.C. 471264 265 Barash I. 347154 Beale S. I. 4318 17 18 26 451129 Berenberg C. J. 5601430 Baas P. 2881187 Barata L. E. S. 210/110 21 11237 578111 21 Berenyi S. 941189 Baas W. J. 161142 Barco A. 144171 Bear C. A. 286169 Beretta M. G. 426190 Berg D. 556166 Baasov T. 3821103 124 127 128 Barczai-Beke M.,941214 215 Beatty W. W. 941265 Berg J. M. 346111 3851404 Bard M. 556165 57819 Beau J.-M. 42518 Baassou S. 191130 Barden T. C. 144134 35 Beauchamp A. L. 941181 Berg L. R. 5591352 Babady-Bila 161141 Bardhan J. C. 2881208 Becher J. 187135 Bergen H. R. 3831149 Berger G. D. 248112 Babcock S. H. 286138 Bardo M. T. 961386 Beck J.451178 179 Babiak K. A. 24/27 Bardshiri E. 346140 523124 Beck J. F. 44/48 Berger L. 941249 Babin D. 382173 Barker A. J. 144154 Beck J.-P. 14/11 5571179 Berger R. G. 5241120 Berger R. V.,961401 Bach T. J. 523114 23 555121 22 Barker W. L. 941268 Beck S. G. 951297 23 556172 Barkigia K. M. 451185 186. 5801 Beck W. S. 471271 Berger Y. 5561136 Bacher A. 461230 164 Becker A. M. 118187 347185 Bergey J. L. 951351 Bachman G. J. 3181109 Barnard G. F. 44/96 556184 86 Becker H. 5241122 Bergman J. 78/30 Badaisha K. K. 3831196 Barnes P. K. 92/49 Becker R. S. 3851345 Bergman R. 159169 70 Bader G. J. 3831151 Baron M. H. 3841315 3851397 Beckett A. H. 2811144 Bergmann K.-H. 451190 191 Baenziger N. C. 161132 Barone G. 14/15 15/43 Beckett G. J. 5581272 Bergquist P.,381123 Baerheim Svendsen A.79/73 119 Barr G. 225139 Beckman C. H. 457135 Bergquist P.R. 4921101 5601420 120 801170 92/68. 931102 18712 Barrabee E. B. 318164 Beckmann S. 286167 Bergweiler P. 451155 Battig K. 144148 55 Barreiro E. J. 219112 4261119 Beckwith A. J. 118198 Berkowitz B. A. 951299 Bagchi A. 1611.54 Barrero A. F. 3831208 Beecher C. W. W. 178133 Berlin J. 118142 510/41. 5241117 Baggio G. 961372 233162 Barrett J. C. 961436 Beg M. F. A. 161174 Berlyn M.B. 3181108 Bahadur G. A. 317/20 318/69 75 Barrie S. D. 457155 Beg Z. H. 523117 19 555/7,8,43 Bermejo J. 1601137 80 Barrnett R. 5591322 49 556164 Bernard M.,382194 Bahadur S. 233140 Barrow S. E. 5591383 Begley M. J. 510171 Bernard-Dagan C. 5231.32 Bahnweg G. 5591354 Bartel J. 5801146 BCguC J. P. 2811114 Bernardi L.78/55 Bahurel Y. 2881219 Bartels K. 3821122 Beier R. C. 457134. 4581111 112 Bernardinelli G. 14/55 2881229 Baile C. S. 96/392 Barthe P. 523172 113 Berndt J. 5551.59 NATURAL PRODUCT REPORTS 1985 1-3 Bernhard K. 382190 Bishop P. D. 4591249 252 Bondarenko L. 492133 Braz Filho R. 21 11222 223 224 Bernhauer D. 9218 941234 Bisseck P. 4921118 Bondarev S. L. 3851343 3861406 233 243 Bernini F. 5571161 Bisseret P.,3851382 Bondavalli F. 2871132 Bredt J. 286179 81 287191 92 Bernotas R. C. 243111 Bisset G. M. F. 451187 Bondi A. 5581305 2881176 180 Bernstein M. 5801140 Bisset N. G. 7812. 791123 931114 Bondinell W. E. 3181129 Bree M. P. 961399 Bernstein P. R. 2871122 Bisson W. 5241122 Bonelli A. 951300 Breedlove R. L. 21 11241 Berry A. 44/64 66 77 Bitsch A.510147 Bonet J.-J. 492192 4931191 Breen M. A. 5591367 Berry D. J. 5571151 Bittler D. 4941229 Bongiorno de Pfirter G. M. 9212 Breining T. 15/115 Berry D. M. 317122 Bjorkhem I. 558/281 290 299 301 Bonin M. 187122 Breitmaier E. 931142 Berset D. 381137 Bjoernevaag S. V. 931178 Bonini C. 5601421 Breitman T. R. 3821141 Berson J. A, 2881201 Bjnrnland T. 381118 36 Bonkovsky H. L. 579139 Brems D. N. 556187 Bertocchi G. 941238 Bjornsson 0.E. 523112 Bonnet B. 3841305 Brendel K. 220159 Bertolini A, 941246 Bjoroy M. 461256 Bonnett R. 5801169 170 Brennan T. F. 160/105 Bertranne M. 492158 Blackwood D. H. R. 233156 Boocock M. R. 3191141 Brenner M. L. 523171 Bertz S. T. 144174 Bladon C. M. 941191 Booij L. H. D. J. 92/48 Brereton R. G. 44/56 451174 461 Bed H.4261104 Blaha K. 248116 Booth H. 318193 237 239 346135. 58011 14 Besso H. 15/77 81 82 Blais C. 5601411 Booth P. M. 425138 Breslow R. 492191 Bessonova I. A, 39918 9 Blaschke G. 92/21 178137 38 Boots M. R. 555134 Brewer H. B. 523119 55517 8 43. Best A. H. 286129 Blasko G. 791100 101 92/30 43 Boots S. G. 555134 556164 Bestmann H. J. 3861438 941214 215 216 217 218 Bopp T. T. 3841270 274 Brewer S. J. 317140 Betancor C. 15/68 4941215 Blaszczyk K. 15/63 Borch G. 381125 34 35 36 Bridge A. W. 491121 Bevan D. R. 43/33 Blatchly H. A. 3861425 Borders D. B. 347175 Bridger W. 225139 Bevelle C. A,. 160/100 Blattel R. A. 2871109 Bordner C. E. 3861484 Brien J. D. 3181109 Beven J. L. 3841244 Bleaney R. C. 317113 15 56 Borenfreund E. 951357 Brien J. F. 92/20 Beverley C. L. 951357 Blizzard T.A. 144143 Borges J. 1611182 Brienne M.-J. 2881190 Bevins C. L. 5571223 Bloch C. B. 457186 Borges-del-Castillo J. 14/18 1601 Briers T. 5601408 410 Beydon P. 560/411 Bloch K. 5561128 129 5571157 123 Brieskorn C. H. 159173. 160/121 Beyerman C. H. 24812 5591313 334 348 Beyersmann D. 578123 24 Block M. A. 451167 Borg-Karlson A. K. 144157 209173 Beytia E. 556175 76 77 Block M. H. 5801189 Boriack C. J. 286163 Brillanceau M. H. 79/65. 178156 Bhagvat M. B. 2881206 Bloem R. J. 159140 Borriello S. P. 209132 37 Brindle P. A. 457171 75 523160 Borris R. P. 78/64 79/84 Brinkman U. A. T. 3871561 Bhakta C. 21 11230 Blohm T. R. 5581249 Borrod G. 3861466 Britton G. 38112 24 382182 83 Bhakuni D. S. 931106 118 126 Blomquist C. H. 5571216 558/255 Borschberg H.J. 78/59 3831227 3861444 450 455 178129 44 233134 44 Bloom F. E. 951334 Bhandari P. 14/19 32 160/128 Bloomer J. R. 451119 Borthwick I. A, 43/10 57812 4 5 Britton R. W. 2101132 163 Bhargava P. 951285 Blum Z. 21911 7 Broadbent H. A. 44/74 Bhat C. S. 556179 82 Blumen G. 961434 Bortnikova V. V. 931112 Brochmann-Hanssen E. 931172 Bhat P. V. 3841255 Blunden G. 4941239 Borup-Grochtmann I. 179/111. Brockmann H. Jr. 451188 461234 347189 236 5801123 Bhat U. G. 160180 Blye R. P. 4931192 Bos R. 1611184 Brocksom U. 21 11217 222 Bhat V. S. 15/89 Bhatia A. V.,941209 Boar R. B. 14/25 26 Bosch J. 79/87 88 Brodasky T. F. 425180 Bhatia K. S. 457/85 Bocchini G. 951319 Boschelli D. 4261125 Brody S. S. 385j381 Bose A. K. 4921121 5581296 Broek A. D. 3821108 3841307 3861 Bhatia M.S. 21 11192 400128 Bockbrader H. N. 4931200 Bosisio G. 78/55 436 Bhatnagar R. K. 961386 Bode R. 51013 24 28 Bostock R. M. 457142 80 81 84 Broniowska B. 3831238 Bhatnagar S. I51108 Bodea C. 382184 4591246 52316 Brooker J. D. 43/10 556171 57812 Bhatnagar S. P. 941187 Bodish C. 425156 Bostrom H. 5581291 7 Bhattacharya M. K. 161201 Bodlaender P. 43/33 Bhattacharyya J. 3991 13 Boeckman. R. K. Jr. 425157 61 Botham K. M. 5581272 Brooks C. J. W. 457152 4591242 Bhattacharyya L. 7819 Boger P. 3861461 462 463 467 Botteghi C. 492185 Brooks D. J. 92/17 Bhattacharyya P. 7818 11 39917 Bohm H. 178130. 579170 Bottomley W. 45617 Brooks D. W. 144142 3831187 14 Boehm I. 3821104 Boucher F. 3851360 Brossi A, 931120 941213 224 961 Bhattacharyya S. C. 286153 74 Bolcskei H.801163 Boudet A. 4581146 422 288/216 Boente J. M. 92/25 55 931162 Boudet A. M. 5lOlSO Broughton W. J. 381150 Bhattacherjee P. 96/425 Borger H. 45611 Bouillant M. L. 4581134 Brown A. E. 457150 51 62 Bhatwadekar S. V. I59/53 Borner H. 4581144 149 4591259 Bounias M. 457159 63 Brown A. G. 1781106 317146 Bhavnani B. R.. 558/271 Boes M. 941200 Bouquet A. 801175 Brown A. M. 318186 87 88 Bhawal B. M. 2101124 Bosterling B. 5581288 Bousquet A, 941203 Brown C. 457147 Bhide. K. S. 400117 Bottger D. 426184 Bouvier P. 5561133 136 138 Brown C. E. 5801152 154 Bhiravamurty P. V. 209179 Bottger-Vetter A, 4261113 Bowden B. F. 159/10 60 18714 Brown C. R. 5581256 Bhosale S. B. 319jl86 Bogdanov V. S. 494:216 2101158 167 Brown D. M. 579179 Bhupathy M. 145/110 Bogdanova K.A, 492147 Bowden G. T. 220160 Brown E. 2101129 130 131 164 Bhushan R. 523/4Y Bogenschiitz O. 3861460 Bowden R. D. 381130 165 Bhutani K. K. 243117 Boger D. L. 2881154 Bower S. G. 3191147 I51 Brown F. C. 287196 Bialek-Bylka G. E. 3851383 Bogomolni R. A, 3851330 Bowers R. J. 317132. 318168 82 Brown H. C. 287/111 Bianchi G. 78/55 951288 Bogorad L. 44/49 461260 Bowman N. J. 178198 317150 Brown J. J. 941195 Bick I. R. C. 78/57 92/74 187130 Bogoslovskii N. A, 4921115 Bowman R. M. 400123 Brown J. T. 951291 Bickelhaupt F. 425150 51 Bohlin L. 78/32 791105 5601417 Boyd G. S. 5571203. 5581230 272 Brown K. 219131 Bidlack J. M.. 94jlY2 422 289 293 Brown K. L. 286145 5801195 Bieganowski R. 461219 Bohlmann F. 144129 57 59 1451 Boyd I. 92/49 Brown K. S. Jr. 219133 Bieri J.H. 382/75. 425131 4261110 116 15911 2 3 11 27 30 31 32 Bradbury A. J. 233157 Brown L. 491115 Biermann J. 248117 34 35 56 62 65 160179 81 82 Bradbury W. M. 961396 Brown M. S. 55514 28 29 30 63 Bigam G.. 15/37 88 89 93 94 95 96 97 101 Bradley A, 1611182 5 561 I06 Bigge C. F. 3821115 107 118 120 129 130 141 143 Bradley C. H. 318196 Brown P. 791144 80jl50 Bigler. P. 381151 158 1611165 175 176 177 18716 Bradley C. V. 451174 Brown R. T. 791103 28613 Biglino G. 5561132 209169 2 I 11207 Bradshaw W. H. 2871102 Brown S. A, 510157 Bignardi C. 171205 Boid R. 5601405 Brady D. R. 5561147 5571148 Brown S. B. 579157 58 73 74 Biguet J. 346/17 Boiko E. V. 232111 Braga R. M. 791107 Brown W. E. 55514 41 Bildsoe H. 580jlr50 Bokel M. 178172 580l136 Braiman M. 3851319 Brownell L.941249 Billet D. 159120 Bokern M. 510141 Bralovic M. 49117 Brownie A. C. 5571213 Billheimer J. T. 5571153 Boll P. M. 187120 24818 Bramley P. M. 3861457 462 463 Brubaker G. R. 28617 Billiet H. A. H. 94/236 Bollag W. 3821142 467 468 Bruce J. M. 3871554 Billington D. C. 14416 4261117 Bollenbacher W. E. 5601404 414 Branca S. J. 4261126 Bruce R. J. 4591206 Bilyard K. G. 458/167 Boiler T. 4591230 245 Brandange S. 187142 Bruenger E. 556187 Bingel A. S. 233143 Bolognese J. A. 555119 Brandlmeier T. 579185 Brumm P. J. 43/25. 44/43 Birch A. M. 144187 Bolt A. J. N. 381158 Brandt K. E. 52319 Bruneton J. 78/18. 79/75 801175 Birge R. R. 382199 118 Bombart P. 5801113 Brandt K. G. 555jll 92/63 233136 Birnbaum D. 510/3 24 28 Bommer J. C. 44/83 Brankiewicz A. J. 425125 Bruse M.578120 Birtwell J. 555119 Bonanno G. 951319 Brannon D. R. 317144 Brutko L. I. 92/33 Bischofberger N. 3831219 220 Bond F. T. 2871143 Branthaver J. F. 461257 Bruun T. 171212 221 223 Bondar 0.P. 3851375 Bratt G. T. 5801156 Bruyant P. 579125 NATlJRAL PRODUCT REPORTS 1985 Bryan R. F. 15/57. 2101132 163 Caldwell C. G. 3861441 Cassidy P. J. 425174 Chapya W. A. 791120 21 11229 Caldwell R.S. 5601424 Castedo L. 92/25 55 931162 961 Chari V. M.,210/90 21 11203 244 Bryant J. E. 4591252 Callahan J. F. 144156 408 233167.4921117 Charles G. 4921118 Bryson I. 457149 Callender R.H. 3841313 3851331 Castelfranco A. M. 451144 Charpentier-Morize M. 2871114 Buchanan G. L. 286180 395 3861419 433 Castelfranco P. A, 43/17 451129 Chasalow F. 5511228 5581262 Buchecker R.381133 39 40 45 Calleri M. 159175 160177 138 142 132 133 142 143 144 578121 Chashchin V. L. 5571206 207 5581 Buchert J. 3861433 Callot H. J. 580/171 579194 96 97 112 263 Buchmann M. S. 5581301 Callsen H. 15/100 Castellano C. 941267 Chatson K. B. 178158 Buchwald W. F. 941194 212 220 Calverley P.M. 951292 Castro V. 160179. 1611177 Chatterjee A. 79/77 209125 Buckel W. 3191163 Calvet A, 492170 Castro C. O. 21 11217 228 234 Chatterjie N.,961382 Buckley D. G. 4311 44/84 Calvin M. 5591308 232120 Chattopadhyay S. K. 931113 2331 Buckner C. 209175 Camadro J.-M. 451109 579145 Catalin C. A. 159167 38 3851392 393 394 Buckner R. C. 219126 Camakaris H. 510129 Catalan C. A. N. 4921104 4931123 Chaturvedi R. 931106 178144 Buda C. 931139 Camara B. 3861448 456 51 1/89 Catalano S.161148 Chau D. D. 580/18l Budde A. D. 457144 45 4591247 Cambie R.C. 210/115 116. 492134 Cattel L. 15/60 5561132 133 5581 Chaudhry A. G. 43/30 44/38. 451 Budesinsky M. 4941240 Camerino B. 381127 302 303 5591314 363 364 111 Buemi G. 3851356 357 Cameron A. F. 159151 Cautreels W. 233163 Chaudhry I. A. 579149 Butikofer P. A. 381133 382178 Campbell A. L. 248127 Cava M. P. 801171 233150 Chaudhuri K. 961407 Bugaenko L. A. 5241130 131 132 Campbell C. E. 559/316 Cave A. 801175 92/59 60,65 931 Chaudhuri P. K. 15/39 Buhler D. R.,219149 220166 Campbell C. S. 178197 318181 110 179 23211 2 5 23218 19 Chaudhuri R. K. 21 11209 Bujtas G. 382185 Campbell I. M. 5571185 21 26 28 30 233146 Chauhan Y. S. 382199 Bulard C. 3841265. 523172 Campbell J. 15/57 Cavenee W. K. 5561141 Chaussin R.,2871139 Bulenkov M.T. 3861410 Camps P. 2101162 Ceccarelli N.,523120 Chauvet J. P. 3851385 386 Bull L. B. 219127 Candaletti S. 951289 Ceccherelli P. 151104 Chavdarian C. G. 187144 Bullerman L. B. 346121 Candrian U. 219150 Cella J. A. 492149 Chayet L. 523136 556199 100 Bullock G. 5581268 Cane D. E. 159168. 347169 84. Celmer W. D. 347159 Che C.-T. 233143 Bu’Lock J. D. 3871.515 523142 53 Cerfontain H. 2881187. 383121 I Cheatham S. F. 21 11241 Bunce R. A. 151116 Canevari A. 951319 212 213 Cheeke P. R.,219149 220161 62 Bunge R. H. 159140 425125 Cannizzaro G. 951349 Cerny A. 78/53 54 63 64 ’ Bunnenberg E. 5801167 168 179 Cannon G. W. 287183 Cerny I. 4931122 209 Cheema A. S. 4591254 Buntinx A. 555jl9 Canonica L. 21 11181 185 Cerrini S. 159150 Chegaeva T.V. 961435 Bunton C. A. 523136 Canovas A. 145199 Cervo L. 951352 Chen C.-C. 209180 Bunyapraphatsara N. 233143 Cantoni L. 579136 38 Ceskis B. A. 4921115 Chen C. H. 931127 Bupp J. E. 3831152 153 Cantore W. A. 3851333 Chachaty C. 382181 3841268 Chen C.-L. 210/118 232114 Burden P. M. 4931167 Cao Z. 14/34 Chader G. J. 381112 3861413 Chen C.-M. 171213 21 11211 Burden R. S. 159157 457137 38 Capitaine J. 492155 Chaisson J. B. 160/154 Chen F. C. 21 11190 39 47 4581108 109 I10 Caprasse M. 78/22 801167 Chait B. T. 580/150 Chen G. 931134 233160 Burdett J. E. 4931192 Capshew C. E. 286162 Chakrabarty M. 44/94 Chen G. C. 3841282 Burger V. T. 5801154 Caputo O. 15/60 61 558/302 303 Chakraberti D. K. 161153 Chen H. W. 555163 5561141 Burger W. 3831151 304 5591363 364 Chakraborty A, 7818 Chen I.-S.,961412 Burgess H.2871113 2881178 Caputo R.,491125 Chakraborty D. P. 7819 209161 62 Chen J. 43/24 35 555jl.5 18 Burghoffer C. 3841280 3851380 Caramiello R.,15/61 5581304 Burgstahler A. W. 2881154 Caras I. W. 5561128 129 Chakraborty T. K. 3831176 Chen K. 161137 Chakravarti B. 178192. 3 1718 33 Chen K.-M. 248120 Burk R. M. 801153 3 18/66 67 76 80 94 Chen L. 233159 Burka L. T. 425122 457119 24 Caravatti G. 941213 Chakravarti K. K. 159153. 2881216 Chen M. 225145 Carde A. 2891235 Burke M. C. 2871130 Cardemil E. 556180 81 83 Chakravarti R.N.,2881207 Chen M. H. M. 347154 Burke P. J. 5801169 Cardinali D. P. 961368 Chalenko G. I. 457177 Chen N. T. 578122 Burke S. D. 144180 Chalmers A. A. 425152 Chen Q. 951344 Burkhart J.P. 5581239 Carey L. 3841267 Chamberlin A. R.,21917 24311 Chen S. C. 49112 Burks T. F. 951287 961377 389 Carey S. C. 382199 Chambers S. M. 5581256 Chen T. K. 161132 Burlingame A. L. 5561118 Cariello L. 471267 Carino M. A, 941253 Chambers W. D. 2871128 Chen T. M.,931127 Burnett E. 2871135 Chan J. C.-S. 451137 Chen W. 225152 Burnham B. F. 44/70 83 Carle J. S. 78/33 Chan J. K. 347158 4261132 Chen W. M. 79/72 Burnham W. M. 931156 Carlon F. E. 492136 Chan J. T. 5561143 Chen X. 93/99 Burns C. P. 5571158 I59 Carlone G. M.,3871546 Chan R. L. S. 3821138 139 140 Chen Y. 791113 1601146 Burrus P. B. 219126 Carlson J. P. 5561112 Chen Y.-P. 210/153 Burton G. 44/53 54 55 70 83 461 Carlson R. E. 44/83. 4581131. 5801 Chan T. H. 18713 78/48 233 244 245 246 140 Chan W. H.2881177 Chen Y. Y. Burton G. W. 3851367 Carlson R. M. K. 4921106. 5601416 Chan W. K. 492186 Chen Z. 161136 225140 Bush L. P. 219126 Carmely S. 171219 220 Chandel R.S. 210/111 Cheng F. W. 5581296 300 Cheng G. 15/55 225151 Bushell M.J. 451187 461215 Carmichael G. L. M. 951292 Chander M. S. 5591320 Cheng J. T. 941257 Buss A. D. 144120 Carnevale A, 941233 Chandra D. 3851395 Buss V.. 3841283 Carnmalm B. 209124 Chandraratna R.A. S. 382199 Cheng P.-T.,243129 Caroli C. 4931174 116 117 118 Chenieux J. C. 178160 Bussmann R.,51 1/78 Carotti A. 491119 Chandrasekaran L. 187116 Chereskin B. M. 451132 142 143 Butler J. R.,3181124 Buttke T. M.,5591334 348 Carpenter D. G. 21 11179 Chandrasekaran S. 3831176 5791112 Butz R.F. 95/29] Carpenter J. F. 160/111 Chang A. 3851405 Cheriyan U.O. 399113 Chang C. 523142 Chernoburova E. I. 4931135 Buu H. P. 346114 426188 95 Carr D. M. 318189 Chang C.-C. 51 1/92 555162 Chernysheva E. K. 3861478 479 Bycroft B. W. 317110 318/Y3 Carriker J. D. 3821119 Byers J. 382186 Carroll F. I. 3821136 137 Chang C.-J. 92/19 178173 347160 Chervenkova V. 931166 51 1/92 Cheshire R. M. 94/257 Bykhovskii V. Ya. 451192 461198 Carroll G. L. 144188 227 SSOjl33 Carroll K. K. 3871505 Chang C. K. 5801164 Cheung H. T. A, 4931167 204 Byon C.. 5571199 Carroll M. 318/113 Chang H.-M. 161130 134 135 Chexal K. K. 346119 29 Carruthers W. 187132 210/118 232/14 42 Chhabra B. R. 523158 Cartaya-Marin C. P. 187131 Chang I. M.,161183 Chi C. 941204 Carter C. G. 248119 Chang K. C.. 92/44 45 Chiang J. Y. 5581291 Carter G.T. 347/75 Chang L. T. 317139 Chiang T.-C. 161130 134 135 Cary L. 346136 Chang. P. 5561145 Chiari G. 159175 160/77 138 142 Chang T.-Y. 5561122. 55715 62 Chiaroni A. 931179 Cabalion P. 92/65. 23215 233146 Casadevall E. 1418 346110 Caballero E. 3831208 Casati R. 18719 151 Chiarotti M.,941233 Chao H. S.-I.,319/176 Chiba M. 1451123. 209117 74 81 Cachia P. 286147 64 71 73 2881 Case M. E. 318/106 161 224 Casellato M. 5591356 Chao W. 3821138 139 140 Chiba T. 15/42 Caerteling C. G. 461225 Cashaw J. L. 92/2Yp 931135 Chao Y. S. 555jlY Chibbar R. N. 578112 Cafmeyer N. 3871537 Casida J. E. 4591265 Chapman D. J. 45/16] Chicarelli M. I. 580/148 172 Cagiano R. 941263 Casinovi C. G. 15/104 159150 Chapman R.A. 2881174 Chichester C. O. 382182 Cain E. N. 3191174 Caspi E.4931154 5561134 135. Chappe B. 3871516 Chichester M. L. 457167 Caine D. 425145 5571194 203 5581233. 5591348 Chappell J. 4581146 4591230 Chichuev Yu. A, 941226 Caldecourt M. A. 951356 Cassani M. 941221 Chapple D. J. 92/50 Chiesara E. 961375 Calder M. R.,5571220 5581234 Casseis B. K. 931164 243126 3991 Chapuis C. 144131 32 2881229 Chiese P.,225/7 Calderon J. S. I60jY9 15 Chapya A. 400134 Chifu E. 3851376 377 378 NATURAL PRODUCT REPORTS 1985 1-5 Chignell C. F. 96/422 Cohen S. A. 233154 Costall B. 233/57 Dafeldecker W. P. 5571212 Chihiro M. 16/llH Cohen T. 145/110 Costerousse G.,491128 Daggett J. U. 145/117 Chin D. J. 555/2Y 30 63 Coker G. G. 92/51 Costes C. 3841280 3851380 Dahiya J. S. 4571103 4581167. 4591 Ching M. 951304 Colau B. 187126 Cotta E.381127 210 Chinsky L. 384/2YY 300 Cole D. F. 961425 Cotton W. D. 287195 Dahl C. E. 5591313 Chintalwar G. J. 51 1/93 523131 Cole J. R. 209123 70 21 lj205 Couch P. 45/110 Dahl J. S. 5591313 Chitrokorn S. 49116 Cole K. W. 318/105 Couldwell C. 28617 Dahlbender B. 510142 43 Chmielewski M. 24811 Cole S. P. C. 471262 Coulomb B. 92/34 Dahmer J. 578120 Chmurny G. N. 347159 Coleman G. J. 95/30] Coulomb C. 457/59 63 Dai S. 951359 Choi J. S. 16jl6.5 Coll J. C. 159/10 60 187/4 Coulomb P. J. 457157 59 63 Dai Z. 93/98 Choi L. S. L.. 178158 Collado I. G. 161/176 Coune C.,78/22 Daie J. 523171 73 Choi M. C. K. 7814 Collin H. A, 5241118 Court W. E. 78/22 79/70 82 Dailey H. A. 451116 117 579146 Choi Y. R. 95/338 Collin S. 5241120 Courtin A. 286180 47 Chojnacki T. 3871540 Collins C.J. 2881196 Courtin J. M. L. 3821108 Dalavoy V. S. 159164 Chon S. U. 92/77 Collins D. J. 4931178 Coustal s.,557/219 221 Dal Fiume D. 579136 38 Chong J. H. 2881222 Collins J. G.,951284 Cover E. C. 457133 Dalietos D. J. 523137 Choplin F. 1451124 Collins M. D. 3871547 Covey D. F. 286115 5571222 223 Dallacker F. 286114 Chopra. A. K. 2881226 Collins P. 209138 210/93 5581238 243 244 253 254 258 Dallas J. L. 451143 220/52 5791 Chow S. W.. 286145 Colombeau C. 2871146 Cowan A, 961404 I12 Chowdhury B K.. 78/11. 39917. 14 Colombo L. 346130 31 42413 4 Cox M. 578124 Dallner G.. 387/540 Chowdhury P. K. 159/54 160/106 426190 I0Y Cox P. J. 791137 Dalton D. R. 287/116 491112. 492168 Colonge J. 288/21Y Coxon D. T. 4581106 124 Daly J. W. 243/12 Christensen C. B. 941211 Colonna M..941263 Crabb T. A. 791124 4941239 Dalzell H. C.,941196 Christensen J. R. 4941223 Comins D. L. 248127 Crabbe P. 49114. 4931149 Dalziel J. 5241103 Christensen S. B.. 347177 78 Comparini I. B. 941182 Craig A. M. 219142 D'Amato R. J. 951342 Christophersen. C. 78/32 33 Concepcion J. I. 4941215 Craig D. C. 2871138 d'Amato T. A, 510123 Christopherson R. 1.. 3191190 Cone E. J. 941194 212 220 Craig G. W. 580j125 D'Ambra T. E. 144141 Christov V. S.,233147 Confalone. P. N. 79/86 Craig I. F. 5571203. 558/293 Damodaran N. P. 144123 Chu D. 3841270 Conk J. M. 2881204 Crandell C. W. 5801167 Danho D. 3821123 Chu. G.-N. 243115 Conklin D. E. 3861484 Crankshaw D. L. 941210 Dani H. M. 961430 Chu H. 493/17Y Connolly J. D. 15/94 159151 1601 Crastes de Paulet A, 5561142 5571 Danieli B.79iY3 136. 801174 1781 Chu. J. Y.-R. 317/51 54 145 286130 2881160 188 59 2881189 Chun B. G. 95!313 Connor W. E. 5601424 Craw M. 3851336 Daniell H. 579103 98 Chung B. C.. 383/200 Conrad H. E. 287/102 103 Crawford M. S. 451138 Danielsson H. 5581273 27Y 280 Conrow R. E. I44116 Crea A. E. G. 16/180 Chung B. H.. 92/71 283 294 298 Chung. J. Y. L.. 21917 24311 Constabel. F. 178158 Creelman R. A. 387/500 523168 Daniewski W. M. 161/18I Chung S.-K. 178lY5 287/114 3171 Contel N. R. 225129 Crespi H. L. 3861443 Danil'chuk D. N. 243127 52 318171 Contreras M. L. 931122 Crich. D. 492131 Danilov L. L. 3871527 528 Churin. A. A, 3841306 Conus M. 457158 Criel G. R. 381147 Danin A. 160186 Cialdella J. I. 426181 Conway E. 209131 Crimmin M. J. 317/5Y 318170 Danishefsky S.4261146 Ciamician. G.,288,!172 Cook J. M. 144174 Crisp T. 9219 Ciborowski. P. 16/187. 5581307 Cooks R. G. 9213 Crist B. V. 2881157 4921101 5601 Dao G. M. 144/31. 2881229 Darbord J. C. 510148 420 Ciccio. F. 1611177 Cooksey. C. J.. 4571103 4581167 Crombie L. 510/71 51 1/79 Darbre T. 7815Y Cicero T. 96136Y 4591210 Cighetti G.,555/60 5561146 Cookson R. C. 287183 113 Cros J. 94/19Y Darby M. V. 4931174 Croteau A. A, 3821107 115 Darby N. 286147 64 287186 107 Ciociola A. A, 94i252 Coolbaugh R. C. 5241104 Croteau R. 52214 523134. 35 38 Darise M. 151107 Ciuffreda P. 492130. 100.493/125. Cooley G. 20913I 40 41 42 49 50 54 da R. Madureira J. 96/4OY 132 4941225 Cools W. 5591326 Clardy J. 15/36 171204. 248136 Cooper A. D.. 523113. 555157 Crouch R.C. 941209 da Rocha A. I. 791135 Crouch R. K. 382/111 3861431. Dartayet G. H. 159167 347154 Cooper B. W.. 5581274 432 434 Darvill A. G.,456110 459/IYY 207 Claret J . 560141I Cooper D. A, 941188 235 Crouch W. W. 288jl55 220 249 253 26Y 270 Clark R. D. 2871126 Cooper J. R. 961396 Clark R. J. H. 3831232. 233 234 Cooper R. 209/85 210187 88 Crouse G.D. 144119 Darwin W. D. 941394. 212 220 Crout D. H. G. 1791107 317/SY Das A. K. 14/20 15/41 Clark S. 951330 Cooper. R. D. G.. 2881225 381130 60 3 18/62 63 Das B. 209125 Clark S. M. 9512Y4 Cooper S. 225139 Crow W. D. 79/13] Das K. 171218 Clark W. G.. 9512Y4 Cooper S. J. 951350 Crowder R. D. 5561147 Das K. G. 2101124 Clarke C. F.. 555,'12 Cooper. T. M.. 382/YY Crul J. F. 92/48 Das M. C. 1411 Clarke E. A. 400 19 Copan W.G. 3841278 279 Cuadros L.. 92/25 Das P. K. 3851345 3YO. 391 3Y2. Clarke G. 951305 Copeland R. J. 346133 Cuadros R. 931162 393,394 Clarke I. E. 3861462. 463 467 468 Copley S. D. 318/133 51018 Cullen D. L. 2881157 Das S. 161/164 Clarke S. I.. 93/15? Coppola G. M. 400/21. 22. 40 Cullum M. E. 384/25Y Das U. N. 961428 Claverie. P. 3851388 Copsey. D. B. 14/26 Culvenor C. C. J. 219127 28 29. Das Gupta C. 80/17Y Clayton J. P. 42Sj5 Corbett K. 317/10 318/Y3 40 41 45 46. 248122 391117 da Silva A. M. Y. J.. 209/68 Clayton R. B. 556'118 Corcoran J.. 31714 Y Cumming S. A, 187/32 da Silva M. L. 21 11243 Cleland W. W. 319/1Y2 IY3 IY4 Cordell G.A. 15/110,161123 781 Cuomo V. 94/263 da S. Pereira M. 0..21 lil88 195 510125 556/6Y 64. 79/66 137 801176 160/100 Cupello A. 951321 Date T.243/3 Clement. R. P. 44/76. 579132 102 122 233143 74 400131 41 Curley R. W. 3821144 Dathe W. 32/63 Clemo N. G. 425134 37 42. 43 5 10156 Curran D. P. 425/11 Datta B. B.. 2881208 Cleveland T. E. 458/187. IYI lY2 Cordova R. 42517 Current S. P.. 287/110 Dauben W. G.,151116 Clezy P. S. 451121 461232 47/34 Corey E. J. 286,'45 287/102 103 Currie S.,555jl5 Daulatabadi N. 791134 187i4. 579149 580!151 167 181. 120 2881215 217. 218 346111 Curry B. 3841307 318 Daum G.,5561113 I83 492152 Curtis M. T.. 95/34U Dauner H.-0.. 44/51 Cline K. 4591205 226 Cori O. 523136. 556/YY 100 Cushman M. 961413 Dave V. 492153 Clive D. L. J. 4261140 Corina D. 45/160 Cutrufello. R.. 961375 Daves G. D.. 5601424 Clough J. M. 381/43 3841267 Corina D. L.. 5581234 Cybulski J. 24316 Davidson.A, 3851401 Cmiel E. 579161 62 83. 84 5801 Cork. M. S. 579154 55 Czapski. J.. 3861473 Davidson A. G. 22515U IIY 124 Cornelis A. 493//8Y Czechowski F. 580/170 Davidson B. E.. 3191172. IXY. IYI Coates R. M. 287,#145 Cornelisse. J. 4931141 Czeczuga B.. 383/225. 22Y 230 5 10120 Coburn W. C. Jr. 3821135 3841 Cornelissen F. 5591326 3861483 Davidson. G.. 961424 272 Cornforth J. W. 3191163 Davidson H. 556171 Cockrum P. A. 248/22 Correas. I. 951320 Davies B. H. 381148 Code R. 961379 Correia C. R. D.. 491114 Davies. R. C. 4317 44/50 Coert A, 209133 Cortes D. 9215Y8 232119 Davies. T. G. 5601405 406 414 Cogdell R. J. 3851335 Cortes M . 15/68 Dabra T. T. 92/26 Davis A. P. 461203 317148 Coggins J. R. 318ilO3 104 126. Corwin. A. H.. 44/73 D'Abramo L.R.. 3861484 Davis B. R.. 286161. 287/118 128 135 137 138. 13Y 319/141 Cory H. T. 5601424 Dabrowska-Bernstein B. 961429 Davis D. V. 9213 5l0115 16 17 Coscia. C. J.. 931174 178140 Dadson W. M.. 286117 65 70 76 Davis K. R. 4591207 Cohen M. R. 951331 Coscia E. M. 931174 178/40 77 Davis S. G.,347180 Cohen R. M. 951331 Costa. G.. 95/28Y Dafeldecker W.. 233158 Davis V. E.. 92j2Y. 931135 1-6 NATURAL PRODUCT REPORTS. 1985 Davis W. A. 233150 Demuth M. 145199 Dieter H. H. 5581261 Drautz H. 426198 Dawson B. A. 144191 Demuynck M. 1451121 Dieter J. W. 144110 Drawert F. 5241120 Dawson M. I. 3821138 139 140 de Napoli L. 5561114 Dieter R. K. 144110 Dreiding A. S. 144136 1451127 Daxenbichler M.E. 248129 Dencher N. A. 3861418 Dietsch A. 5561132 425131 4261110 Dayal B.4921120 121 558l285 Deneris E. S. 523127 Dietschy J. M. 557/186 Dresow B. 461218 296 300 Deng L.-S. 4931182 Dietz A, 425180 Drewes S. E. 219j15 Dayton D. F. 451141 de Nicola Giudici M. 471267 Digel M. 248117 Drews G. 451178 De B.,346111 Denisenko 0. N.,92/22 232118 Dillon J. L. 492171 Drexler S. A, 171204 Deakin J. F. W. 961394 Dennis C. 4581106 Dimbi M. Z. 161144 Drikos G. 3851340 341 342 de A. M. Reis F. 791107 Denniss I. S. 461238 Dimitriadou-Vafiadou A. 5571156 Driver H.E. 220153 de Alvarenga M. A, 21 1/189,217 Denny M.,3821101 3831158 3861 Dimitrov V. 159163 Du H. 171207 222 234 426 Dimmel D. R.,286119 31 2881213 Dua F. K. 93/111 Deana A. A. 4261144 Denny T. P. 4581189 Dinan L. N. 5601406 414 Duarte A. P. 791126 de Bernardi M. 14/12 Deodhar V.B. 159164 Ding S. 92/73 Duax W. L. 941196 491113 4921 Debitus C. 232126 de Ovando F. S. 556176 77 DiNunno C. M. 4931192 105 5581237 DeBold C. R. 555133 de Paiva Campello J. 210/110 DiPardo R. M. 243133 Dubart A. 579131 42 de Bruyn A, 801178 de Paoli M.A. 3851371 DiPietro R. A. 2871143 Dube P. 931170 de Carvalho M. G. 21 11243 de Pascual Teresa J. 15/70 159/4 Direkar P. V.,346116 Ducardus R. 225125 de Castro Dantas T. N. 3831191 160198 233171 3831208 Dirksen R.,941244 Duckworth D. C. 178197 104 3171 de Cian A. 3831206 De Pauw-Gillet M. C. 78/22 di Salle E. 78/55 22 3 18/81 83 de Clercq P. J. 1451121 De Potter W. P. 961393 d'Ischia M. 24814 Duddeck H. 160186 de Costa M. S. L. 159110 Depres J.-P. 144/93 Ditschuneit H. 555125 Dueltgen R. R.,286129 Decsei L.791138 Derdzinski K. 2881170. 3821138 Dittami J. P. 144169 Dugan R. E. 55512 59 Deeg R. 451190 191 140 Divakaran P. P. 4941211 Duggan J. X. 451148 150 151 175 Dtfago G. 4581105 Derguini F. 3821115 3861441 Diven W. 5581275 276 Duggleby R.G. 3191183 de F. Dias A. 209149 De Riso C. 555117 Dixon R. 941240 Duhamel R.C. 220159 DeFeudis F. V. 941245 Derome A. E. 178192 179/107. Dixon R. A. 45619 4581141 142 Dujardin E. 5801113 De Galan L. 941236 318162 63 76 78 79 147 150 159 161 4591209 Duke P. C. 941249 Degenhardt C. R. 2871142 de Roose J. 3841242 Djerassi C. 287/149 4921101 104 Dult M. C. 94/225 Degenhart H. J. 557/198 de Ropp J. S. 3871526 105 106 4931123 5591382 5601 Duma C. 94i239 De Giovanni N. 941233 de Rosa M.,3871514 515 516 517 416 417 418 419 420 421 422 Dumbroff E.B. 3841260 423 5801167 168 179 Dumbroff P. A. 3841260 DeGrip W. J. 3861426 Desai D. G. 21 Ill93 de Groot A. 1451112 de Salmeron M. S. A, 160/151 Djura P. J. 159110 Dumont R. 382169 70 Dehaussy H. 92/62 Descorte G. 2881219 Dmitriev S. M.,3861406 Duncan J. N.,5591367 DeHaven P. A. 578122 DeShong P. 425156 62 Dmochowska-Gladysz J. 2881170 Duncan K. 3181126 138 139 5101 Dehennin L. 209130 Deshpande V. N. 1781102 Do M. N.,1601155 16 17 Dehesh K. 5791108 111 de Silva E. D. 159jlO Dobashi M. 93/91 Duncan W. P. 3831149 151 Dehlaele M. 94/230 De Siqueira N. S. 209157 Dobbelstein D. 3821112 3841278 Deinzer M. L. 219149 Desnick R. J. 44/45 65 Dobberstein R. H. 23217 Dunit7 J. D. 5801190 Deiter S. A. 555145 de S. Ribeiro M. N. 21 11242 Dobler M.,425169 Dunlap N.K. 15j111 112 171210 de Jesus A. E. 78/14 16 178165. Dessinges A, 346131 42414 Dobson W. E. 425125 Duong T. 248139 426193 de Stefano A, 5601426 Docherty J. C. 579157 Duque C. 492/'/04 5571196 203 de Jong G. 79/73 Deus-Neumann B. 3841264 Doddrell D. M.,461211. 178162 Duquette P. H.,941210 961378 de Jonghe J. P. 801178 Deushi T. 961417 418 Dodds M. G. 4931202 203 Durman J. 144125 Dekanosidze G. E. 161169 181 Deutsch E. A, 4261137 138 D& de Maindreville M. 78/35 Durmishidze S. V. 5591321 Delaage M. 3841265 Deutscher K. R.,461209 Dopke W. 25113 5 Durst T. 210/123 286132 Dutky S. R.,346138 5591331 de Laat A. M. M. 4591244 Dev S. 523133 Doering W. E. 2881163 Dutta C. P. 171218 de la Concha A. 3831237 3861457 Deverall B. J. 45613 Dornemann D. 5801118 Dutta P.K. 14/20 468 de Verneuil H. 44/88 92 579140 Doherty M. 457133 Dutton C. J. 461207 208 5801198 de la Fuente A, 951316 42 Dohi S.,941250 951276 Dutton P. L. 3871554 de la Fuente M. 556199 Devi S. U. 555147 Doi M. 580/144 Duval D. 3841265 de la Garza R. 225132 Deviche P. 951348 Doizi D. 382181 Dvolaitzky M. 287194 De La Higuera N. 3 17/54 3 18/95 de Vlaming P. 510/69 Doke N. 457176 78 79 4591212 Dvorackova S. 961419 DeLange R. J. 579179 Devlin J. A. 177117 219131 213 Dworacek B. 225125 de la Peiia A, 4941222 Devreese A. A. 1451121 Dolamore P. G. 4931202 203 Dwuma-Badu D. 791105. 92/26 Delatour T. 3841315 3851397 Dewanckele J. M. 144179 Dolejs L. 931107 Dwyer J. T. 209135 36 Delaude C. 16/14/ 144 78/60 801 Dewar G. H. 92/51 Dolphin D. 5801140 Dyadyusha G.P. 92/82 161 168 de Weck G. 3831222 Dolphin D. H. 458/131 Dybailo Z. V. 4931170 del C. Batlle A. M. 43/11 36 441 Dewey R. S. 425174 Domayne-Hayman B. P. 318178 Dykstra L. A. 941256 961397 68 75 Dewick P. M. 210/105 21 l/lSO 80 Dzelzkalns V. 4318 Delderfield J. S. 31716 183,4581151 152 153 154 155 Dombi G.. 492160 Dzhikiya 0.D. 161169 181 Dele M.L. 3831235 156 157 160 161 170 184 5101 Dominguez D. 961408 de Leenheer A. P. 381147 3841241 I 54 55 51 1/76 Dominguez X. A, 161191 193 242 de Winter M. S.,492173 Domnas A. J. 5591353 DeLeo A. B. 318/111 de Wit P. J. G. M. 457186 459/ Donker-Koopman W. E. 510170 Delfosse M. 346//7 215 216 232 233 Donnelly D. M.X.,1611186 187 Eales L. 461260 Dell A. 4591250 268 DeWitt S. K. 523137 Dsnstrup S. 5801160 Earl R.A, 801181 Delmelle M. 3851361 362 de Wolf M. 3871531 Dorman D. E. 1781104 318/83 Earley W. G. 80/152 de Loof A. 5601408 410 Dey J. A. 220154 Dorn C. R.,493/165 Easton C. J. 178198 317149 50 de Lourdes Quintero M. 160/119 Dey P. M. 45619 4581159 4591209 Dornyei G.,92/30 941214 215 Ebel J. 4581115 116 143 144. 4591 de Loze C. 3841315 3851397 Deyama T. 209176 216 217 218 219 Delprino L. 15/60 61 5561132 Dhal R. 210//31 164 165 Doskotch R. W. 160183 Ebert E. 5591340 133 558l302 303 304 5591314 Dhaneshwar N. N.,160180 523182 Dotan I. 556168 Ebizuka Y.,346132 4~411 2 363 364 Dhar K. L. 209158 21 11192 400128 Do-Trong M. 4931153 Ebrey T. G. 3851331 del Puppo M. 492130 4931125 Dhara J. P. 79/77 Douce R. 451167 Eck C. R.,286146 47 54 DeLuca H. F. 382/144. 3861490 d'Harlingue A.51 1/89 Dougherty R. C. 5801149 Eckardt K. 347174 4931144 Dhasmana K. M. 92/83 Douillard R. 3841280 385/380 Eckart K. 46/242 Demain A. L. 178199 101 105 Dhawan B. N. 233144 Doukas A. G. 3851395 3861419 Eckenrode F. M.,791143 31715 5 16 17 22 27 28 29 30 Dhingra M. M. 3851400 433 Eckenrode M. E. 791143 34 35 37. 318184 102 Dholakia J. N.,3861476 477 Doux-Gayat A, 4581105 Eckhardt G. 243126 de Matteis F. 451120 Dias S. M.C. 21 11232 Dow W. C. 4921106 Edelstein S. 3831156 de Mayo P. 28614 492143 Diaz D P. P. 21 11197 Dowd P. 523121 Eder U. 493/194 Dembinska-Migas W. 161/181 Diaz E. 160/114 154 Dowell D. S. 92/17 Edgar J. A. 219134 248122 Dembitskii A. D. 5241135 Diaz L.,44/79 Downing J. F. 556165 Edinger J. 579188 Demedts P. 941230 Dick A. T. 219127 Doyle M.P. 491117 Edington C. 46/22] 222 240 5801 DeMoss J. A. 3191152 154 155 DiComo F. 5241109 Draber W. 556166 128 156 Diekert G. 461223 224 Drain P. 492182 Edmond J. 5571158 Dempsey M. E. 5561112 5571156 Diener E. 461213 Draper R. W. 492136 79 80 Edstrom E. 941213 162 Dierick W. 3871531 DraSar P. 4931122 209 Edwards M. P. 425166 NATURAL PRODUCT REPORTS 1985 1-7 Edwards 0. E. 15/64 Erge D. 178177 Farrant R. D. 209131 40 Findlay J. W. A. 951291 Edwards,.P. A. 555/8 9* 12 14 27 Erickson K. A. 5571183 Farrow A. 21 11179 Finkel’shtein E. I. 3861409 410 61 Erickson K. L. 160115.5 Farthing J. E. 317140 Finn J. 4261143 Edwards R. L. 425146 Erickson R. R. 961378 Farwaha R. 492143 Finner E. 161180 Egan R. 347173 Erickson S. K. 523113 5551.57 5581 Fatima J.791132 Firl J. 79/81 Egert E. 15/57 288 Fatima K. 791108 Firneisz G. D. 579157 Eggensperger H. 287193 Erm A. Yu. 3831166 Fatima T. 791133 Fischbein A. 471263 Eggerer H. 3191163 555136 Ermakova C. A. 3821102 Fattorusso E. 171203 5561114 Fischer J. F. 288/171 Eglinton D. G. 579/51 Erman W. F. 286168. 2881192 220 Faulkner D. J. 159112 523183 Fischer N. 286124 Eglinton G. 5801147 Ermann P. 3861438 Fausa O. 5581299 Fischer N. H. 160/109 110 111 Eguchi T. 4921113 Ernst L. 461218 240 3821120 3841 Faust J. R. 555129 30 63 5561106 112 Ehrenberg B. 3821103 273 5801155 Fautz E. 4261113 4581116 145 Fischer P. 178172 Eich E. 178179 Errick J. K. 961387 Faux A. F. 5601403 404 Fish S. M. 3181132 Eierman D. F. 5591353 Erwin D. C. 45615 Favinger J. L. 5801122 Fisher M.A. 3191192 510/25 Eikenberry J. N. 2891237 Eschenmoser A, 45/181. 461201 Favre-Bonvin J. 210/172. 4581134 Fishman H. K. 961373 Eilert U. 458/136 137 202 203 212 213 214 216 217 Favrot J. 3841315 3851397 Fishman J. 4931193 5581235 236 Einarsson K. 523118 223 226 471269 270 5561117 Fawcett P. A, 317113 55 56 3181 246 Einav M. 578jIO 580/131 134 190 191 192 96 97 Fiske M. J. 318/110 510/2 Eisenberg R. 210j133 Eschenmoser W. 382171 77 Fayos J. 16/19/ 193 931162 1591 Fleet G. W. J. 187140. 24318 42519 Ekanayake N. 14416 Eshel Y. 4591264 46 1611172 173 Fleischhacker W. 941200 Ekiko D. B. 5571223 Eslava A. P. 3861480 481 Fedeli W. 1591.50 Fleming I. 2881156 426194 Eksborg S. 931155 Esperling P. 492164 Fedorovich I. B. 3851373 Fleming J. E. 451116 Ekstrom A.461255 Espey L. L. 961433 Feierabend J. 3861464 Fleming M.P. 248127 2871137 Ekstrom M. 21911 Essa A. K. 177/9 Feigelson G. B. 144126 Flesch P. 5591355 Ekundayo O. 178j34 523140 Essenberg M. 457133 Feigenbaum J. J. 951273 337 Fleuriet A, 510/52 Elander R. P. 317139 Estevez R. J. 233167 Feingold K. R. 523113 555139 53 Flippen-Anderson J. L. 210/157 Elango V. 931151 Eubanks S. W. 461261 Feinmann-Weinberg R. 3821103 Flitsch S. L. 318180 El-Azizi M. M. 92/26 Eugster C. H. 346115 381133 39 Fekete M. I. K. 951303 Florencio F. 22515 El-Bialy H. 523/50 40 45 382168 71 74 75 76 77 Feldberg W. 951366 Flores H. J. 251/11 I2 Elder G. H. 44/87 Y7 103 104. 78 3841284 Felice L. J. 457119 Floss H. G. 461230. 178173 317158 46/26] 579141 Eustace E. J. 286159 Felix F.57816 3181113 134 3191144 153 160 El-Feraly F. S. 1451105 160183 Evans C. F. 4261140 Felix H. R. 317114 31 41 164 347160. 510,@ 51 1/92 108 21 11241 Evans J. A. 3861458 Feliz M. 79/87 Fludzinski P. 160/113 El-Fishawy A. M. 233142 Evans J. N. S. 579127 Felkova M. 931175 176 Flugy A. 951349 Elgersma D. M. 4581177 Evans J. O. 44/97 103 Fellows B. 523191 El-Hamamy A. A. 492196 Evans W. C. 21 1/183,22512 2881 Fellows P. A. 78/15 Flynn G. A. 4941220 558/240 Fodor G. 225110 El Hamouri B. 579/Y9 153 Fels G. 225/20 El-Hindawi. S. 523150 Evenari M. 209185 Fels J. P. 233163 Fogelman A. M. 55518 9 12 14 Elix J. A, 248135 Everaert J. 3851396 27 61 5571160 Fogleman J. C. 5591317 Evershed R. P. 5801147 148 Feng J. 931100 El-Kawi M. A, 233135 Evidente A, 25114 Feng X.Z. 79/71. 801172 Foley T. 4318 Fong H. H. S. 23217 233143 74 Elliott J. 144/25 Evstigneeva R. P. 382198 I21 Fenical W. 5601422 423 Elliott J. D. 4261128 Fenstemacher R. 3861430 Fong W. C. 286133 Elliott W. H. 43/10 492193 57812 Evteeva N. M. 3861407 408 Fenstemacher R. J. 3831160 Fonken G. A, 2871100 4,5 7 Exon C. 80/148 145196 Fernandes J. B. 21 11232 242 Fonouni H. 178174 Ellis A. B. 383/157 Eyssen H. 317118 Eyzaguirre J. 556176 77 80 81 Fernandes de Azevedo L. 961434 Fonseca S. F. 209150 210/110 Ellis B. E. 524/107 Fernandez A. 233171 Font J. 2101162 Ellis C. 3841253 Fernandez F. 3871547 Fontani G.,951282 Ellsworth R. K. 451139 140 145 Fernandez L. A, 556jlOO Fookes C. J. R. 4316 44/51 52 56 Elmadfa I. 243123 Fernandez de Cordoba H. 232110 57 59 61 63 72 74 80 81.451 121 182 461204 207 208 221 El-Masry S.,160j141 Faden A. I. 941.259 951342 Fernindez G. J. M. 4941222 El-Moghazy S. M. 400139 Fadlallah M. 492166 Ferraboschi P. 4931177 187 188 222 232 240 253 255 579149 El-Sayad H. A, 92/52 El-Sayed A. 79/66. 801176 Faedda G. 492185 Ferramola de Sancovich A. M. 441 580/128 186 93 Forche E. 178142 El-Sayed M. A. 3851322 326 327 Fassler A, 461217 223 226. 5801 Ferramola A. M. 43/36 Ford D. W. 791127 134 135 3861423 Fagbule M. O. 961405 Ferrari F. 961372 233162 Ford W. T. 382194 Elsevier C. J. 492/4/ Fagerness P. E. 44/53 55 461233 Ferrari G. 210/109 Forkmann G. 510/61 62 63 El-Shagi H. 178127 244 245 246 579127 5801126 Ferreira D. 210/117 Formacek V. 178147 Elson A. 178/106 317146 Faghih R.248125 Ferreira S. H. 941247 Formica J. V. 178163 Elwood J. C. 555133 Fahmy M. 951310 Ferrer A, 52318 Formiga M. D. 21 1/188 Elyakov G.B. 15/71 Fairchild E. H. 160183 Ferrer J. C. 492192 Forster M. O. 286116 2881178 Elyakov G.V. 14/30 Fairclough D. P. 3831232 233 234 Ferreri C. 491/25 Fosket D. E. 3861470 471 Elzay T. K. 317124 Fajardo V. 92/61 931148 157 2331 Ferres H. 555137 Foss P. 381119 34 Emanuel N. M. 3861407 70 Ferretti P. 95/288 Fotsis T. 209135 36 Emeric N. 5581266 Fajer J. 451185 186. 580j164 Ferri S. 951289 Foulon C. 346117 Emmanouil V. 4591263 Fajkoi J. 49118 4941227 Ferriere H. 457158 Fournet A. 18718 27 23215 Emmons G.T. 557/185 Falck J. R. 4261145 Ferrigni N. R.,92/14 Fourrey J.-L. 2871141 Emslie N. D. 219115 Falk H. 451155 579187 88 89 90 Ferro E.16/191 193 Fouweather C. 346129 Enderle U. 560/411 5801157 Fesenko L. M. 220165 Fowler M. W. 524/110 Endo A. 347j57 55514 16 29 5561 Fallis A. G. 144164 65 Feser C. 510127 Fowler R. 2871135 70 Falsone G. 16/180 182 171205 Fetizon M. 492158 Fox C. M. J. 425138 Endo H. 951324 425142 206 Feuerstein I. 160186 Fox D. L. 38117 Endo K. 75/64 Fan J. 209147 Feutry A. 5lOj51 Fox K. R. 178162 Endo Y. 78/41 Fan Y. 225140 Feyereisen R.,523179 Frackowiak D. 3851383 Eng R. R. 4931155 Fan Y.-M. 4931182 Fiecchi A. 492130 45 100 4931 Fraga B. M. 161146 191 193 Engel C. R. 492155 Fan Z. 4931179 180 125 132 187 4941225 5561146 Fragen R. J. 92/48 Engel J. 4931208 Fang D. 92/84 88 89 90 93j95 5571161 Frahm A. W. 210197 25117 Engel K. H. 161/183 Fang J. M. 3821139 Fiedler E.3871567 573 Frahn J. L. 248122 Engel R. 556178 Fang J.-R. 179/110 Field F. H. 580/150 Franceschi G. 381127 Engels P. 287/Yl Fang S.-D. 210/150 151 Field F. J. 523110 Franceschi V. R. 451132 Engler D. A, 2871146 Fantini A. A, 347175 Field L. D. 178192 317/7 8 20 Francis J. E. 44/91 579137 Englert E. 44/82 Fardella G. 15/104 I59/50 318/70 73 76 80 94 Francisco C. G. 492175 Englert G. 381139 382/66 Farina V. 941219 Fields K. W. 2871130 Franck B. 578120 5801175 Enikolopyan N. S. 492147 Farines M. 3841245 Figliuolo R. 21 11222 223 Franck-Neumann M. 3831206 207 Enokita R. 425164 Farley C. M. 5571166 Fiksdahl A, 381118 Franco C. M. 225137 Enzell C. R. 3851363 Farmer D. J. 579129 Filer C. N. 233155 58 Franke P. 4931205 Epe B. 1412 15/88 100 I01 Farnsworth N.R. 15/110 161123 Filippova T. M. 3831205 3871552 Franzen L.-E. 459/269 Erdtman H. 346/24 1601I00 Finch A. M. T. 286143 Frasinel C. 5601434 Erdtman H. G. H. 209/24 Farooq S. 461226 Fincke M. 225124 Frecknall E. A, 381144 Eremin S. V. 3821121 Farooqui A. A, 5571209 Findlay J. A. 209143 Freer A. A. 425i70 1-8 NATURAL PRODUCT REPORTS 1985 Freer I. 52315.5 Fukushima H. 5571149 Garcia C. 160/119 Gieselmann M. 2891235 Freerks R. L. 187133 Fukuyama Y.,15/99 159113 Garcia-Blanco S. 22515 Gil G. 555140 Frei B. 3831165 209 210 214 217 Fukuzaki K. 144145 Gardiner S. M.,951367 Gilbert H. F. 556167 218 219 220 221 222 223 Fuller G. 3861445 449 Gardner D. 425170 Gilbert L. I. 5601404 414 Frei R.W. 3871561 Fuller K. W. 5241111 Garegg P. J. 4591221 224 225 Gilbert M.T. 44/82 Freire R. 15/68 492175 Fullerton D. S. 4931199 Gariboldi P. 159174 160176 131 Gilchrist B. M. 3831228 233 234 French J. C. 159140 425125 Fumagalli R. 5571161 142. 492145 Giles N. H. 318/106 108 Freudenberg K . 20914 Fumagalli S. 44/68 Garneau F.-X. 14/31 Gill J. P. 5801147 Frey M. H. 931180 Funakoshi S. 791129 Garnier J. 801159 Gill M. 426199 Freye E. 951327 Funayama S. 233174 400131 41 Garratt P. J. 4571103 4581167 Gill S. 161/181 Freyer A. J. 92/61 63 931148 157 42,43 4591210 Gillan F. T. 3841248 161 233170 399111 Funfschilling P. C. 2871122 Garrett B. J. 220162 63 Gillbro T. 3851349 3861422 Freyssinet G. 451173 Funk R. L. 145/117. 4261136 Garrett K. M. 951306 Gilles H. H. 461223 224 Frickel F. 381/11 3821141 Furihata K. 426185.457199 Garrido-Fernandez J. 38 I15 Gillet B. 791129 Friedlander E. J. 5561129 Furuhata K. 78/41 Carson M. J. 346134 35 Gilman S. 2881161 Friedman N. 3821103 105 128 Furuichi A, 426/102 Garza G. A. 4931190 Gilmore C. 523155 Friedmann H. C. 43/22 25 44/43 Furukawa F. 220155 Gaskin P. 524193 94 97 I01 Gilmore C. J. 2101132 163 5801137 Furukawa H. 171215 78/10 801 Gasparini F. 5571203 Gilmore J. 78/25 Friedrichs E. 931142 164 165 92/67. 233172 346126 Gau C.S. 4941235 Gilmour S. J. 524197 102 Fries D. S. 961388 28 39916 400133 36 425120 Gau W. 3841251 Gilpin M. L. 1781106. 317146 Frischknecht H. R. 96/38] Furukawa J. 347166 67 Gaudilliere J. P. 51 1/89 Giordano G. 3871574 Fritz U. 159134 Furukawa K. 160/157 Gaudin J. 5591340 Giordano 0. S. 160/151 Fritzberg A.3171.55 318197 Furukawa S. 400138 Gaughan R. G. 14/10. 5561103 Girard M. 14/31 Fritzemeier K.-H. 4571104 4581 Furuno T. 15/102 105 Gaul Z. N. 951318 Giri D. N. 4591262 107 51 1/83 Furusaki A. 159141 42 43 44 Gautam V. K. 3831196 Giri V. S. 79/89 Frobel K. 461194 346127 42 347153 Gautheret R. 5241121 Girotra N. N. 4261134 135 Froissios C. 3 I81122 Furusawa F. 3871519 524 Gautieri R. F. 941252 Gladiali S. 492185 Frolik C. A, 381/11 11 Furuya K. 4261107 131 Gauvreau D. 178164 Glasby J. S. 1414 18711 Frolow F. 210/135 Furuya T. 931117 178139 41. 2331 Gavuzzo E. 159150 Glass T. E. 179/111 Frome D. M. 557116.5 41 391123 Gayen A. K. 4921108 Glassel J. A, 961396 Fronczek F. R. 161152 160/109 Fusi F. 579165 Gaylor J. L. 55512 5571149 153 Glazer A. N. 579179 80 81 92 111 119 Fuska J.4941240 155 195 Gleizes M. 523152 Fronza G. 14/12 Futatsugi M. 5241124 Gazelli E. 941182 Click S. D. 225136 Frost J. W. 318/115 120 51015 6 Fuwa T. 15/77 79 81 82 Gebhart G. F. 961386 Glinski M. B. 210/123 Fry S. C. 4591253 Gebreyesus T. 400134 4921106 Gliozzi A, 3871517 Frydman B. 44/78 79 579164 Geewananda Y. 187130 Gloger M. 9218 941232 237 Frydman R. B. 44/78 79 579164 Gehri A, 4591245 Glover W. H. 2871118 Frye J. L. 3821135 3841272 Gabard J. 287185 Geiger H. 286167 Glusenkamp K.-H. 178153 Geigert J. 523137 Fu W. Y. 286119 2881213 Gadher P. 5591326 Geissman T. A, 21919 Glusker J. P. 5801162 Gmerek D. E. 961404 Fuchida M. 14/33 Gaertner F. H. 318/105 3191152 Gelbcke M. 9216 Fuchs A. 457146 Fuchs E. F. 9218 941234 Gartner W. 3821104 106 120 Geller E.B. 951294 Gnecco Medina D. H. 225118 Gellrich B. 381154 Gneuss K. D. 45/191.46/199 3861437 Fuchs W. 161125 Gaeta F. C. A. 286158 Gemmer R. V. 2871110 Gnonlonfoun N. 3831178 Goad L. J. 555120 5591361 362 Furst A, 4931148 Gaete-Holmes A. 5801167 Fuesler T. P. 451132 133 579194 Gagarina A. B. 3861407 408 Gendin D. V. 2871127 365 367 368 5601433 Genin D. 801157 97 Gaines C. G. 3191142 510/12 23 Gennari C.,346130 42413 426190 Godel T. 144131. 2881229 Fuhrer H. 55913411 Gaita G. 210/102 Godelmann R. 5241120 109 Fuhrer J. 4591243 Galbraith M. N. 5601404 Gentien P. 383/226 Godinho L. S. 14/13 Fuhrhop J.-H. 5801180 Galby J. 25119 Georgopapadakou N. H. 471272 Goeb A, 286179 Fuji K.. 187128 Galeffi C. 78/19 791118 120. 1601 Gerats A.G. M. 510170 Goeders N. E. 225135 Fujii H. 3871538 542 136 Gerdes H. J. 17718 Goedken V. L. 160/103 1611174 Fujii K. 461228 Galemmo R. A, 145/100 Germer H. 287191 Goegelman R. T. 555117 Goering H. L. 2891237 Fujii. S. 5581264 Gallacher G. 144164 248110 Gero L. 92/43 Fujii T. 93/96 167 168 169 Gallagher J. 791144 Gerrish C. 4581147 Gorisch H. 319/171 Fujii Y. 4931184 Gallagher R. T. 78/17 Gerteisen T. J. 2871151 Goers S. K. 510/21 22 Fujimori T. 1601124 147 148 1611 Gallagher T. 80/148 150 Gerth K. 347191 425123 77 Goewert R. R. 3871575 Gozler B. 9214. 931104 144 148 188 38 1/57 60 457140. 41. 43 Galli G. 492145 555160. 5561146. Gerwert K. 3851332 Fujimoto H. 14/16. 17 209177 21 I/ 5571161 Gerwick W. J. 178174 149 165 166. 96140.5 399111 177 Galli Kienle M.555/60 5561146 Gest H. 5801122 Gozler T. 931143 147 149 399111 Fujimoto Y. 425124. 492199 5591 Galligan J. J. 951287 Gevorkyan B. Z. 3841303 Goff D. A. 451185 186 461238 3Y0. 5601393 395 396 Galpin. I. J. 5241118 Ghaleb H. A, 391125 Goff H. M. 5801184 Fujimura T. 523156 Galvez E. 2251.5 Ghera E. 210/135 Goldbeck R. A, 5801167 Fujimura Y. 5571226 Gambacorta A. 3871514 515 516 Ghia J. N. 951291 Goldberg A. 580/1Y3 Fujinari E. M. 461247 517 Ghisalba O.,3191169 Goldberg I. 4941234 Fujioka H. 2871123 Gambliel H. 523141 Ghiuru E. 210/102 Colder W. S. 5591377 Fujioka T. 16/I85 14419 4261111 Games D. E. 451110 Ghosal S. 209167 84 210/Y7. 2511 Goldfarb S. 555147 5571192 I I2 Gampe R. T. Jr. 3871530 I 7 8 400127 Goldin B. R. 209135 36 Fujisawa. S. 524198.YY Can L. 14/34 15/54 55 56 Ghosh A. C. 941196 Goldman J. 2881227 Fujisawa T.. 14415 1451106 Ganem B. 243111 319/158 425132 Ghosh A. K. 144/YI Goldschmidt R. 961423 Fujisawa Y. 317142 5 10126 Ghosh P. K. 161201 Goldstein J. L. 55514 28 29 30 Fujita E. 187128 248114 Ganesh K. N. 46/25Y Ghosh-Dastidar P. 233173 63. 556/106 Fujita M. 457122 28 Ganeshpure P. A. 209141 Ghozland F. 941199 Goldstein J. M. 951332 Fujita N. 425147 Ganguli M. 425122 Giacherio D. 3841253 Golebiewski W. M. 177/20 22 Fujita T. l5/109 Ganguli N. C. 931161 Gianotti M. P. 14/12 Golovina L. A, 159147 48 161/174 Fujita Y.. 14/Y Ganguly S. N. 7817 Gibb W. 5571215 Comes M. C. C. P. 21 lj231 Fujiwara J. 144/22 Gani D. 318189 Gibbons. G. F. 523112 555124 5561 Gomez I. 556176 77 Fujiwara. T. 16/11Y I29 Ganjian.I. 1601113 400/2Y 140 141. 5571187 Gbmez J. 4931191 Fukae R. 451172 Ganson R. J. 510123 Gibbs A. H. 451120 Gomez R. 3831227 Fukami H.. 426187 4581117 118 Canter C. 425110 Gibbs M. 3861471 Gomez G. F. 160199 121 Ganti V. 941207 Gibbs P. N. B. 43/34 Gommerson W. 961393 Fukamiya N. 15/1UY Gantron M. 951363 Gibson D. M. 555143 556164 Goncharova N. V. 5801116 Fuke K. 3851368 Ganzinger D. 177112 Gibson J. M. 5601402 Goncharova S. V. 3831197 199 Fukuda H. 16/200 Gao H. 225151 Gibson J. R. 14/24 Gong J. 4931179 Y.-L. 209143 210/150 Gibson K. H. 44/48 Gonzalez A. G. 161146 191 193 Fukui H. 51 ljY0 G~o Fukumoto J. M. 3861423 Gaponova G. I. 5801116 Gibson T. W. 286168 2881213 159138 46 160/137 Fukumoto K. 151117 161118 801 Garas N. A, 457183 4591213 Giencke W.144157 Gonzalez C. M. 16/191 193 180. 2 19/10 Garate A. M. 3831227 Gieren A, 3851364 Gonzalez F. B. 4931194 Fukumura M. 317112 Garber E. D. 38116 Giesbrecht A. M. 209149 21 11189 Gonzalez J. 22515 Fukushi H. 144152 Garcia B. 145/108 234 Gonzalez M. S. 15914 160198 NATURAL PRODUCT REPORTS 1985 1-9 Gonzlilez P. 1611YI Greger H. lS9j21 22 62 18716 Gundy. A. 523154 Halonen A. 287184 87 Gonzalez R.,5561112 209166 Gunji S. 425126 Halsall H. B. 49311.58 Gonzalez Solveyra. C.,961368 Gregg G. 555150 Gunn J. M. 461246 Haltiwanger R. C. 286134 Gooch E. E. 4261x6 Grein A, 381127 Gunsalus I. C. 2871102 103 104 Hamada Y. 251/14 Gooding D.,145/111 Grekin R. 3841253 105 Hamaguchi H. 3841310 311 Goodman D. S. 3Rl/ll,11 Grenz M. 159131 32 Gunzer G.44/51 Hamamoto T.,425126 Goodwin C. D. 5581274 Grevel J. 941248 Guo H. 225146 Hamana K. 384/243 Goodwin T. 523/YO Grey S. 286129 Guo R. 161136 Hamana M. 187143 Goodwin T. W. 38111. 386/446 Gribble G. W. 791128 Guo Y. 941204 Hamano K. 4261131 450 55512 5591368 5601405 406 Grieco P. A. 1451122. 287/121 Gupta A, 3871577 Hamasaki T. 346136 414 2881161 4261143 Gupta A. S. 523182 Hamazaki T. 24815 Goossens J. F. V.. 4581170 4591248 Grieger I. 3851323 Gupta M. M. 961430 Hambley T. 461255 Goossens M. 579131 42 Grierson D. S. 791115 187/21 22 Gupta S. 93/118 178129 233134 Hambley T. W. 580/166 Gorbach S. L. 209135 36 2251I8 Gurll N. J. 95/339 345 Hamill R. L. 248124 Gordon H. 209132 Griffin D. 386/4Y3 494 3871495 Gurne D.,43/35 Hamilton A. D. 441105. 451113 Gordon H.T. 38118 Griffin J. P. 951302 Gurria G. M. 5.56193 Hamilton B. K. 457j33 Gore M. G. 44/3X Griffin R. G. 3841275 276 277 Gurusiddiah S. 346113 Hamilton D. 951355 Gorman M. 3 I7/3 Griffiths W. T.. 451156. 157 5791 Gust D. 382180 81 3841268 Hamilton P. B. 347171 Gorodetzky C. W.. 94ilY4 212 YY 100 103 Gustafson D. H. 2881192 220 Hamilton. R. L. 3841282 Gorovits. M. B. 15/35. 47 48 4Y Grigor'eva N. Ya.. 3871521. 522 Gustafson-Potter K. E. 44/52 57 Hammans J. K. 385'379 50,51 52 53 Grigoriadis D. 233155 Gustafsson B. 209134 Hammer J. 178142 Gorovits T. T. 15:4Y. 52 Grimshaw C. E. 318/131 133. 3191 Gustafsson J. 5581279 280 282 Hammerschmidt F. 461194 Gorst-Allman C. P. 78/14. 178165 181 510/8 I9 283 290 298 Hammerschmidt R. 457142 71 187/3Y. 248122 346125 425115 Grimshaw J.20916 Gustine D. L. 4591256 Hammouda F. M.. 391/25 52 Grinstead G. F. 5571149 155 Gut M. 5571199 Hamon D. P. G. 288'1YI Gossauer A. 44/58 461251 579172 Grinstein A. 4591264 Guthoff C.,451164 Hampton B. L. 286129 77 580jl85 Grisebach H. 45614 458111.5 144 Gutierrez C. 25115 Han A, 5581267 Gosselin P.. 144117. 3831180 148 14Y IS#. 181 182 4591259 Gutman A. L. 451182 5791107 Han C. A.. 4931161 Goswami U. C.. 3861487 48X 51 1/75 77 Gutowski G. E. 80/177 Han J. 951344 961402 Gotarelli G. 941238 Grissom C. B. 319/IYS Gutschow C. 3 191163 Hanack M.. 287/Y3 2881198 Gothoni P.. 225124 Grobbelaar. N. 387139 Gutterman Y. 209185 Hanada M. 24819 Goto. G. 492162 4931175 Groger D. 178160 77 8Y 90 Guyot M. 381120 492/110 Hanafusa M. 556/115 Goto J. 791125 5581236 Groen M.B. 209133 Guziec F. S. 2871140 426192 Hanamoto C. M. 451133 Goto. K. 94/20] 202 225149 Groenewegen A, 3871549 Guzik P. 24811 Hanaoka M. 79/92 801149 151, Goto T.. 78147 510131 Gromov L. A. 951277 931121 122 158 ISY 160 18713 Goto Y. 2111lY1 319/146 148 Croquet A. 941245 Hanbauer I. 225130 579150 Gros E. G.. I59/67 Handa S. S. 78/64 Gotoh Y. 144;s. 145/106 Gross R. 243123 24 Gottlieb. H. E. 210188 106. 135 Grothaus. P. G. 144142 Haag A, 382168 Handy. G. A. 79/66 801176 1601 100 21 l/lXX 231. 232 242 Grotjahn L. 461218 5 10142 Haard. N. F. 456111 45912.54 Haneishi T. 425164. 4261107 Gottlieb 0. R.. 20812. 3 209120. 4Y Grove J. F. 347150 Haataja H. 78121 210/106 113 21 1 1lXfj7 1x7. IXX. Gruber. J. 3821138 Haber S.. 178/105 318184 Haniu M.558j260 1x9 IY7 214 217 222 223. 224 Gruber W. 2881202 Haberlach T.. 459/247 Hanke B.,92/70 225 226. 228 23 I 232. 233 234. Grubmayr K. 5801157 Habermehl. G. 46/258 Hannart J. 80/17X Hansbury E. 5571154 184 I90 237 242 243 Grue-Serrensen G. I77116 Habermehl G. G. 14/23 Hansen J. 187120 248/8 Gottschalk P. 14414 Grumbach K. H. 3861455 465 Hackler L. 492160 Gottschall K. 579,ihY. 70 556172 Hadd H. E. 491/13 Hansen K. B. 3841,791 Hansen M. M. 145,'117 Gottsegen A,. 458i164 Grundon M. F. 24315 20. 25112 6. Haddock B. 3871574 Hansen P. E. 580/1SY Gough M. J.. 24318 4251Y 400/16. 19. 20. 23 5 IO/SY Haddon R. C. 3191175 Hanson. C. 347173 Gough. S. P. 43/18. 578113. 14 IS Grutzner. J. B. 318/101 Haddon W. F. 220152 Could R. G. 555157 Gu. H.-Q.. 4931182 Hadley C.R. 426/139 Hanson. J. R. 492144 52213. 5231 80 81 5591379. 380 Could S. J.. 178174. 179110X IOY Gu L. Q.. 3871553 Hadley M.S. 225/Y Govind N. S..3861475 Gu W. 161136 Hadwiger L. A. 459/197 202 229 Hanson. J. W. 579146 Govindachari T. R.. 80/158.24816 Guaciaro M. A,. 4261126 255 Hanson K. R.. 318,'116 Haedicke. E.. 3821141 Hanson R. C. 384128Y Govindan S.. 426;I2I) Gualandris R. 426/10Y Haegele K. D. 160/112 Hanson R. F. 558!2X6. 2YS Govindan S. V. 1451120 160/116 Guan J.-H. 233155 58 Hauser. I. 5791108 Hanssen H. P. 524'128 Gracen V. E. 4591200 Guedes M. E. M.. 457142. Y3 94 Hafeez M. 791132 Hansson. E.. 951321 Graebe J. E. 523'87. 524iY4 YS Guedin-Vuong D.. 391/18 Hagaman E. W.. 80/173. 177 Hansson. R.. 5581288 2Yl Graf U. 219i50 Guella G.; 1591lY Hagenbach R.287/151 HanuS V. 492/3X Graham. B. D..425125 Giinther. H.. 45/18? Hagens R. 2881175 Hanzlik R. 556/llX Graham S.L. 14312 Guerrant G. O.,3871558 Haginiwa J. 79,'76. 24311'5 Haque M. E.. 17/230 Gramatica P. 21 1/18],18.7 Guerrero C. 160/114 Hagino. K. 21 l/lYl Hara H.. 92/16. 18. 232:15. 233148 Grambow H. J.. 510136 Guerrier L.. 187321 Hagiwara H. 280142. 44 75 2871 4Y 24815 Granat M. 96/43] Guerriero. A. 159jlY Y7 Hara. K. 144/30 Granchelli F. E. 233158 Guesdon J. P.. 3841304 Hagiwara. Y.. 94/270. 248114 Harada H. 78/42 Grand C..510!4Y. 50 Guest. D. I.. 4593260 Hagler. W. M. 347/71 Harada. K. 961417. 418 3841266 Grandchamp. B.. 44iY2 579131 42 Guggisberg A. 79/84 Hagmann M.-L..458/15X. 51 1/75. Harada Y.,425142 Grande. M. 3831208 Guha P. C.,286153 77 Haradahira.T.,491 Y Grandi R.. 523147 48 Guha. R. 209162 Hahlbrock. K.. 458/115. 116. 141. Haraguchi M.. 21 1 226 Grandjean J. 425140 580/113 Guilbaud. G. 941242. 951279. 2x0. 142 144. 145. 146 4.591230 Haraguchi. T. 34733 Granell F. 15'70 363 Hahn E. F. 941,730 Harayama. T. 144iS2 Granick. S.. 43/18 Guilhem J.. 791x3 114. 121. 80/161 Hahn M. G.. 458/1HI. 4591IYY Harbison. G. S.. 384!275 276 277 Granolini G.. 15/104 Guillard R. R. L. 3811lY Hahn. T.-R.,579185 Harborne J. B.. 190. 458i172 524! Grant W. D.. 3871514 515 Guillerm. D. 144111 Hai. M. A. 78/57 134 Grasbeck R.. 580,'IY4 Guiltinan M.. 3861471 Hai. T. T. 471264 579i4Y Harbour G. C.. 78 2.7 Grasmeijer. G 94i228 Guinan D. M. 95/36] Haider B. 93/17] Hardeman E. C.. 555!13. 29 Grassi E. 55W27.5 276 Guinaudeau.H.. 92/56. 57. 5X. 63. Hait. G. N. 459,261 Hardgrave. J. E.. 555154. 55.56 Gray G. R.. 346144 93/'147 161 23211 2 22 Hakanson. E. Y. 5571216. 558i255 Hardie I. R.. 558,',777 Grayson J. I. 78/50 Guittet E. 79/12Y Hakumaki M. 0. K.. 225,26 Hardy D. G. 94iIY5 Cream G. E.. 2881168 Gullo. V. P.. 425174 555/17 Hale. P. D.. 385!3XY Harel E. 43/18 23 Greatbanks. D.,425i70 Gumulka J.. 492146 Hale R..383;151 Hargrave P. A,. 3861413 Greco R. J. 931132 Gumulka. M. 4931152 Haley L. V. 3841286 288 Hargreaves. J. A,. 459'IYH Green N. B.. 17892. Y3. 318176 77 Gunaherath. G. M. K. B. 16/IY4 Halim A. F. 161/165 Harigaya. Y.. 96,1411 Green W. R.. 96;424 IY5 lY6 Hall D.. 286145 Harimaya K. 161!f80 Greenblatt. G. A,. 457134 Gunasekera S. P. 161123 Hall P. F.. 557j224 5581260 Harkar S.161147. 156 Greene A. E.. 143138 93 Gunatilaka A. A. L. l6/lYU IY2 Hall T. W. 144124. 67 Greenfield N. J. 5571213 5.581262 194 195 196. 187145 209168 3991 Haller A,. 287/151 Harkness R. 209132 Harms N. 425151 Greenwood C.,579/51 3 Halley. B. A,. 38413UH Harnik M. 493'164 Greenwood. D. R. 5601407 Gunawardana P. 187130 Halloran L. G. 5581279 2x0 Haroon. Y. 387!560 1-10 NATURAL PRODUCT REPORTS 1985 Harraz F. M. 160183 Hayman E. P. 3861449 Hesse M. 78/58 79/84 177112 Hoare J. T. 51Oj19 Harrer J. M. 458/191 Hazemoto N. 3861442 187115 34 248140 Hobbs A. A. 57817 Harris A, 78/29 Hazra B. G. 210/124 Hetmanski M. 4261128 Hobbs P. D. 3821138. 139 140 Harris C. J. 381130 He R. 941251 Hetru C. 4931133 Hobert K. 492190 Harris E.555115 He S. 92/72 Heumann A. 286130 Hochachka P. W. 38117 Harris G. C. 209124 Hearon W. M. 20918 Heuschmann M. 248/27 Hochberg R. B. 5571203 2U4 Harris J. 951317 Heathcock C. H. 15/116. 14312 Hewitt J. M. 5241127 Hochlowski J. E. 159112 Harris L. S. 22514 2871126. 4261139 Hewlins M. J. E. 791128 Hock C.,225148 Harris M. 791115 Hebborn P. 4931174 Hewson A. T.,4261116 Hocquemiller R. 92/59 931110 Harris R. A. 3851324 Hecht S. M. 15/57 Hexem J. G.,93/180 179 23215 8 19 21 26 30 Harrison D. M. 378169 70 Hedden P. 451161. 524194 Heyde E. 3191184 188 190 Hodge L. C. 558/270 Harrison N. A. 457135 Hedegaard J. 2871103 Heyer D. 492191 Hodgkin D. C. 5801163 Harrison P. J. 461204 206 580/188 Hedstrom L. 3181132 Heyndrickx A. 941230 Hodgson G. L. 44/47 48 84 2861 Hart G.J. 44/63 67 579126 33 Heel R. C. 961387 Hickey D. M. B. 233175 54 Hart P. A, 248131 Heftmann E. 558/305 5591324 Hickman D. L. 580jl84 Hodgson G. W. 471268 Hartley D. L. 178175 76 Hegardt F. G. 52318 555/40 Hicks R. P. 210/155 Hodgson K. O. 580j190 Hartline R. A, 287/105 Heger I. 44/51 Hidaka Y. 3851350 353 Hofle G. 178147. 1791112 347190 Hartmann R. 287/120 Heikes J. 286/25 Hidalgo C. C. 16/152 91 425123 75 77 Hartmann T. 177123 178126 2431 Heikkinen R. 209135 36 Hieke M.. 178160 89 90 Hogberg T. 347173 22 23 Heim J. 178199 101 317/35 Higashiyama H. 251113 Hogenauer G. 5561113 Hartung E. 951327 Heim T.,219148 Higashiyama K. 21913 Hoeksema H. 426181 Haruna M. 209119 21 11206 233172 Heimann M. R. 145198 Higby R. G. 144192 Hoellinger H. 96/420 Harvey O.14/31 Hein F. 286139 Higgins P. J. 95/3-57 Hollriegel V. 5801136 Harwood H. J. 52319 555132 50 Hein M. 523171 Highet R. J. 243112 Holzel C. 187117 Hasan M. 178157 Heinemeyer E.-A, 3861482 Higuchi R. 16/145 185 Hoenig A. 391124 Hasan N. M. 801147 Heinricher M. A. 95/281 Higuchi T. 209177. 21 1/177 Horig J. 461229 5801136 Hasan S. K. 318168 Heinrikson R. L. 3191146 148 Hikichi K. 3871512 Hoesch L. 425131 42611 10 Hase T. 15/93 Heinstein P. 178147 556198 Hikino H. 78/64 159128 160/156 Hosel W. 178142 Hasegawa P. M. 51014 Heisler E. G. 457174 16 1jl85 Hofer O. 159121 22 209164 66 Hasegawa S. 15/92 171227. 523/67 Heitefuss F. 459/234 Hikino Y. 1611185 Hoffman C. H. 555115 18 Hashagen U. 556199 Heitz M. P. 3831206 207 Hilario A.-L. 457160 Hoffmann H. M. R. 144153 Hashimoto C.78/51 52 Helfrich J. S. 9213 Hildebrand E. 3861438 Hoffmann J. J. 209/23 70 Hashimoto F. 233148 Helgeson J. P. 457144 45 48. 4591 Hildebrandt P. 3851328 329 Hoffmann R. W. 2881228 Hashimoto K. 92/39. 220155 247 Hilderson H. E. L. 387/531 Hofheinz W. 144160 Hashimoto M. 187133 243114 318/ Hellberg L. H. 492/48 Hilderson H. J. J. 3871531 Hofman J. E. 4591216 85 347153 Heller R. A, 523118 Hilgenberg J. C. 92/47 Hofmeister H. 491116. 492159. 4941 Hashimoto S. 2871131 Heller W. 4581158 510127 51 1/77 Hilgenberg W. 7813 229 Hashimoto T.,4931199 Helmchen G. 2891230 Hill B. C. 579151 Hogan I. T. 7815 Hashimoto Y. 161158 159 144152. Helmlinger J. 7813 Hill D. L. 95/335 Hogenkamp H. P. C. 461241 5801 21 11195 196 199 Helper B. R. 941227 Hill J. 492/96 156 Haslam E.3181123 130 389 5101 Helton E. D. 491113 Hill M. W. 15/Yl Hogge L. R.. 5241136 45 Hemming F. W. 3871501 Hill R. A, 346133 4261129 130 Hokimoto K. 159133 Haslam J. M. 556165 Hemscheidt T. 178147 Hill R. K. 318198 3191143 Holaday J. W. 941259 951342 343 Haslanger M. F. 286125 Henderson G. B. 461206 426/129 Hillard R. L. 111 931131 Hotenstein J. E. 346148 Hasler H. 347/84 130 5801188 Hilliker K. S. 220154 Holker J. S. E. 346120 29 36 Hassan I. 801147 Henderson L. J. 92/Y Hillyard S. A. 95/334 347179 425127 28 30 Hassan S. M. 225/50 Henderson R. W. 471264 580/181 Hilpert K. 461203 214 217 580/ Holland A, 951316 Hassanali A. 400134 Hendriks H. 161/184 191 Holland H. L. 491122 492129 5571 Hassel C. H. 2881183 Hendry G. A. F. 471273 Hilton G. L. 178187 347185 193 5581231 232 Hasselstrom T.286172 Henfling J. W. D. M. 4591246 Hinchcliffe D. J. 346/33 Hollander I. J. 178199 317135 Hassner A. 2871134 288/184. 4921 Henggeler B. 3831210 Hinchigeri S. B. 451136 137 5791 Hollands C. 451120 71 Henkin J. 3191156 95 Hollebone B. R. 579129 Hata S.,556/104 559/328 329 337 Hennig B. 523/10 Hinderer W. 510/60 Hollenstein R. 44/59 341,342,343 344,375 Henning R.,144153. 248127 Hinds P. A. 225136 Hollinshead D. M.,144112 3831185 Hatakeyama S.,4931136 Henning V. T. 457133 Hino T. 78/34 Holloway T. 92/49 Hatano A. 425143 Henrick C. A. 289/235 Hinotozawa K. 248125 425178 Holmberg C. 225121 22 Ha Thanh Co 3841255 Henry M. J. 5591326 Hintsche R.,4931205 Holmberg I. 5581288 Hatsui T. 3831170 Hensens O. 425174 Hirabayashi K.458/118 Holmes C. P. 14417 Hatta S. 383/170 Hensens 0. D. 555115.18 Hiraga K. 492162. 493/f75 Holmes 1. B. 555/19 Hatton I. K. 555137 Herbert E. W. 5601401 Hirai N. 382/64 384/266 Holmlund C. E. 559/336 Hattori H. 144158 Herbert R. B. 17711 3 4 5 11. Hirama M. 426/141 142 Holroyd J. A. 579173 74 Hattori M. 21 11240 178146 82 3191165 166 34611 Hirano H. 523151 Holt D. L. 4581111 Hattori T. 457129 51 1/95 96 5591387 Hirano R. T. 243125 Holtan D. W. 220163 Hatzold T. 243123 Herchen S. 1781105 317116 29 Hirano Y. 492199 113 Holtzman J. L. 941210 961378 Hauback B. C. 931178 3 18/84 Hirata T. 3871533 534 535 5231 Holubek J. 78/54 Hauschka P. V. 3871560 Herin M. 5561116 28 5241124 558/306 Holuigue L. 556jlU0 Hausinger R. P. 5801132 Herlihy P. 94/196 Hirata Y. 78/42 79/99 102 15919.Holy N. 2871135 Havel C. 557/184 Herlt A. J. 178187 347185 2101153 Holz W. 287/92 Havel M. 4931122 209 Herman R. L. 95/332 Hirayama N. 426191 Holzapfel C. W. 347155 Havemann U. 951275 Hermans B. 96/393 Hiroi M. 160192 209118 Homberger K. 187134 248140 Havinga E. 4931141 Hermes J. D. 3191192 193 194 Hirono I. 159171 72 Homma E. 951284 Hawk C. 951294 5 10125 Hirose Y. 17/227 159116 1601133 Hommer D. W. 941271 Hawkes A. D. 78/17 Hermodson M. A. 319/150 Hirota H. 15/102 103 Honda K. 3851384 580/143 Hawkins A. R. 318/125 Hernandez A. 209148 Hirsch A. L. 493/139 Honda T. 16/118,178158 21913 Hawkins G. A. 286129 Hernandez L. L. 95/333 Hirsch M. 3191157 251113 Haworth R.D. 20811 Hernandez R. 15/68 49217.5 4941 Hirsenkorn R. 425135 Honeybourne C.L. 451118. 5801 Haxo F. T. 381152 215 Hirshfield J. 555115 120 Hayakawa Y. 2871110 Herold P. 144146 Hirsjarvi P. 287184 Hongu A, 5801143 Hayami H. 4921116 Herold T. 2881228 Hisada S. 209117 22 74 78 81 82 Honig B. 3841313 3861419 Hayase Y. 383/215 Heron D. K. 288/173 Hitotsuyanagi Y. 78/39 41 Honkan V. 144174 Hayashi K. 160/150 187133 3471 Herrinton P. M. 144114 Hiwatashi A. 558j2.59 Honty K. 791100 101 53 3831164 179 Herrmann K. M. 51014 Hlubucek J. R. 383/193 Hood J. D. 1781106 317146 Hayashi N. 57813 Herron J. N. 145/115 Ho I. K. 951322 Hood W. F. 5581238 243 244 Hayashi S. 16/140 43/20 4581121 Hertz F. 941245 Ho P.-T. 425167 Hoogerbrugge J. 5571198 5581297 Hertzberg S. 381122 25 Ho T.-L.,144124 67 4261124 Hoogsteen K. 55511.5 Hayashi T. 15/76 187143 425/42 Herz J.E. 4931134 Ho W. K. K. 951354 Hook D. J. 178/73. 317139 Hayashi Y.,171226 144162 159158. Herz W. 160/90 91 103 116 135 Ho Z. Z. 3841289 Hook J. H. 461222 220155 161/164 174 391/19 Hoaki Y. 951312 Hook J. M. 461240 Hayashida S. 510132 Herzfeld J. 3841275 276 277 Hoare J. H. 3191178 181 Hootele C. 187126 NATURAL PRODUCT REPORTS 1985 1-11 Hopen G. SSSjZY9 Huemme B. 4591234 Iijima H. 42411 Ishiguro T. 2101160 Hopen H. J. 5791106 Huennekens F. M. 461228 Iimori K. 951311 312 Ishii H. 92/67 961412 417 418 Hopf H. 3821104 106 122 3841 Huff J. 555115 Iimura Y. 243110 Ishii K. 3831165 209 556185 273 3861437 Huffman J. C. 801148 150 Iinuma H. 248132. 425144 Ishii Y. 5571208 Hopla R. E. 5561121 Hufford C. D. 248136 Iitaka Y. 14/14 15/85 102 103 Ishikawa K.941268 3851399 402 Hoppe H. H. 4591234 Hug G. L. 3851390 391 161157 171227 229 18/38 1611 Ishikawa S. 4581129 Hoppe H.-U. 425173 Hugel G. 791141 180 2101138 139. 248132 251114 Ishikawa T. 14/27 961412 418 Horak R. M. 347182 Hughes M. T. 286155 346132 42412 425144 4931143 Ishikawa Y. 346132. 42412 Horcher L. H. M. 145/117 Hughes R. G. 78/25 Iizuka H. 4941238 Ishikura M. 248138 Horgan R. I59118. 3861493 494 Hughes-Fulford M. 523113 Iizuka M. 225138 Ishikura N. 510132 5241123 3871495 496 Huguet J. 1451127 Ikeda K. 15/42 Ishimaru K. 78/13 Hori H. 161/180 Huizing H. J. 391120 Ikeda T. 248138 5601412 Ishiwata H. 1601126 Hori M. 2871123 Hulbert P. B. 210/104 Ikegami S. 144190 94 4931160 Ishizone H. 16/1-58 159 Hori T. 17/23] Huling S. 556174 Ikegawa S.4931193 Ishizu K. 3871563 564 Horikoshi K. 4261102 Hull L. W. 961403 Ikekawa N. 491124. 492154 99 Isida T. 159116 Horita A. 941253 Hull W. E. 78/14 801174 178159 111 113 4931127 131 5571183 Iskrenova E. S. 232129 Horiuchi S. 3851354 65 3191179 426193 196 203 5591390 5601393 394 Isler O. 38113 Horn D. H. S. 560/403 404 Huls R. 161141 144 395 396 397 398 412,415 Ismail S. I. 391125 Horsburgh R. S. 14/26 Hulse G. K. 951301 Ikenoya S. 3871559 Isobaev M. D. 92/66 Horton M. 144/50 Humber D. C. 4931202 203 Ikeuchi M. 451155 5791103 Isobe K. 144162 579167 Horvath G. 951303 Hummel I. 425173 Ikeuchi T. 3871564 Isobe M.,248126 Horwitz J. S. 3851352 Hummel W. 556166 Ikeya Y. 2101134 136 137 138 Isoe S. 3821146 3831215,216 Hoshino O. 92/16 18 232115 2331 Hundt H.K. L. 22513 139 140 141 142 143 144 145 Isono K. 347187 48 49 251114 Huneck S. 17/211 159151 146 147 148 149 154 Isono M.,457156 Hoshita T. 4921110 4931137 5581 Hunkler D. 4261113 4581114 Ikura M. 3871512 Israilov I. A. 92/13 22 23 931109 30 I Hunt E. 44/47 Ikushima K. 425141 232116 17 18 23 24 25 233132 Hoshu Y. 951311 Hunt J. E. 5801149 Ilias A. M.,5601424 Itai A, 14/14. 15/102 103 161157. Hosokawa T. 225149 Hunt N. A. 178/105. 317116 28 Iljin S. G. 15/71 171229 78/39. 4931143 Hosomi A, 144118 29 318184 Illi V. 491120 Itatani Y. 425114 Hosozawa. S. 44/53 55 Hunt V. 555/15 Ilyasova K. T. 791110 Ito I. 457120 523159 63 Hosztafi S. 941185 186 189 Hunter B. K. 461254 Imada Y. 4941233 Ito K. 951298. 209119 52 211/206 Hou C. F. 387/545 Hunter C. F. 555152 Imai Y.93/91. 556/111 215 216 240 233172 Hou D. 931134 Huong P. V. 3841289 291 297 Imamura N. 248125 Ito M. 243125 3821133 143 145 3841257 271. 3871536 Houben J. 288,’176 300 301 314 3851328 397 Imanaka H. 425141 426197 Houee-Levin C. 3841291 Hurley T. R. 425125 Imanishi T. 79/92 801149 151. Ito N. 3871510 Houen G. 578113 Husain A. 78/43 187129. 457189 Ito R. 523159 Hough L. 24319 Husain S. 492172 It6 S. 14/76 Houghton J. D. 580/120 Hussain M. 287199 Imfeld M. 461199 Itoh M. 3851368 Howard J. B. 5571156 Hussain S. F. 92/11. 931148 Imooka M. 209118 Itoh S. 3851339 4931166 579167 Husson H.-P. 79/65 67 115 801 Inanaga J. 2871121 Itoh T. 5591323 359 5601418 Howarth 0. W. 171217 172. 1781.56 187121 22 225118 Inano H. 5571227 5581265 Itoh Y. 425164 426197 107 Howbert J.J. 145197 Hutchins C. W. 941198 Inayama S. 1611180 Howe C. R. 187144 Hutchins M. 92/28 Ingebritsen T. S. 555143 556164 Itoi K. 1419 Howe J. 556198 Itokawa H. 1601127 Howell C. R. 159155 Hutchinson C. R. 347151 Ingersoll A. W. 286138 Ittel I. 21 1/200 Howell S. C. 144j12. 3831185 Hutchinson J. H. 286151 78 2871 Ingham J. L. 4581165 166 170 Iturraspe J. B. 159167 Howes J. F. 941203 115 119 134 138 2881179 223 171 173 175 176 185 Iuchi Y. 382196 224 2891232 233 234 240 Ingold K. U. 3851367 Ivanenko T. I. 492189 Howlett G. J. 3191189 Hutchinson M. 524193 Ingolia T. D. 57819 Hoyte R. M. 5571204 Hutin M. 23218 Ingram T. J. 5241101 Ivanov B. 93/93 Hsiao J. 941240 Iversen S. D. 941266 Hsieh C. L. 3851322 326 327 Hutterer F. 5581291 Inokuchi T.425145 Ivie G. W. 4581111 113 Huxtabie R. J. 220158 59 60 Inoue A. 159158 Hsieh W.-C. 2881212 Hveding-Bergseth N. 171212 Inoue H. 457123 523159 64 Iwadare S. 425165 Iwado S. 425164 Hsing A. S. 45/145 Hwang K-J. 145/113 Inoue J. 5241125 Iwai J. 5791103 HSU,C.-T. 4261133 Hylands P. J. 15/58 59 7812 791 Inoue K. 209180 511186 87 Iwai Y. 425143 HSU H.-Y. 210/153 40012.5 123. 1601122 Inoue M. 171224 79/92 801151 931 Iwakawa T. 160/156 HSU J.-S. 210/150 151 Hylemon P. B. 523117 121 159116 210195 Iwakiri M. 1601157 Hsu K. S. 39916 Hynes M. D. 951299 Inoue S. 3871518 519 524 425119 Iwakuma T. 92/27 Hsu T. C. 961437 Hynninen P. H. 461235 5801142 Inoue T. 160187 Iwami M. 425141 426197 Hsu W. J. 3861449 Inoue Y. 451153 5791103 Iwamoto M. 161185 Hu C. 93/94 Y5 98 152 153 Inouye H.178154. 209180 51 1/86 Iwasa K. 931124 145 146 178135 Hu C. K. 287/110 87 523143 44 46 5241119 36 Hu Q.-Y.,287/114 Inturrisi C. E. 941239 Iwasa T. 3821114 3861440 Hu S. 951283 Inubushi Y. 144152 187133 Iwasaki M. 931158 159 Hu T. 92/87 Iasiello I. 25114 Ionescu F. 21 11205 Iwasaki S. 347166 67 86 Hua Z. 161126 219137 Ibata K. 3871503 504 520 Iorio M. A. 961422 Iwashita M. 4261142 Huang C. T. 160183 Ibers J. A. 580/165 Iqbal J. 426194 Iwashita T. 15/93 159116 Huang D.-D.,578115 Ibragimov A. A, 24813 Ireland R. E. 492151 Iwata C. 457188 89 Huang F.-C. 209175 317155. 3181 Ibraham N. G. 579145 Irgashev T. 92/13 Iwata M. 457197 98 99 97 Ibrahim R. K. 510166 Irie H. 4581118 Iwata R. 425143 Huang H.-C. 209/lY Ibrahim Y. E. 1601143 Irngartinger H. 159163 Iwata T.187128 382j145 Huang L. 248128 555117 Ibuka T. 187133 243115 Irokawa T. 171229 Izaki K. 248121 Huang M. 209147 Iccho K. 5581306 Irschik H. 179/112 347190. 425123 Izquierdo I. 951358 Huang M.-F. 15/36 37 209143 Ichihara A. 2101168 169 170 175 77 Izui K. 5561105 210/150 151 152 21 11176 220 347153 56 425117 Irwin A. J. 461193 19Y Izumi A. 5571172 Huang Z. 92/72. 931105 Ichikawa Y. 961417 5581259 Isa R. B. M. 556173 Izumi K. 5241106 Huault C. 579125 Ichimura M. 3871497 Isaac O. 4931208 Hubbard J. L. 951353 Ichino K. 21 11216 240 Isaev M. I. 15/35 50 51 52 53 Huber H. 209173 Ida Y. 15/78 951311 312 457188 161173 Huber P. 382/142 Ife R. J. 318/130 Isaka Y. 5601397 Hubert E. V. 5571185 Igglessi-Markopolou O. 425163 Isamukhamedova M. 161’366 167 Jabalquinto A.M. SSSl59 556175 Huckstep L. L. 1781104 317122 Iglesias D. I. 159167 168 76 77 80 81 83 24 54 3 18/83 Y5 Ignatov N. V. 579/101 Ishbaev A. I. 243127 Jack I. R. 210192 Huddleston J. A. 317113 15 21 Ignatyuk V. K. 3871523 Ishibashi M. 151102 103 105 106 Jackman L. M. 2881225. 381130 25 56 57 3 18/69 Iguchi H. 144118 Ishibashi T. 5571157 Jackson A. H. 44/83 93 94 95 Hudec J. 286155 2871144 Ihara M. 16/118 80/180,219110 Ishida T. 171224 961417 418 2101 97 104 106 45/110 120 579176, Hudlicky T. 144173. 145/120 4261 Ihn W. 347174 95 5801173 120 Iida H. 243119 21 31 4581120 Ishidate M.,286182. 287198 Jackson D. E. 210j105. 21 1/180, Hudson D. W. 2881190 Iida M. 4941238 Ishige T. 232115 510154 55 Hudson G. S. 3191189 191. 510/20 Iida T. 14/27 209119 52 2111215 Ishiguri Y.4571102 Jackson E. M. 5571166 Hudspeth J. P. 248127 216 240 426191 Ishiguro M. 492/111 113 Jackson F. B. 177111 1-12 NATURAL PRODUCT REPORTS 1985 Jackson J. R. 44/97. 451110 Johansen J. E. 381122 25 Kadoshnikov S. I. 3851383 Kappas A. 44/88 579140 Jackson J. T. 451118 Johansen T. 187135 Kadota S. 92/46 210/114 Kapriyanov A. N. 160/140 Jackson S. W. 457119 Johanson C. E. 225132 Kaegi H. H. 381/11 3831151 152 Karakozova E. I. 492147 Jacob G. 2871147 Johansson L. B. A. 3851401 153 Karavaeva K. A. 457177 Jacob G. S. 579156 Johansson M. 931155 Kafer E. F. 951291 Kardos Z. 9215 Jacob J. J. C. 961380 John E.-M. M. 31717 8 36 Kagan H. B. 2881174 Karimova S. UL,-92/22 931109. Jacob K. 5801139 Johne S. 177112 187115 Kagarlitskii A. D. 1601140 232118 23 24 25 Jacob L.556195 Johns R. B. 3841248 Kagaya M. 160184 Kariv-Miller E. 4931172 173 Jacob R. 220157 Johns S. R. 161143 198 Kagei K. 400133 Karli P. 941261 Jacobs H. J. C. 4931141 Johnson B. A. 2881163 Kageyu A. 3871504 Karlsen J. 791120 Jacobs J. M. 45l108 109. 579143 Johnson B. L. 317121 Kainulainen A. 287184 Karlsen R. L. 941241 Jacobs N. J. 451108 109. 579143 Johnson C. K. 2881196 Kaiping S. 511/88 Karlson P. 5601409 Jacobsen D. W. 461228 Johnson D. W. 44/84 Kaiser M. 160186 Karlsson L. 92/37 Jacobson A. E. 941197 961422 Johnson E. F. 5581261 Kaiya T. 161199 200 Karmilova L. V. 492147 Jacobson N. 2881227 Johnson J. H. 286149 62 Kajiwara A. 2871123 Karpf M. 144136 1451127 Jacquemin H. 79/68 69 1611186 Johnson M. A. 2871137 510153. Kajtar J.382185 Karrer A. 425169 187. 18718 10 232126 233136 523134 38 Kajtar M. 382185 Kartha G. 92/15 Jacques J. 2881190 Johnson R. A, 2871100 Kakemi M. 92/76 Karube A. 160185 Jacquesy J.-C. 2881193 Johnson S. M. 286136 Kakitani H. 3841313 Kasai R. 15/75 77 79 80 81 82 Jacquesy R. 78/61 2881193 Johnson W. M. 457133 Kakitani T. 3841313 3851403 3861 83 161178 Jacquier M.-J. 78/60 801161 168 Johnston J. O. 5581239 240 419 Kasajima T. 93/91 Jaenchen R. 461223 224 5801131 Jolad S. D. 209170 21 11205 Kakooko A. B. 159114 Kasal A, 4941219 230 Jaenicke L. 171221 222 381153 Jolles C. 79/68 Kakutani Y. 3841243 Kasamatsu S. 79/96 97 54,55 Jonckheere J. A. 381147 Kalan E. B. 457167 74 Kase F. 558/28l Jaerbe T. U. C. 941255 Jondet M. 209130 Kalaus G. 801154 155 156 Kasemir H.5791104 Jaffe E. K. 3191173 578122 Jones A. J. 248122 Kaleem S. 791133 Kashiwaba N. 171231 232 Jaffer J. A. 4941239 Jones C. 451111 461194 215 5791 Kalikhman I. D. 2871127 Kashiwagi K. 5571210 212 Jahangir 492129 44 Kalinovskaya N. I. 14/30 Kashman Y. 171219 220 347154 Jahnke K.-D. 5591354 Jones C. R. 92/53 54 Kalinovskii A. I. 14/30 4931164 Jain G. K. 161149 Jones D. H. 510138 Kalisshevskaya T. M. 92/79 Kasina S. 4931156 Jain M. P. 400130 Jones D. M. 579176 Kalles I. 5581292 294 Kaspar P. 492178 Jain S. 178129 44 Jones K. 461201 216 Khlman A. 801154 Kasprzyk Z. 161187. 5581307 Jaiswal D. K. 209167 Jones M. F. 791103 Kalsi P. 523158 Kastner R. E. 248124 Jakobsen H. J. 5801159 160 Jones M. S. 451112 Kalsi P. S. 160/163 Kasum B. 931152 Jakubowski A.A. 426192' Jones 0.T. G. 451112 118 128 Kalvoda J. 492167 Kasymov Sh. Z. 1611168 169 170 Jakupovic J. 15912 3 27 30 31 5801 I20 Kamat S. Y. 2881216 Kasymov T. K. 243127 56 62 160179 82 95 96 97 129 Jones P. G. 346134 Kamat V. 3861425 Katagiri K. 178161 381142 161/175 176 177 209169 21 11207 Jones P. S. 4931202 Kamat V. P. 159164 Jones R. C. F. 425158 59 60 Kamber M. 381138 3841250 Katagiri M. 5571226 Jalali-Naini M. 144111 Katagiri T. 3831168 James I. 555119 Jones T. A. 219126 Kamei J. 225149 Jonsson L. M. V. 510168 69 70 Kameoka H. 159129 Katai M. 161151 James J. C. 347175 Katan J. 4591264 James K. J. 441102 Jordan P. M.,4312 13 14 15 30 Kamernitskii A. V. 4931135 4941 Kataoka T. 3871533 523128 James M. J. 3871532 31 34 44/37 38 53 54 55 62 216 64 66 70 77 83 98 45/111.461 Kametani T. 15/117. 161118 801 Katatsuji E. 4931199 Janardanarao M. 3831161 233 245 579144 Katayama C. 159/41 Janardhanan K. K. 78/43 Jorn D. 555117 180. 21913 10 251113 Katayama K. 92/76 3871559 Janero D. R. 5591322 Joselow M. M. 471263 Kameyama T. 941262 Katayama M. 144158 Jankowski K. 1601154 Joseph J. M. 5601434 Kamin H. 557120.5 209 Katayama T. 381141 Katayama-Fujimura Y. 3871555 Janowsky D. S. 951334 Joseph-Nathan P. 14/18 5571191 Kamiya K. 461243 Jansen J. A. 941211 Joshi B. S. 210/107 Kamiya T. 318185 Katner A. S. 801177 Jansen R. 425175 77 Joshi D. P.,233152 Kamiya Y. 524195 99 Kato H. 457195 Kato K. 1601124 147 148. 1611 Janssen H. F. 951341 Joshi G. C. 286121 2871109 124 Kammerer P. 44/51 188 381160 3871551 457140 41 Jarvis B.B. 144139 159139 128 Kamo N. 3861442 Jarvis T. 2881223 Joshi V. S. 15/89 Kamogawa H. 3831190 203 43 Jaun B. 461223 5801135 Joshua H. 555l15 18 Kamori T. 161185 Kato N. 457120 523163 Jaworska R. 4931138 Joska J. 4941227 Kan C. 79/67 71* 801172 Kato S. 225134 Jayatilake G. S. 31712.5 33 318170 Jossang A. 92/65. 232128 233146 Kan S. K. 79/65 67 69 71 801 Kato T. 144128 29 159135. 381159 Katoh K. 160178 160 75 80 94 Jouillie M. M. 248120 172 178156 Jefford C. W. 2871116 136 Jousselin A. 79/68 Kan-Fan C. 79/65 178156 Katsikas H. 3871565 566 Jeffrey G. A. 21 11218 Joy A. M. 382180 Kanaho Y. 93/96 Katsui N. 457165 66 70 Jeffrey S. W. 3861451 Joyard J. 451167 Kanai S. 210/169 170 Katsuki H. 5561104 105. 5591328 Jeffs P. W. 187111 Jozefowicz M.492170 Kanakala R. D. 209179 329 335 337 338 341 342 343 Jeger O. 3831165 209 210 214 Jubb J. S. 3861443 Kanazawa T. 187124 344 375 21 7 218 219 220 221 222 5561 Judd L. L. 951334 Kanbayashi M. 951295 Katsumi K. 931129 117 Jurgens U. 451188 461234 Kandutsch A. A. 3871532 555163 Katsumura S. 3831216 5561141 5571165 169 171 173 Katsuno T. 251110 Jenck F. 941261 Juttner F. 3861460 Jeng I. 3871557 Juillard D. E. 951317 175 176 177 178 Katsuragawa B. 425119 Jenke H. S. 555113 59 Juillerat M. 579152 Kane J. 555161 Katsuyama M. 381132 3861486 Kattenberg M. 3841293 294 Jenkins R. M. 579176 Juknat de Geralnik A. A. 44/68 Kane J. F. SlOl2 Jennings L. J. 555137 75 Kane J. M. 248127 Katz J. J. 5801149 152 154 Katzenellenbogen J. A. 2881217 Jensen K. M. 931154 Julia M.382173 3871525. 556195 Kane J. P. 3841282 Jensen N.-H. 3841290 291 Jung L. 286123 77 Kaneda M. 78/13 Kauffman G. B. 286140 Jensen R. A. 3l8/110. 3191142 Jung M. 1781105 317157 318166 Kanekiyo T. 2881164 Kaufman C. 523121 510/12 21 22 23 67 69 84 Kaneko C. 78/20. 425153 Kaul P. N. 42515.5 Jensen S. E. 317119 23 32 318182 Junnarkar M. R.. 3851395 3861419 Kaneko H. 457140 Kaur G. 1601163 Jeong H. J. 941223 Jurcic K. 15/87 Kaneko I. 55513.5 Kavka J. 160/151 Jeyaraman R. 187116 Jurczak J. 243128 Kanemoto S. 4921116 Kawada K. 171216 Ji R. 225116 Jurd L. 399/2 Kang S. S. 21 11203 244 233143 Kawada M. 14413 30 382196 97. Jiang H. 92/87 Jurgec M. 78/56 Kannangara C. G. 578113 14 15 3831169 Jiang M. 92/84 88 89 90 Jurlina 1. L. 144191 Kannangara T. 523176 Kawagishi H.,210/175 Jiang Z.4931180 Juve H. D. 3831177 Kanner J. 3851374 Kawagishi M. 21 11220 Jie K. 4931204 Kansal V. K. 791129 Kawaguchi H. 24819 Jin D. F. 4591229 251 Kanyicska B. 951303 Kawahara N. 4931166 Jin G. 93/99 136 139 140. 225144 Kanzaki M. 93/96 Kawai K. 78/38. 346128 Jin H. 4931197 Kanzaki T. 317142 Kawamata T. 161/180 Jin J. 15/55 Kabasakalian P. 2881165 Kao Y.-L. 210/151 152 Kawamoto I. 426/91 Jin M. 92/89 Kabat M. M. 4931195 196 4941 Kaouadji M. 2101172 Kawamura H. 492150 Jindal S. P. 9217 2871109 218 Kapil R. S. 801162 160/153 Kawamura M. 3191146 148 Jing P. 4931179 Kachroo V. 161147 156 Kapinus L. N. 961435 Kawanabe E. 92/67 961417 418 Jochum P. 3841252 Kadonaga J. T. 318/115 51016 Kaplan D. 5801157 Kawanishi K. 21 11195 196 199 NATURAL PRODUCT REPORTS 1985 1-13 Kawanishi S.44/89 Kihara M. 4931199 Kjonaas R. 523135 Kohda H. 15/83 107 Kawanobe T. 383/164 Kihira K. 4921119 5581301 Kjasen H. K. 171212 Kohl W. 179/112 347173 90. 3811 Kawara T. 144/5 Kihlberg J. 159/70 Klassen J. B. 34616 7 26 425123 Kawasaki T. 16/145 185 209154 Kikuchi G. 4319. 57813 Klaus M. 3821142 Kohli J. C. 3831196 Kawashi T. 171218 Kikuchi H. 16/119 78/64 Klawans H. L. Jr. 951273 337 Kohmoto S. 425148 Kawashima M. 14415 Kikuchi M. 14/27 Klee W. A. 941197 Kohne B. 3821129 Kay I. T. 210/93 Kikuchi T. 92/46 210/114 5591318 Kleijn H. 492142 Kohno Y. 951311 312 Kaye P. T. 219115 Kim C. Y. 5581264 Klein O. 43/19. 578119 Kohout L. 4941230 Kayser H. 381135 3861485 Kim H. K. 4931192 Kleinfelter D. C. 2871151 Kohsaka M.1781105,317127 29 Kayser R. H. 557/223 Kim J. C. 233153 Kleinig H. 381150. 3861454 3871 426197 Kayser V. 941242 95/279 280 363 Kim S-W. 1451123 572 51 1/91 523126 Koike K. 78/23 28 Kazlauskas R. 381123 Kim S. I. 92/77 Kleinschmidt T. 44/39 Koike Y. 3871508 509 510 511 Kazmaier P. M. 318/68 Kim T. H. 3821146 3831215 Kleinsek D. A. 55519 59 Koizumi H. 15/78 Keen N. T. 45615 4591196 201 Kim Y. 579171 Kliger D. S. 3851352 Koizumi J. 555125 227 228 235 Kim Y. H. 3831200 Kline T. B. 941213 Koizumi N. 491124 4921111 Keeping J. W. 317126 Kim. Y. S. 161183 Klingenberg A. 5241128 Koizumi T. 92/76. 425136 Keesey J. Jr. 319/155 156 Kimata H. 161163 178 Klischies M. 21 11178 184 Kojima I. 558126.5 Kehres L. A. 45/184 580l125 167 Kimble S. N. 941229 Kloosterman J.1601149 1611184 Kojima M. 49119 510139 40 177 Kimbu S. F. 15/94 Kluender H. 317155 318196 97 Kokke W. C. M. C. 286127. 2881 Keilbaugh S. A, 491118 Kimizuka Y. 79/76 Klunder A. J. H. 4261127 153 4921104 5601416 422 423 Keim P. S. 3191146 148 Kimura I. 92/42 46 Klusener A. R. 286162 Kokshake M. 318184 Keinan E. 491/27 Kimura K. 492174 Klussmann U. 4941236 Kokubo T. 22015.5 Keinath S. H. 95/294 Kimura M. 92/42 46 Klyne W. 210/104 2871146 Kokubun S. 161163 Keith M. L. 555/40 42 Kimura R. 21 11176 Knabe J. 92/69 70 Kolb V. M. 2881181 Keithly J. H. 44/99 Kimura Y. 24815 Knapp H. 286112 Kolek T. 288/170 Kelleher W. J. 178133 Kin K. C. 931136 Knapp J. E. 92/26 Kolev V. D. 3851337 Keller P. J. 461230 178151 Kindl H. 4571104 4581107 51 1/81 Knierzinger A.5801167 Koleva M. 93/93 Keller R. K. 3871537 82 83 Knight D. W. 14416 4571100 Kollar L. 22516 Keller R. M. 45/126 King F. D. 243132 Knoch F. 219135 Kolodziejczyk P. 178158 Keller-Juslen C. 425139 King H. D. 425139 Knoche H. W. 5591351 376 Kolonits P. 791101 Keller-Schierlein W. 426198 King J. F. 286132 2881201 Knoefel H. D. 5241100 Kolot F. B. 4941231 Kelley G. J. 243118 King R. M. 15913 11 27 31 32 Knoeppel E. M. 55518 Kolpak M. X. 179/111. 347189 Kellner D. 144/70 34 65 160188 89 97 101 107 Knogge W. 510167 Kolster K. 3841283 Kellogg R. M. 144/61 118 120 129 130 158. 21 11207 Knowles J. R. 3181115 120 131 Komatsu Y. 187114 Kelly C. T. 160/105 King T. J. 15/95 42515 133,3191173 181 182 510/5 6 8 Kominami S. 5571225. 5581259 Kelly M. J. 288/229 Kinghorn A.D. 15/110 18 19 Komives T. 459/265 Kelly T. R. 2891231 425155 Kinghorn J. R. 3181125 Knowles P. F. 3181129 Komori M. 3841292 5591342 Keltjens J. T. 46/225 Kingston D. G. I. 179/111 347189 Knox L. H. 28617 18 26 Komori T. 161145 209154 318185 Kemertelidze E. P. 15/35 161169 Kini A. 3821101 3841270. 3861426 Knudsen C. G. 382199 381142 425141 181,209121 26 Kinnear J. F. 5601403 Kobaru S. 24819 Komura H. 51 1/84 Kemoklidze Z. S. 16/169 Kinnel R. B. 5601421 Kobatake Y. 3861442 Kon K. 3821146 Kemp M. S. 159157 457137 38 39 Kinney W. A. 144/19 ,Kobayashi G. 187137 Kon S. 471263 458jl08. 109 110 Kinoshita T. 209178 Kobayashi H. 2101136 138 141 Konda Y. 425178 Kende A. S. 210/133 Kinsella J. E. 3851374 142 143 146 149 347186 Kondo H. 381159 Kennard O. 461243 Kinter M.T. 225/53 Kobayashi J. 78/25 15919 Kondo K. 151109. 425145 Kennedy E. 3831187 Kintya P. K. 161170 171 172 Kobayashi K. 425129 523146 Kondo M. 4931130 Kennedy L. 225/30 Kintzinger J. P. 580l171 Kobayashi M. 14/29 1601159 2091 Kondo S. 931173. 4261100 Kennelly P. J. 555j11 42 Kipping F. S. 286135 36 2881190 71 3871536 4931171. 51 1/84 Koningstein J. A. 3841286 287 Kenny P. T. M. 161/187 Kirby G. W. 941191 178180 81 Kobayashi R.,2871110 288 Kerimova N. K. 225/27 Kirby M. L. 951309 Kobayashi S. 92/42 251110 4261 Konishi M. 24819 Kerkenaar A. 559/330 Kircher H. W. 5591316 317 146 Konno F. 92/40 41 Kern H. 346148 4581105 Kirchner R. M. 457167 Kobayashi T. 451153 346132 4241 Konno H. 5561111 Kerr C. R. 941254 Kirfel A. 219136 38 2 49119 5791103 Konno M. 5801143 Kerr K.A, 93/163 Kirk D. N. 209127 31 32 40 2871 Kobayashi Y. 15/85 4931140 5581 Kono S. 3851365 Kerwin J. F. 426/146 146 4921107 4931162 163 183 259 Kono Y. 457195 96 Kesler E. 159/69 Kirk J. R. 3841256 Kober W. 2871125 Konoma K. 346127 Kessel D. 580/196. 197 198 Kirk M. C. 3821135 3841272 Koblicova Z. 248116 Konomi T. 178/105 317116 29 Kester A. S. 3841249 Kirkup M. P. 15/57 Koch M.,78/19 35 79/83. 187110 Kononenko G. P. 51 1/80 Kettenes-van den Bosch J. J. 1601 Kirmse W. 2881202 38 399112 Konoshima T. 161160 161 162 149 Kirsch J. H. 14/23 Koch P. 4921112 Konowi T. 3 18/84 Keve T. 80/163 Kirson I. 491127 Kochetkov N. K. 3871527 528 Koolman J. 5601409 411 Keyhani E. 45/122 123 Kirst H. A. 2881217 Kochhar K. S. 187112 Koomen G.-J. 79/91 187140 Keyhani J.45/122 123 Kiryakov H. G. 232129 Kochi H. 5571150 Kopanski L. 78/26 Khadzhidekova. V. 93/93 Kiryakov K. L. 931165 Kochubei L. N. 961435 Kopp B. 178178. 5591385 Khafagy S. M. 159i1 1601143. 1611 Kisic A, 5571165 166 172 178 Kocienski P. 3831183 426182 83 Koppenhagen V. B. 461218 171 Kisiel W. 160/161 209172 Kocor M. 4941218 Koreeda M.,145195 49111.5 Khalmirzaev M. M. 791110 111 Kiso Y. 159128 KoEovsky P. 49118 492137 38 Koroly M. J. 5571162 Khan L. 92/11 Kissin I. 94/2-74 Koda S. 425141 KorSiE J. 78/56 Khan M. Y. 931171 Kissinger J. C. 457167 Kodama A. 3821143 3841257 271 Koseko Y. 3861421 Khan R. H. 21 11230 Kistler H. C. 4581194 195 Kodama H. 1601148 381160 Kosela S. 171226 Khanna I. 347!73 Kita T. 555128 Kodama K. 92/67. 4261107 Kosemura S. 346128 Khanna N.M..161149 Kitagawa I. 14/29 33 15/44 45 Kodama M. 144176 Koshihara Y. 78/64 Khanna P. 931115 46 76 161129 138 155 176 177 Kodama O. 457195 96 Koshiji H. 4261102 Khanum S.,19/109 1601159 2871123 Kodde E. 4591233 Koshimizu K. 382164. 3841266 Khasanov T. Kh. 159/23 Kitagawa S. 346132 42412 Koek W. 941258 Koshoev K. K. 4941216 Khodonov A. A. 382198 I21 Kitagawa Y. 2871131 Koelling E. 3821120 Koskinen A. 791105 Khodzhimatov M. 92/66 Kitahara K. 3841247 Koeppler H. 1611183 Kos-Kuyck E. 79/73 Khokhar A. G. 287/144 Kitahara T. 161163 3831167 Koermer G. S. 2891237 Kossa M. 161/183 Khripach V. A. 4931129 Kitahata L. M. 951284 Kost H.-P. 451161 579160 61 62 Kost N. 951314 Khuong-Huu F. 79/85 Kitamura K. 92/76 144181 1451 91 Kostochka L. M. 22518 Kibayashi C. 243119 21 31 103 Koester J.51 1/78 Kosugi H. 4261121 122 Kibby J. J. 178187. 3191167 168 Kitano Y. 381/59 Kost-Reyes E. 579191 Koszyk F. J. 233151 4261120 347/85 Kitchen J. L. 286129 Koft E. R. 4261149 Kotai E. 951286 Kido F. 425149 Kitchen S. E. 557/209 Koga K. 187140 210/160 161 Kotani E. 2lOl121 Kido M. 160/159 Kitchin J. 178/105 318184 Kogami K. 3831164 179 Kotera K. 251114 Kienzle F. 381/3 Kito M. 3841297 298 Kogan T. P. 14/37 Kotick M. P. 941203 Kieslich K. 287/101 Kiyohara H. 931117. 178/41 2331 Kogekar R. G. 1781102 Kotler M. 44/68 Kigoshi H. 34/7 41 Kogure T. 3831195 Kotts C. E. 5571216 5581255 Kiguchi T. 78/51 52 Kizu H. 161164 Kohashi M. 44/76. 579130 32 Koube T. 21 11206 1-14 NATURAL PRODUCT REPORTS 1985 Koul G. L. 161147 156 Kulp T.1451120 Lai J.-J. 579153 Lave D. 3871525 Koul S.K. 209158 Kumada K. 209116 Laine R. A. 457180 81 82 Lavens P. 381147 Kovachev G. 5601432 Kumamoto J. 5241137 138 Laing D. G. 2881169 Lavie D. 15/62 67 209185 210187 Kovganko N. V. 4931129 Kumar C. V. 3851392 393 394 Lakshmikantham M. V. 801171 88 Kowalski C. J. 2871130 Kumar P. 931126 Lal B. 801177 Lavoie A. C. 144121 Kowanko N. 178/85 Kumar R. 15/86 4931206 Lal G. S.,4261124 Lavoie L. 3851360 Koyama S. 95/364 Kumar V. 161188 189 Lal K. 492132 Law S.-J. 233158 Koyama T. 3871536 538 542. 5561 Kumar Y. 25111 Lalezari I. 400129 Lawrence D. K. 5241103 96 102 Kumashiro 0..961426 Lallemand J.-Y. 791 129 1441 If, Lawrence D. S. 286158 Koyama Y. 78/39 41 3841292 Kunesch N. 801146 173 187/10 Lawrence S. M. 317124 296 297 298 310 Kunihara M.951295 LaLonde R. T. 24314 Lawson A. M. 209127 31 32 36 Kozhukhova A. I. 3871552 Kunimoto J. I. 92/67 Lam E. 3851355 37 Kozikowski A. P.,78/48 145/11Y Kunitomo J. 233169 Lam M. 286160 76 Lawton M. A, 4581141 142 4591 4261118 Kuniyoshi M. 492156 Lam Y. K. T. 555117 209 Kozlov E. I. 3861409 Kuno A, 16/11Y La Magnen J. 951328 Layer H. 248117 Kozlov N. G. 3831201 Kunugi M. 5241125 Lamb C. J. 456/9 4581116 141 Layne D. S. 5581257 Kozlova 1. V. 3871552 Kunze B. 425177 142 147 150 459/209 5791105 Lazarovitz G.,4591258 Kozlovsky A. G. 78/44 Kuo D. 2881223 Lamb N. 286156 287188 89 Le A. T. 556192 Krautler B. 461212 220 226. 5801 Kuo P. C. 21 1/22] Lamba D. 159j.50 Leander J. D. 941256 134 135 IY0 Kuo S. C. 400125 Lambert C. 3851336 Lear S.R. 555/3Y Krafcik J. M. 556189 Kuo Y. H. 21 I/2lY 221 Lambert J. L. 286115 Leary J. D. 243118 Kramer A, 382172 Kuoh C.-S. 17/215 78/10 39916 Lambert R. 3861461 Leblanc R. M. 3851360 Kramer M. 941183 400133 Lamberton J. A. 161143 198 1871 Leboeuf M. 92/59 60 65 23211 2 Krane B. D. 961405 Kupchan S. M. 210/132 163 21 I/ 30 24317 I3 19 28. 233146 Krane J. 461256 229 Lambeth J. D. 5571202 205 209 Lechat P. 233163 Krasnovskii A. A, 3851369 Kupka J. 178/YY. 317122 34 37 Lamed R. 4931164 Leclercq J. M. 3861416 Kratky C. 461216 226. 580j135 Kuprina S.,5571207 Lamm L. 58011.36 Lecornte J. 3861429 Kraus G. A. 15/113 14414 Kurahashi K. 317/Y Lamm V. 3851364 Leddet C. 5241121 Kraus W. 288/IYY Kuraishi H. 3871555 Lan H.-Y. 233170 Lednicer D. 2871102 Krausch B.178149 Kuramoto J. 5581301 Lan S. F.,55518 12 14 27 Lee C.-L. 209115 44 Krauss G. 178160 Kuramoto M. 558/301 Land E. J. 382181 3851335 344 Lee D. I. 951338 Krebs E.-P. 426194 Kuramoto T. 492/11Y. 4931137 385 386 Lee F. C. 3871576 Kreek M. J. 941239 Kurata K. 159141 42 43 44 Landen G. L. 580/157 Lee J. 457118 21 523161 62 Kreiser W. 4931153 Kurbanov D. 399/Y Landers G. M. 3841254 Lee J. H. 3851327 Kiepelka J. 78/54 Kurbanov M. 92/66 Landry D. W. 144151 Lee J. J. 3181134. SlOjY Krepkova L. V. 931112 Kurda E. 159163 Lang R. W. 5601418 Lee J. S. 21 1/190 Krepski L. R. 492171 Kurek A. 4931152 lY6 Langbein A. 941205 Lee J. Y. 461246 Kresken J. 161/17Y Kuribara H. 225142 Lange E. 178/88 Lee K. 318/134 SlOjY Kreuz K. 3861454 523126 K uriyama K . 187128 Lange G.L.. 2881204 Lee K.-H. 16/133 209/IY K reuzaler F. 4581 145 Kuriyama M. 16/15Y Langenbeck-Schwich B. 5 10136 Lee R. H. 941223 Krick W. 17/22] 222 381153 54. Kuron G.,555/15 Langenburg J. P. 3871562 Lee S.-C.,4591236 237 55 Kurosaki A, 400138 Langenskiold T. 225121 22 Lee S. D. 18713 Kurosaki F. 458/1YO. 4591240 241 Langlois N. 801157 Lee S. M. 5591386 Krief A. 14/21 5561116 Kurosawa E. 159141 42 43 44 45 Langlois. Y. 801157 Lee T.-C. 382182 Krieg M.. 579163 Kurth M. 288/22Y Kriemler H.-P. 45/IY0 191. 46/IYY Kurz W. G. W.. 178155 58 Langmann B. 209156 57 Lee T. H. 21 11182 Lee W. Y. 3831173 Krinsky N. I. 3841240 Kusano G. 14/14 15/38 3871508 Langry K. C. 461247. 580jl82 Leenstra W. R. 385138Y Kristiansen K.N. 510165 50Y 510,511 Lankin D. C.233143 Kritskii M. S. 3861478 47Y Kuschinsky K. 951275 Lannoye G. 144174 Leeper F. J. 44/67 57811 579126 Krivorotov S. V. 951277 Kushner J. P. 44/70 YO Lansard J.-P.. 144138 Leet J. E. 92/61 233170. 399111 Kroll K. O. 3861491 Kuster B. F. M. 4591267 Lansinger J. M. 4261106 Leete E. 17712. 10 178185 510146 Kropf A, 3861426 Leets K. 3831166 Kutchan T. M. 931174 178140 Lantz M. S. 931104 Kroppenstedt R. M. 3871556 Kutner A. 4931138 Lanzetta R. 14/15. 15/43 Lefer A, 225148 Lefer A. M. 931132 951340 Krow G. R. 2881163 Kutney J. P. 145/107. 178158 524/ Laonigro G. 14/15 15/43 Lefevere M. F. 3871561 Kruger C. 145/YY 108 Lapalme R.. 2881222 Krueger R. J. 931174 178140 Kuwabara T.. 4261101 Lapko A. G.,5571207 LeFevre J. W. l79/111 347/8Y Legrand J.-C. 5581266 Krug C.5801136 Kuwajima I. 144145 2891238 Lapko V. N. 5571207 Legrand M. 4591235 Kruglaya 0.A,. 2871127 Kuwano H. 4261131 Largeau C. 346110 Kruglikova R. I. 3821102 Kuznetsov. Yu. B. 931112 LaRochelle M. C. 5581254 Lehman W. R. 382180 81 Krumperman P. H.. 219149 Kuznetsova T. A, 14/30 Laronze J. Y. 791140 Lehrnann H. 159117 382161 62 523169 74 Kubelka W. 5591385 Kuzovkina I. N. 178189 400135 Larrahondo J. E. 209/45 Kubiak C. 2101133 Kwok C. T.. 5581277 Larraza M. I. 251/11 I2 Lehrnann T. 580/180 Kubitzki K. 21 III87 234 Kyburz R. 78/58 Larroque C. 557/1Y7 Lehner H.,579/YI Lehoczki E. 3861459 Kubo H. 425136 Kyler K. S.. 15/112.4921114 4931 Larsen S. D. 219116 Kubo I. 159114 160/113 207 Larson D. L. 961388 Lehtinen M. 225124 Kubo S. l6l/188 4.57140 41 43 Kyogoku Y.14/2Y 160/15Y Larson E. R. 210/15Y Lehtonen E.-M. M. 317120 Leistner E. 17718 346141 Kubota H.. 457/8Y Kyriakidis N. 78/15 Larsson B. 225128 Kubota. T.. 15916 7 160/157. 4561 Lascelles. J. 451131 Leitao Filho H. F.. 791107 16 Lascombe. J. 3841289 2Y1 2Y7 Leland D. L. 9412003 Kuc J. A, 457132 42 72 73. 80. 300 301 314 3851328. 397 Leluan. G..510/48 XI. 82 83 84 86. 4591213 217 Lash T. D. 441106 Le Marechal P. 318/118 122 Le Men-Olivier. L. 78/60 79/79 246. 52316 Labadie R. P. 346141 Laskay G. 386/45Y Kuchin A. V. 4941226 Labbe P. 4511UY Laskovics F. M. 556/8Y YO 114 121 801161 168 Kuchkova K. I. 381/16 Labbe-Bois. R.. 57818 Lassak. E. V. 161145. 185 Lemke P. A, 318/101 Kudela M. 52313Y Lablache-Cornbier A. 346117 I8 Laszlo P. 425140 493/18Y 5801113 Lemongello D.555/Y 61 Kudo K . 209154 Labler. L. 4931148 Latimer L. H. 4261133 Lempert U.,451162 523184. 5801 Kudrnkt S. 78/53 Lacadie J. A, 317/52 Lattes A,. 3871191 11.5 Kuenzi M. T. 178/103 317138 Lachance P. 492/55 Lattmann R.. 461201 Lenz. F. 3841246 Kuehne M. E.. 801152 Lack L. 5581250 Lau C. K. 145/114 Lenz G. R.. 233151. 49111 4931165 Lau P. C. K. 5581257 Lenzlinger. M. 2871117 Kueng W. 3821142 Lacombe S. 492176 K unstler K . 20915 Lacroix. A, 3841,755 Laughlin M. E. 5581244 Leone-Bay A. 144175 Kuenzig M. 951362 Lacy M. E.. 3861432 Laurent A, 492176 Leoni S. 523113 Kuhadja M. 579/Y3 Ladd J. I59163 Laurent C. J. C. M. 941236 Leopold E. J. 1415 556111Y Kuhn D. H. 4581145. 146 Ladner W . 2 191 14. 2881228 Laurent H. 491116 492159.64. 4941 Le Page-Degivry M. T. 384/265 Kuhn M. 425139 Lafont. R. 5601411 228 22Y LePoire D. M. 491117 Kuhn P. J. 457171 Lafranconi W. M. 220/5X 5Y Lautens M. 18717 Le Quesne P. W. 791108 160/105 Kukolja S. 1781104 317124 318183 Laghai A,. 43/15 Lauterwein J. 3841269 18715 209145 Kukovetz W. R. 555jlY Lagrou A.. 3871531 Laval. J. P. 383/1Y1 Leriverend. P.. 2871139 Kulanthaivel. P. 160/Y0 YI 135 Laha. S. 17/208 Lavaud C. 791114 Leroux P. 559130Y 1611164 Lahita R. 941239 Lavault M. 79/75 233136 Leroy J. 2871150 NATURAL PRODUCT REPORTS 1985 1-15 Leshem M. 943264 Lim C. K. 44/71 82 85 86. 2101 Lopes L. M. X. 209120 210/113 Mabuchi H. 555125 Lesma G. 79/93 104 136 103. 579134 35 5801138 Lopez F. J. 251111 I2 McCammon M. T. 5591374 Lester H. H. 510164 Limanek J.S. 55515 62 Lopez M. B. 555115 18 McCarthy S. A, 451152 169 Lester R. 5581275 Lin C. 144156 Lopez-Nieto M. 178/100 McCarty R. N. 286141 62 2881183 Lesuisse D. 243114 Lin D. S. 5601424 Lorenc L. L. 492133 McColl K. E. L. 5801193 Letouze R. 5lOj.51 Lin H.-J. 179/10Y Lorenz R. 2871135 McCorrnack D. K. 556171 Leube J. 4581148 Lin J. K. 92/45 Lorenzetti B. B. 941247 McCorrnick A. M. 3861491 Leumann C.,461203. 214 580jl91 Lin L. D. 400125 Lorenzi R. 523120 McCorrnick J. D. 3191157 I92 Lin L. H. 5561126 Loriot M. 2101129 130 McCorrnick S. 160/104 Leung S.-L. 579182 Lin L.-J. 317151. 318199 100 5101 Lorsbach T. 5571156 McCoy J. W. 219143 Le Van N. 160/8I 248133 56 Loschke D. C. 4591197 202 255 McCoy K. E. 5571156 Le Van Q. 461230 Lin L.-Z.233164 65 Lotter H. 209151 210190 McCrae K. R.,5561122 Le van Thuc 471264. 5801151 183 Lin M. 92/85 Lotter H. L. 400/41 McCrindle R.,2861.30 Level M. 3181122 Lin N.-H. 2871121 Loudon J. D. 286111 McDermott I. R. 492140 5571218 Lever 0. W. 941209 Lin S. C. C. 951306 Lounasmaa M. 79/67 71 105 801 McDermott J. P. 317124 Levere R. D. 579145 Lin S. H. 3841289 172 225121 22 23 McDonagh A. F. 579166 68 Levesque J. 78/61 Lin S. T. 21 1/21Y 221 Lounkokobi J. 78/60 79/79 MacDonald A. B. 5571210 Levin S. 471263 Lin T. P. 400125 Lourenco E. J. 3181127 51017 McDonald E. 4316 44/47 48 51, Levine S. G. 2881210 Lin Y. M. 21 ljl90 Louw W. K. A, 347155 52 56 57 59 61 69 84 102 Levine Y. K. 3841293 294. 3851379 Lindberg B. 4591221 224 225 Love C. J. 2871110 105 451110 192 461197 198 200.Levisalles J. I 5/90 2881152 492170 Lindblad B. 44/44 Lovel C. G. 178194 318172 178143 579149 Levitt R. A, 961395 Lindblom L. 187142 Lowe D. A, 317110 McDonald I. A. 3191167 Levy D. 492182 Lindemann N. J. 941210 Lowe P. 318/130 MacDonald P. E. 4571Y2 Levy E. C. 209185 210187 88 Lindig C. 492157 4931201 Lowenstein P. R. 961368 MacDonald R. J. 555163 Levy J. 78/35. 791114 139. 140 Lindley P. F. 14/26 Lowmaster N. E. 425162 Mace M. E. 457136 141 80/161 187113 Lindman B. 3851376 Lowry T. M. 28618 13 2871113 Macedo de Abreu P. 14/13 Levy P. 2881176 Lindner B.. 4581182 Loya Y. 171220 McElroy A. B. 144125 Lew M. J. 225131 Lindstedt S. 44/44 Loyal R. 4581143 Macfarlane R. D. 347161 Lewendon A.. 3181135 138. 139. Lingaardh G.,95/296 Lozano R.5591347 McFaul S. J. 457133 510116 17 Lingens F. 178172 Lu F. 93/94 95 Macfoy C. 400134 Lewer P.. 524196 Linger B. 44/39 Lu H. 4931179 McGaugh J. L. 941268 Lewin A. H. 3821136 137 Lipinski A. 5801123 Lu L. 961402 McGee L. R. 79/86 Lewinski A.. 951325 Lipp M. 286114 Lu S.-T. 23213 4 MacGregor W. S. 20918 Lewis A.. 3851311 Lipp P. 286112 Lu Y. 5801167 Lewis D. N. 2871148 Lipton J. M. 9512Y3 Luche J.-L. 144138 Macharia B. W. 286116 2881197 Lewis J. R. 209112 248113 Lis R. 4261143 Luche M.-J. 144193 Macheix J. J. 510152 66 Lewis J. W.. 385.352 Lisker N. 457132 4591217 264 Luckner M. 52211 Machida K. 92/10 Lewis K. G. 171109 Lister S. G.,425166 Luduena F. P. 22514 Machin I. 4931203 Lewis N. 524iY3 Litman D. J. 941223 Ludwig G.-W. 15913 Macias F. A, 161/176 Lewis.N. G.,461200. 215 178158 Little R. D. 344188 92 Ludwig-Kohn H. 5591354 McInnes A. G. 178/85. 34619 3471 Lewis N. J. 46j212 216 Litto W. J. 951302 Liithy B. 5801117 51 5591358 Lewis R. G. 2881220 Litvin F. F. 451154 5791101 Liithy J. 219148 50 3191162 McIntyre C. R. 346146 47 425/28 Lewis. W. 425/33 Litvinova G. E. 4921115 Liitke-Brinkhaus F. 3861454 3871 523177 Lewton M. A. 5791105 Liu B. 92/86 572 5 I 1/91 Mackay M. F. 159161 219129 40 41 391117 Ley S. V.. 144112. 13 383/185,4251 Liu C. 92/75 93197 141 Liitz C.,451155 McKay T. 4931174 38 66 Liu C.-S. 210/151 152 Lugaro G. 5591356 MacKenie A. R.,233i75. 400118 Leyson J. E. 9613Y3 Liu G.,931Y7. 225141 Luger P. 248115 Lugtenburg J. 3821108 109 110 McKenzie D. C. 523136 Li B. 248128 Liu H.-J..2881177 203 112 147 148 3841275 276 307 Mackenzie N. E. 461245 579127 Li G.. 931Y4 95 Liu. J.-S. 15/36 37 951306 209143. 316 318 3851320. 3861435 436 5801126 Li H.-T. 4921105 5601418 2 I01150 Li. J. 931Y11 140 225/44 Liu K.-P. 5571150 Luis J. G. 161146 Mackie H. 523155 Lukacs G.,248125 346131 42414 McKittrick B. A, 21 11202 Li L. 931134 Liu. M. 941204 Lukton D. 3831159 3851398 MacLachlan L. K. 15/96 Li L. N. 560/4111. 4lY Liu R.. 931141 2101153 Lurnonadio L. 78/27 McLaren M. 359151 Li M.. 5601421 Liu R. S. H. 382192 101 3831158 Lumsden. J. 3181103 104 McLauchlin W. R. 178157 Li S. 951344 160 3841270 274. 3851344. 3861 Lundell D. J. 579179 80 81. 82 McLaughlin C. L. 961392 Li S.-W.,347/5/ 411 426 428 430. 439 Lundell K. 55812Y4 McLaughlin J. L. 9213. 14 19 2091 Li X.492/101 5601420 Liu S. 159137 Lunnon M. W. 5591378 60 Li Y. 92/86. 209147 Liu T.-Y.,3841317 3861428 Luo S.. 78/24 McLaughlin P. J. 961383 385 Li Z. 941193 4931180 Livingston D. A, 580jl31 Lupon P. 492192 4931191 MacLean D. B. 931128 153 Liaaen-Jensen S. 38 I 118. 19 22. Livingston K. E. 93/156 Lusby W. R. 5591352 McLean S.. 79/90 23 25. 28 29 34 35 36. 52 3821 Ljungdahl I. 5581288 Lusinchi X.. 492139 4941212 MacLeod J. K.. l5jYl 67 8Y Lo C. W. 951354 Luskey K. L. 555129 30 63 McLeod. R. J. 5581293 Liang. D. 931119 Lo D. S. T. 941225 Lussiana J. P. 92/34 McManus I. R. 5571185 Liang T.-C. 347184 Lo K. K. N.. 3851344 Lutstorf M. 1791107 317159 60. McMillan. D. E. 951307 Liang X. T. 79/72 Lobo A. M.. 14/13 3 18/62. 63 MacMillan J. 346113 523188 8Y.Liao. R. 931105 Lobo A. P. 286141. 62. 2881183 Lutz M. 384129Y. 300 524193 94. 96 97 101 102 5591 Libby L. 951336 Locci R. 457172 Lutz R. P.. 2881194 3 78 Libman J. 2881200 Lochte W. L. 2881155 Lutz. T. 9217 McMorris T. C. 5591381. 383 Lichtenthaler H. K.. 523114 5551 Lockley W. J. S.. 5601405 406 414 Luu B. 14111. 4921112 4931133 McMurray R. G.,951361 21 22 23 Lockwood G. B.. 17719 Lwande W. 400134 McMurry J. E. 941219. 144168. Liddell P. A.. 382180 81. 38412611 Lodato. D. T. 457167 Lyiveke I. A, 3831166 2871129 492169 Lidstrom B. 558/2Y4 LoKelhardt. W. 559/385 Lynch. W. C. 951330 336 McMurtey K. D. 92/29 Lie. T. S. 931177 Loeffler R. S. T.,4581108 Lyness W. H. 941243 McNeil. M.. 4591'223. 249 250 269, Lieberman S.. 5571203 213 5581 Loeh. H. J. 461155 Lynn D.G.. 15/57. 16/131 2 70 262 Losel W.. 178180 Lynn W. S. 15/57 McPhail. A. T. 161133 801164. 173 Liebeskind L. S. 210/133 Lotjonen S. 461235 580j152 153 Lyon. G. D.. 4591207 208 1451105 347361 Liebezeit G. 580/146 Loew G. H. 5801167 Lyon-Joyce A. J. 219132 MacPherson D. T.. 4261116 Liebman A.. 383i151 Lowel M. 555i59 Lyubechansky L. 318182 Macquet. J. P. 941181 Liedvogel B. 3861454 387/572 Loewenthal H. J. E. 144170 McQuillin F. J. 2871111) 51 ljYl Logel. J. 555126 McRitchie-Ficknor D. 22514 Liesch J. 555/15 Lohr I. B.. 43/22 Lieser. Th. 287/Yl Lok C. M. 3871549 MacSweeney D. F. 286154 Light R.W.. 95,360 Loliger J.. 3l8j9.5 Ma C. L.. 287190 Madden C.,961374 Madhusudanan K. P.. 931118 Lightner. D. A. 288:/57 579166 London M. 510171 Ma J.-S. 58011.57 Madkour M.K. 391125 68 5801157 I58 Longuernard. N. 3841245 Ma S. 2331611 Madras B. K. 931156 Likhachev Yu. V. 384/306 Lonitz M. 209164' Maat L. 931177 24812 Madyastha K. M. 94/187. 5241126 Liljeqvist L. 523118 Loomis C. W. 92/20 Mabe J. A,. 178173 317144 Madyastha M. K. 4941241 Lillie T. S.. 4261106 Loosli H.-R. 425139 Mabry T. J. 159149. 160/104 2091 Maeda. A, 386/411. 439 Lilly L. 233155 Loozen H. J. J. 492173 10 Maeda K. 93/YI 1-16 NATURAL PRODUCT REPORTS. 1985 Maeda M. 491/Y Mann D. F. 3191153 Maruyama S. 5601393 398 Mauch F. 4591245 Maeda N. 14/47 Mann J. 178182 210/125 319/166 Marvin M. J. 385/330 Maxwell J. R. 461254 5801147 Maeda Y. 385/39Y 491126 51 I/Y5 96 Marx J. N. 4261115 148 172 Maekh S:Kh. 232111 233133 45 Mann R. L. 219115 Marzilli L.G.,5801162 May B. K. 43/10 57812 4 5 7 Maeno S. 3871512 Manni P. E. 178173 Mas P. 457158 60 May D. L. 46/26] Maentele W. 3851332 Manning J. W. 951364 Masamune S. 492186 Mayama S. 4581117 118 IIY 120 Mlrki-Fischer E. 38 1/33 39 40 Manoharan T. 941187 Masamune T.,457165 66 70 90 121 122 123 45 382177 Manresa M. T. 161/182 91 4581127 128 129 130 132 Mayer D. 556166 Maes C. M. 347181 Manresa-Ferrero M. T. 160/123 133 Mayer F. 57814 Maessen P. A, 4931141 Mansfield J. W. 4581124 125 Mascarenhas Y. P. 21 11214 Mayer H. 382166 YO Magalhaes M. T. 21 11217 Mansour E.-S. S. 15/58 59 Mascaretti O. 347160 Mayer N. 951286 Magauer K. 5801157 Mantegani S. 78/55 Mase S. 457/Y7 YY Mayol L. 5561114 Magno S. 5561114 Mantele W. 3851334 Mase T. 144/Y0 Mazdiyasni H.144142 Magnolato D. 4581180 Mantle P. G. 78/15 Mash E. A. 556191 93 94 Mazur Y. 2881200 3821129 Magnus P. 791142. 144 801148 Manugian V. 951364 Masnyk M. 4941210 Mazzola E. P. 144139 359139 40 150 145/Y6. 4931142 Manulis S. 347154 Mason J. I. 5571203 5581230 Mead J. F. 523127 Mahalanabis K. K. 209139 Manushakyan. M. A, 92/23 2321 Masood M. 92/31 32 Medugorac I. 220157 Mahanta P. K. 160/Y5 16 17 Massane G. M. 1611176 Meegan M. J. 44/51. 161/186 Mahato S. B. 1411 248115 Manzardo G. G. G. 144136 Massey I. J. 4921105 Meek B. 941195 Mahendran M. 159/10 Mao G. 15/56 Massiot G. 78/60 79/94 95 114 Meerwein H. 2881197 Mahmoud Z. 160/141 Maoka T. 381131 32 42 121. 801161 Meeschaert B. 317118 Mahon M. 144112 13,3831185 Mapelli S. 3841261 Massiot. J. 801168 Meganathan R.3871570 Mahrenke R. L. 286120 Mapleston R. E. 451157 Massotti M. 951274 Meguri H. 16/151 Mahuteau J. 80115Y Marais J. C. S. 219130 Massoussa B. 801168 Mehri H. 79/130 Mahutte C. K. 951360 Marandici A, 5581267 Masuda K. 15/72 73 171223 224 Mehta A. R. 5601413 Mai L. 78/24 Marano E. 96/37] 225 Mehta B.. 3861475 Maia. J. G. S. 21 11225 232 233 Marasas W. F. 0..248122 Masuda T. 78/47 248132 425144 Mehta G. 144189 243 Marchetti. M. 492185 Masuoka M. 492162 Mehta R. R. 382/Y5 Maier V. P. 387/4YY 523165 67 Marco J. 951320 Masuoka Y. 492162 Meier W. 4931148 Maier W. 178177 Marconi. G. 3841312 . Mata R. 92/IY Meijer. J. 492142 Mailer K. 451113 Marcos I. S.. 15/70 Matcham G. W. J. 4316,44/57 59 Meinwald J. 286180. 287/10Y 2881 Mailman. D. 95/2Y0 Marcotte P. A, 5581241.242 61 63. 72 80 52 56 461198 200 I74 Maiti B. C. 79/85 Marcuccio S. M. 248135 Mateescu G. D. 3841278 279 Meisch H.-U. 578116 17 Maiti M. 961407 Mardirosyan Z. 931166 Matern U. 4571101. 4581114 148 Mejia G.,557/1Yl Maitra U. S. 318111Y 557jl50 Marecek J. F. 492183 84 5 I0127 Melaja A, 287184 559132Y Marekov N. 5601432 Mathews W. S. 288118I Meldrum B. S. 233156 Maizumi H. 961436 Marfaing-Jallat P. 951328 Mathewson J. H. 44/73 Mele L. 951274 Majetich G. F. 1451122 2871121 Margolis S. 5581274 Mathies. P. 3831165 20Y Melega W. P. 2871142 Majumber S. 209161 Margulies L. 579/Yl Mathies R. 3841275 276 307 318. Melian D.,492175 Majumdar S. K. 80/17Y Marini-Bettolo G. B. 78/IY. 79/ 3851319 320 346 Melikov F. M. 233132 Majumder M. S. I. 5601402 118. 120 456112 Mathies R.A. 3841317 3851324 Meller E. 43/18 Majumder P. L. 161154 17/208 Marino C. A, 4931156 330 Mellerio G. 14/12 Mak T. C. W. 16/134 135 286!64 Mariott. M. S. 5591326 Mathis P. 382181 Mello N. K. 9613YY Mak V. 51 ljY2 Markham K. R. 4581171. 173 175 Mathur S. N. 523110 Mel'nikova V. I.. 492/47 Makarov. V. V.. 5241130 Marks G. S. 471262 Matida. A. K. 15/67 Melo C. 510124 Maki Y. 3871551 Markwell. R. E. 44/48 84 Matile P. 5801117 Menachery M. D. 160/105 Makimoto N. 45712Y Marner F.-J. 17/22! 222 381153 Matlin. S. A. 579176 Mendelson J. H. 96/3YY Makin H. L. J. 4921107 54,s5 Matos M. E. O. 161175 Mendez A. M. 17/211 Makin S. M. 3821102 Marnette J. M.. 78/22 Matson. J. A, 3871530 Mendis A. H. W. 5601402 Makino A. 21912 24312 Maroko P. R.. 931132 Matsuda M.93/YI MenendeL A. M.. 4941212 Makleit S. 941185 186 I8Y Maroni. P. 94/IYY Matsuda R. 160/145 Menet A.. 28812lY Makover A. 3831156 Maroti I.. 3861459 Matsuda S. 178154 523143. 44 Menon A. S. 555147 Maksimov G. V. 3841306 Marpeau A,. 523152 Matsuda Y. 187137 Mentberger. J.. 523139 Maksoud H. M. 233158 Marples B. A.. 4931151 Matsuhashi Y.. 3871519. 524 Merand Y. 492155 Malcolm A. J. 160/10Y. 110 111 Marquet A, 287185 Y4 55712IY. Matsui K. 21 ljlY8 Mercer E. 523/YO Maldonado. E. 160//15 221 Matsui M.. 931173 3831164 Mercer E. H. 4581174 Malick. M. E.. 95/.?32 Marrero. H. 3851333 Matsuki K. 78/34 Mercer E. I. 5591326 Malik A. 79/78 Marriott P. J.. 5801147 Matsumiya. N. 941250 276 Merendi C. 346130 31,42413 4 Malik S. 78/63 Marsden R. 931128. 153 Matsumoto H..44/53. 55. 160/127. Merienne C. 78/61 Malikov V. M. 791110. 159123 24 Marshal R. D. 961394 3861426 430 3871512 Merillon J. M. 178/60 25 26 47 48 66. 2lOjY6 Marshall J. A, 144116 Matsumoto T. 14/27 144/15 82 Merlin J. C. 3831235 3841302 Malingre T. M. 391120 Marshall J. H. 381149 83. 84. 86. 159114 41 42 43. 44 Merola D.,3871513 Malinovskaya G. V. 15/71 Marson S. A. 141.5. 556/11Y 346127 42 347153. 3831184 3871 Mersh. J. D. 46/25Y Mallams A. K.. 347161 Marti U.,381145 512 5591323 35Y Mertens R. 3841263. 264 Mahvardpu G. R.. 161150 Martin-Yangy J. 458i135 Matsumoto Y. 1611.57 Mervii.. M. 2101135 Mallik A. K. 15/3Y Martin. A. 233143 Matsumura Y.. 187124. 21912 24312 Merz H. 941205 Malloy J. M.. 5571185 Martin. C.,4581135. 510144 Matsunaga I. 493/145 Messana I. 78/IYs 791118 120 Malmberg A.G.,457168 Martin G. E.. 3871530 Matsunaga S. 171214. 159133 Messing R. B. 961384 Malmberg C. 94/lY6 Martin. J. D.. 159/38 46 Matsuno. T. 381121. 31. 32 42 3861 Mester. I. 400IJY Malmer M. 55812Yl Martin L. L. 178173 486 Metcalf B. W. 558123Y 240. 249 Maloney A. P.. 317110 3181Y3 Martin. M.. 248336 Matsuo. A,. 359136 Metra P. L. 159/8 Malte A. M. 2881181 Martin M. D. 560/403 Matsushima. S.. 1601147 Metzger P. 1418 Manara L. 9.51288 Martin M. G. 2881198 Matsushita K.. I SjlOS 159171 72 Meucci M. 95/28? Manasse O. 2881205 Martinii. D. 3831206. 207 Matsuura. H. 15/79 Meyer B. N. 9213 Manchand P. S. 160/102 Martinez. A. G. 288llYN Matsuura. I.. 425142 Meyer E. R.. 96/36Y Manchanda R.. 961430 Martinez. M. 160/11Y 2251.5 Matsuura. T. 15916 456116 Meyer H.D.. 58Ojl3Y Mandai. T. 14413 30. 382/Y6 Y7. Martinez M. A,. 16/1Y/. IY3 Matsuura Y. 4581117. I20 Meyer. W. L.. 286141. 62 2881183 383116Y Martinez-Ripoll. M. 931162 Matsumki T. 346177 Meyers A. I. 210/101 248177 Mandal S. B. 492iN4 Martinez V. J. C. 21 1/23] Mattheis J. R.. 45!141 16Y. 170 Meyers C. Y.. 2881181 Mander L. N. 44/84 Martinkus. K. J.. 179/1OX Matthews D. E. 4581183 lY3 Meyerson. L. R. 92/2Y Mandrile. E. L.. 9212 Martinoni B.. 46/2OY Matthews. P. S.,4581174 Mezher H. A. 243/Y Mane R. B. 21 lily3 Martins J. M. S. 457193 Matthiesen. U.. 161/178 Mialocq. J. C. 382181 Manecke G.,4941236 Martsev S. P. 5581263 Mattiasson. A. 225128 Miao A,. 233/60 Mangeney P. 79112Y Martynenko Z. 5801176 Mattio T. G. 951304 Miao Z. 225147 Mangiantini M.T. 523!13 Marumo S. 144158 159115 Mattocks A. R. 220153 Miceli D. 951328 Mangion M. M. 288/157 Maruoka. K. 144122 2871131 Mattson J. 92/37 Michael M. 79/13] Mangoni. L. 14/15 15/43. 3871513 Maruta. E. 79/Y6 Matuoka S. 3851350. 3.53. 3861420 Michael M. A. 187135 Maniara G.,457182 Maruyama. K . I44i47 Matwiyoff. N. A, 46/24] Michael R. P.. 951329 Manitto P. 21 I/l81 IHS Maruyama M. 160/8S Matz J. R. 145/110 Michalski. T. J. 580/14Y NATURAL PRODUCT REPORTS 1985 1-17 Michel S. 187138 Miyabo S.. 4931184 Moppett C. E. 347159 Mueller J. 426/96 Michiels T. M. 951360 Miyachi S. 43/14 Mor U. 5581305 Miiller K. O.,45611 2 Michulla R. N. 96/40] Miyahara K. 171218 Moradpour A. 2881174 Mueller M. 39911 Miciak A, 555/3l Miyahara Y. 15/65 66 Morais M. L.457193 Miiller N. 579188 89 58Ojl57 Middleton A, 555131 Miyakawa S.,425142 Moralishvili R. 96/373 Mueller P. 524/100 Middleton B. 555/31 Miyake Y. 5581264 Moreau S. 346117 18 Miiller P. M. 461226 Midgeley J. M. 4931146 Miyamoto K. 4931145 Morecombe D. J. 317151 51 Mueller R. H. 243133 Midiwo J. O. 359139 Miyamoto O.,3871519 524 Morel A. 248117 Miiller R. K. 3821YO Midol-Monnet M.. 92/34 Miyasaka T. 248114 3851384 Morel E. 492/110 Miiller T. 4581164 Miettinen T. A. 557118') Miyashita K. 80/151. 457188 Morelli I. 16/148 Mugrage B. B. 145/11Y Mihailovii. M. L. J. 492133 Miyata O. 79/99 102. 425135 Moreno D. S. 2891235 Muhammad N. 24314 Mihashi S. 1601127 Miyauchi M. 523146 Moreno Valle M. A, 16O/Y8 Mujumdar R. B. 400117 Mikami K. 4261103 Miyazawa M. I59/29 Morera E.492187 Mukai C. 931122 158 159 Mikaya G. A,. 209121 26 Mizobuchi K. 3831169 Moreth C. 931110 Mukai K. 3871563 564 Mikerin I. E. 3821102 Mizsak S. A. 78/25. 425180. 426181 Moretti C. 79/75 80jl59 187127 Mukai T. 2881188 Mikheeva M. N. 92/33 Mizuguchi H. 210/161 Miki K. 210/173. 21 11210 238 Mizukami M. 510134 232121 Mukai Y. 3841310 Morgan D. M. L. 209132 Mukataev Zh. 3831197 198 Miki T. 286142 492162 4931175 Mizukawa K. 371228 159116 4571 Morgan G. S. 44/69 Mukhamedova S. 233133 45 Milani F. 18719 21 523161 5561139 Morgan J. 286115 Mukhametzhanov M. N. 160/140 Milborrow B. V. 3841262 3861451 Mizuno H. 225149 Morgan L. W. 187144 Mukherjee D. 492155 452. 453 387/4Y8 523166 70 Mizuno M. 3871503 504 520 Morgan N. L. 451157 Mukherjee K. C. 233144 Milicua J. C.G. 3831227 Mizuno T. 5601412 Miljkovic D. 2881186 Mizuno Y. 458/118 Morgan P. J. 1791107 317159 60 Mukherjee K. S. 161201 Mukherjee M. 7817 Miljkovic M. 2881186 Mizutani J. 4581185 3 18/62 63 Milkova T. 492190 Morgans D. J. Jr. 144126 Mukherjee M. M. 161153 Mukherjee S. 7817 Miller D. D. I44168 Mizutani K. 15/107 Mori F. 3871520 Miller D. W. 491113 Mnatsakanyan V. A, 92/23 2321 Mori H. 159/52 Mukhopadhyay S. 79/66. 137 1601 16 17 Miller G. W. 43/24 451135 Mo F. 16/IY7 931178 Mori K. 144/9 251114. 3831167 122 233174 Miller J. C. 801177 Mo Y. 961421 4261111 112 4931124 126 128 Mulamba T. 79/94 Y5 Miller J. M. 2871151 Mocek U. 4261104 130 Mular M. 2881168 Mori M. 144163 248138 Mulchandani N. B. 243116 51 1/74 Miller L. H.. 95/33 Modde J. F. 560/411 Mori R.43/21 Mulder P. P. J. 3821147 148 3841 Miller L. R. 5571167 170 172 Modenaar F. 941228 Morimoto C. 3871563 564 275 307 318 3851320 Miller M. J. 451125 Modi V. V. 3861475 476 477 Morimoto Y. 425141 Mulhauser M. 3871525 Miller R. D.. 178/104 317124. 3181 Moellefors K . 951296 83 Morin R. A, 941243 Mulheirn L. J. 347179. 4581176 Morin R. B. 31713 39 SSSjl Miller R. W. 209160 21 1/22Y Moeller K. D. 144/Y2 Morin R. J. 523111 555148 5561 Mullah K. B. 361139 Miller S. A. 461255 580j166 Moens L. 381147 Miller V. 78/53 Moesta P. 4581181 182 127 Muller-Eberhard U.,5581261 Milliet. P.. 4941212 Moffatt F. 2881229 Morino A. 92/76 Mulry M. C. 3841256 Mills 0.S. 288/1YO Momer M. H. 555jY Morisaki M. 5571183 196 203 Mulvena D. P. 7816 Mills R. W.. 286146 54 Mohacsi E.941184 5601393 394 395 396 397 398 Mumtax M. 209139 Milovanovic A,. 492/33 Mohamed S. E. N. 4581163 Morisaki Y. 382197 Munakata K. 21 ljlY8 Min Z.. 93/14] Mohan V. P. 5571150 5591329 Morishita T. 4931131 Mune N. 161162 Minailova. 0.N. 492189 Mohanraj S. 3841258 391/19 Morison J. F. 510125 Munoz L. 4581129 Minakata H.. 187133 Mohnhaupt M. 2881229 Morita A, 4571102 Munoz M. A. 399115 Minale L. 5601415 Mohr P. 144146 Morita M. 92/10 Muntz R. L. 286136 Minami S..931169 Moiseenkov A. M. 3871521. 4921 Morita R. 171214. 159133 Muradin-Szweykowska. M. 3821 Minard R. D. 9214 63 931143 I I5 Morita T. 15/75 83 108 109 112 3861435 436 Minaskanian G.,4261114 115 Mol P. C. 457146 Moritome N. 51 1/87 Murae T. 15/102 103 Minato A, 209/16 Moldowan J. M. 17/210 Moriyama Y.161157 171229 Mura'eva D. A, 92/22. 931103 Mincheva A, 93/93 Molinari M. 941247. 961422 Morizawa Y.,4921116 Murai A. 457165 66 70 YO 91 Minguez Mosquera M. I. 38115 Molinski T. F. IS191 Moron J. 44/48 Murai S. 287/110 Minker E. 92/43 Moll J. 5801131 Moroney S. E. 3 18/67 73 Murakami K. 5581291. 297. 5591 Minnetian 0.M. 58Ojl82 Mollov N. 931165 Moronova M. I. 931112 390 Mino M. 5241133 Molnar I. 941189 Morris D. G. 287196 Murakami. S. 4511.55 Minter D. E. 92/17 Molnar P. 381146 382188 Morris H. R. 461198 Murakami T. 171213 21 l/211 Miozzari G. F.. 319/14Y Molot P. M. 457158 60 Morrison G. A. 491121 Murakawa K. 2871123 Mirand C. 78/60 Molteni A. 220156 Morrison J. F. 3191183 184 185 Murakoshi I. 243125 30 Miranda. C. L. 220166 Mombelli L. 441105 461215 186 187 188 IYO 192 Muralikrishna E.16/150 Miranda E. C. 79/13 Momma Y. 492150 Morton G.O. 941195 Murano K. 3851365. 366 Mirza. A. H. 5801183 Momoi K.. 5581264 Morton J.. 15/87 Murari G.. 95j289 Misawa M. 225149 Monaco P. 3871506. 507 513 Morton K. O. 45/11Y Murata. H. 21 1/206 Mishima H. 347i86 Monaghan R. L. 555115 17 Morton T. C.. 161143 198 Murata K. 2871144 Mishra N. 951285 Monder C.. 4931161 558/267 Morys P. 3851340 342 Murata S. 145/104 Miski M. 159149 Mondon A. 1412 15/88 100. 101 Moschetto Y.. 3841305 Muratake H. 78/46 Miskolczi Z. 94/185 186 Moneger R. 3861448. 5 I I 189 Moser A. H. 555139 53 Murav'eva. D. A.. 232118. 233132 Mislankar S. G. 145/95 Money T. 286117 46 47 51. 54. Moser M. 78/26 37 Misra R. 425176 56 60. 64. 65 70 73 76 77 78.Moss C. W. 3871558 Murfet I. C. 5241101 Misra T. N.. l6/120 121 287186 88. 89 YO+ 107 108. 115 Moss G. P. 2881226 381130 382166 Murillo F. J. 3831237 3861457 468 Misso N. L. A,. 5591361 119 134 138 2881170. 223. 224 Mostad A.. 791120 Murphy B. D. 523176 Mistry A. N.. 791132 2891232. 233 234 Motherwell W. B. 492131. 77 4931 Murphy D. L. 951331 Misuraca. G. 24814 Monger D. J.. 5571168 150 Murphy G. J. P. 523175 Mita T. 524/105 Monks R. 492188 Motidome M. 21 11226 Murphy J. A.. 1781Y2 Y3 100 3181 Mitchell E. D. 523122 Monroe S. H. 510153 Motl O. 159j50 67 76 77 78. Y4 Mitchell F. L. 209127 Montazer-Zouhoor. A, 5791106 Mott G. E. 5571166 Murphy M. T. 95/2Y4 Mitchell R. E. 931163 248131 Monteleone P. 961370. 371 Motto M. G. 3861441 Murphy S. J. 451140 Mitenko P.A, 941249 Montforts F.-P.,461201 Motzkus M. 579/111 Murphy W. S.. 20917. 210/126. 127 Mitoma Y. 16/163 Montgomery C. T.. 931164 Mourao J. C. 21 11214 Murray A. M. 287/Y6 Mi tra A, 2891236 Monti. D. 21 IjlXl I85 Mouriiio A, 4921117 Murray K. E. 248122 Mitropoulos K. A,. 5561140 Moody C. J. 233175 400118 Mousdale D. M.. 3181137 510j15 Murray M. 461254 5801120 172 Mitscher L. A. 347173 Moon B. H. 951273. 337 Mpuza K. 161144 Murray M. F. 2881163 Mitsner B. I. 382jY8 121 Moore A. L. 382180 81 3841268 Msonthy J. D. 791120 Murray-Rust J. 210/8Y Mitsuhashi H. 160/150. 4931171 Moore D. R. 2871121 Mtetwa E. 31716 Murray-Rust P. 210/8Y Mitsui S.,555135 Moore F. H. 580/163 Mubiru N. K. 159114 Murtiashaw C. W. 144i80 Mitsui Y. 187133 Moore J. M. 941188 235 Muccio D. D. 3841278 279 Murty A.N. 144189 Mitsunobu O.,318/91 Moore. L. 145/111 Mucha R. F. 941266 Muscio 0.J. 556194 Mitsura H. 209146 Moore. R. N. 347158. 425130 4261 Mudd J. B. 3861471 Musilek. V. 4261105 Mittal D. L. 3851376 132 523177 78 Muecke W. 5591340 Muthusubramanian P. 78/33 Miura I. 14/33 15/99. 145/102 Moore T. A. 382180. XI 3841268 Miiller G.,44151 451190 191,461 Muto O. 3861425 103. I 59/52 16 I 1/80 3851358 35Y 199 215 580/126 I29 Muto V. 3861489 1-18 NATURAL PRODUCT REPORTS 1985 Muzaffar A. 791134 Nakazato M. 5801143 Newton M. D. 2881213 Noguchi H. 346132 347165 42411 Myers A. B. 3851320 324 Nakkady S. 92/11 Ng A. S. 144164 2 555135 Namba T. 21 11240 Ng D. L. K. 941225 Noguchi K. 801180 Nanasawa M. 3831190 203 Ngo Le-Van 160181 248133 Noguchi M.579159 Nanavati D. D. 15/89 Nguyen H. D. 21917 24311 Noguchi T. 43/20 21 Nanayakkara N. P. D. 161190 192 Nguyen Hoang Nam 961420 Nohara T. 209154 Naab P. 461201 Nancarrow C. D. 5581251 Nguyen L. T. 318188 90 Nokami J. 144130 Nabeshima T. 941262. 951322 Nanda B. 523182 Nguyen-Ngoc-Suong 151108 Nolan A. M. 961403 Nabeta K. 523156 5241123 Nandi D. L. 43/12 16 28 29 Nguyen Phuong Tung 3821102 Noland B. J. 555154 56 5571154 Nabiev A. A. 159123 25 26 Nandi R. 961407 Nichols B. P. 3191149 Noma Y. 4931137 Nachman R. J. 1601152 Nanjundiah C. 4931172 Nichols D. E. 9213 Nomi R. 78/13 Nader F. 20915 Nano G. M. 159174 1601131 Nickisch K. 4941229 Nomoto K. 171228 5561139 Nadler K. D. 44/99 Naoki H. 15/93 159116 Nickolson R. 4941229 Nomura K. 492/81 Naemura K.2881172 Naora H. 151102 Nickon A. 286115 Nonaka F. 4571102 Nafradi J. 951365 Nap I. 492142 Nicoara E. 382184 Nonhebel H. M. 510137 Nagahisa A. 5571200 Napier J. J. 425157 Nicol M. 3851322 326 327 Nonoyama M. 21 11245 246 248 Nagai F. 4921119 Napoli J. L. 3861491 Nicolaus B. 3871514 515 516 Nordlov H. 44/54 55 70 83 Nagai J. 5591341 Naqvi K. R. 386/424 Nicoletti M. 791118 120 160/136. Nordmann R. 5801190 Nagai M. 160187 Narasaka K. 391118 17718 Nordmann Y. 44/92 579131 42 Nagai Y. 400133 Narasimhan N. S. 187136 Nicollier G. 161184 Norgard S. 381128 Nagakura I. 1451114 Naruchi K. 2881164 Nicolson I. T. 177111 Norin J. 161139 Nagakura N. 178127 28 31 32 Narula A. 523133 Nicotra F. 5591356 366 388 389 Norman A. W. 4931142 34 5241119 Narula A. S. 2881221 5591369 5601391 392 Norman S.M. 3871499 523165 Nagami K. 93/12] 370 371 Nielsen B. 931172 Noro Y. 209/52 Nagamine M. 578118 Nash C. H. 317154 3181101 Nielsen L. T. 209150 Norte M. 159138 46 Naganawa H. 178186 248132. 4251 Nasser A. M. A. G. 78/22 79/70 Nieminen A. 0. K. 78/21 Noshiro M. 5581297 44 4261100 Natori S. 78/31 Nigam M. C. 523130 Nothnagel E. A. 4591250 Nagano H. 3181112 347153 Natsias K. 3841273 Nigam S. S. 161124 Noto T. 425142 Nott A. P. 4571100 Nagao K. 1451123 Natsume I. 346142 Nii H. 1601157 Nagao S. 4581127 128 129 130 Natsume M. 78/46 187125 Niino N. 4581130 132 Novak J. 931107 Nagao Y. 248114 Natu A. A. 160195 Nijhuis G. M. M. 941244 Novikova M. A. 3871521 Nagaoka M. 4931159 181 Nauss-Karol C. 951318 Nikaido T. 209178 Nowicky W.961410 Nagasaki N. 951311 312 Navon G. 5801157 Nikiforov G. A, 492147 Noyori R. 2871110 Nagata K. 4931166 Nawata Y. 4931145 Nikonov G. K. 523129 Nozaki H. 161133 160192 2871131 49211 16 Nagavi B. G. 400130 Naya Y.,457118 523162 Nilsell K. 523118 Nagumo M. 3851327 Nayak U. R. 159164 Nilsson L. 159169 70 Nozawa K. 78/38 Nagumo S. 160187 Nayeshiro H. 51 1/86 87 Nimgirawath S. 233166 Nozoe S. 14/14 15/38 347152 3871 Nahasampagi B. A. 160180 Naylor R. J. 233157 508,509,510 51I Naik N. C. 2881154 Nee P. B. 457167 Nimit Y. 931135 Ninagawa Y. 1419 3871520 Nriagu J. O. 471263 Nair A. M. 5601400 Neef G. 492165 4931194 Ninomiya I. 78/51 52 79/98 99 Nuckles E. 4591246 Naito A. 4261107 102 931129 130 961406 415 416 Niiesch J. 1781103 317114 38 41 Naito T.79/98 99 102 931129 Neelakantan S.. 159159 Ninova 248116 3 191169 130 961406 415 416 Neeman E. 43/23 Nakagawa A, 425143 Neese A. S. 318161 Nio N. 21 11176 Niirrenbach A. 3821141 Nakagawa K. 4261131 Negrel J. 510144 Nugent M. J. 3181124 Nisbet J. J. 317113 56 Nugent R. A. 144178 Nakagawa M. 78/34 Negrete R. 243126 Nishi A. 4581190 4591240 241 Numata A. 159133 210/119 251110 Nakagawa R. 95/31] 312 Neidhart W. 44/58 5591318 319 Numata H. 4921102 4931136 Nakagawa T. 160/150 Neidleman S. L. 523137 Nishibe S. 209117 22 74 78 81 Numata Y. 2101168 169 Nakahara S. 4581185 Neier R. 461197 198 200 82 Neijenesch H. N. 3821147 Nishida T. 1419 3871520 Numazawa M. 492174 4931159 Nakai A. 801149 I51 181 186 Nakai H. 187128 Neill E. A. M. 92/50 53 54 Nishide H.171226 Nuraliev Yu. M. 92/66 Nakai S. 161140 Neill S. J. 159118. 3861493 494. Nishiguchi Y. 79/98 Nurgozhaev K. Kh. 3831197 198, Nishikawa M. 286142 44 50 57 199 Nakai T. 4261103 3871495 496 Nakajima K. 2101134 Nelis H. J. C. F. 381147 3841241 75 287197 Nurmukhamedova M. R. 1611168 Nakajima R. 159/6 242 Nishikawaji S. 1601147 Nussbaumer C. 461199 212 215 Nakajima S. 78/38 Nelson D. W. 579195 Nishimaki K. 347152 220 78/59 5801130 Nakajima T. 78/13 Nelson E. C. 382194. 3841308 Nishimitsu H. 286144 Nussberger R. 461212 Nakajin S. 5571208 224 5581260 Nelson J. A. 5561122 123 124 Nishimoto N. 161140 Nutt R. F. 248120 Nishimura A. 2871149 Nwaiwu J. 931114 Nakamura E. 144145 Nelson P. 1611167 Nakamura H. 951298. 15919 Nelson P. A. 5581233 Nishimura S.,492150 Nwankwo J.O. 7814 248132 425144 Nelson S. H. 92/80 Nishino C. 209165 Nyburg S. C. 243129 Nakamura M. 5561125 Nelson W. H. 3841295 Nishino T. 5561104 105 5591328 Nakamura N. 3831222 Nemeth G. A. 382180 81 3841268 329 335 337 338 341 342 343 Nakamura S. 78/13 Nemeth M. A. 225133 344 375 Oba K. 457118 22 25 26 27 28 Nakamura T. 4941238 Nemethy E. K. 5591308 Nishino Y. 4931194 29 523159 62 Nakamura Y. 210/170 175 Nemoto H. 145/101 102 103 Nishio T. 3831165 209 214 Obase H. 2881167 Nakanishi K. 15915 1601125. 3821 Nes W. D. 3861445 449 523123 Nishioka I. 523151 Obayashi A. 2481.92 425144 Nishizawa M. 171226 159/58 Obert K. A. 55516 11.5 119 125 134 3831154 155. 5581305 5601434 Nitsche B. 5801119 Oberti J. 1611174 3861425 431 433 441 457118 21 Nes W.R. 5571183 5591345 346 30 31 523161 62 347 5601434 Nitta I. 78/42 Obol’nikova E. A. 3871552 Nakanishi T. 159152 Ness G. C. 55519 10 44 45 5561 Nitta K. 346115 425147 O’Brien D. F. 3861414 Nakano M. 510131 64 Nivard R. J. F. 2871140 O’Brien E. 425127 28 30 Nakashima R. 24815 Neszmelyi A. 15/87 Niwa H. 1451125 159171 72 2191 O’Brien J. H. 951297 Nakashima T. 161163 426187.4581 Netting A. G. 3861453 11 425165 79 Ocampo R. 4931134 5801171 118 Neuberger A. 43J7. 44/50 Niwa M. 2111245 246 247 248 Occolowitz J. 317154 Nakashima T. T. 347158. 4261132 Neuhaus D. 92/74 346126 425120 Ochi H.,558/259 523157 Neukomm G. 187115 Niwa N. 1417 Ochi M. 15/99 Nakata H. 160184 Neumann D. 178160 Nixon L. N. 44/48 O’Connor B. H. 5801163 Nakata T. 4261101 Neumann H. 941232 234 237 Njar V.C. O. 4931154 523140 Oda K.,2101168 Nakatani M. 15/93 Neumeyer J. L. 233154 55 56 57 5241113 Oda T. 523156 5241125 Nakatani Y.,3851382 4921112 58 Noack K. 381138 39 Oda Y. 5591341 4931133 Neu-Miiller M. 3861474 Noble N. 555148 Odani S. 5561111 Nakatsu K. 161158 961376 Neuss N. 801177. 178191 97 104 Noble N. A. 523111 Odani T. 15/84 Nakatsuka S. 78/47 3 1713 22 24 54 3 18/81 83 95 Noble P. 159173 1601121 Odashima S. 161140 Nakayama A. T. 3841274 101 Nockolds C. 5801163 O’Dell C. A. 382/135 3841272 Nakayama K. 16/163,493/143 Neves V. A. 3181127 51017 Noda Y.,425149 Odinokov V. N. 3871523 Nakayama M. 159136 160192. 5581 Neville H. J. 951334 Nodes B. R. 3861431 O’Dowd M. L. 2871130 301 Newkome G. R. 3191143 Noga G. 3841246 Oehlschlager A. C.5591339 349 Nakayama R. 492162 Newmark R. A. 178185 Nbgradi K. 80/155 372 373 Nakazaki M. 2881172 Newton J. 0.E. 951307 Nogradi M. 4581164 Oelbermann U. 15/88 101 NATURAL PRODUCT REPORTS 1985 1-19 Oelrichs P. B. 15/91 Okano M. l5jl09 Oshima Y. 78/64 159128 160/156 Paramonova L. I. 3851369 Oertli E. H. 458/111 112 113 Okazaki H. 425142 Oshio H. 5241106 Parchet M. 4581135 Oesterhelt D. 3821104 106 120 Okazaki M. M. 9311.56 Osianu D. 382/84 Pardini V. L. 382195 3851364. 386/437 Okazaki T. 4261131 Osmanov Z. 24813 Pardo. A. D. 451132 Oztekin A. 23218 30 Okech M. 400134 Ossowski P. 4591221 224 225 Pardo C. 287/114 Ofner S. 461201 202 Okikawa T. 5591325 Ostrove S. 555118 Pardoen J. A. 3821112 147 148. Oftebro H. 5581299 Okogun J. I. 187/18 248134 Ostrovskii M.A. 3851373 3841275 276 307 318 3851320 Oga K . 457/26 Okorie D. A. 187118 248134 O’Sullivan A, 383/218 Paredes W. 225139 Ogasawara K.. 219113 4921102 Oksuz S. 160/162 O’Sullivan J. 31714 15 43 45 Parfeinikov S. A. 931103 233137 4931136 Oku H. 457156 Osumi T. 5591337 338 Parikh V. D. 5581238 Ogata K. 144128 Okuda A. 5581287 Otake N. 43/19 426185 457199 Parish D. W. 461247 Ogawa M. 187125 Okuda K. 558j284 287 290 291 Otaki S. 219113 Parish E. J. 49115 6 5571165 166 Ogawa S. 3841243 29 7 Otera J. 14413 382196 97 3831169 168 169 171 175 177 178 Ogawa T. 451153 Okuda R. K. 159112 Otoguro K. 248125 Park C. W. 92/45 Ogihara Y. 15/85 Okuda S. 347166 67 86 Otomasu H. 21913 243125 30 2511 Park J. C. 3831173 Ogino T. 579167 Okuno T. 346142 3871512 I3 Park K.H. 524198 Ogiso A. 555135 Okuyama A, 178186 Otsuka H. 220155 Park 0.S. 3831173 Ogle C. W. 95/39 Okuyama E. 425129 Otsuka S. 5561115 Park R.J. 5581230 Ognyanov I. 159163 160/134 Okuyama T. 161162 Ott A. C. 2881163 Parker D. 34618 Oguakwa J. U. 79/118 Okwute S. K. 187118 Ott S. 15/87 Parker J. M. R. 426189 Ogundana S. K. 4581106 Olaniyi A. A. 210198 Ottolenghi M. 3821103 105 113 Parker R. A. 555143 Oguntimein B. 248/36 Olay L. P. 92/68 Ouchi S. 457156 Parker S. R. 3821136 137 Ourisson G. 14/11 2871147 3851 Parker T. S. 556178 Ogura H. 78/41 O’Leary M. A. 5591379 380 382 4921112 5561136 137 138 Parks L. W. 5591327 348 374 Ogura K.. 3871536 538 542 5561 O’Leary M. H. 3191192 193 5101 85 96 101 102 25 5571 I79 Parnell C. A. 931131 Ogura M. 161158 159 Oleinikova G.K. 14/30 Ovcharov R.,951272 Parnell J. C. 210/115 116 Ogura Y. 4931186 Oliveira-Campos A. M. 791128 Ovchinnikov Yu. A, 3861412 Parodi B. 161182 Oh C. J. 951313 Oliver J. E. 286115 Overman L. E. 801153. 187133 Parrilli M. 14/15 3871513 O’Hagan D. 347183 Oliver R.P. 578114 579199 243114 Parry R. J. 346114 426188 95 96 O’Hanlon P. J. 42515 6 Olivier E. J. 360/110 Overton K. H. 2881160 523155 Parsons W. H. 144178 O’Hara E. P. 3851358 Olivigni F. J. 346121 Owen F. D. 96/394 Parthasarathy P. C. 92/15 Ohashi A. 4319 Olson J. A, 381/11 13 3821131 Owen J. A. 941222 249 Partridge C. W. H. 318/106 Ohashi H. 510134 132. 3831149 3841254 259 3861 Owen J. D. 4581110 Partridge J. E. 45615 Ohashi Y. 426191 492 Owen L. N. 28612 Paryzek Z. 15/63 64 Ohba H.5571227 Olson R.E. 3871571 575 576 Owens D. P. 961369 Pascal R. A. 5561144 145 5571 Ohba M. 931167 168 169 Oluwadiya J. 159169 Owens W. 2871121 169 170 173 174 176 Ohba S. 159172 Omar A. A. 160/143 Owusu P. D. 931111 Pascard C. 15/68 108 791114 121. Ohbayashi H. 251110 Omarkulov T. O. 3831197 198 199 Ozaki M. 951326 80/161 161/187. 18718 209125 Ohfune Y. 1451122 2871121 2881 Omura S. 248125 425143 74 78 Ozaki N. 171227 Pascual A, 3831214 16 I 426192 Ozasa S. 5581289 Pascual C. 209148 Oh-hama T. 43/19 Onan K. D. 160/105 18715 492171 Ozeretskovskaya 0.L. 457/77 Pasternak G. 941208 Ohira S. 5581301 Onanga M. 79/85 Pasternak G. W. 941259 951342 Ohiri F. C. 791120 931102 Onda M. 961411 425178 Pastore M. P. 160/105 Ohizumi Y. 17/228 15919 233139 Onderka D. K.318/113 3191144 Paaren H. E. 4931144 Patamia M. 791118 5561139 160 Pacakova E. 951314 Patchett A. A. 55511.5 18 Ohkawa S. 3871551 O’Neil T. H. 492151 Pache W. 425139 Patel N. 178/100 Ohki T. 161200 O’Neill M. J. 4581168 169 Packer L. 3851355 Patel N. J. 318166. 3861450 Ohkura T. 161/180 O’Neill T. M. 4581124 125 Packer N. 5791109 110 Patnaik G. K. 233144 Ohloff G. 381156 Onishi N. 248121 Pacquer D. 2871139 Patoiseau J.-F. 2881193 Ohmiya S. 243/25 30 Onishi S. 579167 Padmawinata K. 232128 Paton B. 555147 Ohmoto T. 15/42. 78/23 28 209178 Ono H. 92/39 Page J. A. 92/20 Paton B. C. 3871577 Ohnishi E. 5601412 Ono M. 79/97 347186 457191 Pagliosa F. M. 21 11225 Patra A. 399111 Ohnishi S. T. 93/92 Ono T. 5561111 Pagnoni U. M. 523145 47 48 Patrick G. 951305 Ohnishi Y.3871533 523128 Onoda M. 5571224 Painuly P. 171202 Patrick V. A. 78/57 Ohno M. 286/45 Onur M. A. 931143 Pajewski T. N. 5571167 Pattenden G. 144150 54 87 3811 Ohno N. 160/104 Ookawa N. 210/145 154 Pak C. S. 5601416 43 44 3841267 425134 37 Ohnuma T. 24313 Ooms P. H. J. 2871140 Paknikar S. K. 159153 64 Patterson G. W. 5591352 5601430 Ohsawa T. 801180 219/10 Opella S. J. 931180 Pakrashi S. C. 79/89 233173 43I Ohshima T. 95j295 Opie C. T. 510145 Pal S. C. 24817 Patterson J. W. 46/26] Ohta S. 15/74. 171229 3831217 Opitz G. 286/24 Palfreyman M. N. 4261128 Patton M. L. 951345 Ohta T. 78/10. 801164 165 347152 Oplinger J. A. 144180 Palings I. 3841307 Patwardhan S. A, 523182 Ohta Y. 161159 160/133 209171 Oppolzer W. 78/50 961414 144131 Palm D. 3 18/74 Paukert J. L.31911.55 156 51 1/84 85 32 48 55. 2881229 Palmer B. D. 425166 Paukstelis J. V. 286116 2881197 Ohtani K. 225149 Or Y. S. 382/111. 3861434 Palmer L. A. 579166 68 Paul 1. C. 286136 Ohtsuka T. 144186 Ordaz C. 92/14 Palmer T. N. 951356 Pauly G. 523152 Ohuchi S. 178186 Orenstein L. 555148 Palmieri B. 961427 Paupordin C. 5241121 Oikawa H. 347153. 56 Oriente G. 3871548 Palmisano G. 79/93 104 136. 2881 Pauptit R. A. 286170 Oishi H. 425142 Oritani T. 3831162 174 175 3871 189 Pavone F. 941267 Oishi T. 791125 4261101 102 497 Paltauf F. 5561113 Pawelka K.-H. 801174 178159 Oiwa R. 425174 Orito K. 801146 Palumbo A. 24814 Pe W. 941231 Ojewole J. A. O. 791116 951308 Orlandi G. 3841312 Palumbo G. 491125 Pearce C. J. 179/110. 347164 4251 Ojhara B. 14416 Orlandini M.523172 Pande A. J. 3851331 54 Ojika M. 1417 159/71 72 425165 Orme-Johnson W. H. 5571200 Pande J. 3861433 Pearce G. 4591249 252 79 579156 5801132 Pande L. M. 2871124 Pearl J. 22514 Ojima I. 383/195 Ornstein P. L. 3831171. 4261147 Pandey P. C. 3851387 Pearson H. 461231 Oka T. 426191 Orshi R.,951326 Pandey P. S. 44/63 80 81 Pech B. 78/18 Okabe H. 15/65 66 Orsini F. 210/109 Pandey R. C. 425176 Pechy P. 92/30. 941214 215 Okabe K. 209122 81 Ortar G. 492187 Pandey R. K. 579175 5801176 178 Peczynska-Czoch W. 4941218 Okachi R. 426191 Ortega A, 160/115 117 119 Pandit U. K. 79/91 187140 Pedersen J. I. 5581281 290 299 Okada K. 288/188. 4931126 Ortiz de Montellano P. R.,5571179 Pandita K. 400128 Pederson R.C. 5571213 Okada M. 931146 Ortmann R. 458j115 . Pang C.-P. 179/107 317133.3181 Pederson R. R. 2881163 Okada N. 346128 Osada A. 457170 62 63 Pedro J. R.,145/108 Okada S. 579/50 Osawa E. 144183 Pang G. T. M. 210/116 Pegg G. F. 4591203 204 Okada Y. 161162 558/291 Osawa Y. 4931181 5581237 245 Panizza S. 15/67 Pelizzoni F. 210/109 Okamoto H. 3841310 311 55512.5 Osborne M. G. 5241114 Pant K. K. 951285 Pelletier J. C. 233150 Okamoto M. 426197 5581264 Osborne N. N. 3861413 Paoli G. 3871517 Pelter A, 209138 63 65 83 86 Okamura M. 3871533 523128 Osei T. P. S. 961374 Pappalardo P. 791142 144 210189 91 92 93 128. 28613 Okamura W. H. 382193 99 116 Osei-Gyimah P. 941192 Paquette L. A. 144119 75 85 1451 425133 117 118 3831181 4931147 Oshima K. 4921116 100 2871142 Penco S. 381127 1-20 NATURAL PRODUCT REPORTS 1985 Peng B.92/87 Pietrzak B. 491126 Posey B. L. 941229 Quantin-Martenot E. 5591372 Pennetreau P. 4931189 Pigott H. D.,2871145 Posner G. H. 144137 Queener S. W. 178191 97 104 Penning T. M. 5571222 223 Pilard S. 187123 Poss A. J. 144178 31713 22 24 318181 83 Pennock J. F. 3871569 Pilbeam D. J. 219132 Posselt K. 4931208 Quijano L. 160199 117 Pepperberg D. R. 3861431 Pilla N. N. 4261126 Post R. M. 225129 Quinn P. 178169 70 Perales A. 16/1Yl 193,931162 Pillay S. P. 5581277 Posthumus M. A, 457146 Quinn P. J. 3871565 566 159146 160199 161/172 173 Pilotti A. 187142 4591221 224 225 Potenza D. 4261109 Quirke J. M. E. 5801120 148 Percy-Robb 1. W. 5581272 Pinar M. 161/172 173 Potgieter D. J. J. 347155 Qureshi N. 55512 Pereira A. L. 219112 Pinder A. R. 145/115 Potier P. 79/68 69 71 83 129 801 Pereira J.M. G. 961409 Pinetti A, 523145 47 48 172 187127 Pereira R. 5591336 Pinhey J. T. 492161 Potter J. E. R. 3871532 Perera P. 791106 117 801160 Piniella J. F. 492192 Pougny J.-R. 42518 Pereyra E. N. 961368 Pinkerton F. D. 5571172 Pouilhes A, 80/157 Rabe T. 557/211 Perez J. J. 425156 Pinnick H. W. 187112 Poulson R. 441107 451113 Rabi J. A. 491/14 Perez L. M. 556/YY 100 Pinten P. 286181 Poulter C. D. 14/10 55512 556189 Rabie C. J. 346122 Perez R. 159138 46 Pinto W. J. 5591346 347 90 91 92 93 94 103 Rabii J. 951302 Perez-Ossorio R. 288/IY8 Piper S. E. 210/125 286176 78. Poulter M. 961394 Rabiller C. 3821123 Peri I. 5581305 2881179 223 224 Poulton J. E. 510168 Racagni G.,941263 Perkins E. J. 579/Y3 Piper W. N. 44/76 579130 32 Poupat C. 79/68 69 83.187127 Radics L. 381146 382185 88 Perlman J. I. 3861431 Pirkle W. H. 286136 Pouzar V. 49118 4931122 209 Radin D. N. 3861470 471 Perrier M. 3831188 Pirola B. A. 57814 5 7 Powell D. A, 951333 Radmer R. 44/49 Perrin D. R. 45617 Pirozhkova N. M. 161170 171 172 Powell G. P.. 2871144 Radyuk V. G. 5571206 Perrot B. 3191184 Pirrung M. C. 14312 Powell J. W. 21O/Y8 Raffauf R. F. 160/105 18715 2091 Perry C. W. 3831151 Pittard A. J. 3181107 Powell R. G. 209113 14 60 45 Persico D.,5601425 Pittard J. 510129 Powers M. A, 38513.52 Rafikov S. R. 3871.523 Personova E. R. 451154 Pitteloud R. 1441.55 Poyser J. P. 425170 Ragg H. 4581145 Rahal S.,5581268 Pert A. 941271 Pivnitskii K. K. 492147 8Y Prabhakar S. 14/13 Perveen N. 79/132 Pizzi P. 5591389 Pradhan B. P. 161153 Rahier A.5591314 315 369 370 Pervushina E. A. 382/Y8 Placheta P. 951286 Pradhan S. K. 4941211 371 Peseckis S. M. 425168 Plant J. E. 461238 Prager R. A, 248139 Rahkamaa E. 78/21 Raich N. 579/31 Petcher T. J. 42513’) Plat M. 79/7Y 130. 92/34 Prager R. H. 9311.52 Railton I. D.,523191 Peter H. H. 317131 Platt R. V. 510145 Prakash A, 400127 Rainer J. D. 961373 Peters A. J. M. 382/10Y Plattner R. D. 209113. 14 60 Prakash O. 92/83 Peters T. J. 580jl38 Plavac F. 14312 Pramanik B. N. 4921121 5581296 Rajagopalan M. S. 4931162 Petersen J. L. 144188 Pleuvry B. J. 951323 Prange T. 15/68 108 161/187 1871 Rajagopalan V. 159159 8 20912.5 Rajamahendran P. 233143 Petersen J. S. 225/1Y 20 Plieninger H. 579169 70 Prasad A. V. R. 161122 179 Rajamanickam P. 400124 Petersen M.510160 Ploschke H. J. 384/251 Rajananda V. 461250 5791.58 Peterson B.. 18717 Podschun T. E. 580jl2Y Pratesi R. 579165 Rajaraman R. 233150 Peterson F. J. 941210 Poggi A. R. 286122 Prati R. 941238 Prebble J. N. 3861458 Rajeswari S.,8Ojl58 Peterson G. E. 425158 SY 60 Pohland A. E. 391125 Preckel M. M. 425116 Rajkovit M. 492133 Peterson H. I. 92/37 Poisson J. 801146 173 Preclik G. 555125 Rajkumar K. 523176 Peterson J. E. 219145 Polazzi J. O. 941203 Preininger V. 931107 138 233161 Raju M. S. 558/235 Petrier C. 144138 Polglase W. J. 441107 Preiss A. 17/211 159117 232110 Ram V. J. 233156 58 Petrovic J. 2881186 Poli G. 346130 42413 382161 Petrow V. 558j2.50 Polian-Bouin C. 457157 Premila M. S. 24816 Ramage R. 2881169 Ramaiah P. A, 209183 Petry T. W. 220160 Policastro P.P. 319/159 Petryka Z. J. 580/141 Poling S. M.,3861449 3871499 Prestwich G. D. 4921108 10Y. 5601 Raman H. 287jl09 3Y9 Raman P. V. 159j.59 Petts H. V. 95/323 523167 Preus M. W. 5591381 Ramasarma T.. 555/47 556179 (I2 Petzoldt K. 4941228 22Y Pollack R. M. 5571223 Preusch P. C. 38715.50 Ramaswami S. 286174 Pfaltz A, 461216 217 223 226 Pollini G. P. 144171 Previtera L.. 387/506 507 513 Ramaswami S. K. 286174 580/131 134 135 174 190 Polonski T. 286128 Prewo R. 382175 425131 4261110 Ramdahl T. 381122 23 25 Pfdnder H. 38 1/37 38 51 382169 Polonsky J. 15/108. 161/186 187 Priestap H. A. 44/78 Rameseshan S. 5801163 70 72 7Y. 3841250 18718 Prince R. C. 3871554 Ramesh M. 400124 Pfauth E. C. 391120 Polyakova N. K. 92/82 Prior S. 93jl50 Ramesh S.,4251.56 Pfeiffer B.556/YS Pomerantz I. H. 2881184 Prota G. 24814 Ramirez F. 492183 84 Pfeiffer E. F. 951316 Pommer H. 382165 Prousek J. 4941240 Ramirez J. S. 492139 Pfennig. N. 580/125 Ponder J. W. 346111 Prout K. 28617 Ramirez-Munon M. 387/525 Pfenninger A. 461215 Ponder M. 3851346 Provenzano P. M. 951349 Ramos C. M. 51013 Pfitzner A.. 79181 178148 4Y 50. Ponnamperuma C. A,. 471268 Prudnikova I. V. 580/116 Ramsey K. P. A. 22512 51 Pons. J. L. 510148 Prugh J. D.,4261144 Ramsteiner K . 5591340 Pfrunder B.. 2871146 Ponsati O. 2lO/l62 Pryde L. M. 44/53 54. 55 Ran C. 931105 Pham H.-P. 580j181 Ponsold K. 492135 Pryor J. S. 555jlY Rana J. 177114 IS 18 19 21 Philibert D. 491128 Ponticorvo. L. 5571150 5581262 Psenak M. 45113.5 Randaccio L. 5801162 Philip G.. 44/Y4 Pontikis R.961420 Puar M. S. 347161 Randazzo C. 25114 Philipp. B. W. 555146 Ponty. A. 492lY0 Puff H. 93/14? Rando R. R. 3831159 3851308 Philippi U. 178179 Pontzen R. 4591214 Puga A. 961408 405 3861427 Philippot J. R. 3841305 Popa D. P. 381116 Puglissi Allegra S. 941267 Rang H. P. 92/78 Phillipps G. H. 4931202. 203 Pope. W. J.. 28619. 35 36. 37 2881 Pulkinnen E. 287184 Ranganathan S. 2871109. 3871.577 Phillips G. B. 42517 lY0 Pullinger C. R. 523112 555124 Ranise A, 2871132 Phillips S. E. V.. 286148 6Y Popjik G. 426/13Y 556178 84. 86. 5561140 141. 5571187 Ranjeva R. 51014 Phillips W. R. 160/145 110 5571160 Purcell N.. 4261128 Ranu B. C. 144173 Philogene E. 187127 Pople M.. 347150 Purkis S. W. 381/58 Ranzi B. M. 5591366 Phinney B. O. 524/Y3 102 Popli S. P.. 801162 1601153 Purushothaman K .K . 15/40 2 I I / Rao A. M. 209186 Phirwa S.,492/1OY. 560/3YY Popov S. 4921106. 5601432 204 Rao B. V. G. 210/Y2 108 I20 Piattelli M. 3871548 Popova M.. 931107 Purwin C. 4581116 Rao E. V. 209163 7Y. 210/YY Piazza G. J.. 5591308 Popravko S. A,. 51 IjXO Pusset J. 79/79 Rao G. S. K. 3831189 Pichat L. 96/420 Porcheron P. 5601411 Putter I. 555117 Rao G. S. R. 347173 Pickar D. 951331 Porlock D. E. 94/1Y6 Putun E. 160/162 Rao H. S. P.. 426196 Pickardt J. 360/12Y Porra R. J. 43/IY. 578116. IY Pyke D. A, 951366 Rao K. R. N. 44183 95 451120 Picken. D. 523155 Porreca F. 961377 38Y Pyser J. P.. 3l8/8Y Rao K. V. 209153 2101174 Picker K. 7816 Porrskamp P. A. T. W. 286134 Rao P. N. 4931190 I92 Pickering R. A. 491117 Port C. D.,220/56 Rao P. S. 178180 Picot D.451126 Porter. A. E. A, 4581124 Rao R. R. 210/128 Pierce. A. M.. 5591339 34Y 372 Porter B.. 791135 Rao V. J. 3831160 3 73 Porter J. W. 381/10. 3861445 5231 Qian Z. 225140 Rao V. K.. 209186 Pierce H. D.,5591339. 34Y. 372 25 55512 Y SY 556/69 Qiao G. 93/11Y Rao Z. 93/11Y Piers E. 144166 1451114 Portilla G. 556jY9 100 Qin C. 161136 Raphael R. A, 210/15Y 425112 Pierson-Goeger M. L. 220161 Portius. H. J. 4931205 Quail P. H. 579185 Rapoport H. 451125 941198 2251 Pietra F. l59jlY Portoghese P. S.. 961388 3Y0 3YI Quain D. E. 556165 19 20 579171 80 81 82 NATURAL PRODUCT REPORTS 1985 1-21 Rasamizafy S. 93/110 Renna. G. 941263 Robbel L. 5591355 Romandini S. 951352 Rasetti V. 461201 202 216 217 Renstrram B. 523149 Robbiani C. 961414 Romeo P.-H.579131 42 Raskin V. I. 579/101 Rentzepis P. M. 3851348 351 396 Robbins M. P. 4581147 Romero J. R. 187122 Rasmussen S. K. 578114 Renwick A. G. C. 55Sj256 Robbins W. E. 5601400 Rorno de Vivar A, 160/115 117 Rassat A,. 2871146 147 Renz P. 461229 5801136 Robert G. M. T. 79/68 69 I19 Rast D. M. 425131 426/110 Repke K. R. H. 4931201 205,4941 Roberts A. B. 381/11 Romussi G. 161180 182. 171205 Rastetter W. 318/Y5 210 Roberts J. D. 2881194 206 Rastogi K. 801162 Reshetova I. G. 493113.5 4941216 Roberts J. K. M. 52317 Ronald R. C. 346113 4261106 Rastogi R. C.. 160/Y5 Restivo R. J. 2101132 163 Roberts J. S. 457149 Ronchetti F. 5591356 366 388 Rastogi R. P. 14/IY 32 1601128 Reszka A. 5801169 Roberts M. F. 4581168 169 389 5601391 392 2l0/lll 21 11208 385/387 Retamar J.E. 159167 Robertson E. N. 92/48 Rood J. I. 3191184 186 Ratcliffe A. H. 523180 Retey J. 318165 3191162 179 180 Robertson G. B. 187130 Rosa J. 579131 42 Ratcliffe N. M. 144112 383/185 Rettig S. J. 286156 Robertson J. S. 287199 Rosazza J .,4941240 Raudino A. 3851356 357 Reum L. 5601409 Robeson D. J. 346143 44 45. 4581 Rosazza J. P. 791143 5241127 Raulais D. 159/20 Reuning R. H. 4931200 172 Rose I. A, 318/116 Raulston D. L. 555138 5571171 Reusch W. 14/24 4941223 Robey D. 28617 Rose M. E. 5591367 Rausch T. 78/3 Reuss R. H. 2871134 Robien W. 159j21 22 Rose S. 44/78 Rautenstrauch V. 381156 Revial G. 145/104 Robin J.-P. 2101129 130 131 155 Roseboom P. H. M. 4591232 Rautio M. 78/21 Revol J-M. 144173 156 164 165 Rosen T. 4261139 Ravao T. 791121 Revuelta J. L. 3861480 481 Robins D.J. 177113 14 15,17 18 Rosenbach V. 3821103 105 113 Ravasi M. 4931177. 187 188 Rexhausen H. 5801185 19 21 178180 81 21914 5,6 31 126 Ravelo A. G. 16/IYI IY3 Reychler A. 28616 Robins M. J. 426189 Rosenblum E. R. 5571185 Ravi B. N. 187/4 580/l81 183 Reyes J. 161152 Robinson C. H. 492140 5571152 Rosenfeld J. P. 95/28] Ravi K. 3871505 Reynolds A. H. 3851348 351 217 218 5581241 242 Rosenstein R. D. 21 Ij2l4 218 Ravikumar P. R. 209/75 Reynolds D. G.,951345 Robinson H. 15913 11 27 31 32 Ross D. 961373 Ravindranath K. R. 210/107 Reiribek K. 78/54 34 65,160188 89 97 101 107 Ross H. N. M. 387/515 Ravishankar G. A. 5601413 Rezhepov Zh. 931125 118 120 129 130 158,21 11207 Rossetti M. V. 44/68. 75 Ravn-Jonsen A, 941211 Reznikova S. A, 5241130. 131 132 Robinson J.A. 318165 347183 88 Rossi M. 5801162 Rawal. N. 95/2Y6 Ribes V. 57818 Robinson R. P. 248118 19 Rossman R. R. 347161 Rawal. V. H. 80/17/ Ricca A. 14418 4261108 Robinson T. J. 4591211 Rossotti F. J. C. 286/7 Ray A. B. 931113 233138 Ricci P. 451158 4581134 Roblot F. 931179 23218 21 26 Rotenberg S. L. 3181114 117 Ray L. 80/17Y Rice E. 45615 Roby M. R. 219143 Roth R. A, 220154 Ray S. 492132 Rice K. C. 931120 197 213 Rocchetti M. 951288 Rothrock J. 555115 Razdan R. K. 941106 Richard B. 79/79 121 Rocchi P. 3841261 Rothschild J. M. 3191168 Razdan T. K. 161147 156 Richards B. A. 555163 Rocek I. 523139 Rothschild K. J. 3851325 333 Read J. 286/Y 37 Richards J. C. 17716 7 Rochat C.,791130 Rouessac F. 144117 210/155 156 Read R. W. 210/15# 167 21 11201 Richards.K. E. 43/32 Rockley M. G. 3841308 3831178 180 188 Reay S. 14/25 Richards W. R. 451136. 137 5791 Rockley N. L. 3841308 Rouse J. 791124 Rebeiz. C. A. 451130 131 141. YS Rodebaugh R. K. 2871116 Roush W. R. 144141 43 44 4251 146 147 148 149 150,151 152 Richardson A. C. 243/Y Rodenburg L. J M. 3861435 68 16Y 170 173. 175 579193. Y8 Richardson K. G.,347171 Rodewald H. 159163 Rousseau J. 5571197 106,112 Richarz R. 16/128 Rodig 0.R. 286166 2881195 Rousset C.,492176 Rebeiz C. C. 45/14] Riche C.. 931179 Rodionov A. P. 22518 Roux-Schmitt M.-C.,492163 Rebek J. 78/49 Richmond R. E. 144127 Rodkird S. 1601122 Roux D. G. 210/117 Recchia M. 95i288 Richomme P. 233136 Rodman H. 3841313 Rovnykh N. V. 14/30 Rector D. H. 3821136 137 Richter M. L. 451134 Rodrigo R. 210/116 Row L.R. 209183 86 210191 108 Reddy D. B. 145i120 Rickard T. M. A, 171217 Rodrigues M. 2 1 11214 Row T. N. G. 159164 523182 Reddy D. S. 144/8Y Rickards R. W. 178187 3191167 Rodriguez B. 161/172 173 187142 Rowan D. D. 457/Y2 Reddy G. S.,79/86 168 347185 Rodriguez D. B. 382182 Rowe B. A. 492161 Reddy K. S. 15/57 Rico M. 161/172. 173 Rodriguez M. L. 161193 159138 Rowell P. M.. 457147 458/150 Reddy M. P.. 383;INY Rideau M. 178160 Rodriguez R. J. 5591327 348 Rowold J. 5801136 Redfearn R. 187/// Rideout J. M. 44/82 85,86 5791 Rodriguez de Lera A, 92/25 55 Roy S. 7819 209161. 62 Redfern J. R. 4511 10 34 35 Rodriguez-Luis F. 160/123 161/ Royer J. 187121 Redlinger T. E. 451155 Ridge R. J.. 471264 182 Rozas S.,931122 Redmond J. W. 3191163 Ridigion. J. M. 2881153 Rodriguez-Ubis J.C. 14/18 Rozsa 2..400135 Redpath J.. 492/Y7 Ridley D. D. 7816 Rodwell V. W. 523/Y 55514 11 Ruangrungsi N. 1601122 Rees C. W.. 233175 400/18 Rieff L. 941211 40 41 42 50 52 Ruano J. Z. 159138 Rees H. H. 55512 5601402 405 Riegman R. L. M. 78/2. 791123 Roe J. 931172 Rubchinskaya Yu. M.. 3861409 406 407 414 Rienits K. G.,451134 Rider E.. 219135 36 38 391124 Ruberto G. 3871548 Reese J. H. 9613Y6 Riggio G.,96/38] Roelofs W. 2891235 Rubin J. L. 3191142 510112 Reese P. B. 492144 Rigter. H.,961384 Romer A. 178188 3191165 166 Rubin L. B. 384i306 Reese W. G.. 951307 Rijk H. 961384 Roemer J. 4931168 Rubio-Arroyo. M. F. 4941222 Reggit. S. J. 286152 Rilling H. C. 55512 556187. 88 Y4 Roennbaeck L..951321 Rubio-Poo C.,4941222 Regler H. 286/3Y I0Y Ronsch H. 232110 Rubly N.951283 Rehm H. J. 178178 Rimbault A, 5 10148 Roper U. 451155 Rubottom G. M.. 3831177 Reichenbach H. 1791112 347/YO. Rimbault C. G.,2871136 Roeske C. A,. 319/IY3 Ruchirawat S. 931135 381/26. 425123 77 4261113 Rinehart K. L. Jr. 78/25. 179/110 Roessler F. 177/12. 187115 Rutman R. 78/56 Reichenthal J. 319il57 286136. 347164 70. 425154 Rossler H. H. 3871541 Ruddat M. 38116 Reichlin D. 144131 2881229 Rink E. 178130 Roettger P. M. 161/178 Rudney H. 3871571. 577. 555/40 Reichling J. 5241122 Riopel J. L.. 16/131 Roeymans H. J. 4581177 Rudoi. A. B. 45/1SY Reid. D. G.. 17x162 Rios L.. 961380 Rogers D. 286141 Rudqvist U. 4931169 Reid J. B. 524/lO/ Rios T. 16O/YY 117 Rogers D. H. 555140 Ruecker G. 209156. 57 Reider P. J. 248127 Rip J. W. 3871.505 Rogers N.H. 42515 6 Ruediger E. H. 144/66 Reifenstahl G. 425/77 Ripka W. C. 210/100 Rogers Q. R. 220163 Riidiger W. 451161 162. 163 164. Reiffsteck A, 209130 Ripp E. 319/17Y Roggero J. P. 457163 166 168 523184 579183. 84 85, Reigle T. G.. 941268 Risch N. 451183 461236 Rohlfing E. A. 21 11229 5SOjll5 117 Reinle W. 578117 Rispe. R. 233163 Rohmer M. 5561136 137 138 5591 Riieger H. 21918. 391122 Reisch J.. 39911 400/3Y Risse H.-J. 3871541 360 Riiffer M. 178127 28 34 Reischig D. 233iSX Ritacco R. P. 382182 83 Rohrer. D. C. 493/1YY Ruegg R. P. 523179 Reischl W. 383/18/ Riva R. 791136 Roitelman J. 523115 16 Rueppel H. 3851340 341 342 Reis Luz A. I. 79113.5 Rivas S. 931122 Roitman J. N. 219139 44 391121 Riittimann A. 382166 90 91 Reiter L. A, 580//87 Rivera P. 1.59138 Roizin L.96/373 Ruggieri R. 579136. 38 Remberg. G. 15/88 Rivett D. E. A, 510157 Rojas C. 556/Y9 Ruhter G. 2871140 Renard. M. 3851361. 362 Rizk A. M. 391125 Rojas M. C. 523136 5561100 Ruigrok C. L. M. 79/73 Renaud R. L.. 5591349 350 Rizzardini M. 579138 Rokem J. S. 4941234 Ruis H. 5591333 Renauld F. 346118 Rizzardo E. 3191174 Roland. D. M. 248127 Runnebaum B. 5571211 Rendell N. B. 5591367 Rizzi R. 961375 Rolando C. 556/Y5 Rupe H. 2871117 151 Rendina A. R. 319/IY4 Roark J. L. 161131 Rolfs C. H. 51 1/81 Rupreht. J. 225125 Renganathan V. 5241126 Robaire B. 5581248 Rolfsen W. 791105 Ruscoe M. A. 7814 1-22 NATURAL PRODUCT REPORTS 1985 Russell D. W. 556171 71 Salcher O. 178172 Satake K. 425121 Schmidt C. lSjl15 Russell R. 210/115 Salemink C.A. 92/12 Satake T. 21 11211 Schmidt J. 171211 159117 382161 Russo G. 5591356 366 388 389 Salen G. 4921120 121 558l285 Sathyamoorthy N. 3861445 523125 Schmidt K. 3861482 5601391 392 296 300 Sato A, 951298 457170 555135 Schmidt R. H. 3841256 Rutledge P. S. 492134 Salhanick H. A. 5511210 212 Sato F. 931116 Schmidt R. R. 425135 Ruveda E. A. 209150 210/110 Salisbury P. 287186 89 107 Sato H.,78/20 346127 3841247 Schmidt W. E. 4581143 21 11237 3831186 Salituro G. M. 318192 Sato K. 160185 251110 3811518 Schmierer R. 2891230 Ruvio B. A. 951342 Sallanon M. 931139 519,524,4591238 239 523159 Schmitt P. 941261 5591309 310 Ruzicka L. 5561117 Salowe S. P. 578122 Sato M. 3851365 4921116 311,312,315 369 370 Ruzziconi R.,3821100 Salvapati G. S. 3831161 Sato R. 5561125 5591333 Schmitz E.9215 Ryan C. A. 4591229 231 249 252 Salvati P. 78/55 Sato R. I. 425157 Schmitz J. A, 220163 Ryan E. R. 2881171 Samanin R. 951352 Sato S. 4261107 Schmoeker P. F. 961369 Ryan J. 555129 Sammes P. G. 1451118 Sato T. 93/96 14415 1451106 1591 Schmuff N. R. 492198 Rychener M.,381151 Samokhvalov G. I. 3831205. 3871 13 178158 2811149 2881167 4001 Schneider A. 555/25 Rychlewska U. 1601132 552 4921115 33 426191 Schneider E. 5801126 Rycroft D. S. 159151 Samonina G. E. 225126 Sato Y. 14/22 28 951298 5241125 Schneider G. 492160 Ryder D. J. 44/106 Sampathkumar P. 3191185 187 5511180 181 182 183 Schneider J. A. 15915 1601125. Ryder N. S. 555120 Samuel E. 2881205 Satoh J. Y. 492181 41/18,21 30 31 523161 62 Ryhage R. 3851363 Samuelsson G. 791106 Satoh M.,233169 Schneider M.M. 44/54 Rylett R. J. 92/78 Sanada M. 3831168 Satoh Y. 492156 4941214 Schneider R. A. 2811109 Sanada S. 15/78 Sattar A, 78/43 Schneider S. 519161 62 83 84 91 Sancassan F. 171205 Satyanarayana P. 209138. 210192 Schneiders G. E. 210/166 Sanchez A. M. 21 11181 108 120 Schnoes H. 311155 318197 Sanchez I. H. 251/11 12 Sauer G. 492165 Schnoes H. K. 4931144 Saa J. M. 92/25 55 931162 961 Sancovich H. A. 43/36 44/93 Sauers R. R.,287/110 2881159 Schoch S. 451162. 5801117 408 233167 Sanda V. 4941230 Saulnier M. G. 791128 Schoellmann G. 3831202 Saab D. B. 451173 Sandberg A. 558/250 Saunders J. 44/47 Schoelm R. 209164 Sabine J. R. 3871532 Sandberg F. 191117 Savin I. G. 220165 Schonauer K. 4921103 Sabri N. N. 161/171 Sand berg G. 510135 Savin J. 510171 Schonenberger B.425110 Sadd J. S. 381158 Sanders B. 5191109 Sawada M. 425142 Schoenfeld W.,4941210 Sadee W. 941248 Sanders J. K. M.,461237 238 239 Sawada T. 161160 161 162 Schoenleber R. W. 579/71,80,81, Sadek M. 159161 219140 41. 254 259 Sawada Y. 311117 28 30 82 391117 Sanderson T. F. 209124 Sawai K. 346142 Schoenmakers H. J. N. 5601427, Sadler I. H. 318189 Sandifer R.M. 14/10 5561103 Sawaki S. 251114 428,429 Sadoff S. 5511223 Sadowski R. A. 3861469 Sandmann G. 3861462 463 467 Sawamura K. 346142 Schopp E. 78/58 177/12 468 Sadritdinov S. 931125 Sandra P. 5561116 Saxena P. R. 92/83 Schoppner A. 511/82 Saeedi-Ghomi H. M. 523157 Sandris C. 425163 Sayre L. M.,961388 391 Scholten A. H. M. T. 3871561 Sburlati A. 44/78 Schoiz B. 451180 Saeki S. 181143 Sanghvi A.555/58 5581275 276 Scahill T. A. 78/25 Schopfer P. 5791105 Sagami H. 556185 Sanguinetti M. C. 92/38 Scala A. 492145 Schow S. 2881222 Sagami I. 3871536 Saniewski M. 3861473 Scallen T. J. 555154 55 56 58 Schram A. W. 510168 69 70 Sagar P. 931170 Sagawa T. 3851365 366 Sankawa U. 209117 78 210/171 5571154 159 184 190 Schramm E. 9215 346132 347165 42411 2 Schreiber J. 451181 461214 5801 Sagitdinova G. V. 159124 66 Sannai A. 1601124 381157 Schaber P. M.,5801149 Sahai M. 491127 Sc haber-K iechle M . 286167 130 191 Sahija M. 931115 Sano S. 44/40 40 89 100 Schacter B. A. 579157 Schreiber K. 232110 Schafer E. 4581116 Schreiber S. L. 425121 Sahlberg I. 5801142 Sano T. 318191 Sahu P. N. 248115 Sansoulet J. 287/114 Schaefer G. J. 951329 Schreiner A. 5581299 Schaefer W.5801119 Schrader K. 178/73 Saidkhodzhaev A. I. 159/24 47 Santacroce C. 171203 48 66 Santander P. J. 5801126 Scharnagl C. 579191 Schroeder W. P. 248129 Saifah E. 243118 Santaniello E. 18119 4931177 187 Schatz G. 4591259 Schroepfer G. J. 55513 38 5561 Schatzman G. L. 5581249 143 144 145 5511165 166 167, Saiki K. 382187 3841296 297 187 188 Schaumann E. 287/140 168 169 170 171 172 173 174 Saiki Y. 111213 210190. 21 11211 Santavy F. 961419 Saini K. S. 25117 8 Santel H.-J. 451155 Scheer H. 5581248 519191 5801 175 176 177 I78 119 124 Schrott E. L. 3841252 Sainsbury M. 171217 7815. 92/28 Santhanakrishnan T. S. 5241129 Scheeren J. W. 2811140 Sainte-Marie J. 3841305 Santiesteban H. L. 951364 Schuber F. 5591371 Scheid F. 5591311 360 Schubert C. A. W. 3871560 Saito A.523142 556188 96 Santikarn S. 580/114 Scheidegger A. 178/103. 3 17/38 Schubert W. 5241117 Saito M. 15/44 45 161129 138 Santos A. C. 92/68 176 177 144118 Santus R. 3851385 386 Schenk D. 286110 Schuda P. F. 145198 Schenk G. K. 951327 Schubel H. 178152 Saito S. 3841284 285 309 Shpi J. 801154 155 Schenk H. E. A. 3861474 Schuette H. R.,3861447 523132 74 Saito T. 4591238 239 Sapini O. 78/55 Saito Y. 159172 Saplay K. M. 144123 Schenker J. G. 961431 Schulten H. R.,209154. 580/119 Saitoh S. 5801143 Sarada A. 15/40 21 11204 Schenone P. 2811132 Schultz A. G. 14/69 Saitoh T. 151117 Saragai Y. 3811533 535 Schepers G. 951348 Schultz G. 451165 166 3811567 Sakabe N. 78/42 Saragi Y. 523128 Scherer K. V. 286133 573 510147 51 1/88 Scherer P. 5801136 Schultz G.W. 3851371 Sakaguchi S. 381121 Saran A. 3851400 Schemer R. A. 286145 Schultz J. A. 144140 Sakai S. 17/216. 78/36 39 41. 791 Sardina F. J. 4921117 76 96 97 Sarg T. M.,1601143 Scheuer P. J. 159112 5601421 Schulz A. 510113 14 Sakai T. 425148 Sariaslani F. S. 791143 Schiavoni E. S. 5561122 Schulz G. 5561113 Schick R.,951316 Schulze P.E. 491120 Sakakibara A. 209117 2101173. Sarin V. 556178 178128 21 11238 Sariyar G. 92/24 23219 Schiebel H.-M. 171123 580/119 Schumacher H.-M. Schiedt K. 382191 Schumann G. 347174 Sakakibara J. 161199 200 Sarkozi L. 471263 Sakakibara M. 4931124 128 Sarni F. 5lOl50 Schiff L. J. 3821138 139 140 Schurtenberger H. 382179 Sakakura T. 391118 Sartoretti J. 1451124 Schiff P. L. Jr. 92/26 64. 931111 Schusdziarra V. 951316 Sakamoto M.961417 418 Saruwatari Y.-I. 15/77 79 81 82 113 233131 35 38 42 Schuster A. 15912. 160182 96. 21 11 Sakamura S. 2101168 169 170 Sasa T. 451171 172 177 578118 Schiff S. 225139 207 175 21 11176 212 213 220 3461 519/102 s80/1zi 144 Schillinger E. 4931 194 Schwab J. M. 34/15 7 27 34/53 56 42511 7 Sasada Y.,426191 Schimmer O. 219147 Schwabe K. 4931198 Sakane S. 144122 Sasaki H. 2101134 425142 Schimz A. 3861438 Schwartz C. C. 5581279 280 283 Sakata T. 92/36 Sasaki J. 144118. 3811545 Schipper D. 425150 51 298 Sakdarat S. 21914 Sasaki K. 144118 Schlageter M. G. 2881222 Schwartz J. A. 209138 Sakharovsky V. G. 78/44 Sasaki N. 3851354 Schlatter C. 219148 50 Schwartz S. I. 951362 Sakurai A. 524198 99 Sasaki T. 457199 Schlecht M.F. 151116 Schwarz H. 461242 Sakurai H.144118 Sasamori H. 15/57 Schlessinger R. H. 14/40 78 Schwarzkopf E. 5241100 Sakurai I. 425113 4581190 Sasaya T. 2101173 21 11210,238 Schlosser E. 458/107 51 1/83 Scolastico C. 346130 31 42413 4 Sakurai S. 9311.58 159 Sashida H. 251114 Schlosser M. 382/100 426190 109 Sakurai T. 425129 Sashida Y. 160184 Schlude H.-J. 3851364 Scopacasa F. 961370 Sakushima A, 209117 Sassa S. 44/88. 579140 Schmeda-Hirschmann G. 1611177 Scopes D. I. C. 92/28 Salama O. 21 11209 Sastrapradja S. 159158 Schmelzer E. 4581144 Scopes P. M. 210/104 Salazar J. A. 492175 4941215 Sastry K. V. 209163 79 210199 Schmid G. 144160 Scora R. W. 5241137 138 NATURAL PRODUCT REPORTS 1985 Scoto G. 951289 Seto S. 556196 102 Scott A. D. 49115 Seuron N. 492163 Scott A. I. 44/53 54 55 58 70 83 Sevenet T.78/19 79/79 130,921 461 193 199 233 244 245 246 60 232128 399112 471272 1781.57 95 96 3 171 12 52 Seybert D. W. 5571205 53 318171 34613 523124 579127 Seyden-Penne J. 492163 5801126 Seyed-Mozaffari A. 941190 192 Scott D. 951291 Shabanowitz J. 15/57 Scott D. B. 951292 Shabd R. 3851387 Scott F. E. 346149 Shafiullah 492172. 4941213 Scott L. T. 287195 Shah S. N. 555151 Scott W. J. 2871129 492169 Shahak I. 2871140 Scourides P. A. 471264 265 Shaker-Jomaa R. M. A. 14/25 Scriba G. 92/21. 118137 38 Shakespeare V. 5571163 Seaman F. C. 160/112 Shaligran A. M. 159153 Sebek 0. K. 4941232 Sham C. R. 4931204 Sebrosky G. F. 941227 Shamma M. 9214 I I 61 63 931 Secor H. V. 187/44 104 143 144 147 148 149 151, Sedee A. G. J. 492194 157 161 164 165 166 961405 Sedlmeier R.5801126 233170 39911 I Sedmera P. 931107 961419 4261 Shang D. 941251 105 Shankar V. 557/150 Seeger. A, 49 1/20 Shankaranardyan R. 178195 3181 Seehra J. S. 43/31. 44/37 38 62 71 66 98 Shanks C. A. 931101 Seeman J. I. 187141 44 Shanmugam P. 400124 Seeman P. 233155 Shannon H. E. 961398 Sefton M. A, 178180 Shannon P. V. R. 791128 Segal D. S. 951334 Shao K. 161136 Segal G. M. 4921115 Shapiro D. J. 555146 Segal R. 160186 Shapiro R. 2881222 Segal R. A. 160/100 Shapiro R. H. 225153 Segall H. J. 220152 Shapiro R. M. 225136 Segawa M. 159145 Shard M. A. 5581251 Seguin E. 79/83 Shariff A, 79/90 Seiber J. N. 5591386 Sharma 0.P. 931115 Seichter F. S. 286129 Sharma P. N. 931120 224 961422 Seidel U. 4581182 Sharma R.961430 Seidl G. 5561113 Seif El-Din A. A, 161/171 Sharma R. P. 159154. 160/106 1611 Seifert W. K. 171210 164 491111 12 492168 Seifert-Schiller E. 3821104 Sharma S. 1601163 Seitz. H. U. 510/60 Sharma S. C. 15/69 86 Seki H. 92/67 Sharma V. 233152 Seki Y. 44/89 Sharova E. G. 22511 Sekita S. 78/31 31 801166 Sharp J. K. 4591221 222 223 Sekiya M. 2871133 Sharpless K. B. 5561118 Sekizawa Y. 457/97 9# 99 Sharpless N. 225139 Sekula B. C. 5591345 347 Shaskus S. 523142 Seligmann O. 161165 209151 21 I/ Shavrygina 0.A. 3821102 203 233164 65 Shaw A. K. 7817 Selvaraj Y. 5591320 Shaw G. J. 5801148 Selvardjan N. 3851390 Shchelochkova A. P. 4941216 Sembdner G. 382163 524/100 Shealy Y. F. 3821135 3841272 Semenovskii A. V. 3871521 522 Shearer J. D. 58OlI4.5 49211I5 Shechter I.523115 16 555161 5561 Semmelhack M. F.. 2881215 68. 5571160 Sen A, 4931206 Sheets J. J. 5571201 Sen A. K. 15/41 Shefer S. 4921120 121 SS8l285 296 300 Sen D. C. 287/140 Sen M. 171218 Sheggeby G. 219142 Sen P. K. 317151 Sheldrick G. M. 15/57 Sen R. 3831154 I55 Sheldrick W. S. 580/161 Senanayake U. M. 21 11182 Shelton J. C. 286180 Senciall I. R. 5581268 Shemin D. 43/27 29 32 33 35 Sener B. 9214 931108 44/41 42 Senger H. 580/11# Shen D. 92/73 Sengupta P. 111218 Shen Q. 4931180 Seo S. 461196 556/130 131. 5591 Shen Y.-Q. 178199 101. 317134 35 357 384 37 3181102 Seoane E. 145/10# Shen Y. 233160 Sepulveda-Boza S. 931142 Sheng Z.-C. 461195 205 206 5801 Sequeira L. 4591247 266 188 189 Serchi G. 286122 Shen-Miller J.523192 Serebryakov E. P. 492195 Sheppard D. M. 44/87 Sergeev A. V. 3841303 Sheppard R. N. 92/74 Serita K. 42618.5 Sheps D. S. 951361 Serizawa N. 4261131 Sheth J. P. 145/120 Serizawa S. 4261131 Sheves M.,3821103 105 113 124 Serkerov S. V. 1601139 125 126 127 128 129 3831156 Serrou B. 5561142 385 1404 Serur L. M. 399113 Shi D. 92/87 Setchell K. D. R. 209127 28 29 Shi J. 225147 31 32 34 36 37 Shibaev V. N. 3871527 528 Sethi D. S. 2881202 Shibanoki S. 941268 Sethi M. L. 931137 Shibaoka H..524/105 Sethi S. P. 2881221 Shibasaki M. 144190 94 Seto H. 43/19 346132 3871508 Shibata K. 451153 511. 42411 2 425126 426185 4571 Shibata N. 78/36 99 Shibata S. 161162. 210/171 Shibuya H. 2871123 Shichida Y. 3851350 353 3861420 Shieh H.M. 4921108 Shieh J. 451135 Shieh T.-L. 178173 3181134 51019 Shields J. E. 178197 318181 Shigemasa Y. 24815 Shiiya K. 24313 Shikita M. 5571196 203 208 Shima K. 209/81 510158 Shimada Y. 555135 Shimagaki M. 151113 Shimizu H. 92/10 425143 Shimizu I. 161119 Shimizu K. 161162. 248127 425164 5571229 5591318 Shimizu M. 2891238 Shimizu N. 5591359 Shimizu S. 425113 Shimizu T. 510139 Shimoda C. 3841247 Shimoji K. 492152 Shimomura H. 160184 Shimono Y. 144177 Shimura M. 457197 98 99 Shin H. 801149 Shin K. I. 951338 Shin M. R. 951313 Shing T. K. M. 187140 42519 Shingu T. 21 01114 233169 Shinkai Y. 144152 Shinoda M. 5571208 5581260 Shinoki H. 233149 Shinzawa K. 5571225 Shiobara Y. 51 1/86 Shioi Y. 451171 172 177 578118 5791102 5801121 I44 Shiojima K.15/73 171223 225 Shiokawa H. 161119 Shiomi K. 3841292 Shiosaki K. 225120 Shiota M. 492150 Shirahama H. 144182 83 84 86 Shirahata K. 426191 Shirai R. 92/18 Shiraishi M. 3871551 Shiraishi T. 457156 Shirasawa E. 558l2.52 Shirata A. 4581127 129 130 132 I33 Shirley R. L. 961437 Shiro M. 187128 Shiroo M. 5571226 Shishibori T. 3871534 Shishido H. 941201 202 Shishido K. 15/117 461246 523124 Shitole H. R. 159164 Shive D. 288l15.5 Shively J. E. 5581260 Shivji A. 5801140 Shizuri Y. 1417 1601126 210/153. 21 11235 346126 28 425120 65 79 Shkumatov V. M. 5571206 Shkuropatov A. Ya. 3851383 Shlyk A. A. 451159 5801116 Shner V. F. 4931170 Shoeb A, 160/153 Shoji J.15/75 78 Shoji N. 171228 233139 5561139 Shono T. 187124 21912 24312 Shoolery J. N. 161153. 461193 Short R. P. 144173 Shoyama Y. 523151 Shrewsbury M. A. 555157 Shu A. Y. L. 5801167 I68 Shudo K. 78/39 41 Shue Y. K. 78/49 Shukla A. K. 233140 Shukla V. 159154 Shukuya R. 579150 Shuster A. 1601129 Sica D. 5601418 Sickles B. R.,21 11229 Sidebottom P. J. 461246 Sidjimov A. K. 233147 Sidyakin G. P. 1611166 168 169 170 Sieben R. 178179 Siebert F. 3851332 334 Siefert E. 461218 Sieg S. 510141 Siegel L. M. 461193 Siegfried B. 961381 Sielinsak-Stasiek M. 161/181 Sierra M. G. 3831186 Sietsma J. H. 391120 Siewinski A, 2881170 383/210 Sigaut F. 791139 187113 Sigurdson E. R. 2871107 Sih C. J. 209175 317/55 318196 97 4261133 Siirde K.E. 3831166 Siiteri P. K. 5581247 Silber P. 2881172 Sillesen A. H. 3841291 Silva M. 251/9 Silverstone T. 951347 Silverton J. V. 425176 sim G. A. 791137 425170 Simanek V. 931107 138 961419 23316 I Simard J.-L. 14/31 Simchen G. 2871125 Simmonds D. J. 451118 Simmons D. P. 801146 Simon H. 451182. 318174 Simon L. 3841283 Simongi A. 951303 Simoni D. 144171 Simoni R. D. 555113 29 Simonsen J. L. 28612 2881153 206 Simonsen O. 187/20 24818 Simpson G. M. 523/76 Simpson K. L. 382182 83 Simpson T. J. 34611 I 2 13 22 23 36 40 46 47 49 425127 28 523124 77 78 5591378 Sims J. J. 45615 Sinay P. 42518 Sinclair J. F. 579139 Sinclair P. R. 579/3Y Sinensky M. 555126 Singer G.961374 Singh A. K. 145/107 3821130 3831 155 194 3861417 Singh B. B. 941187 Singh N. 951285 Singh P. 1781105 Singh P. D. 317117 26 29 30 318166 67 84 Singh R. S. 161120 I21 Singh S. 251/1 Singh S. B. 3851387 Singh V. P. 3861472 Singleton K. A, 248110 Sinha A. K. 4591261 262 Sinha J. N. 951285 Sinha Roy S. P. 209161 Siniscalco Gigliano G. 9211 Sinnwell V. 15/88 Sipat A. B. 556173 Siperstein M. D. 5231 13 555139 53 556174 Sipes G. I. 220160 Sipma G. 160/149 1611184 Sippel C. J. 3871575 Sirokman F. 941183 Sironval C. 58OlI13 Sisler H. D. 346/37 38 5591326 331 332 Sit S.-Y. 425172 Sitar D. S. 941222 249 Sitges M. 555140 Siva P. J. 1611174 Sivam S. P. 951322 Sivasothy R. 580/140 Siwapinyoyos T.4261123 Sizto N. C. 941223 Sjoblom T. 78/32 Sjoerdsma A. 5581249 Sjostrand U. 5601417 419 Sjovall J. 493/178 Sjoevall S. 209134 Sjolander N. O. 3191157 Skaltsounis A. L. 78/19. 187138 Skare K. L. 3861490 Skipp R. A. 457192 Skjenstad T. 38 1/52 1-24 NATURAL PRODUCT REPORTS. 1985 Skjetne T. 461256 Sommer J. M. 2881152 Stapley E. SS5j15 Streckenbach B. 4931205 Skoldinov A. P. 22518 Sommer R. 578123 Starchenko V. M. 232111 Street L. J. 1451118 Skone E. J. 3861457 468 Sommerville R. L. 510/30 30 Stark E. 951303 Strickland S. 3821141 Skrede S. 558j299 301 Son B. W. 160/159 Stark W. M. 178181 Strickler R. C. 5581253 254 258 Skrukrud C. 5591308 Sondengam B. L. 15/94 Starostin A. V. 3851373 Strobel G. A. 346143 44 45 3471 Skryma R.N. 951277 Song M. K. H. 5571156 Stary I. 492138 54 Slachman F. N. 3871575 Song P.-S. 579185 Staunton J. 45/110 17718 346133 Strombom J. 791105 Slade C. J. 4931183 Sonoda N. 287/110 34,35 Stroink J. B. A, 3871549 Slangen J. L. 941258 Sonoda Y. 14/22 28 5571180 181 Steardo L. 961370 371 Stroman D. W. 425180 Slater R. 961394 182 183 Steare S. E. 951356 Strong P. D. 491113 Slatkin D. J. 92/26 64 931111 Sood U. K. 523149 Steckbeck S. R. 5561123. 124 Strube E. 4931153 113. 233131 35 38 42 Soon C. Y. 5581256 Steele M. J. 4581153 160 161 Struchkov Yu. T. 15/71 Slaunwhite W. D. 4931174 Sopena Y . 43/36 Steele V. 2871113 Strunz G. M. 4261124 Slavik J. 931109 Ssrensen 0.W. 5801160 Steen G. 44/44 Struzinsky R. 3841314 Slavik Yu. 232125 Sorgeloos P.381147 Steen L. 3871531 Strzalkowska-Grad H. 951325 Slaytor M. 7816 Soria J. J. 251/11 12 Stefancic V. 3861433 Stuart J. D. 457167 Slechta L. 426181 Sosa V. E. 1611174 Stefanovic M. 49117 Stuart K. L. 178158 Sleeckx J. 801178 Sost D. 510113 14 Steffens J. C. 161131 Stubbs K. 44/82 Sleigh S. K. 178158 Soter N. A. 951310 Steffens P. 178131 Stubbs W. A, 951366 Slikker W. 491113 Sotheeswaran S. 92/64 209168 Steglich W. 78/26 4261104 Studelmann R. J. 346115 Slobbe W. 457146 Soulier J. 3841245 Stehouwer P. M. 492141 Stuening M. 3841263 Smirnov A. M. 400135 Soulier R. 3841245 Stein P. D. 4261118 Sturiale E. R. 24314 Smit N. 510169 Sovocool G. w. 5591353 Stein R. A. 523127 Stusser R. 286110 Smith-Verdier P. 22515 Spada A. P. 144144 Steinbereithner K. 951286 Su J.225148 Smith A. B. 111 144127. 1451126 Spagnuolo S. 523113 Steiner R.,580jl24 Suami T. 243110 4261114 125 149 Spakovskis A. 318180 Steinke I. 4941217 Suares H. 161143 198 Smith A. G. 44/91 579137 Spalink J. D. 3851348 351 Steinman C. E. 42512.5 Suarez E. 15/68 492175. 4941215 Smith A. N. 4261126 Spalla C. 38 1/27 Steinrucken H. C. 3181136. 3191 Suau R. 92/25 55. 931162 961408 Smith B. B. 451141 Spanevello R. A, 3831186 140 510/10 I1 233167 Smith B. W. 3181123 Specht J. 951316 Steinsland 0.S. 92/80 Subden R.E. 5591349 350 Smith C. R. 209160 Spector A. A. 5571158 159 Stella A. M. 43/11 36 Subrahmanyam P. 210192 Smith D. A, 4581183 187 188 Speedie M. K. 178175. 76 Stella L. 3831163 Subramaniam L. R. 2881198 191 192 Speers L. 2881163 Stelzig D. A, 457185 Subramanian P.S. 391119 Smith D. G. 178185 Spencer G. F. 2101157 248129 Stenlake J. B. 92/51 Subramanian V. 510133 Smith G. C. 961432 Spencer R. B. 5801154 Stenzel D. J. 425127 28 523178 Suckling K. E. 5571203. 5581293 Smith G. D. 941196 3191170 174 Spencer R.W. 5571200 Stephens R. L. 347161 Suehiro K. 159141 Smith G. J. 3851370 372 Spencer T. A. 2881211 5561122 Stephenson L. M. 287/110 Suemura K. 171229 Smith J. E. 225135 123 124 Stermitz F. R. 219143 232120 Suga T. 3871533 534 535 523128. Smith J. L. 248125 Spengler I. 25115 Sterner O. 159169 70 5241124 5581306 Smith K. M. 451184 185 186 187 Spenser I. D. 17716 7 16 20 22 Stevens C. M. 317143 Sugahara T. 187114 46/23] 238 239 247 21 11194. Spensley C. R. C. 42519 Stevens K. L. 21 11229. 52315 Sugai S. 4931160 579153 75 5801125 173 176 177 Sperandei M.791120 Stevens R. V. 286158. 2881222 Sugama K. 160/150 178 182 Sperling W. 3851340 348 351 Stevenson R. 209141 210/112 166 Sugano N. 5591318 Smith L. L. 492146 3861438 21 11202 Suganuma M. 161158 Smith L. R. 941254 Spero L. 931156 Steward O. 961423 Sugden M. C. 951356 Smith L. W. 219128 40 41 248122 Speroni E. 95/28!) Stewart M. D. 556167 Sugisawa H. 523156 5241123 Smith P. A. S. 2881158 Spessard G. O. 492186 Stewart P. S. 3841244 Sugiura M. 426192 Smith P. W. 24318 Spike T. E. 5561143 Steyn P. S. 78/14 16 17. 178165 Sugowdz G. 3831193 Smith S. 3821138 Spikman G. 4591215 68 71 187/39 24/22 346122 23 Suh M. P. 5801165 Smith S. B. 5571223 Spiller S. C. 451144 25 347155 81 82 425115 18. 52 Suhara K. 5571226 Smith S.G. 44/83 95 104 106 Spindler C. D. 55519 44 426193 Suire C. 1601144 45/110 Spiteller G. 187117 Stibbard J. H. A. 425112 Sullivan B. 523183 Smith S. L. 5601414 Spitznagle L. A, 4931155 156 Sticher O. 21 11209 Sullivan B. W. 5601417 Smith S. O. 3841275 276 318 3851 Spivak A. Yu. 4941226 Still B. 1451120 Sultana M. 791145 801147 319 320 330 Sponsel V. M. 524197 Still W. C. 145/104 2891236 Sultanbawa M. U. S. 161188. 189 Smith T. 5571220 Sporn M. B. 381111 3821135 141 Stillman M. J. 457153 190. 187145 Smitka T. A. I59/40 425125 Spray C. 5241102 Stipanovic R. D. 159155. 457134 Sultanbawa S. 92/64 Snatzke G. 4941217 Spreafico F. 318/134. 51019 Stirchak E. P. 151114 Sumi M. 492162 4931175 Sneddon M. K 3191183 186 Sprecher E. 5241128 Stiso S. N. 941223 Summermatter W.42.5110 Sneden A. T. 210/155 21 11229 Sprecher M. 2881200 3181129 Stiver S. 4941224 Summers M. C. 17718 Snider B. B. 187131 42517 4261 Spribille R. 510162 63 Stockburger M. 3851323 328 329 Summers M. F. 580j162 137 138 Springer G. 461258 Stockhaus K. 941205 Sun R. 225146 Snieckus V. 209139 Springer J. P. 145/100 347154 Stoddard R. G. 492148 Sunagane N. 92/36 Snipes C. 346119 555115 18 Stiickigt J. 79/81. 801174 178147 Sunagawa M. 3471.52 Snow R. J. 461216 5801186 Sprinson D. B. 318/111 114 117 48 49 50 51 52 59 2111178 Sunder N. 951310 Snyder W. C. 347170 119 121 129 557/150 5591329 184 Sundstroem V. 3851349. 3861422 Soblosky J. S. 3871557 Spry D. O. 3 17/24 Stossel P. 458/180 4591257 Sundt T. M. 951353 Sodano G. 5601425 426 Spurgeon S. L. 381/10 3861445 Stoessl A, 346148 347168 457153 Sunshine I.941227 Soejarto D. D. 160/102 233/43 523125 54 69 458110.5 Supavita N. 79/74 Soerum H. 931178 Srikantaiah M. V. 523111. 555148 Stoilov I. 5601432 Supphayen D. M. 44/95 Sogo S. G. 3181131 133 3191181 5561127 Stone T. W. 951278 Surber B. W. 425116 51018 19 Srinivasan C. V. 2871109 Stonik J. A. 523119 55517 8 43 Surendrakumar S. 187145. 39913 Sohoni S. S. 2871109 Srinivasan P. R. 3191161 49 Susan A. B. 3831149 151 3841278 Sokolova S. A. 51 1/80 Srinivasan R. 286136 5591372 Stoodley R. J. 4261128 Susani M. 5591333 Sokolovskii V. Yu. 3861478 479 Srivastava G. 43/10 57812 4 5 7 Storer R. 400126 Sutheimer C. 941227 Sokolskii D. V. 3831197 198 199 Srivastava H. C. 161174 Storm C. B. 461257 Sutherland M. D. 159/8 Solaja B.49117 Srivastava R.S. 209184 Stothers J. B. 144191 346148 3471 Sutter A. 4581115 Solas D. 144133 49 2881214 Srivastava S. D. 161124 68 457153 54 69 4581105 Suttie J. W. 3871543 550 Soler M. 556175 Srivastava S. K. 161124 Stotz G. 510/61 63 Sutula T. 961423 SOH,J. 451165 166. 3871567 51 1/88 Stachon D. 578115 Strack D. 510/41 42 43 Suyunbaev U.,3831197 198 199 Solli H. 461256 Stachulski A. V. 178143 Straight R. C. 44/82 Suzich J. A. 51014 Solliday N. H. 220156 Stacpoole P. W. 555132 Straka J. G. 44/70 90 Suzukamo G. 2881219 Solo A. J. 4931174 Stafford H. A. 510164 Strange G. A. 492134 Suzuki A. 457198 99 Solomon N. A. 178/101 31715 17 Stahl E. 21 11200 Strange R. N. 4571303. 4581167 Suzuki E. 425119 Solov’eva A. B. 492147 Stajic M. 2881186 4591210 Suzuki H.161133. 209119 3851347 Solyom S. 4941221 Stammer C. H. 426186 Stransky H. 3861474 399 402 3861421 Somanathan R. 187145. 21 11194 Stampwala S. S. 425125 Straub K. M. 451143 5791112 Suzuki K. 14/16 17. 209116. 2871 Somei M. 78/20 425153 Stange E. F. 555125 Strauch B. 3841314 123 133. 382196 425142 Somme-Martin G. 560/411 Staples A. B. 5581295 Streaty R. A, 941197 Suzuki K. T. 5241125 NATURAL PRODUCT REPORTS 1985 1-25 Suzuki M. 92/67 159141 42 43 Takahashi T. T. 492181 Tanaka H. 14/17 425143 426197 Terayama Y. 21 11176. 3861442 44 45 3841266 426186 Takahashi Y. 425143 4261121 122 Tanaka K. 210/114 Termini J. 3821107 Suzuki S. 3871520 Takai M. 161157 Tanaka M. 95/31I 312 243121 31 Terpstra J. W. 491117 Suzuki T. 159141 42 43 44 45 Takamatsu S. 21 11212 4261131 Terriere C.387/574 4931145 Takane K. 5571203 Tanaka N. 171213 Teshima S. 560/431 Suzuki Y. 941270 l59/28 457197 Takani M. 233168 Tanaka O. 15/75 77 79 80 81 Teutsch G. 491/28 Svechnikova A. N. 15/47 48 49 Takano S. 187114. 219113 248132 82 83 107 161163 178 Thappa R. K. 21 11192 400128 Svendsen A. B. 79/73 119 120 425144 4921102 4931136 Tanaka R. D. 55518 12 14 Thauer R. K. 461223 224 5801131 801170 92/68 931102 18712 Takao H. 15/93 Tanaka S. 159115 2881164 5lOl58 Theander O. 457168 Svenneby G. 941241 Takao M. 3821114 3861440 Tanaka T. 78/34 385/382 457189 Thebtaranonth Y. 4261123 Svetlaeva V. M. 3831205 Takao N. 931124 145 146 178135 Tanaka Y. 381141. 3871502 503 Thein-Schranner I. 425173 Svoboda J. A. 5601400 401 36 504 520 529 Theis A. B. 318161 Swain T.209/11 3191180 Takaoka D. 160192 209118 46 Tanazawa H. 15/84 Theobald N. 5601416 Swanson S. 523155 Takase K. 1451109 Tandon J. S. 15/69 171202 Thepenier P. 78/60 801161 168 Swaringen R. A, 92/52 Takasu A. 5601395 Taneja S. C. 209/58 Theriault R. J. 347173 Swayze J. K. 347173 Takasu Y. 233168 Tang C. 233160 Theuns H. G. 92/12 Swedberg M. D. B. 941255 Takasugi H. 248137 Tang J. 951344 961402 Theuring C. 178126 243122 Sweet F. 5581251 Takasugi M. 4581127 128 129 Tang S. 219137 Thibier M. 209130 Swell L. 5581279 280 283 298 130 132 133 Tang X. 931100 Thieme H. 209174 Swenson D. C. 491113 4921105 Takatsuji H. 5561104 105 Tang Y. 161126 Thieme P. C. 382165 Swenson K. E. 4931172 173 Takatsuto S. 492154 4931127 131 Tange K. 5581306 Swepston P. N. 58Oj165 Takaya H.2871110 Tani K. 5561115 Thiemer K. 4931208 Swick R. A. 220151 62 64 Takaya T. 248137 Thierbach G. 425177 Swift I. E.. 386/45/ 452 453 Takayama H. 4931143 145 Tani T. 4581117 118 120 121 Thierman J. 95/355 122 123 Swinburne T. R. 457150 51 Takayanagi I. 92/40 41 Tani Y. 4261101 Thies R. W. 3821138 Sworin M.,801153 Takazawa O. 3831179 Tanida K. 3831167 Thind I. S. 931171 Thirion P. 3851362 Sybesma C. 38119 3831238 3851 Take K. 144162 Tanis S. P. 144114 Thiruvengadam T. K. 1791109 386 Takeda A. 425148 Taniuchi H. 451127 579152 Thoison O. 187/27 Sybrecht G. W. 961401 Takeda E. 791125 Taniuchi M. 451127 Thomas A. F. 2871109 149 Sysko R.J. 286166 2881195 Takeda K. 144177 3841281,425136. Taniyama T. 15/76 Szabo L. 791100 801154 155,156 5591357 Thomas A.J. 425161 Szabolcs J. 381/46. 382185 88 Takeda M. 92/27 Tann C.-H. 1791108 Thomas E. W. 425157 Tanoguchi M. 2101119 Thomas G. A. 43/25 Szalay L. 3861459 Takeda N. 3841266 Tanoguchi T. 210195 Szalontai B. 3841301 Takeda R. 159116 160178 133 Tantivatana P. 1601122 Thomas I. L. 492188 Szantay Cs. 79/100 101 801154 160 555125 Thomas J. A. 4261139 155,156 163 9215 30 941214 Takeda T. 15/85 Tanzawa K. 556170 Thomas J. L. 5581254 215 216 217 218 Takeda Y. 51 1/92 Tapiolas D. M. 159110 60 18714 Thomas M. 451188 Szczepanik-van-Leeuwen P. 5581 Takehara T. 21 11238 Taschner M. 151113 Thomas P. 4581162 163 286 Takeki T. 961436 Taschner M. J. 4261139 Thomas R. 286133 31716 347172 Thomas V. J. E. 92/49 Szejtli J. 791138 Takemori A. E. 951326 961388 Tashiro H.2891235 Szendrei K. 400135 390 391 Tashiro N. 457197 Thommen W. 381156 Szilagyi K. 4941221 Takemori S. 557j225 558l259 Tasker R. 961376 Thompson A. C. 161184 Szilasi. M. 791138 Takemoto J. Y. 43/24 Tasumi M. 384/284 285 309 310 Thompson C. W. 92/50 311 Szucs M. 941183 Takemoto T. 15/38 161140. 171228. Tatematsu A. 3841266 Thompson H. E. 243133 159113 1601144 145 161/185 Tatsuno T. 425124 Thompson H. J. 510157 209181 233139 5561139 Thompson M. 451192 461197 198 Takemoto Y. 457189 Tavale S. S. 159164. 160180 523182 178153 579149 Taafrout M.. 2lO/l55 156 Takemura N. 92/10 Tavani A. 951288 Thompson M. D. 14/10 5561103 Tabacik C. 5561142 5571188 Takemura T. 159133. 251110 Tavernier D. 801167 169 Thompson M. J. 5601401 Tabata M. 510/58 51 1/90 Takeo Y.44/40 Taylor A. R. H. 15/97 Thompson R. E. 3841249 Tabba H. D. 451184,461247. 5801 Takeshita H. 3831170 Taylor D. A. H. 15/95 96 97 98 Thomson A. E. R. 961429 I 76 Takeshita M. 55812.52 Taylor F. R. 5591327 Thomson A. J. 579151 Tabe M. 24313 Taketani S. 451114 115. 5591344 Taylor G. F. 2881191 Thomson G. A. 178196 317153 Tabuneng W. 187119 579148 Taylor G. J. 5581231 232 Thomson R. H. 39913 Tada Y. 79/98 931129 130 Takeuchi A. 523159 Taylor G. W. 4591268 Thomson W. W. 3861471 Tadano K. 92/42 243110 Takeuchi M. 425164 4261107 Taylor J. B. 941195 Thoren S. 2871146 Tadokoro S. 225142 Takeuchi S. 457195 96 Taylor J. C. 461255. 5801166 Thorn-Gray B. E. 961395 Taga T. 187133 Takeuchi T. 248132 425144 Taylor L. C. E. 461242 Thornton E. R. 491118 Taguchi H. 2101134 136 137 138 Takeya T.210/121 Taylor L. E. B. 144164 Thornton J. C. 471263 139 140 141 142 143 144 145 Takido M. 209117 2101171 Taylor M. D. 1451126 Thorpe M. C. 3821135 3841272 146 147 148 149 154 Takigawa T. 2871121 3871503 520 Taylor N. F. 209131 Thorsen A, 457124 Taguchi K. 941270 Takiguchi Y. 347186 Taylor P. B. 347184 Thorup N. 187120 Taguchi T. 4931140 Takii T. 3841296 297 Taylor P. V. 579154 55 Threlfail D. R. 3871568 457171 75 Tahara S. 4581166 185 Takino Y. 15/84 Taylor R. 28617 523160 Tahara Y. 3871544 545 Takubo K. 941201 Taylor R. F. 381148 3831239 Thummler F. 579183 84 85 Tai D. F. 78/49 Tal B. 4941234 Taylor R.T. 287/142 Tidbury R. 425112 Taillefer R. 2871109 Tal D. M. 492193 Taylor W. C. 2101158 167 2111 Tidwell T. T. 2871109 Taira M. 178139 Talalay P.557/223 201 233166 76 Tiemann F. 2881166 Taira Z. 15/38. 171228 5561139 Talapatra B. 15/39 931161 Tazaki H. 425117 Tietjen K. G. 4571101 4581114 Tait A. D. 5581270 Talapatra S. K. 15/39 931161 Tazaki K. 510132 148 Tajima K. 145110Y Talekar R. R. 178180 Teeple E. 951291 Tietze L.-F. 178145 53 Takabe K. 3831168 172 4261148 Tallirada R. J. 951294 Tegtmeyer G. 78/26 Till C. P. 210194 Takada M. 3871559 Talvitie A. 144157 Teitelbaum P. 94/257 Tillekeratne L. M. V. 209/68 Takagi A. 14/33 15/44 2871123 Tam C. C. 426192 Telnaes N. 461256 Tillequin F. 78/19 35 187110 38 Takagi N. 161140 Tam J. C. L. 2881175 Telschow J. E. 287/146 399112 Takagi S. 3841281 Tamada T. 171223 Temperilli A, 78/55 Tillman A. M. 159168 523153 Takahashi A. 14/14 Tamao K.209116 Tempesta M. J. 209170 Tilov B. O. 3841306 Takahashi H. 248121 Tamaoka J. 3871555 Templeton J. F. 4931204 Timkovich R. 579154 55 Takahashi I. 556jlOI Tamaoki B. 5571227 5581265 Templier J. 346110 Tin Y. 951315 Takahashi K. 161162 144174 2331 Tamaoki T. 347162 Tencer Y.,558/305 Ting H.-H. 178192 93 94 317133 68 347176 4581127 129 130 132 TamPs J. 791101 801154 Teng C.-Y. P. 3191158 510126 318172 73 76 77 78 79 80 133 5561111 Tamir H. 3191161 Tensho A. 161119 Tint G. S. 4921120 121 5581285 Takahashi M. 220155. 3851366 Tamm C. 144146 2871146 346119 Terada Y. 21 11236 245 246 248 296 300 524195 Tamura C. 4261107 Terahara A. 425164 4261131 Tippett J. 17718 Takahashi N. 524195 98 99 106 Tamura M. 2881219 Terai T. 161151 Tipton P. A. 3191192 510125 Takahashi S.425164. 426185 107 Tamura T. 14/27 5591359 Teranishi M. 4931184 Tirilly Y. 160/149 Takahashi T. 15/74 102 103 105 Tanabe M. 178184. 346136 347163. Terao M. 347186 Tishler M. 426192 106 161157. 171229 78/46 144181 425171 Terao S. 3871551 Tits M. 801169 92/62 1451101 102 103. 3851365 366 Tanahashi T. 801174. 178159 5241 Terao T. 510134 Tiwari K. P. 92/31 32 4941214 119 Terasawa T. 492199 Tjaden U. R. 3871562 1-26 Tjamos E. C. 457173 84 52316 Tkacz T. 243128 Tobe S. S. 523179 Tobert J. A. 555119 Tobias B. 558/253 258 Tobinaga S. 2101121 Todaro L. J. 160/102 Todd M. 3831183 426182 83 Toder B. H. 4261114 Todorova M. 159163 1601134 Toke L. 791100 101 Toh H. T. 4931147 Toivonen N. J. 287184 87 Tokousbalides M. C. 346138 Tokunaga F.3821 114 38513.54 365 366 3861425 440 Tokunaga R. 451114 115 579148 Tokutake S. 425153 Tokuyama T. 243112 Toldy L. 4941221 Tollari S. 79/93 104 136 Tolman G. L. 492151 Tolmann R. 248125 Tolstikov G. A. 3871523 4941226 Tom H. K. 941223 Tom R. 3851358 Toma L. 5591366 388 389 5601 392 Tomaro M. L. 579164 Tomassini T. C. B. 161175 Tomer K. B. 225153 Tomii A. 931124 178135 36 Tomiie Y. 78/42 Tomimori T. 161164 Tominaga Y. 187137 Tomioka K. 187140. 210/160 161 248/27 Tomita F. 347162 76 Tomita K. 16/119 129 21 11214 218 227 24819 Tomita Y. 5561130 131 Tomiyama K. 4591212 Tomoaia-Cotisel M. 3851376 377 378 Ton J. M. N. C. 941260 Tookey H. L. 248129 Toong Y. C. 492143 Tooptakong U.187130 Tooyama Y. 425149 Toporowicz M. 579191 Torgov I. V. 4921115 Tori K. 5561130 131 5591384 Tori M. 15/74 17/229 Torii S. 425145 Torikata A. 425164 Tormanen C. D. 555156 Toros S. 22516 Torrance S. J. 209123 Torres G.R. 39911.5 Torres R. 232127 Torssell K. 2881227 Toscano P. J. 5801162 Toscano R. A. 160/115 Tosirisuk V. 161129 155 Tosti E. 47/267 Toteberg-Kaulen S. 225119 Toth G. 941183 Toth J. 225110 Toth J. O. 14/11 Tournemine C. 49 1/28 Tourwe D. 187126 Tovey J. A. 44/87 Towers G. H. N. 524/109 Towley E. R. 288/165 Townend J. 492196 Towner P. 3821104 106. 3861437 Townsend C. A, 318161 64 86,87 88 90 92. 347177 78 80 Toyota M. 1601144 145 Tozuka Z. 248137 Trafford D. J. H.4921107 Trager W. F. 4931155 Trahanovsky W. S. 425116 Traldi P. 159119 Trammel] M. 3841270 Tran-Giac Nguyen. 555136 Trantow T. 144159 Trautmann A. 92/81 Trautmann D. l5/101 Trautwein K. 347178 Trave R. 523145 47 48 Treichler H. J. 317131 Trenchard E. 951347 Trentalance A. 523113 Tressel R. 161/183 Tresselt D. 347174 Trifonov L. S. 425131 4261110 Trigo G.G.,22515 Trihbes R. 510147 Trimble L. A. 346147 49 523177 78 Trimino Z. 2511.5 Tripathy R. N. 400132 Trojanek J. 248116 Tropp B. E. 556178 Trost B. M. 144121 18717 2871122 383/171,426/147 492198 Trotter J. 286148 52 56 64 69 70 Trowbridge S. T. 5561143 Trowitzsch W. 347/91 Troy F. A. 3871526 Trull F. R. 579166 5801157 158 Trulson M. E. 9219 Trung Quang Tran 2871138 Truscott T.G. 3851335 344 385 386 Tsai I.-L.,23213 4 Tsai L.-S. 3861445 449 Tsai M.-D. 317158 3191164 Tsai T. Y. R. 4931197 206 Tsamo E. 15/94 Tsankova E. 161/175 Ts'ao C. H. 2201.56 Tsay Y-H. 145199 Tschesche R. 161186 Tschiersch B. 4931198 Tse J. 44/76 579130 32 Tso J. Y. 3191145 147 150 Tsoi A. T. A. 79/73 Tsubata K. 21912. 24312 Tsubuki M. 4931206 Tsuchiya T. 2871149 Tsuda A. 95/31] 312 Tsuda M. 3851331. 3861442 5571 171 178 Tsuda Y. 171230 231 232 Tsuji E. 3871508 Tsuji H. 457123 523164 Tsuji J. 144181 145/101 102 103 Tsuji M. 4931181 Tsuji T. 425126 Tsujii S. 2871123 Tsujimoto K. 3821114 3851365 366 3861440 Tsujita Y. 4261131 Tsukamoto H. 209/82 Tsukamoto I.44/40 Tsukida K. 38114 382187 133 143 145 3841257 271 296 297 Tsunakawa M. 24819 Tsunezuka M. 21 11240 Tsunoda H. 425124 Tsunoda T. 144176 Tsuritani I. 5591319 Tsutsumi K. 3831222 Tsuyuki T. 15/74 102 103 105 106. 16/157 171229 Tucker D. J. 171209 Tuckey R. C. 5571209 Tudos F. 791138 Tu Hoa Ai 4931167 Tukamoto T. 286182 Tunac J. B. 425125 Turabelidze D. G. 209121 26 TureEek F. 248116 49118 492138 Turelli M. 457/63 Tur-Kaspa I. 96/43] Turkish S. 95/3-50 Turnbull B. A. 951335 Turner A. B. 4931176 Turner B. L. 5241134 Turner D. L. 347183 Turner M. J. 318/123 Turner M. K. 317140 Turner N. J. 318178 79 80 Turner S. P.D. 461207 5801189 Turner W. B. 34614 5 NATURAL PRODUCT REPORTS 1985 Turpin P.Y. 3841299 300 Vader J. 145/112 Turski L. 951275 Vaidyanathan C. S. 510133 Tuttle R. C. 5591368 Vainer H. 3841304 Tyler J. W. 42516 Vajna de Pava O. 14418 4261108 Tyobeka T. E. 31716 Vakulova L. A, 3831205 Tyrrell A. W. 555137 Valasinas A. 44/78 79 Valdes-Iraheta S. 1601123 Valencia E. 931157 Valensin G.,941182 Valent B. 4591219 222 Ubukata M. 347187 Valente D. 941221 Uchida K. 219/2 24312 Valimae T. 3831201 Uchida S. 457189 Vallejo C. A, 317120 26 318166 Uchimaru T. 391118 67 Uchiyama M. 5591330 Vallely P. J. 15/91 Uda H. 2871103 4261121 Valli K. 4941241 Uda U. 4261122 Valverde S. 209148 Uebelhart P. 382171 van Amsterdam L. J. P. 3821110 Ueda E. 961417 418 112 3861435 Ueda M. 3851368 van Beek E. 5601408 Ueda S.51 1/87 523146 van Beek T. A. 7812 791106 117 Uedo N. 24815 119 123 801160 170 92/68 Uegaki R. 1611188. 381157 457140 van Bochove A. C. 579/100 103 41,43 van Cleemput M. 3191149 Uei M. 4261141 van Dam K. 3861435 Ueki Y. 78/13 van Dam W. 492173 Uemura M. 144162 Vandenbaviere H. 3841242 Ueno K. 3851338 van den Bossche H. 5591326 Ueno S. 4581129 van der Baan J. L. 425/50 51 Ueno T. 426187 4581117 118 121 van der Bend R. L. 3861435 436 Uesato S. 178154 523143 44 46 Van der Meer M. J. 22513 Uguen D. 3871525 van der Verren J. 941230 Uhara Y. 2111195 196 199 van der Vies J. 209133 Ukachukwu V. C. 425145 van der Wel H. 3831211 212 Ulla J.-K. 161139 Vanderwende C. 951318 Ullman E. F. 941223 van Dessel G. 3871531 Ullrich V. 2871106 Vande Velde V.15/62 67 Ulrichova J. 93/138 233161 van de Ven M. 384/293 294 3851 Ulrichs K. 286114 379 Ulubelen A, 159149 210190 399110 Vandewalle M. 144179 1451121 Umadevi P. 3821113 van Diepen J. 510169 Umarova R. U. 15/47 48 49 van Dijk H. F. 461225 Umehara K. 426197 van Dijck P. W. M. 3861436 Umetani Y. SlOl58 Umeyama A. 171228 233139 5561 van Eijk G. W. 4581177 139 Vanelli G. 951300 Umezawa B. 92/16 18. 232115 van Etten H. D. 4581174 183 186 233148 49 25 1/14 189 193 194 195 Umezawa H. 178186 248132. 4251 van Ginkel G. 3841293 294 44 4261100 van Grondelle R. 5791100 103 Une M. 4921119 Vanhaelen M. 78/27 Unrau A. M. 559/339 349 372 van Heerden F. R. 78/14 16. 373 178165 426193 Uomori A. 5591357 384 van Henegouwen G. M. J. B. 4921 Uosaki Y.219/11 94 Uotani K. 4261100 van Heyningen S. 44/41 Upadhyay B. M. 3851387 van Huystee R. B. 578112 Upadhyay J. 161120 121 van Koningsveld H.,931177 Uppal S. K. 523158 van Kooten A. M. 461225 Upton R. M. 4931146 van Laere A. J. 4581179 Ura T. 3851347 van Leersum P. T. 4931176 Urakov A. L. 92/35 van Lier J. E. 5571197 Uramoto M. 346136 van Loon L. C. 4591244 Urano S. 178184. 347163 425171 van Pee K.-H. 178172 Urban-Grimal D. 451109 57818 van Riel M. 3851379 Uritani I. 457118 20 22 23 25 van Rooyen P. H. 346122 26 27 28 29 4591238 239 5231 van Tamelen E. E. 14/5 6 5561 59 62 63 64 118 119 120 121 Urones J. G. 15/70 233171 Vanzetti G. 94/22] Urquhart A. J. 579141 Vargish T. 951345 Urrea M. 78/50 Varkevisser F. A. 286127 Urrechaga E.3831227 Varley M. J. 4921107 4931162 Uruno T. 92/36 Varnado C. E. 555132 Urwin J. 92/51 Varon Z. 1611186 Urzua A. 23216 27. 233170 Varro V. 951365 Usher J. J. 178192 93 317113 20 Varshney I. P. 161174 21 56 57 318166 67 75 76 77 VaSitkova S. 4931122 80 Ushijima Y.,510131 Vatakencherry P. A. 2871120 Usui S. 144/15 3831184 Vaughan G. T. 3841262 523170 Utaka M. 425148 Vaughan W. R. 286129 43 Uthemann H.. 493/208 Vaultier M. 187123 Utley J. H. P. 382195 Vaverkova S. 931175 176 Uusvuori R. 225123 Vaz A. D. N. 3831202 Uvais M. 92/64 Vazquez P. 1611182 Uvarova N. I. 15/71 Vazquez-Bueno P. 14/18 1601123 Uyehara T. 144128 29 159135 Vecchi M. 381139 382190 91 Uzar H. C. 461211. 580/127 Vecchietti V. 210/109 Uzawa J. 347187. 425124 Vedejs E.219116 2871146 NATURAL PRODUCT REPORTS 1985 Vederas J. C. 34/47 49 347158 Vonarx V. 5581266 425130 4261132 523177 78 von Baer E. 243124 Vegh A, 92/43 von Dippe P. 492182 Velgova H. 491 123. 4941230 Vondracek M. 4261105 Veloso D. 451127. 556169 579152 Vondrackova J. 4261105 Vendrig J. C. 4591248 von Hugo H. 556166 Vonk Noordegraaf C. A. 209133 Venkatachalam K. V. 523135 Venkatachalam S. R. 243116 von R. Schleyer P. 287/112 Venkatanarasimhan M. 15/40 von Schutz J. U. 451179 Venkateswarlu R. 209183 210/91 von Wartburg A. 425139 93 Voogt P. A. 5601428 429 Venn R. F. 961396 Vordermaier G. 9218 Venton D. L. 23217 Vormayr G. 579189 Voyle M. I5/1ll 112 Vercauteren J. 791114 Vrudhda V. M. 159139 VereS K. 49118 Vugalter M. M. 161169 Verhaar L.A. T. 4591267 Vuilhorgne M. 15/108 187/10 Verlaak J. M. J. 4261127 Vulfson N. S. 209121 26 Verma S. P. 384/305 Vyalimyae T. K. 3831166 Verma V. K. 951285 Vyas A. V. 51 1/74 Vermeer P. 492141 42 Vyazankin N. S. 2811127 Vernon D. I. 579173 Veronee C. D. 3861432 Verpoorte R. 7812 79/73 105 106 117 119 120 123 801160 170. 92/68 931102 187/2 Wachtmeister C. A. 34/24 Versluis G. G. 5591330 Wada A. 5241106 Verwer W. 3841294 301 3851379 Wada K. 159115 Veselovskii V. V. 3811521 Wada M. 318191 Vettore O. 941247 Wada N. 3851347 Veysey S. W. 3841259 Wada Y. 161140 79/92 Vezhnik F. 232125 Waddell W. H. 3861429 Vezitskii A. Yu. 451159 Wade A. P. 5591367 Veznik F. 931109 Wadischatka R. 461213 Vial J. 3861466 Wadsworth H. J. 5591379 380 Vicente S.15914 Waegell B. 286130 Vick B. A, 67/87 Waeghe T. J. 4591270 Vickery L. E. 5511201 Waespe H. R. 1415 5561119 Vidal M. C. 92/25 55 Waespe-Sarcevic N. 5591382 Vidari G. 14/12 Wagner C. 347174 Vieira P. C. 210/106 Wagner G.C. 225137 Viel C. 92/34 Wagner H. 15/87. 161165,209151 210190 2 1 11203 244 233164 65 Vierstra R. D. 579185 400141 4931168 Viger A. 557j219 221 Wagner R. 161186 Vigne-Maeder F. 3851388 Wagoner W. 4591197 255 Vigo C. 3871539 Wahlberg I. 3851363 Villar A. 160/136 Waibel R. 209159 Villarreal M. C. 92/17 Waigh R. D. 78/62 92/51 Villegas R. J. A, 510140 Waight E. S. 161147 78/15 Viloria I. 94/199 Waiss A. C. 21919 Vincze I. 225110 492160 Wakamatsu K. 159171 72 Vining L. C. 178185 Wakasa Y. 225134 Vinogradova 0.M. 961435 Wakeel M. 5561108 Vinogradova V. I. 931125 Wakselman C. 287/150 Viola F. 15/60 61 558l302 303 Waleh A. 5801167 304. 5591364 Wales E. E. 44/82 Viovy R. 3851385 386 Walkeapaa L. P. 382199 Vishnoi S. P.,1601153 Walker I. C. 44/82 Visser C. P. 3831211 212 213 Walker M. A. 3841260 Visser J. 941228 Walker M. S. 3191154 Viswanathan N. 2101107 Walker R. P. 159112 Vita-Finzi P. 14/12 Walker T. E 461241 Viterbo D. 159175 160177 138 Walker V. 5571178 142 Walker-Simmons M. 4591229 231 Walkup R. D. 24/27 Vitols K. S. 461228 Viviers P. M. 210/117 Wallace B. J. 3181107 Vlahcevic Z. R. 523117 5581279 Wallace J. A. 4931158 280 283 298 Wallace J. C. 57812 Vlasenok L. I. 5801116 Wallace P.M. 24/10 Vlasov P. V. 523169 Wallach D. F.H. 3841305 Vlckova D. 78/54 Waller D. P. 233143 Vleggaar R. 78/14 16 17. 17118 Waller G.,3191180 178165 68 71. 187139 248122. Wallis J. D. 7814 34/22 23 25 347182 42511.5 18 Wallis S. R. 2871146 426193 Wallmeyer M. 159156 Vlietstra E. J. 92/12 Walsh C. 5801132 Walsh C. T. 3191159 Vnek J. 3181129 Walsh R. C.. 5591332 Vogeli U. 382179 4591245 Walter E. 451181 Voelter W. 161125. 248117 Walter J. A. 17818.5. 34619. 347151, Vogel C. 5591340 5591358 Vogens G. D. 461225 Walterova D. 931138 233161 Vogt. W. 5801139 Walton D. C. 3861493 494. 3871 Vokoun J. 961419 495 Volland C. 57816 Wan T. S. 311111 47 318169 84 Vollhardt K. P. C. 931131 Wan T. 178/105 Volpe J. J. 55516 Wan Z. 931119 Vol'pin I. M. 492195 Wang B. 161136 Volz V. 178126 243122 Wang B.C. 78/48. 1451119 Wang C.-L. J. 210/100 287/121 Wang D. 961421 Wang H. K. 15/44 45 46 161129 138 155 176 177 Wang H. W. 14/33 Wang J.-F. 15/81 Wang K. C. 4941235 Wang M. 171207 931141 Wang M. C. 4591201,227 Wang N.-Y. 4261133 Wang Q. 161127 931134 Wang W.-L. 4931185 Wang W.-Y. 451138 518115 Wang X.,931136 140 Wang Y. 931100 Wang Y. S. 558/250 Wang Z. 4931180 Wani M. C. 3821136 137 Wanner M. J. 79/91 187140 Warburg C. F. 5561107 I08 Warburton D. M. 225143 Ward A. D. 931152 Ward D. 4581153 Ward E. W. B. 451154 55. 4591258 Ward J. P.,3871549 Ward R. S. 20919 38 63 65 83 86 210189 91 92 93 108 120 128 Ward W. F. 220156 Ware R. S. 347159 Wareing P. F. 381117 3871495 Warin R.,161141 144 Waring M.J. 178163 64 Warne P. A. 5511213 Warner S. A. 5591353 WarnhoR E. W. 286121 2871109 128 492153 Warren S. 14/20 25 Warty V. 5581275 Wasada N. 2871149 Waser P. G. 961381 Wasserman H. H. 248111 12 18 19 Watanabe C. 78/39 Watanabe H. 21 11191 Watanabe K. 78/13 209146 2101 114 211/191 4571102 Watanabe M. 1451106 233155 3831174 400138 Watanabe N. 57813 Watanabe T. 961417 418 3831174 47/97 99 5801143 Watanabe Y.,931173 243119 21 Waterhouse D. V. 3841278 Waters J. M. 5801163 Waters T. N. M. 5801163 Waterton J. C. 461238 259 Watson D. G. 457152 4591242 5241I15 Watson D. J. 210189 Watson J. A. 5511184 Watson T. R. 4931167 204 5591 377 Watson W. H. 25119 Watt D. S. 15/111 112#171210 4921114 4931207 Watt R.A.4931146 Wattanasin S. 2101126 127 Watts A. E. 225113 Watts D. I. 951356 Watts E. A. 22519 Watts M. J. 5241118 Watts P. C. 347159 Wawraun A. 161/181 Way S. C. 555llO Wayne A. W. 44/82 Wazeer M. H. M. 161192 Webb J. K. 5241115 Webb L. E. 28617 Weber H. 46121.5 Weber H. P. 425139 Wedege E. 941241 Wedekind E. 286110 Wee A. G. H. 5801167 168 179 Weedon B. C. L. 2881225 226. 38 1/30 382166 Weerasinghe S. 451120 Weeratunga G. 161188 189 Wege D. 2881168 Wegmann H. 78/50 Wegner P. 1451116 Wehrli W. 311114 41 Wei J. 15/81 Wei X. 219137 Weibel F. 178166 Weidenhammer K. 5571211 Weigt E. 14/99 Weijman A. C. M. 4581177 Weiler E. W. 3841263 264 Weiler L. 3831182 Weinberg D.S. 2871149 Weingartner H. 951331 Weinges K. 20914 5 Weinheimer A. J. 3811530 Weinstein J. D. 578111 Weinstein L. I. 47/64 Weisleder D. 209160. 24/29 Weiss U. 941187 51 1/94 Weissenbijck G. 510167 Welankiwar S. 3841240 Weller D. D. 15/114 191127 Weller H. N. 2881222 Wellman E. 4581115 Wels C. M. 317/10 318193 Welshman I. R. 5571158 159 Weltring K. M. 4581184 186 Welzel P. 426184 492190 Wen H. L. 951354 Wen R. 791140 Wender P.A. 145197 Wendisch D. 161128 1611179 Wendler N. L. 4261134 135 Wenkert E. 791135 801146 173 177 144172. 2111188 Wentworth W. A. 2881184 Were S. T. 248139 Wernly J. 3841269 Werstiuk N. H. 2811109 Wesner K. 225143 Wessels P. C. 248122 Wessels P. L. 78/14. 178165. 3471 55.425118 West C. A. 4591206 229 236 237 251 523191 92 West C. H. K. 951329 West J. L. 3861429 West T. C. 92/38 Westlake D. W. S. 317119 23 32 3 18/82 Westmijze H. 492141 42 Weston R. J. 2101116 Wexler B. A. 4261114 Weyler V. 159146 Wezelman B. E. 451132 Whalley A. J. S. 425146 Whalley W. B. 4931146 Wheeler C. J. 4261106 Wheeler H. E. 4581192 Wheeler M. H. 346139 Whipple E. B. 3471.59 Whitaker R. J. 3181110 White A. H. 78/57 White C. T. 14312 White D. A. 555131 White J. D. 941213 3831172 4261 148 White R. D. 219149. 220162. 64 White R. J. 347175 White R. L. 179/107 31717 8 20 21 33 36 57 3 18/62 63 69 70 75 80 Whitehead I. M. 4581159 161 Whitehead T. R. 523117 Whitesides G. M. 2871148 Whitfield F.B. 3831193 Whiting D. A. 210194 4581162 163 510171 Whitlock H. 209175 Whitlow K. J. 441107 Whitney J. G.,317144 Whittaker N. 5591336 Whitten D. G. 579163 Whitten K. R. 318194 Wicha J. 4931152 195 196. 4941 210 218 Wickberg B. 159169 70 Wicker K. J. 317144 Wickham P. S. 555ll0 45 1-28 NATURAL PRODUCT REPORTS 1985 Wicks C. E. 219142 Woggon W.-D. 461198 201 Wyse R.,523171 73 Yang C.-C. 347169 Widera W. 161186 Wojtasiewicz K. 24316 Yang J. 791113 1601146 Wider de Xifra E. A. 43/11 36 Wolf H. C. 451179 Yang L. 4941237 Widlanski T. S. 3191181 3831154 Wolf H. R.,3831165 209 210 222 Yang M. 931105 510/19 Wolf M. 78/26 Widmaier R.,556198 Wolf u.,578117 Xaasan C. F. 171203 Yang R. 161137 Xia G. 92/84 89 Yang T.-R.15/75 80 83 Widman B. 951296 Wolfe S. 178199 101 317119 23 Xiao J. 225140 Yang X. 161136 Wiechert R. 491116 492159 65 32 34 35 37 318168 82 102 Xiao P. 92/75. 93/97 Yang Y. 225117 45 4931194 4941228 229 Wolff G. 3851382 Xie B. 225152 Yang Y.-L. 4261145 Wieckowski S. 3831238 WolfT G. A. 461254 580/148 172 Xie J. 225117 Yanofsky C. 3191149 Wiedenfeld H. 219135 36 38 Wolfram J. 187111 Xie L. 225141 Yanotovskii M. Ts. 3831205 39 1 124 Wolfson A. 55712003 5581262 Xie R.,233160 Yao M. 171207 Wiegrebe W. 931150 Wolinsky J. 144133 49 145/111. Xie R.-G., 4931182 Yao W. 92/84 88 Wieland P. 492167 286120 29 31 59 2881213 214 Xiong G. 225145 Yarborough C. 5581245 Wiemer D. F. 161132 Wolkow P. M. 34/37 Wiersig J. R.,5591382 Wollmann T. 5801175 Xu J.931136 140 225144 Yasuda M. 4921111 Xu X. 161126 219137. 248128 Yasuda S. 931121 158 160 Wieschhoff H. 5801119 Woloshuk C. P. 34/37 38 5591 XU,Z.-B. 78/48 145/119 4931185 Yasunaga K. 93/96 Wiesner K. 4931197 206 331 XU Z.-W. 161127 Yata N. 161163 Wigand W. 92/69 Wolschann P. 579187 Xue J. 961421 Yates P. 2871109. 2881175 202 Wiggins P. L. 556192 Wolters B. 4581136 137 4941224 Wiggins T. E. 5591326 Wong C. F. 24314 Yazawa N. 4931131 Wight C. 5581275 Wong C. G. 3861427 Yeh Y. 555134 Wightman R.H.,451110 Wong C. Y. 951359 Yemul S. S. 492183 Wijesekera R.0. B. 233143 Wong E. 510172 73 Yabusaki Y. 5591335 344 Yeowell D. A. 92/52 Wijnberg J. B. P. A. 145/112 Wong 0.-H. Yadav J. S. 523133 441105 Wikvall K. 5581273 278 288 291 Wong R. J. 556171 Yagi N. 801149 187129 Yi M.93/98 292 294 Yagihashi F. 457165 66 Yin D. 225116 Wilce P. A, 555/50 Wong R. Y. 219139 39912 Yagudaev M. R.,791110 111 122 Ying B. 5601394 Wong T. 5581271 159147. 2 10196 24813 Yokoi T. 2101114 Wilcott R. M. 286163 Wong V. 319/191. 5lOl20 Yakimov G. 931165 Yogo M. 400136 Wilder P. 2881212 Wong V. G. 961424 Wiley M. H. 555139 53. 556174 Wong W. C. 961413 Yamada J. 144128 29 159135 Yokose K. 78/39 Wiley R.A. 1601112 Yamada K. 1417 78/47 92/27 931 Yokoyama H.,3861449 Wiliquet P. 78/22 Wong Y.-S. 451142 579194 96 97 169 262 1451125 159171 72 1601 Yokoyama T. 579167 Wilkerson K. 3841253 Wong-Ng W. 243129 126. 219111 225138 2881164 4251 Yokoyama Y. 2871121 161 Yoneda F. 243115 Wilkes M. C. 425116 Woo S. O. 941225 65 79 Wilkie J. S. 5601403 404 Woo W.S. 161165 21 11203 244 Yamada M. 3821114 3861440. 4571 Yoneda K. 159152 Yoneyama Y. 5581252 Wilkomirski B. 161187. 5581307 Wood G. 391125 88,89 5591365 Wood J. L. 144178 Yamada S. 161119 4921102 4931 Yoo S. E. 31715.2 Will G. 219136 38 Wood R. K. S. 4591211 263 136 143 145 Yoshida K. 791125 426197 Yamada T. 187128. 3831168 Yoshida M. 178/105,209120 2101 Willbrandt R. 3841290 291 Woode K. A. 15/57 Willcott M. R.,3871530 Woodgate P. D. 492134 Yamada Y. 931116 3871544 545 113 21 11189 197 214 222 225 226 231 317116 29 30 318184 Willeke U. 4581186 Woods J. H. 225133 5241133 Willemsens G. 5591326 Woods M. 209135 Yamagata E. 159152 425148 Yoshida N. 78/13. 1601150 Willhalm B. 2871149 381156 Woods R.A. 5591339 373 Yamagishi H. 931158 160 Yamaguchi H.961411 210195 119 Yoshida O. 3861421 Williams D. C. 44/69 84 579128 Woodward M. D. 4581178 Williams D. E. 220166 Woodward R.B. 2881156 185 Yamaguchi I. 524198 106 Yoshida T. 178161. 3841292 579159 Yamaguchi K. 78/39 92/67 21 11 Yoshida Y. 5591325 328 329 333 Williams D. H. 178162 580/114 Worcester D. L. 3861443 341,343 Williams D. J. 14/13 25 347172 Worth B. R.,178158 212 213 555137 Worthington P. A, 144112 3831185 Yamaguchi M. 21 11191 Yoshifuji S. 931169 Williams D. R. 425172 Wortmann R.,2881197 Yamakawa M. 93/91 Yoshihara K. 145/104 15915 4571 Yamakawa T. 5581269 579167 21,31 Williams G. C. 558/286 295 Woudenberg M. 425118 Yamamoto A. 381141 Wratten S. J. 248133 Yoshihara K. 523161 Williams J. R.,144156. 210/112 Wray V. 461234 178142 347191 Yamamoto D.3851338 Yoshihara T. 209155 21 11212 213 Williams R.C. 43/32 Williams R.E. 3831231 5 10142 52411 I7 Yamamoto H.,144/22 287/131. 3851399 402 Williams R.N. 961425 Wriede U. 2871140 2881218 Yoshihira K. 78/31 Williamson D. G. 558l2.57 Wright C. L. 5581239 240 Yamamoto K. 251110 Yoshii E. 144177 425136 Willing R.I. 161143 198 Wright D. J. 44/71 82 85 86 5791 Yamamoto M. 2881164 Yoshikawa M. 14/33 15/44 45 Willis B. T. M. 5801163 34 Yamamoto N. 21 11191 46 76 161129 138 155 176 177 456/6,459/201 227 228 Willis C. L. 5241101 Wright J. L. C. 178185. 34619 5591 Yamamoto O. 961415 416 Yoshikawa N. 51 1/90 Willis G. L. 961432 358 Yamamoto R. 4581121 Willmer N. E. 425125 Wright J. N. 5571220. 5581234 Yamamoto Y. 144147 2871123 Yoshikawa T. 931117 178139 41 Wills R.B.H. 21 11182 Wright L. A. Jr. 451132 346132 42412 425113 14 47 233141 Willuhn G. 1611178 179 Wright P. E. 43/19 578119 Yamamura S. 2101153 21 11235 Yoshikoshi A. 425149 236 245 246 247 248 346126 Yoshimura T. 425114 47 Wilmoth G. J. 381149 Wright S. W. 5801145 28 425120 Yoshimura Y. 5561131 5591357 Wilson B. J. 425122 Wrobel J. 14/74 Wrobel J. E. 425132 Yamanaka E. 78/36 79/76 96 97 384 Wilson G. 51 1/86 Yamane T. 3821133 384/257 271 Yoshinaga T. 44/40 100 Wilson J. M. 510172 Wrobel J. T. 24316 Yamano T. 5581264 Yoshioka H. 161158 3871545 Wilton D. C. 5561107 108 5571 Wszolek P. C. 556/118 Yamanouchi S. 209117 2101171 Yoshioka K. 4931199 163 164 Wu C. H.,400125 Yamasaki K. 78/13 Yoshizaki M. 92/46 2101114 Wilton J. H. 160183 WU,C.-L. 159137 Yamashita J.3841297 298 Yoshizawa I. 4931166 Wiltshire C. W. 4581110 Wu D. 161137 Yamashita K. 3831162 174 175 Yoshizawa T. 3851350 353 354 Wingen U. 3841283 Wu H. 15919. 225141 3871497 3861411 420 425 439 Wink M. 177123 178124 25 26 Wu J. 3831204 Yamashita M. 425141 Yosioka I. 2101134 136 138 140 243122 23.4581138 139 Wu S. M. 579193 106 112 Yamauchi K. 171213 141 142 143 144 145 146 147 Winkel C. 3821148 3841276 3851 WU,T.-S. 171215 78/10 801164 Yamauchi T. 15/65 66 148 149 154 320 165 39916 400133 36 37 Yamawaki S. 941253 Younes U. E. 3861429 Winstein J. D. 43/26 Wu W. 15/55 56 Yamazaki M. 14/16 17. 144194 Young D. H. 4591203 204 Winters L. J. 2881171 Wu W. H. 43/32 425129 4931184 Young D. W. 178183. 3 17/51 51, Wintersdorf P. 492148 WU W-N. 209153 Yamazaki N.4591253 3 18/89 400126 Wirthlin T. 161128 Wu Y. 219137 Yamazaki Y. 178167 Young L. G. 3191170 Wirz J. 3831223 Wuensche C. 3841251 Yamiya Y. 523186 Young M. 5601434 Wistrand L.-G. 21911 Wiithrich K. 451126 Yan S. 318198 Young N. M. 3831231 Withers N. W. 5591368 5601423 Wunderlich J. A. 286136 Yan Y. P. 79/72 Young R.,5801164 Witkin J. M. 941256 Wunderwald M. 492135 Yanada K. 92/46 210/114 Young R.N. 2881191 Witte L. 177123 178124 26 2431 Wurziger H. K. W. 44/51 102 Yanagi T. 382197 Yu A. 225144 22 23 4581139 5241117 Wuthier D. 426198 Yanagita T. 225134 Yu B. 225116 3831204 Witzel H. 492178 Wydra W. 15/63 Yanai J. 951273 337 Yu C. A, 287/104. 3871553 Wloch E. 3831238 Wylie I. W. 3841287 Yanami T. 2871121 Yu J. 14/34 225145 Worner G. 44/51.461199 5801126 Wynn S. 209131 40 Yanaura S. 225149 Yu L. 931140 225144 3871553 NATURAL PRODUCT REPORTS 1985 1-29 Yu R.,41/28 Yu S. 171207 Yu X. 92/85 Yu Z. 225147 Yuan P. M. 5581260 Yuan S.-S. 4931157 Yuki S. 159136 Yunusov A. I. 1611166 Yunusov M. S. 92/13 22 23 931 109 125 232116 17 18 23 24 25 Yunusov S. Yu. 79/110 110 111 92/22. 931109 22511 232111 12 13 16 17 18 23 24 25 233133 45 24813 39918 9 Yusupov M. I. 1611169 170 Yusupov Sh. 243127 Yuzuriha T.. 387659 Yu-Ito R. 457127 Zabza A, 2881170 Zaccai G. 3861443 Zahner H. 425173 Zafra-Polo M. C. 1601136 Zagalsky P. F. 3831224 228 232 Zaghloul A. M. 1611165 Zagon I. S. 961383 385 Zaikin V. G. 209121 Zaitseva N. I. 461227 5801133 ZajiEek J. 4941227 Zakelj M. 5591362 Zakusov V. V. 22518 Zalkin H. 318/112 319114.5 146 233 234 236 147 148 150 151 160 Zaman Z.43/13. 44/101 Zamarlik H. 3831178 Zambakhidze N. E. 5591321 Zamureenko V. A. 3831205 Zanarotti A. 21 11239 Zanetti L. 471267 Zanoli P. 961427 Zanoni T. A, 5241136 Zappia J. M. 47/67 Zaragoza T. 1601137 Zard S. Z. 492177 4931150 Zartner G. 2881199 Zass E. 451181 Zavarzin G. A, 461227 Zawadzki M. E. 3831157 Zbiral E. 4921103 Zdero C. 159111 62 65 160188 89 93 94 101 107 118 130 143 158 161/165. 18716 Zdrojewski W. 161187 5581307 Zeches M. 78/60 79/79 121 Zee J. 492155 Zeeck A. 425173 Zeelen F. J. 492197 Zeevaart J. A. D. 387/500 523168 Zehnder B. 461202 Zelle R. E. 4261143 Zeller W. E. 4261136 Zelnik R.,15/67 Zelt D. T. 471262 Zemach D. 4931172 173 Zemlyanskii V. N. 210196 Zenk M. H. 178127 28 31 32 34 2111184 511186 5241119 Zennie T. M. 18715 Zerr R.2871108 Zhang C. 941251 225117 Zhang D. 951315 Zhang F. 931140 Zhang H. 951344 Zhang M. 941193 Zhang S. 225147 Zhang W. 941251 Zhang X. 93/99 Zhang X.-M. 4931146 Zhang Y. 4581188 Zhang Z. 171207 93/99 233160 Zhao H.-M. 4931182 185 Zhao J. 161127 92/88 Zhao S. 931141 Zhao T. 171207 Zhao X. 171207 Zhao Y. 225117 Zhao Z. 233159 Zheng X.-H. 4931185 Zhidkova T. A. 3831205 Zhilina T. N. 461227 580/133 Zhong J. 225152 Zhong L. 4941237 Zhong Z.-Z. 4931185 Zhou G. 16/126 Zhou J. 15/75 79 80 83 Zhou W. 14/34. 15/54 55 56 Zhou X. 225147 Zhou Y. 248128 Zhu B. 931133 Zhu C. 941204 Zhu X. 941251 Zhuang L.-G.,209151 Ziegler E. 4591214 Ziegler F. E. 1451113 209138 Ziegler M . F. 21 01132 163 Ziesche J. 15911 56 160/141 Zikhn V. 78/54 Zimmerman D. C. 457187 Zimmerman S. B. 425174 Zimmerman S.C. 5801189 Zimpfer A. 3871541 Zimpfer M.,951286 Zingoni J. P. 3841270 Ziyaev R.,232112 I3 Zong X. 92/89 Zoretic P. A. 21 11230 Zou C. 92/85 86 Zozulya A. 951314 Zrunek U. 579187 90,580/157 Zsako J. 3851377 Zuccarello F. 3851356 357 Zuder G. 55611 13 Zulaica E. 19/87 Zulueta M. A. 951320 Zutterman F. 14/48 79 Zviadadze L. D. 161181 Zvonkova E. N. 382198 Zwanenburg B. 286134 4261127 Zwitkowitz P.M. 346112 Zylber-Katz E. 961431 Zymalkowski F. 92/71 Zsadon B. 791138 Subject Index The names of compounds have been taken from the text and no attempt has been made to re-index every compound under its synonyms. Where the name of a genus in the plant Kingdom is typographically identical with the name of a genus in the animal Kingdom or the bacterial Kingdom no attempt has been made to show if the name of a species is that of a plant [e.g.Polypodium aureum (Pteridophyta Filicopsida)] or of an animal [e.g. Polypodium hydrifbrme (Coelenterata Hydrozoa)] and entries such as ‘Nerine sp.’ and ‘Bacillus spp.’ may include page numbers for citations of members of those genera in two Kingdoms. However the entry for the name of an organism or enzyme shows the numbers of all pages on which it is mentioned under any of its synonyms if two or more synonyms have been identified on any page in this Voiume; such page numbers are marked with an asterisk. Names of teleomorphic and anamorphic phases of some fungi [e.g. Gibberella fujikuroillrusarium monilgorme and Pleospora betae/Phoma betae] have not been treated as synonyms. If I.U.B. recommended names have been used for enzymes they are those in the 1984 edition of ‘Enzyme Nomenclature’.A25822B 544 Abies sachalinensis 148 abietatriene 522 Abrus cantoniensis 9 Abrus precatorius 9 abrusgenic acid 9 abruslactone A 9 abscisic acid 148 349 353 365 366 370 376 445 453 abscisic acid biosynthesis 518 abscisic acid 6-deoxy- 376 Acanthagorgru sp. 554 acanthocarpan 449 acanthotoxin 195 Acer buergerianum 499 Acer pseudoplatanus 454 526 acetaldehyde 3,4-dihydroxyphenyl- 166 acetaldehyde 4-hydroxyphenyl- 166 acetate-CoA ligase 526* acetate thiokinase 526* acetoacetyl-CoA 338 Acetobacter pasteurianus 533 acetophenone 3,4-dimethyl- 276 acetyl-CoA 295 acetyldehydrorishitinol 432 acetylgynuramine 2 I8 achalensolide 157 158 Achillea ligustica 182 Achillea ochroleuca 148 Achillea spp.522 Achl-va amhisexualis 550 Achlya heterosexualis 550 Aciculites pulchra 473 554 acifluorfen 456 a-acoradiene 11 1 acoragermacrone 133 acorane 111 Acremonium sp. 50 acridone alkaloids 397 acridone alkaloids biosynthesis 174 acridone alkaloids dimeric 398 Acronychia haueri 397 acronycine. 398 acrylochlorin 566 actamycin 174 342 actinidiol 3-OXO- 367 actinidiolide 367 actinidiolide ( +)-3,4-dihydro- 366 actinidiolide 3,4-dihydro- 367 Actinomaduru azurea 344 Actinomaduru mudurae 379 Acrinoplanes philippinensis 4 10 Acrinopyga agassizi 3 activity antispasmodic 147 ACV tripeptide 174 175 acyltetramic acids 408 Adenostyles glubra 2 18 S-adenosyl-L-methionine :magnesium- protoporphyrin 0-methyltransferase 32 569* Adharoda casica 396 adlumidiceine 86 adlumine 86 Aegilops ottata 195 aeginetolide 367 Aegle marmelos 245 Aerobacter aerogenes 62- 1 496 Aerobacter aerogenes 308 3 14 3 15 Aesculus x carnea 503 affinine 16-epi- 62 aflatoxin B, 340 Ajraegle paniculata 393 Agalinis purpurea 9 agarospirol 138 Agathosma puberula 501 Agelas sp.147 agelasidine A 147 Ageratum conyzoides 503 Ageratum jastigiatum 147 149 agmatine 163 agroclavine (+)- 53 agroclavine hydroxylase 173 agroclavine (k)-6,7-seco- 53 agroclavine-I 53 ailanthone 7 Ailanthus altissima 7 52 Ailanthus glandulosa 7 A iptasia pulchella 554 Ajania jastigiata 157 ajmalicine 169 ajmalicine (-)- 59 ajmaline 170 ajmaline alkaloids 61 ajmaline-type alkaloids 169 aklanonic acid 338 AK-toxin I 413 AK-toxin 11 413 akuammigine pseudoindoxyl 57 alangicine 87 Alangium lamarckii 168 alatusamine 154 alatusine 154 albane 104 albene 104 105 106 Albertisia papuana 83 Alcaligenes eutrophus 315 Alcyonium sp.157 aldosterone biosynthesis 542 aleuriaxanthin 354 Alisma plantago-aquatica var. orientale 156 alismol 156 alismoxide 156 alkaloids hemiterpenoid tricyclic 394 alloalantone 155 allo-+-codeine 88 allocryptopine 86 86 allocryptopine 13-hydroxy- 84 allocryptopine N-oxide 86 91 allocryptopine 13-0XO- 84 alloibogamine (*)-16-hydroxy- 73 alloisolongifolene 150 allomuscarine 245 Allomyces macrogynus 104 allopseudocodeine 88 allopumiliotoxins 238 alloyohimbine ( & )- 6 I alloyohimbine 17-epi- 56 alloyohim bine 10-methoxy- 1 7-epi- 56 Alstonia angustiloba 64 Alstonia boonei 64 Alstonia pneumatophora 64 Alstonia yunnanensis 56 61 Alternaria carthami 436 437 438 453 Alternaria chrysanthemi 33 1 Alternaria helianthi 330 Alternaria kikuchiana 41 3 Alternaria solani 3 3 5 404 Alternaria sp.330 alternaric acid biosynthesis 335 alterperylenol 330 aluminium phosethyl 456 AM-6201 412 Amanita muscaria 182 Ambrosia cumanensis 158 Ambrosia elatior 3 americanin 208 americanin-B 208 americanin-D 204 6-(~-a-aminoadipyl)-~-cysteinyl-3,4-didehydroa-valine 295 6-(L-a-aminoadipyl)-L-cysteinylglycine, 300 6-(L-a-aminoadipyl)-D-cysteinyl-D-valine, 293 6-(D-cr-aminoadipyl)-L-cysteinyl-D-valine, 304 1-aminocyclopropane-1-carboxylate synthase 453 5-aminolaevulinate synthase 19 56 1 * 5-aminolaevulinate synthase cDNA sequence 561 8-aminolaevulinic acid 19 6-aminolaevulinic acid biosynthesis 20.56 1 6-aminolaevulinic acid dehydratase 2 1 *. 562* 6-aminolaevulinic acid synthase 19 561 * amino-oxyacetic acid 439 456 Amphidinium carterae 375 P-amyrin 533 544 Anacampta angulata 71 Anacystis nidulans 322 anatoxin-a (+)- 222 anatoxin-a (-)- 222 Anchusa oficinalis 11 12 ancistrocladidine 81 ancistrocladisine 8 1 ancymidol 520 andibenin B biosynthesis 518 Andrographis paniculata 5 17 521 Androsace septentrionalis 11 androsta-5,16-dien-3P-o1, 539 androsta-1 ,4-dien-3-ones1 10-hydroperoxy- 485 5cr-androstane 3p-acetoxy- 17P-cyano- 470 5a-androstane 30-acetoxy- 17a- methoxycarbonyl- 17P-methyl- 18-nor- 468 5cr-androstane 3P-acetoxy- 17P- methoxycarbonyl- 17cr-methyl- 18-nor- 468 5a-androstane 1Sa-azido-3P,17P-di-benzoyloxy- 14P-bromo- 464 kandrostane 14P-azido-3P 17P-di- benzoyloxy-1 5a-iodo- 464 Sol-androstane 2P-iodo-3a-thiocyanato-, 464 Sa-androstane 3a-iodo-2P-thiocyanato- 464 5a-androstane-3,17-dione, 4-ethenylidene- 465 5a-androstane- 16,17a-dione 3-hydroxy- 17-aza-D-homo- 489 androstanes syntheses 483 5a-androstan- 17p-01 3P-benzoyloxy- 14a 15a-epimino- 464 1-32 5a-androstan-l7p-ol 3P-benzoyloxy-l4p 150-epimino- 464 androstan-3-one 50-benzoyl- 17P-hydroxy- 19- nor- 468 5or-androstan-3-one 17P-hydroxy- 541 Sa-androstan-17-one 1P,30,5,W-tetra-hydroxy- 483 5or-androst-2-ene 17p-t-butoxy- 467 androst-5-ene 17P-(2-furyl)-3P-methoxymethoxy- 487 androst-5-ene-3P,17a-diol, 539 androst-5-ene-3P1 17P-dio1 539 androst-4-ene-30 14P-dio1 17P-(3-pyridyl)- 48 7 androst-4-ene-3,17-dione, 471 538 539 540 554 \ androst-4-ene-3,17-dione, 19,19-difluoro- 541 androst-4-ene-3,17-dione, 4-hydroxy- 541 androst-4-ene-3,17-dione, 19-hydroxy- 490 androst-4-ene-3,17-dione, 19-nor- 485 5a,14P-androst-l6-en-3-one, 484 androst-Cen-l7-one 3P,6P-diacetoxy- 465 androst-l( IO)-en-5-one 3P 17P-diacetoxy-19- nor-5 I0-seco- 464 androst-4-en-3-one 65,14a-dihydroxy- 49 I androst-5-en-l7-one 3b-hydroxy- 539 5a-androst-1-en-3-one 1-methyl-l9-nor- 472 5a-androst-l-en-3-one 5( 1hl)abeo-l-methyl-l9-nor- 472 Anemonia sulcata 369 anguidine 108 anhydrolutein 375 anhydromevalonolactone 109 Aniba burchellii 205 206 Aniba ferrea 206 206 Aniha lancijolia 204 208 Aniba megaphylla 206 Aniba sp.204 206 Aniba williamsii 206 anibine 186 anisodinic acid (-)- 222 Anodonta cygnea 554 anomaline 66 anomaline 12-O-methyl- 66 Anomalocera patersoni 370 ansamycins 31 3 342 ansamycins biosynthesis 174 antheraxanthin 350 357 37 1 Anthocephalus chinensis 56 anthocyanidin 03-glucosyltransferase 503 ant hocyanid ins biosy nt hesis 502 anthocyanin Os-glucosyltransferase 503 ant hocyanins biosyn t hesis 502 anthracyclines 338 anthranilate synthase 3 12 498 anthranilic acid 31 2 anthranilic acid biosynthesis 498 anthranilic acid N-methyl- 174 Anthriscus nemorosa 193 antibiotic A47934 247 antibiotic A 258228 488 antibiotic AM-6201 412 antibiotic CI-920 404 antibiotic FR-900109 407 antibiotic M 139603 407 antibiotic M-230B 247 antibiotic ML-263B 525 antibiotic PD 1 13,270 404 antibiotic PDI 13,271 404 antibiotic SEN-215 247 antibiotic U-56407 413 antibiotic U-62162 41 3 antibiotic X-l4547A 410 41 1 Antidesma pentandrum 8 antirhine 18,19-dihydro- 56 antirhine ar-methoxy- 56 Aphanamixis polystacha 7 Aphanamixis rohituka 7 aphidicolin biosynthesis 519 apigenin 502 apiocarpin 449 Apios tuberosa 449 Apis mellijera 552 Apium graveolens 438 522 Aplysia dactylomela 149 aplysistatin 98 100 apocarotenals 374 apocavidine 84 apomorphine 88 aporphines 227 aporphinoids dimeric 230 apparicine 75 apparicine alkaloids 64 aptosimol 196 aptosimone 196 Aptosimum spinescens 195 196 Aquilaria malaccensis 149 Aquilaria sinensis 156 Aquilaria sp.149 156 arachidonic acid 433 451 Arachis hypogaea 437 498 506 561 562 araliangine 199 araliopsine 395 aranotins biosynthesis 173 Araucaria angustijolia 194 arboreol 196 arbusculin la,3a-dihydroxy- 155 arbusculin-C 138 arctigenin 193 arctiin 204 Arctium lappa 202 arctolide 157 Arctotis grandis I57 arenine 82 Argemone grandflora subsp.grandflora 87 Argemone mexicana 81 84 arginine 176 aricine pseudoindoxyl 56 aristolactams 232 aristolane 156 aristolarine 54 Aristolochia indica 229 232 A ristolochia longa 23 2 Aristolochia taliscana 204 Aristolochia triangularis 195 aristolochic acid IV 232 aristolochic acids 232 aristoserratine 54 Aristotelia alkaloids 54 Aristotelia peduncularis 54 aristoteline (+)- 55 Armoracia rusticana 49 Arnica chamissonis I58 Arnica montana 158 arnicolide G 158 aromadendrane 141 158 aromatase 539 540 541 aromoline 83 arphamenines biosynthesis 173 artapshin 156 arteincultone 147 Artemia sp. 351 370 artemin 138 Artemisia absinthium 195 Artemisia barrelieri 154 Artemisia canariensis 154 Artemisia cretacea 154 Artemisia filijolia 1 50 Artemisia fragrans 154 Artemisia herba-alba 152 Artemisia inculta 147 Artemisia paucijlora 154 Artemisia spp.522 Artemisia tripartita 148 Artemisia umbellijormis 154 155 artemisin 134 artepaulin 156 NATURAL PRODUCT REPORTS 1985 Arthrobacter simplex 490 Ascidia sp. 247 Asclepias curassavica 551 ascochitin 326 ascochlorin 100 41 7 Ascochyta viciae 4 17 ascofuranone 98 4 I7 asjanin 245 aspartic acid 3-methyl- 335 Aspergillus amstelodami 171 Aspergillus clavatus 509 Aspergillus flaws 34 1 449 Aspergillus janus 245 Aspergillus melleus 328 329 Aspergillus multicolor 325 Aspergillus niger 44 1 453 499 Aspergillus oryzae 148 Aspergillus parasiticus 340 341 Aspergillus stellatus 404 Aspergillus tamarii 53 Aspergillus terreus 173 401 403 405 407 420 Aspergillus ustus 326 327 341 401 404 405 Aspergillus variecolor 404 518 Aspergillus versicolor 341 asperlactone biosynthesis 328 aspertetronin A 406 aspidocarpine 15a-hydroxy- 66 Aspidosperma excelsum 57 64 66 76 Aspidosperma gilbertii 64 Aspidosperma marcgravianum 56 65 75 77 Aspidosperma oblongum 56 62 64 Aspidosperma sp.56 aspidospermidine 69 aspidospermidine (-)- 67 aspidospermidine N,-acetyl- 69 aspidospermidine 1,2-didehydro- 67 aspidospermine alkaloids 65 Aspilia pluriseta 154 Aspilia spp. 154 aspterric acid 114 aspyrone biosynthesis 328 astaxanthin 369 370 375 asteltoxin 404 astepyrone 325 403 Asterias rubens 554 asticolorin A 325 asticolorin B 325 asticolorin C biosynthesis 325 Astragalus galegqormis 3 Astragalus membranaceus 3 4 11 Astragalus sieversianus 4 Astragalus taschkendicus 4 asukamycin 41 3 atherosperminine N-oxide 23 1 Atkinsiella dubia 546 atracurium 82 84 atropine pharmacology 223 atropinium bromide N-isopropyl- 222 Atro-uima afzeliana 9 Atta cephalotes 9 attenuol 197 attenuol (*)- 199 aubergenone 434 aucuparin 437 aurochromes 356 aurocitrin 416 aurodox 41 1 austdiol 401 austdiol biosynthesis 326 austin 404 405 austinol 404 austocystin D biosynthesis 341 autumnaline 168 autumnolide 6-epi- I58 Avena satica 503 Avena spp.438 avenaciolide 408 avenalumin I 438 NATURAL PRODUCT REPORTS 1985 avenalumin 11 438 avenalumin 111 438 averantin 340 avermectins 337 averufmin 341 averufin biosynthesis 340 Axinella polypoides 554 Axinella verrucosa 554 AY-9944 536 544 546 9b-azaphenalene alkaloids 242 azatetrahydroberberine 85 azukisapogenol 9 bacchara- 12,2 1-diene 13 Bacillus circulans 245 Bacillus suhtilis 379 440 495 528 bacteria methanogenic 40 bacteriochlorophyll a 35 42 571 bacteriochlorophyll h 35 571 bacteriochlorophyll c 35 bacteriochlorophyll d 35 bacteriochlorophyll e 35 bacteriochlorophyll g,, 57 1 bacteriochlorophyllide a 35 bacteriochlorophylls 35 bacteriochlorophylls c h.p.l.c.57 i bacteriophage hspcl 309 bacteriopheophorbide a 35 bacteriorhodopsin 360 37 1 372 373 375 Bahia opposititolia 1 57 baimuxinal I56 baimuxinic acid 156 bakuchiol biosynthesis 509 Balunophora japonica 204 balanophorin 204 Balfburodendron riedelianum 393 395 Baptisia australis.24 1 barrelin 155 basidalin 247 407 bastaxanthin c 349 bastaxanthol b 350 batatasin I biosynthesis 506 batatasin 111 506 bazzanene 107 Bazzania ungusti/dia I48 Bazzania ,fuuriana 148 Beaureria hassiana 41 1 Beaureria jelina 4 16 Brauseria tenella 41 1 beccapolydione 230 Bellendena montanu 223 benomyl 456 benzindanoazepine 167 benzofuran phytoalexins 438 benzoic acid 499 benzoic acid 3-amino-5-hydroxy- 174 3 13 342 benzoic acid 2,3-dihydroxy- biosynthesis 499 benzoic acid 5-hexaprenyl-3,4-dihydroxy- 38 1 benzoic acid 4-hydroxy- 507 benzoic acid o-succinyl- biosynthesis 507 benzoic acid 3,4,5-trihydroxy- biosynthesis 498 benzophenanthridines 90 benzoxazinone phytoalexins 440 benzylaminopurine 445 453 benzylisoquinoline alkaloids biosynthesis 166 benzylisoquinolines 82 berbamine 84 berberine.84 90 167 berberine i3-methyi- 85 berberines 84 Berheris actinacantha 85 232 Berheris hraniana 167 Berheris huifoliu 83 232 Berheris darbtinii 86 87 Berberis spp. 167 bergapten 438 betaenone A biosynthesis 334 betaenone B 334 betaenone C 334 Betula costata 5 betulaprenol 376 betulaprenols 377 bibenzyl phytoalexins 437 bibenzyl synthase 506 bibenzyl 3,3’,5-trihydroxy- 437 506 bibenzyl 3,4’,5-trihydroxy- 506 bicuculline 86 bicuculline (?)- 86 bicyclofarnesanes 100 147 bicyclohumulane 150 bicyclo[3.3.I]nonane-l,3-exo-dicarboxylic acid 6-exo-hydroxy- 314 bigelovin 140 bilane 22 bilane 1-aminomethyl- 23 bilane 1-hydroxymethyl- 22 563 564 bilanes 27 bile acids 483 526 543 bile acids biosynthesis in vertebrates 542 bile pigments biosynthesis 566 bile pigments I5N n.m.r. 575 bilindiones 2,3-dihydro- 569 bilirubin 42 bilirubin biosynthesis 566 biliverdin 42 biliverdin biosynthesis 566 biliverdin IXa 566 biliverdin reductase 566 biliverdins 30 biliverdins XIII 566 biochanin A 450 biochanin A 7-O-glucoside 505 biphenyls polychlorinated 564 bipolarin 341 Bipolaris sorokiniana 263 341 2,3’-bipyridine 3,4’-dihydroxy- 187 bisabolane 100 148 or-bisabolene 101 102 or-bisabolene (Z)-,100 P-bisabolene 100 10 1 102 y-bisabolene 101 517 a-l-bisabolol 100 bisbenzylisoquinoline alkaloids 166 bisbenzylisoquinolines 83 bisindole alkaloids 74 bismurrayafoline-A 74 bismurrayafoline-B 74 bisnorargemonine 84 bispiperidine alkaloids 186 bispyridine alkaloids 187 bispyrrolidine alkaloids 182 bisvertoquinol 41 7 bityrosine 498 Blukeslea trispora 375 blumenol A 353 blumenol C 353 blumenol C 6,7-didehydro- 353 Bocconia corduta 86 Boenninghausenia albrfora 397 Bohadschia hitittata 2 boldine 6a,7-didehydro- 228 Bomhyx mori 551 553 Bonellia ciridis 38 bonellin 38 577 Boraginaceae alkaloids 2 I7 bornanesultone 10,2-e.uo- 279 borneol ( -)-3-e.xo-hydroxy- 263 borneol 5-endo-hydroxy- 263 borneol ( -)-5-endo-hydroxy- 263 borneol ( +)-5-e.uo-hydroxy- 263 borneol ( -)-5-e.xo-hydroxy- 263 borneol ( -)-6-em-hydroxy- 263 bornyl acetate (+)- 263 1-33 bornyl acetate (-)- 262 263 bornyl acetate 5-exo-hydroxy- 263 bornyl acetate ~-oxo- 262 bornyl acetate ~QXO- 262 bornyl methyl ether 6-exo-allyl-5-oxo- 267 bornyl methyl ether 5-OXO- 267 borrerine 52 boschnaloside 5 15 Boswellia carteri 12 botryococcenes 1 Botryococcus braunii 1 322 Botryodiplodia theobromae 325 botryodiplodin biosynthesis 325 Botrytis cinerea 437 439 448 449 547 Branchinecta packardi 370 Branchipus stagnalis 370 Brasilia sickii 148 152 157 158 Brassica elongata 247 Brassica pekinensis 49 brassicasterol 549 brassicasterol 22,23-dihydro- 546 brassinolide 479 brassinosteroids 46 1 brefeldin A 453 brefeldin A biosynthesis 332 Brevibacterium iodinum 3 14 Brevibucterium linens 350 bromocodide 88 brothenolide (+)- 155 Broussonetia papyriferu 440 Broussonetia zeylanica 187 393 broussonetine 393 broussonin A 440 broussonin B 440 Bryonia dioica 4 548 Buchenavia capitata 183 Buchenavia macrophylla 183 buchenavianine 188 bufadienolides syntheses 486 bufalin 487 14wbufalin 14-deoxy- 487 bulbodione 228 P-bulnesene 139 Bupleurum falcatum I 1 Bupleurum longerudiutum 1 1 buprenorphine 88 90 burseran (+)- 202 buthiobate 545 546 butyric acid 3-hydroxy- 335 buxifoline N-formyl- 228 buxifoline N-methyl- 228 c.p.450 350 c.p. 473 350 cacalone acetate 156 cadalene 2,7-dihydroxy- 429 cadambine 56 cadaverine 163 164 165 cadinane 114 149 cadinenes 100 Caesalpiniu digyna 246 caesalpinine A 246 cajanin 447 cajanol 447 Cajanus Cajun 437 447 y-calacorene I 17 calamenene 1 17 calamenene ( -)-7-hydroxy- 430 calamenene ( +)-8-hydroxy- 150 calamenenes 7-hydroxy- 1 17 calciol (3&7R,8R)-3-0-acetyI-7,8,25-tri-hydroxy-7,8-di hydro- 480 calciol (3S)-3-O-acetyl- 10!&19,25-trihydroxy- 10,19-dihydro- 481 calciol 5,l O-didehydrod 19-epidioxy- 5,6,10,19-tetrahydro- 480 calciol 1,25-dihydroxy- p-D-glUC0- pyranosides 483 calciol 6,19-epoxy-(5E)- 480 1-34 NATURAL PRODUCT REPORTS 1985 calciol 0-D-glucopyranoside 483 camphor 5-exo-hydroxy- 262 capsidiol 13-hydroxy- 43 1 calciol 6-hydroperoxy-4,5-didehydro-5,6-camphor 3-endo-methyl- 256 266 capsorubin 350 354 dihydro- 480 camphor 3-exo-methyl- 266 capsorubone 354 calciol 1-hydroxy- 6-D-glucopyranosides camphor 3-endo-methyl-3-exo- Caraipa densifolia 8 483 trideuteriomethyl- 266 carbendazim 456 calciol 25-hydroxy- P-D-glucopyranosides camphor 3-exo-methyl-3-endo- P-carboline 4,8-dime thoxy- 142-48 3 trideuteriomethyl- 266 methoxyethy1)- 51 calciol la-hydroxy-25-methyl- 482 camphor 3-(phen ylt hiome thyl)- 269 P-carboline 4,9-dimethoxy-l -vinyl- 5 1 calciol (6R)- 10~,19,25-trihydroxy-6-methoxy-camphor rearrangement 273 P-carboline 1-ethyl- 51 3,5-cyclo-3-deoxy-5,6,10,19-tetrahydro- camphor ring-cleavage reactions 270 P-carboline 1-ethyl- N,-oxide 51 480 camphor ( +)-3-endo,9,9-tribromo- 255 256 P-carboline 1-(2-hydroxy-l-methoxyethyl)-4-calciols 19-~arboxyalkyl- 482 camphor (+)-3-endo,9,10-tribromo-, 260 methoxy- 52 calciols 19-carboxyalkyl-(SE)- 482 camphor 3-trimethylsilyl- 268 P-carboline-I -propionate ethyl 51 Caldarielia acidophila 3 77 * camphor 3-trimethylsilyloxy- 269 P-carboline-1-propionate ethyl N,-oxide 5 1 Calendula oficinalis 1 1 375 544 camphor 3-trimethylsilylperoxy- 269 Carcinus maenas 369 372 californidine 84 camphor 8,9,10-trinor- 266 cardenolide glycosides 55 1 Callichilia subsessilis 76 camphor benzenesulphonylhydrazone,276 cardenolides syntheses 486 callichiline 76 camphor enol acetate 267 Carduus getulus 10 Calliphora stygia 552 camphor enol t-butyldimethylsilyl ether 267 carinatidin 204 Calliphora oicina 553 269 carinatidin (2S,3S)-2,3-dihydro- 204 calycinine N-methyl- 228 camphor enol triethylgermyl ether 267 carinatidiol 207 Calypogeia granulata 15 1 157 camphor enol triethylsilyl ether 267 carinatin 204 calysterol 23,24-dihydro- 554 camphor enol triflate 267 carinatinol 2,3-dihydro- 204 Calyx niceaensis 554 camphor enol trimethylsilyl ether 264 267 carinatol 204 camelliagenin A 10 269 carinatone (-)- 204 campesterol 544 camphor-y-homoenol 259 carinatonol 204 campesterol biosynthesis 547 camphor hydrazone 270 Carissa edulis 195 camphane-2-endo,3-e.uo-diol 270 camphor morpholine enamine 268 carissanol 195 camphane-2-e.xo,3-endo-diol, 269 camphor nitrimine 268 carissone 134 camphane-2,3-diols trans- 269 camphor piperidine enamine 268 carlosic acid (S)-,407 camphanone 3,5-cyclo- 262 camphor pyrrolidine enamine 268 Carnegiea gigantea 8 1 camphene 253 camphorquinone 270 279 carnegine 8 1 camphene biosynthesis 5 15 camphor-9-sulphonic acid (+)- 254 carolic acid 407 camphene I-hydroxy- 253 camphor-9-sulphonic acid (-)- 254 255 carotane 111 149 camphene sultone ( f)-exo- 279 camphor- 10-sulphonic acid 254 a-carotene 357 camphenilone 104 106 camphor-9-sulphonic acid (+)-3-endo-a-carotene 4-hydroxy- 357 camphor (+)- 5 16 bromo- 254 255 P-caroten-8’-al1 8’-apo- 354 357 camphor 10-benzoyloxy-3-endo-bromo-, 260 camphor-9-sulphonic acid 6-endo-bromo- <-carotene 35 1 375 camphor 3-benzylidene- 268 255 P,P-carotene 357 370 371 372 373 374 camphor (+)-3-endo-bromo- 254 255 264 camphor-9-sulphonyl bromide 256 375 266 269 camphor-9-sulphonyl bromide 3-endo- P,P-carotene 5,6;5‘,6‘-diepoxy-5,6,5‘,6‘-camphor 3-e.uo-bromo- 266 269 bromo- 256 tetrahydro- 356 camphor ( -)d-endo-bromo- 275 camphor-I 0-sulphonyl bromide 253 P,P-carotene (5S,6R)-5,6-epoxy-5,6-dihydro-, camphor 8-bromo- 257 259 camphor tosylhydrazone 270 356 camphor (+)-9-bromo- 255 266 camphor trisylhydrazone 270 P,P-carotene (5S,8R)-5,8-epoxy-5,8-dihydro-, camphor (-)-9-bromo- 255 Campovassouria bupleurijolia 152 157 357 camphor 10-bromo- 253 camptothecin 77 P,P-carotene (SS,SS)-5,8-epoxy-5,8-di hydro-, camphor 3-endo-bromo-8-deuterio-,256 camptothecin (f )- 77 357 camphor ( +)-3-endo-bromo-lO-deuterio- Campylobacter jetus 379 P,P-carotene-2,2’-diol 350 276 Campylobacter jejuni 379 P,P-carotene-3,3’-diol 35 1 camphor ( -)-6-endo-bromo-8-deuterio- 276 canadaline 84 85 P,P-carotene-4,4‘-diol1 (4R,4’R)- 354 camphor 3-endo-bromo-3-e.uo-methyl- 266 canadensolide 408 P7P-carotene-3,3’-diol (1 52)-5,6;5’,6’-di- camphor 3-exo-bromo-3-endo-me t h yI- 266 canadine 14-methoxy-8,13-dioxo- 86 epoxy-5,6,5’,6‘-tetrahydro-, 35 1 camphor 9-bromo-3-endo-methyI- 256 260 candicine chloride 0-methyl- 8 1 P,P-carotene-3,3’-dio17 5,6-epoxy-7’,8’-di- camphor ( +)-9-bromo-3-endo-methyl- 256 Candida albicans 4 16 dehydro-5,6-dihydro- 375 camphor 9~bromo-6-endo-methyI- 256 Candida maltosa 495 498 P,P-carotene-3-3’-diol 5,6-epoxy-5,6-dihydro- camphor 3-t-butyldimethylsilyloxy- 269 Candida parapsilosis 529 350 camphor C(3)-functionalization 264 Candida utilis 31 P,P-carotene-3,3’-diols 5,8-epoxy-5,8-di-camphor C(5)-functionalization 262 cannabinoid acid propyl- biosynthesis 5 16 hydro- 351 camphor C(8)-functionalization 257 Cannabis sativa 437 5 I6 P,P-carotene-4,4-dione 35 1 369 camphor C(9)-functionalization 254 canthaxanthin 351 357 369 370 P,P-carotene-3,3‘-dione 4‘,5’-didehydro-4,5’-camphor C( 10)-functionalization 253 canthine-2,6-dione 3-methyl- 5 1 retro- 375 camphor 3P,8-cyclo- 257 canthin-6-one 5-hydroxymethyl- 52 P,P-carotene-4,4-dione 3,3’-dihydroxy- 369 3,4,3’,4’-tetra-camphor 8-deuterio- 256 cantoniensistriol 9 P,P-carotene-2,2’-dione camphor 3-diazo- 262 capillarisin 503 dehydro- 354 camphor 3,3-dibromo- 254 257 262 capitogenic acid 10 P,P-carotene-3,5,6,3‘,5‘,6’-hexaol, 5,6,5’,6’-camphor (+)-3-endo,8-dibromo- 260 capnellane 128 tetrahydro- 349 camphor (+)-3-endo,9-dibromo- 255 260 capnellene 128 P,P-carotene-4,9,4-triol,357 5’,6’-epoxy-6,7-camphor 3-endo 10-dibromo- 260 capnellene A9(’3- 106 128 143 P1P-carotene-3,5,3’-triol camphor (-)-6-endo,9-dibromo- 255 275 capnoidine 86 didehydro-5,6,5‘,6‘-tetrahydro-,375 5‘,8‘-epoxy-6,7-camphor (+)-8,lO-dibromo- 260 capsanthin 350 354 P,P-carotene-3,5,3’-triols 351 camphor (+)-9,lO-dibromo- 260 266 capsanthone 354 didehydro-5,6,5’,8’-tetrahydro- camphor 3,3-dibromo-8-deuterio-,259 capsicannol 43 1 p,ecarotene 357 camphor 3,3-dibromo-9-deuterio- 259 Capsicum annuum 375 375 43 1 507 P,&-carotene-3,19-diol 357 camphor 9,1 O-dibromo-3-endo-methyl- 260 Capsicum annuum var.grossum 205 P,~-carotene-3,19-diol (3R,6‘R)- 350 camphor 3-endo,9-dichloro- 259 Capsicum spp. 449 P,~-carotene-3’,8‘-dione,3,6‘-dihydroxy-7,8-camphor 5,6-didehydro- 267 capsidesmol 43 1 d ide h yd ro-7’ 8’-d i h yd ro- 349 266 capsidiol 431 P,~-carotene-3,19,3’-triol, camphor 5,6-didehydro-8,lO-dinor- (3R,3’R,6’R)- 350 camphor 5-endo-hydroxy- 262 capsidiol 1-deoxy- 43 1 P,~-carotene-3’,6’-dione,354 NATURAL PRODUCT REPORTS 1985 P,tc-carotene-3’,6’-dione 3-hydroxy- 354 P,~-carotene-3’,6’-dione 3-sulphate 3,19,17’- trihydroxy-7,8-didehydro-,349 p,$-carotene 351 P,$-carotene 1’,2’-epoxy-l’,2’-dihydro-, 371 p,$-carotene (2’S)-1’,2’-epoxy-l’,2‘-dihydro- 350 354 P,$-carotene-l’,2’-dioI, (2’S)-3’,4’-didehydro-1‘,2‘-dihydro- 354 ~,~-carotene-3,3‘-diol, (3R,6S,3’R,6’S)- 350 ~,~-carotene-3,3’-diol, (3S,6S,3’S,6’S)- 350 &,$-carotene 351 ~,~-carotene-6,6‘-dione, 3,3’-dihydroxy- 350 ~,~-carotene-3,6,3’,6’-tetraone, 354 $,$-carotene (72,7‘2)- 351 $,&carotene (72)- 351 $,$-carotene-3,3’-diol 350 $,X-carotene (72)- 351 $,$-carotene 351 $,$-carotene (72,92,7‘2,92)- 351 $,$-carotene 7,8-dihydro- 35 1 $,$-carotene 1,l ’-dimethoxy-3,4,3’,4‘- tetradehydro-l,2,1’,2’-tetrahydro-, 372 $,$-carotene (2S)-1,2-epoxy-l,2-dihydro- 350 354 $,$-carotene 7,8,11,12,7’,8’-hexahydro-, 35 1 $,$-carotene l-methoxy-3,4-didehydro-1,2,7’,8’-tetrahydro- 372 $,$-carotene 7,8,11,12,7’,8’ I 1’,12‘-octahydro- 351 $,$-carotene 7,8,7’,8’-tetrahydro- 351 $,$-carotene-4,4’-dioate,diglucosyl 4,4- diapo- 351 $,i,b-caroten-4-oate-4‘-oic acid glucosyl 4,4-diapo- 351 carotenoid-protein complexes 369 carotenoids 349 carotenoids absorption spectra 372 carotenoids assay 370 carotenoids biosynthesis 375 carotenoids infrared spectra 371 carotenoids metabolism 375 carotenoids n.m.r.spectra 371 carotenoids photoacoustic spectra 373 carotenoids Raman spectra 37 1 carotenoids separation 370 carotenoids synthesis 354 P,P-caroten-2-01 350 P,P-caroten-3-01 35 1 P,P-caroten-3-01 3’,4’-didehydro- 357 375 P,P-caroten-3-olI 3’,4’ 7’,8’-tetradehydro- 349 P,P-caroten-l9’,1 1’-olide 3-acetate 5’,6’- epoxy-3,5,3’-trihydroxy-6,7-didehydro- 5,6,5‘,6’-tetrahydro- 10,11,2O-trinor- 372 P,P-caroten-8-one 3’-acetate 5,6-epoxy- 3,3‘,5‘-trihydroxy-6’,7’-didehydro- 5,6,7,8,5‘,6‘-hexa hydro- 374 P,P-caroten-4-one 3,6-epoxy-3’,4,7‘,8‘- tetradehydro-5,6-dihydro-, 349 P,P-caroten-2-one 2‘-hydroxy- 350 P,y-caroten-3-01 3’,4’-didehydro- 357 P,~-caroten-3’-01 (3’R,6’R)- 350 P,~-caroten-3-01 2’,3’-didehydro- 357 P,K-carotend’-one 3,3‘-dihydroxy- 350 P,~-caroten-6’-one (3’S,S’R)-3’-hydroxy- 354 P,$-caroten-3-01 350 P,$-caroten-2’-01 l’ 16’-didehydro-I’,2’-di-hydro- 354 P,J/-caroten-Cone 3,l ‘-dihydroxy-3’,4‘-di- dehydro-1’,2’-di hydro- 350 y,e-caroten-8-one 3,6,3’-trihydroxy-7,8-di-hydro- 349 $,$-caroten-1-01 I ,2-dihydro- 375 $,$-caroten-1-01 1’-methoxy-3’,4-didehydro-1,2,7,8,1’,2’-hexahydro-, 375 $,+-caroten-2-one l-methoxy-3,4-didehydro-1,2,7’,8’-tetrahydro- 372 carotenoproteins 369 carpesiolin 140 1-35 Carpesium abrotanoides 152 cheilanthifoline 84 Carthamus tinctorius 436 453 chelerythrine 91 carvone 133 137 chelidonine 90 carvoxime 522 chelidonine (*)- 91 caryolan- 1-01 120 chelilutine 90 caryophyllane 119 150 chemotaxonomy 522 caryophyllene 120 123 133 chenodeoxycholic acid 542 caryophyllene biosynthesis 5 17 Chenopodium ambrosioides 5I4 caryophyllene 10-hydroxy- 5 19 Chenopodium rubrum 499 caryophyllene oxide 522 chicanine 194 casbene synthetase 453 454 chilenine 87 Cassia torosa 335 chillanamine 83 castanospermine 237 chiloenamine 232 castasterone 479 chiloenine 232 catechin (+)- 502 Chiloscyphus polyanthos 154 155 cathafoline 2-epi-16-epi- 63 chiogralactone 479 catharanthine alkaloids 71 chitinase 451 Catharanthus roseus 56 57 62 66 77 169 chitosan 453 170 171 515 Chlamydomonas reinhardtii 32 544 561 Catharanthus trichophyllus 67 Chlorella pyrenoidosa 322 cathenamine 169 Chlorella regularis 562 cationomycin 344 Chlorella sp.32 33 Caulerpa prolifera 1 529 chlorin 36 565 cavidine (+)- 84 chlorins 38 576 577 Cecropia juvenile hormone 98 chlorogenic acid 499 cedrane 111 chlorophyll a 34 35 42 374 565 cedrane-8 ICdiol 111 chlorophyll a 132-hydroxy- 570 a-cedrene 1 11 114 chlorophyll b 35 42 570 Cedrus deodara 205 chlorophyll oxidase 570 cedrusin 205 chlorophyll RC1 570 cedrusin 4’-O-glucoside 205 chlorophyll synthetase 34 Centaurea clementei I57 chlorophyllase 34 Centaurea kotschyi 157 chlorophyllide a 8’ ,82-didehydro- 570 Centratherum punctatum 152 152 chlorophyllide a esterification 34 570 cephaeline 168 chlorophyllide b 35 Cephalaria gigantea I1 chlorophyllide 17,18-didehydro- 32 cephalosporin C 176 295 chlorophyllides 33 cephalosporin C deacetoxy- 293 294 295 chlorophylls biosynthesis 3 1 569 cephalosporin C deacetyl- 299 chlorothricin 334 cephalosporin C 3-exomethylene- 299 Chloroxylon swietenia 393 cephalosporin C 7a-hydroxy- 175 295 chola-5,22-dien-24,2O-olide, 3P-cephalosporin C 7a-methoxy- 295 methoxymethoxy-21 -nor- 487 cephalosporins 293 5P-cholan-24-oic acids 3a,7a 12a,23-tetra- cephalosporins biosynthesis 174 293 hydroxy- 479 Cephalosporium acremonium 175 176 293 SP-cholan-24-oic acids 3a,7a,23-tri hydroxy- 294 295 296 299 300 302 304 479 Cephalosporium aphidicola 5 19 chol-5-en-24-oic acid (20S)-3P-hydroxy- Cephalosporium caerulens 4 13 22,23-didehydro- 479 cepham 3P-hydroxy- 299 cholesta-3,5-diene 3,6-dinitro- 469 cephamycin C 175 5a-c holes ta-8,25-d ien-3P-01 (24 R)-4a 14a 24- cepharanthine 83 84 trimethyl- 2 Ceratocystis jimbriata 154 428 429 517 5a-cholestane 3P-acetoxy-6P 19- Ceratocystis ulmi 430 diethoxyphosphinylimino- 489 Cercospora rosicola 148 376 5 18 cholestane 5a-acetoxy-3a,6P-dihydroxy-, 462 cerulenin (+)- 413 5a-cholestane 2P-amino-3a-fluoro- 469 Cespitularia sp.150 157 5a-cholestane 3a-amino-2a-fluoro- 469 cetocycline biosynthesis 338 5a-cholestane 3a-amino-2P-fluoro- 469 chaenorhine (&)- 247 5a-cholestane 3P-amino-2a-fluoro- 469 Chaerophyllum maculatum 193 193 5a-cholestane 2a-bromo-3a,5a-epoxy-5- Chaetomium amygdalisporum 74 methyl- 489 Chaetomium cochliodes 74 cholestane 3a,5a-epoxy-4aP-hydroxy-4,4-Chaetomium elatum 74 dimethyl-a-homo- 462 Chaetomium globosum 440 cholestane 6k-et hy l-3a 5a-c yclo- 489 Chaetomium murorum 74 cholestane Sa-fluoro-6P-hydroxy-3fl-chalaurenol 503 methoxy- 462 chalcomoracin 439 5a-cholestane 4-hydroxy-3P-methyl-4-aza-, chalcone isomerase 441 442 504 488 chalcone synthase 441 442 454 502 506 5a-cholestane 3P-hydrox ymet hyl-A-nor-, chalcone 2’,4,4’,6‘-tetrahydroxy-, 445 biosynthesis 554 chalcone 2’,4,4-trihydroxy- 441 442 445 5P-cholestane 3a,7a 12a,25-tetrahydroxy- chamaecydin 13 543 chamaecydinol 13 5P-cholestane 3a,7a 12a,26-tetrahydroxy- Chamaecyparis obtusa 13 543 chamigrane 149 cholestane- 301 Sa-carbolactone 467 chamissonolide 158 5a-cholestane-2,3-dini trile 2,3-seco- 470 chamomillol 522 cholestane-3P,5<-dio1 6c-alkoxy-5{,6c-epi- chanoclavine 53 dioxy-5,6-seco- 465 Chasmanthera dependens 84 88 cholestane-3P,24c-diol 4a 14a-dimethyl- chatferin 150 9p 19-cyclo- 3 1-36 5a-cholestane-22,25-diol 2I ,26,27-trinor- 478 5a-cholestane-1,6-dione 489 SP-cholestane-l,7-dione, 489 cholestane-l,7-dione 1(Ib5)abeo- 489 5a-cholestane-l I 1Sdione 3P-acetoxy-8a,9a- epoxy- 14a-hydroxy- 465 5P-cholestane-3a,7a 12a,24,26-pen taol 27- nor- 479 cholestanes syntheses 472 choles tane te traol 26-de h yd rogenase 543 cholestane-30 5a,6P-triol 537 cholestane-3P,24c,25-triol,4a 14a-dimethyl- 90 19-cyclo- 3 cholestane-3P,5~,6<-triol, 5<,6<-epidioxy-5,6-seco- 465 cholestanetriol 26-mono-oxygenase 543 cholestan-3-oic acid 5-oxo-4-nor-4,5-seco- 467 SP-cholestan-26-oic acid 3a,7a 12a,24<- tetrahydroxy- 478 5P-cholestan-26-oic acid 3a,7a 12a-tri- hydroxy- 542 543 5a-cholestan-3P-ol 554 5a-cholestan-3P-ol 24-alkyl- 1!+nor- 554 cholestan-3P-ol 25-aza- 550 5a-cholestan-3f3-ol 4a,24-dimethyl- 549 5a-cholestan-3P-ol (24.!+4a,24-dimethyl- 474 cholestan-3P-ol 5,6-dioxo-5,6-seco- 465 5a-cholestan-15-one 3P-acetoxy-8a,9a- epoxy- 14a-hydroxy- 465 5a-cholestan-3-one bis(diphenylphosphin0- methy1)ethylene ketal 470 5a-cholestan-3-one 2a-bromo-5- bromomethyl- 489 cholestan-3-one 2a-bromo-4a,5a-methylene- 489 SP-cholestan-3-one 2P-chloro- 468 5a-cholestan-3-one 4a-chloro- 468 cholestan-6-one 3cr,5a-cyclo- E-oxime 489 cholestan-3-one 2,2-dibromo-k,5a- methylene- 489 5a-cholestan-3-one 2a,4a-dichloro- 468 5P-cholestan-3-one 2(3,4P-dichloro- 468 5a-cholestan-3-one A-homo- 467 5P-cholestan-3-one A-homo- 467 5a-cholestan-4-one A-homo- 467 5P-cholestan-4-one A-homo- 467 SP-cholestan-1-one 7-hydroxy-5 ~P-cYc~o- 489 5P-cholestan-7-one I a-hydroxy-lP,5-cyclo- 489 5a-cholestan-3-one 2a-(p-methoxyphenyl)- 468 5P-cholestan-24-one 3a,7a 12a,25-tetra- hydroxy- 478 5a-cholestan-3-one 2,2,4a-trichloro- 468 SP-cholestan-3-one 2P,4,4-trichloro- 468 cholesta-5,7,24-trien-3P-o1, 550 cholest-5( 10)-ene 3P-acetoxy-6P-(2-fluoro-ethyl)- 19-nor- 46 I cholest-Sene (24R,25S)-30,26-dibenzoyIoxy-24,25-epoxy- 463 cholest-5-ene 3<-ethyl- 489 cholest-5-ene-3P,7a-diol 3P-dehydrogenase 542 cholest-4-ene-3,17-dione, 6p 19-epoxy- 490 5a-cholest-2-eno[2,3-b]azete,3c-hydroxy-1’-phenyl- 1’,2,3,4’-tetrahydro- 472 5a-cholest-8-en-3P-ol 537 5a-cholest-22-en-3P-ol 24-alkyl- 19-nor- 554 cholest-5-en-3P-ol 22,25-epoxy- 478 5a-cholest-7-en-3P-ol 4a-methyl- 535 cholest-8( 14)-en-30-01 4a-methyl- 533 cholest-4-en-3-one 554 cholest-5-en-3-one 46 1 cholest-20-en-3-one 4a 14a-dimethyl-9P 19- cyclo- 3 NATURAL PRODUCT REPORTS 1985 cholestenone 5cr-reductase 54 1 Ciona intestinalis 477 cholest-5-en-3-one 4-thia- 489 Cissus rheijolia 239 cholest-5-en-7-one 6-thia- 489 Cistus libanotis 5 (501-c holest- I 4-en-3a-yl)trimethylammonium citreopyrone 326 m-iodobenzenesulphona te 472 ci t reot hiolac tone 404 cholesterol 525 526 529 534 537 542 543 ci treot hiolactone biosyn thesis 326 549 ‘551 552 554 citreoviridin 404 404 cholesterol acyltransferase 526 citrinin 326 401 cholesterol 25-aza- 550 citrinin biosynthesis 327 cholesterol biosynthesis in vertebrates 534 citronellol 10-hydroxy- 515 cholesterol 24,26-cyclo- 478 Citrus decumana 397 cholesterol (22R)-20,22-dihydroxy- 537 Citrus sinensis 528 cholesterol (23R)-23,25-dihydroxy- 477 Citrus spp.522 cholesterol (23S)-23,25-dihydroxy- 477 Cladosporium fulvum 453 cholesterol (24R)-24,25-dihydroxy- 477 Clausena heptaphylla 49 cholesterol (24S)-24,25-dihydroxy- 477 clausenapin 49 cholesterol (25R)-25,26-dihydroxy- 477 Claviceps fusiformis 173 cholesterol (255‘)-25,26-dihydroxy- 477 Claviceps paspali 547 cholesterol 20-fluoro- 475 Claviceps purpurea 173 cholesterol 22-fluoro- 475 clavicipitic acid I (*)- 53 cholesterol 24-fluoro- 475 clavicipitic acid 11 (*)- 53 cholesterol 25-fluoro- 475 claviculine 82 82 cholesterol 26,27-hexadeuterio- 474 clavukerin A 156 477 Clavularia koeliikeri 156 cholesterol 24c-hydroperoxy-24<-vinyl- cholesterol 7a-hydroxy- 542 cleistanthoside A 196 cholesterol (22R)-22-hydroxy- 537 Cleistanthus collinus 197 cholesterol (23R)-23-hydroxy- 477 Cleistanthus patulus 196 cholesterol (23S)-23-hydroxy- 477 Clematis chinensis 11 cholesterol (24R)-24-hydroxy- 477 clementein 158 cholesterol (24S)-24-hydroxy- 477 Clerodendrum inerme 200 cholesterol 25-hydroxy- 477 525 526 529 Climacoptera transoxana 1I 537 543 clionasterol 547 cholesterol 23-hydroxy-25,26-didehydro- clionasterol 29-fluoro- 476 477 Cliuia miniata 249 478 cliviasindhine 249 cholesterol 25-hydroxy-7,8-didehydro- cholesterol 20-hydroxy-23,24,25,26,27-clivorine 21 7 pentanor- 542 clonidine 85 cholesterol (23R)-23-methyl- 474 Clostridium aerofoetidum 500 cholesterol (23S)-23-methyl- 474 Clostridium spp.176 cholesterol 23-methylene- 474 Clostridium tetanomorphum 2 1 39 57 1 cholesterol 24-methylene- 546 547 551 clovane 119 554 clovene 120 cholesterol 7a-mono-oxygenase 526 542 clusin (-)- 195 cholesterol mono-oxygenase (side-chain- cneorin NP36,6 cleaving) 537 cobester 38 42 cholesterol U-nor- 537 cobyric acid 41 cholesterol 22-0xo- 538 cobyrinic acid 38 39 573 cholesterols 24-methyl- 547 552 cobyrinic acid biosynthesis 36 40 571 cholesteryl diazoacetate 462 cocaine biosynthesis 163 cholesteryl nitrite 462 cocaine (-)- mass spectra 225 cholic acid 543 cocaine pharmacology 223 cholic acid biosynthesis 542 Coccuius laurifolius 229 cholic acid 12,24-1actone 462 cochliodinol 74 Chondrostereum purpureum 438 coclaurine 82 166 chorismate mutase 314 316 497 coclaurine N-methyl- 82 82 chorismic acid 3 12 3 16 497 $-codeine 88 Chromatium vinosum 40 555 571 codeine 90 88 chromone alkaloids 247 codeinone 89 chrysanolide 134 15 1 codeinone 14-amino- 88 Chrysanthemum cinerariaefolium 152 codeinone I+-amino- 88 Cicer arietinum 505 codeinone I-bromo- 89 Cichorium intybus 502 codeinone lChydroxy- 89 cimiacerol 0-methyl- 3 coenzyme A acetyl- 295 CimicGuga acerina 3 coenzyme A (3S)-3-hydroxy-3-methyl-cimilophytine 76 glutaryl- 525 Cinchona alkaloids 77 coenzyme A malonamyl- 338 Cinchona alkaloids biosynthesis 170 coenzyme B * 298 Cinchona ledgeriana 77 coenzyme M methyl- 574 trans-cinnamate 4-mono-oxygenase 44 1* CofSea arabica 434 500* colchemid 91 cinnamic acid 437 499 colchiceinamide N-deace tyl-N-formyl- 9 1 cinnamic acid 4-hydroxylase 441 * 500* colchicine 91 9 cinnamic esters biosynthesis 499 colchicine N-acetoacetyl-N-deacetyl-,I cinnamolide 100 colchicine biosynthesis 168 Cinnamomum camphora 193 colchicine N-deacetyl-N-formyl- 91 Cinnamosma madagascariensis 197 Colchicum autumnale 9 1 168 cinnamoyl-CoA reductase 500 colletodiol 324 cinnamyl-alcohol dehydrogenase 500 Colletotrichum lindemuthianum 437 441 442 cinnamyl alcohol p-hydroxy- 500 445 456 NATURAL PRODUCT REPORTS 1985 Colletotrichum lini 49 1 Colubrina asiatica 6 columbamine 84 colysanoxide 13 Colysis elliptica 13 Colysis pothifolia 13 Commelina undulata 5 Commiphora molmol 150 154 156 compactin 334 41 8 420 5 13 525 compactin (+)- 423 424 Compositae alkaloids 217 compressanolide 140 confertifolin 100 a-conhydrine 182 P-conhydrine 182 coniferaldehyde 500 coniferyl alcohol 500 coniine 182 Convallaria majalik 55 1 convoline 22 1 Convolvulus krauseanus 22 1 conyzorigun 503 copalyl diphosphate 5 19 copro’gen I 29 copro’gen 11 29 copro’gen 111 27 28 copro’gen IV 29 coprobiliverdin 111 566 coproporphyrin 111 tetramethyl ester 24 coproporphyrinogen 111 biosynthesis 564 coproporphyrinogen oxidase 28 coproporphyrins 27 Coptis deltoides 84 Coptis japonica 84 coptisine 84 Cordia alliodora 9 Cordia obliqua 8 Cordia verbenacca 5 cordialin A 5 cordialin B 5 cordrastine 86 Coreopsis jasciculata 148 coreximine 84 85 coreximine 00‘-diacetyl- 84 corgoine 82 coriolin 129 131 132 corledine 86 corlumine 86 86 coromandaline 2 16 coromandalinine 217 coronamic acid 413 coronaridine 73 coronaridine desethyl- 67 coronaridine 3-hydroxy- 73 coronaridine hydroxyindolenine 73 coronaridine 5-hydroxy-6-oxo- 73 coronaridine 3-OXO- 73 coronaridine 5-OXO- 73 coronaridine 6-0xo- 73 coronatine 41 3 corphin 39 corrin 40 corrins 574 corticoids 483 corticosteroids 1 a,l1 a-ethano- 469 corticosteroids biosynthesis 541 corticosterone 542 corticosterone 18-hydroxy- 542 corticosterone 18-hydroxy-l l-deoxy- 541 Cortinarius injractus 51 cortisol 542 corydaldine N-methyl- 8 1 corydalic acid 91 Corydalis bulbosa 228 229 Corydalis claviculata 82 87 167 Corydalis meijdia 84 86 87 90 Cory dalis oph ioca rpa ,84 Corydalis spp.167 Corydalis stricta 81 82 84 86 90 corydalisol (-)- 85 corynantheidol (&)- 59 corynantheine alkaloids 55 corynantheol 3,4,5,6-tetradehydro-18,19-dihydro- 56 Corynebacterium poinsettiae 350 370 Corynebacterium sp.5 18 corypalline 8 1 corypalline chloride N-methyl- 8 1 Coryphantha greenwoodii 81 coryphanthine chloride (+)- 81 coscoiine 83 coscoline 0-methyl- 83 cosculine 83 costaclavine (?)- 53 costal 429 costal 7-hydroxy- 429 costol 429 costol 7-hydroxy- 429 costunolide 138 151 cosynthetase 22* 564* cosynt he tase mechanism 25 Cotoneaster lactea 438 cotonefuran 438 4-coumarate-CoA ligase 441 m-coumaric acid 437 506 m-coumaric acid 2,3-dihydro- 437 506 o-coumaric acid 499 p-coumaric acid 439 499 500 coumarins biosynthesis 501 coumarins prenylated 514 coumestrol 444 crassifoline 82 Crassostrea virginica 554 Crepis capillaris 157 crinosterol 472 Crinum latijolium 249 Crinum oliganthum 249 Crinum pratense 249 Crioceras dipladeni$orus 77 crispatic acid 216 crispatine 21 3 Crithidia oncopelti 31 croalbinecine 214 crocetin 357 372 crocetin P-gentiobiosyl P-neapolitanosyl ester 351 crocetin di-(P-neapolitanosyl) ester 35 1 crocetindial 354 Crocus neapolitanus 351 Crotalaria aegyptiaca 2 18 Crotalaria cephalotes 218 Crotalaria cunninghamii 2 18 Crotalaria globijera 2 18 Crotalaria nitens 2 18 Crotalaria paulina 2 18 Crotalaria recta 21 8 Crotalaria virgulata subsp.grantiana 218 a-crustacyanin 370 P-crustacyanin 370 y-crustacyanin 370 crustulinol 3P-acetyl-2a-(3-hydroxy-3-methylglutary1)- 1 Crypthecodinium cohnii 549 554 cryptocapsin 354 cryptocapsone 354 cryptofauronol 139 Cryp tomer ia japonica 52 2 cryptopine 86 cryptopleurine 239 cryptosporiopsin 418 cryptosporiopsinol 41 8 a-cryptoxanthin 350 P-cryptoxanthin 35 1 374 375 376 cuauhtemone 154 cubebane 149 cubebol (+)- 150 Cucumis sativus 5 543 Cucurbita maxima 4 5 519 520 544 548 1-37 cucurbitacin C 543 cucurbitacin S 4 cucurbita-5,24-dien-3P-o1, 5 culacorine 82 cularicine 82 cularicine 0-methyl- 82 cularidine 82 cularine 82 cularines 82 Cunninghamella elegans 490 cuparane 106 cuparene 107 cuparene biosynthesis 5 17 a-cuparenone 107 curacutine 83 curassanecine 21 7 curassavinine 21 7 Curcuma longa 148 curcumene 148 curcumene ar- 102 curlone 148 cyanidin 503 Cyanidium caldarium 561 562 568 cyanocobalamin biosynthesis 36 57 1 Cyanophora paradoxa 375 Cyclas formicarius 453 cycleanine 84 cyclizidine 41 1 cycloartanol 25-aza- 549 cycloartanol 24-methylene- 544 cycloartenol 543 544,546 547 549 550 550 cycloartenol 24-methyltransferase 549 cycloastragenol 3 a-cyclocitral 367 P-cyclocitral 367 371 y-cyclocitral 365 cycloeucalenol 544 cycloeucalenol 24,28-dihydro- 544 0-cyclofarnesoyl chloride 368 0-cyclogeraniol 366 0-cyclogeranoic acid 4-OXO- 367 a-cyclogeranoyl chloride 366 P-cyclogeranoyl chloride 368 cyclohexanecarboxylic acid 2,2,3-trimethyl- 4-OXO- 279 cyclohex-2-ene-1-propanoic acid 1-carboxy-4-OXO- 316 cyclohex-5-eno[ 1’,2’ :8,14]codeinone 7,8-di- hydro-5’,6’-dimethyl- 90 y-cyclohomogeranial 365 cyclokievitone 447 cyclokievitone hydrate 448 cyclolaudenol 547 cyclomevalonic acid 5 13 a-cyclopiazonic acid 408 (3-cyclopiazonic acid 408 cycloroylenol 6 cyclosadol 547 cycloseychellane 139 cycloseychellene 141 cyclosieversigenin 3 Cylindrocladium ilicicola 173 335 41 1 a-cyperone 6-epi- 137 Cyperus scariosus 517 Cystoseira caespitosa 379 cytisine alkaloids 239 Cytisus canariensis 166 24 1 Cytisus purpureus 24 1 Cytisus spp.239 cytochrome a 565 cytochrome b 30 cytochrome h5 535 536 539 543 546 cytochrome c 565 cytochrome P-450 30 534 537 539 541 545 546 cytochrome-b reductase 535 cytochrome-c oxidase 30 565 cytochrome-c synthetase 3 1 565 NATURAL PRODUCT REPORTS 1985 cytochromes 30 565 cytochromes c 31 cytoporphyrin 3 1 cytoporphyrin dimethyl ester 565 Dacrydium intermedium 197 Dahlia spp.502 DAHP synthase 308* 495* daidzein 444 445 504 dalbergioidin 447 a-damascone 366 a-damascone (E)-,369 a-damascone 9-oxo-8,9-dihydro- 366 P-damascone (a-, 369 P-damascone 3-hydroxy- 353 0-damascone 4-hydroxy- 353 dammara-20,24-diene 5 dammara-13( 17),24-diene (20R)- 5 dammara-l2,25-diene 3P-acetoxy- 5 danaidone 215 Daphne tangutica 194 daphnoline 83 darlingine 2,3-dihydro- 223 Dascyllus aruanus 148 Datisca glomerata 4 datiscosides B-H 4 Datura innoxia 500 Datura stramonium 500 Daucus carota 441 450 495 502 544 daunorubicin 338 dauricine 84 daurinol 196 dauriporphine 231 davanone 98 deacetoxycephalosporin C 175 deacetoxycephalosporin-C synthase 298 deacetylakuammiline 62 deacetylisoipecoside 168 Decachaeta thieleana 157 decaketides biosynthesis 338 decanoic acid (3R)-3-hydroxy 32 1 decarbomethoxynauclechine ( &)- 59 dec-2-enoic acid (2E)- 321 dec-3-enoic acid (32)- 321 dehydroaustin 404 dehydrocavidine 84 dehydrocheilanthifoline 85 dehydrocorydaline iodide 85 dehydrodiconiferyl alcohol 205 dehydrodi-isoeugenol ( & )- 204 205 dehydrodiscretine 84 85 dehydroepiandrosterone 538 539 dehydroepiandrosterone 16a-hydroxy- 490 dehydrohuanshanine 230 dehydroisothebaine 228 dehydrolappaol A dimethyl ether 203 dehydrololiolide 367 dehydromonocrotaline 2 19 dehydromoracin C 439 d e h ydronorc he1 idon ine 90 dehydropentenomycin I 41 8 dehydropredicentrine 228 dehydroproline 336 de h yd roquinase 309 3-dehydroquinate dehydratase 309 3-dehydroquinate synthase 308 495 dehydroquinic acid 308 309 dehydroretronecine 215 dehydrosafynol 436 dehydrosenecionine 2 19 dehydrotelobine 83 dehydrothalifaberine 230 dehydrovomifoliol 518 delphinidin 503 delphinidin 3-O-[(p-coumaroyl)rutinoside] 5-0-glucoside 503 demethoxyanomaline 66 demethylcoclaurine 166 Dendrilla spp.519 dendrillane biosynthesis 5 19 Dendrobates alkaloids 238 Dendrodoa grossularia 49 dendrodoine 49 Dendrodoris sp.147 dendrolasin 98 dendrolasin 6-hydroxy- 428 dendrolasin 6-0xo- 428 dendrolasinolide 6-0xo- 429 densiflorine 87 dentatin acetate 155 denudatin A 205 206 denudatin B 205 deoxophylloerythroetioporphyrin,575 deoxoprephenic acid 3 16 3 17 3-deoxy-~-arabino-heptulosonate-7-phosphate synthase 308* 495* deoxycholic acid 12,24-lactone 462 deoxycorticosterone 483 deoxyisosikkimotoxin 198 deoxyluteins 357 deoxynojirimycin (+)- 237 deoxynupharidine methiodide 236 deoxynupharidine methiodide 7-epi- 236 deoxypodophyllotoxin 501 deoxypodophyllotoxin 1,2,3,4-tetradehydro- 196 deoxypodorhizone (+)- 202 deoxyradicinin 330 deoxyradicinol 3-epi- 330 deoxytrisporone 366 deoxytubulosine (*)- 61 deoxyvomifoliol acetate 369 desacylchrysanin 155 desacyltanapsin 155 deserpidine 61 desethylvincadifformine,68 desformocorymine 63 desmocarpin 448 Desmodium gangeticum 448 desmosterol 473 537 546 549 552 desmosterol 7,8-didehydro- 473 desmosterol 24,25-epoxy- 530 desoxycordifolinic acid 56 desoxyiripallidal 353 Desulfovibrio desuijiuricans 38 Desulfovibrio gigas 38 diadinoxanthin 375 diamine oxidase 163 165 dianthalexin 440 Dianthus caryophyllus 440 Diaptomus castor 375 diasesartemin (+)- 195 diatoxanthin (3R)-3’,4’-anhydro- 349 Dicentra peregrina 229 Dicentra spectabilis 229 dichomine 73 Dichotomomyces cejpii 509 8,8’-dicorypalline 8 1 Dictyopteris undulata Okamura 1 15* Dictyopteris zonarioides Farlow 1 15* P-dictyopterol 137 Dictyostelium discoideum 379 digitoxigenin 14,15-anhydro- 486 digitoxigenin a-L-arabinofuranoside 486 digitoxigenin (3-D-galactoside 486 digitoxigenin P-D-glucoside 486 digitoxigenin 3-O-P-glycoside 486 3-dihydroabscisic acid 353 3a-dihydrocadambine 56 dihydrocarvone 276 dihydrocarvoxime 522 dihydrochrysanolide 134 dihydrocodeine 14-flUOrO- 89 di h yd rocode i none 89 dihydrocodeinone 1-bromo-7-oxo- 89 dihydrocodeinone 8-(3-hydroxypropyl)- 89 dihydrocodeinone 8-methyl- 89 dihydrocodeinone 1,7,7-tribromo- 89 di hydrocompact in 525 dihydrocorymine 63 dihydrocorymine 3-epi- 63 dihydroflavonols biosynthesis 502 dihydro-y-ionone 365 dihydromauritine A 247 dihyd romevi nolin 525 dihydromorphinone 89 dihydromorphinone 14-hydroxy- 89 dihydrophaseic acid 3-O-P-~-glucoside 353 dihydrophenanthrene phytoalexins 437 dihydrosanguinarine 90 dihydrosanguinarine 8-acetonyl- 90 dihydrosanguinarine 8-methoxy- 90 dihydrosesamin (-)- 194 dihydrosirohydrochlorin 38 574 dihydrospiniferin-1 100 P-dihydrothebaine 88 dihydrotigogenin diacetate 16a-ethoxy- 461 dihydrovindoline 68 dihydrovindoline 3-hydroxy- 68 dihydrovindoline ~-oxo- 68 dihydrowyerone 436 dilignans 202 dimethylallyl diphosphate 527 528 dimethylallyl pyrophosphate 527 528 dimethylallyltranstransferase,527 dimethylcurine (&)- 84 dimoracin 439 dinklageine 187 dinochromes 35 1 dinosterol 554 dinosterol biosynthesis 549 Dioscorea floribunda 544 Dioscorea macruora 506 Dioscorea rotundata 437 506 Dioscorea spp.490 507 Dioscorea tokoro 550 Dioscoreophyllum cumminsii 84 168 229 diosgenin 490 550 dioxoaporphines 23 1 diphosphomevalonate decarboxylase 527 diphyllin 4-O-[~-~-glucopyranosyl-( 1+2)]-P-3,4-di-O-methyl-~-xylopyranoside Diphysa robinioides 446 diphysolone 446 Diplazium subsinuatum 12 Diplodia macrospora 325 403 diplodiatoxin 334 diplophyllolide ent-5cr-hydroxy- 155 diplophyllolide ent-7a-hydroxy- 155 diploptene 533 diplopterol 533 diplosporin 403 diplosporin biosynthesis 325 diprenorphine 90 diptamine 247 Diptychocarpus strictus 247 dipyrrocorphins 39 diquat 514 Dirinaria aegialita 12 Discaria febrijiuga 246 discarine C 246 discarine D 246 discoguattine 228 discretine 84 ditabersonine 77 diterpenoids biosynthesis 5 19 diumycin 41 3 diumycinol 367 41 3 dodeca-a-1,4-galacturonide 454 dolichol 376 dolicholactone biosynthesis 5 15 dolicholide 479 dolichols 377 379 dolichosterone 28a-homo- 479 dopa 166 dopamine 166 168 Doriopsilla sp.147 NATURAL PRODUCT REPORTS 1985 doronine 219 douglanin acetate 155 Drechslera oryzae 456 Drechslera ravenelii 332 drimane 147 drimatrienes 367 drimenin 100 Dryopteris crenata 12 duguenaine 229 Duguetia obovata 228 229 230 duguevanine 228 duguevanine N-formyl- 228 duguevanine N-methyl- 228 Dulacia guianensis 159 182 Dysdercus jasciatus 552 Dysidea jragilis 148 Djjso.uylum acutangulum 150 Dysoxylum alliaceum 150 ebelactone A 416 ebelactone B 416 eburnamenine (-)- 68 eburnamine (+ )- 76 eburnamonine 69 ecdysone 553 ecdysone 2-deoxy- 479 553 ecdysone 20-hydroxy- 552 553 ecdysteroids 55 I 552 ecdysteroids biosynthesis 553 echinofuran B 507 echinomycin biosynthesis 17 1 echinoside A 24,25-didehydro- 3 echinosporin 41 3 echinulin 171 echinulin biosynthesis 171 echitamidine 64 echitamidine N,-formyl- 64 echitamidine N.,-formyl-l2-methoxy- 64 egenine 86 Elaeodendron balae 11 Elaeodendron glaucum 1 1 elaeokanine A 235 elaeokanine C 235 elaiomycin 41 5 elemane 134 153 elemanolide 153 elemanolides 136 0-elemenone 134 fi-elernol 134 ellagic acid biosynthesis 499 ellipticine 65 ellipticine alkaloids 64 ellipticine 17-OXO- 65 Elodea canadensis 377 elwesine 25 1 elwesine 3-rpi- 25 I elymoclavine (i-)-,53 emetine 87 p-l,3-endoglucanase 452 Enkianthus cprnuus 12 5-enolpyruvylshi kimate-3-phosphate synthase 309 496* 497 enterolactone 193 194 enzyme immobilized 19 enzymes active-site-directed agents 2 1 enzymes in biosynthesis of alkaloids 164 165 166 167 170 172 174 175 ephedrine 81 85 epiacetylaleuritolic acid 10 epiaschantin 195 epicatechin (-)- 503 epicubenol 1 15 epidihydrofumariline 87 epiglaufidine 228 epigomisin 0,200 epi-isopodophyllotoxin ( &)- 198 epilubimin 432 epilupinine 235 epimagnolin 195 epiophiocarpine 84 Eugenia kurzii 12 epioxylubimin 432 eugenol 204 epipinoresinol mono-P-D-glucoside (-)- 195 Euglena gracilis 19 21 24 25 27 29 31 epiprecapnelladiene 128 32 35 562 563 564 570 epiprezizaene 149 Euonymus alatus var.striatus 154 episesartemin A (+)- 195 eupalestin 503 episesartemin B (+)- 195 Eupatorium adenophorum 149 episterol 546 eupha-7,24-diene 6 epoxyagroclavine-I 53 Euphorbiu lathyris 544 epoxygermacrane D 154 Euphorbia royleana 6 2,3-epoxysqualene lanosterol-cyclase 533 Euphorbia supina 12 epoxyzinamultifloride 153 Euphrasia rostkoviana 205 EPSP synthase 309 496* 497 Euplexaura erecta 157 ercalciol 5,lO-didehydro-6,19-epidioxy-eupodienone-l 200 202 5,6,10,19-tetrahydro- 480 eupodienone-2 200 ercalciol p-D-glucopyranoside 483 eupodienone-3 200 ercalciol 6-hydroperoxy-4,5-didehydro-5,6-eupomatenoid-1 204 dihydro- 480 eupomatenoid-3 204 ercinamine 62 eupomatenoid-4 204 ercinaminine 62 eupomatenoid-5 204 eremophilane 138 156 eupomatenoid-6 204 eremophilone 138 eupomatenoid-7 204 a-ergocryptine 2-bromo- 54 eupomatenoid- 13 204 ergopeptine synthetase 173 Eupomatia laurina 200 202 ergosterol 527 547 Eurema hecabe mandarina 25 I ergosterol biosynthesis 545 546 550 Eurycoma longijolia 8 ergosterol 22,23-dihydro- 546 eurycomalactone 8 478 eurycomanol 7 ergosterol 25-hydroxy-7,8-dihydro- eurycomanone 7 ergosterol-triazoline adduct 465 euryfuran 100 ergot alkaloids 53 ergot alkaloids biosynthesis 173 eusiderin-B 208 Eriobotrya japonica 437 eusiderin-C 208 eriodictyol 502 eusiderin-D 208 eriolin 152 Eutreptiella gyrnnastica 349 Ervatamia coronaria 66 eutreptiellanone 349 Erwinia carotovora 453 454 Evodia grauca 6 Erwinia spp.440 erythromycin A biosynthesis 342 faberidine 230 erythromycin B biosynthesis 342 faberonine 230 Escherichia coli 30 306 312 315 316 321 factor F-430 40 574 381 432 441 495 496 497 555 564 565 factor I 36 576 Escherichia coli strain RB791 308 factor 11 36 Eschscholtzia californica 84 86 168 229 factor 111 38 571 Eschscholtzia tenuijolia 166 factumycin 41 1 eschscholtzine 84 Fagara heitzii 393 esculetin 501 Fagara mayu 393 esculin 502 fagaronine 90 91 estafiatin 140 Fagonia indica 12 etaconazole 546 falcarindiol 449 ethrel 431 falcarinol 449 et h y1 3,5-d imethylorsell inate 405 faranal 98 ethyl monate C 401 402 fargesin I95 ethylmorphine 89 fargesin 2-epi- 195 ethyl retinoate 360 fargesin demethyl- 195 etiohaem 575 farnesane 98 147 etioporphyrin 111 575 0-farnesene 98 102 etioporphyrin 111 132,15-cyclo- 575 p-farnesene trans- 5 16 etorphine 90 farnesic acid 98 eucannabinolide 133 I33 farnesoic acid 9-hydroxy- 429 Eucommia ulmoides 195 farnesol 36 eudesmane 136 154 farnesol 9-hydroxy- 428 eudesmol 137 farnesol 9-oxo- 428 Eudiaptomus amblyodon 375 farnesyl diphosphate 527 Eudistoma olicaceum 5 1 Fatsia japonica 11 eudistomin A 51 fatty acids biosynthesis 32 1 eudistomin C 51 fatty-acid-binding protein 536 eudistomin D 51 faurinone 158 eudistomin E 51 fauronyl acetate 139 eudistomin G 51 fecosterol 546 eudistomin H 51 fecosterol 14a-methyl- 545 eudistomin I 51 fenarimol 544 546 eudistomin J 51 fenchol (-)-endo- biosynthesis 515 eudistomin K 51 fenchone (+)- 276 eudistomin L 51 fenchones dibromo- 260 eudistomin M 51 ferreirin 447 eudistomin N 51 ferrochelatase 30 564 eudistomin 0 51 ferruginol 522 eudistomin P 51 Ferula elaeochytris 149 eudistomin Q 51 Ferula karatavica 148 Ferula lapidosa 149 Ferula lehmannii 148 Ferula microloba 148 Ferula penninervis 157 Ferula tschatcalensis 1 50 trans-ferulate 5-mono-oxygenase7 500 ferulic acid 439 499 ferulic acid 5-hydroxy- 500 501 ferulic acid 5-hydroxylase 500 feruloyltyramine 500 Festuca arundinacea 218 ficaprenol-1 1 376 flavan 7-hydroxy- 439 flavan phytoalexins 439 flavanone 3-dioxygenase 502 flavanones biosynthesis 502 flaviolin 329 flavone glycosides 438 flavones biosynthesis 502 flavonoids biosynthesis 502 flavonoids glycosylation 503 flavonoids methylation 503 flavonoids prenylated 5 14 flavonol 03-glucosyltransferase 503 flavonols biosynthesis 502 flavopereirine 58 flavopereirine 5,6-dihydro- 58 Fleischmannia pycnocephala 195 Flexihacter elegans 417 Flexibacter sp.350 flexirubin 41 7 flexixanthin 350 flourensic acid 138 Flustra joliacea 52 flustramine B (-k)-,52 flustramine B (+)-debromo- 52 Foeniculum culgare 5 1 5 Fomes annosus Cooke 424* formononetin 441 442 446 504 formononetin 7-O-glucoside 505 Forsythia suspensa var.jortunei 204 fraxetin 501 fredericamycin A 41 2 Frullania brotheri 154 frullanolide (+)- 155 frustulosin 4 16 fruticarpin 448 fucosterol 546 547 550 55 1 552 554 fucosterol 24,28-epoxides 55 1 552 fucosterol 29-hydroxy- 550 fucoxanthin 374 fulvine 213 fumaramidine 86 fumaramine (E)-,86 fumaramine (Z)-,86 Fumaria densflura 84 86 Fumaria densijolia 8 7 Fumaria gaillardotii 84 86 87 Fumaria oficinalis 84 87 Fumaria parijpora 86 Fumaria r-aillantii 81 82 84 86 87 90 fumaricine 87 fumaricine (-)- 86 fumariline 87 fumaritine 87 fumaritrine ( )- 87 fumarofine 87 fumarofine O-methyl- 87 fumarophycine 0-methyl- 87 fumigaclavine A 53 0-funaltrexamine 90 funebrine 181 fungi compatible 433 fungi incompatible 433 funiculosin 41 1 furanomycin 324 41 3 furocoumarin phytoalexins 438 furoquinoline alkaloids 396 furylindolizidine alkaloids 235 furylquinolizidine alkaloids 235 fusarentin 332 Fusarium culmorum 263 264 Fusarium larvarum 332 Fusarium martii 332 Fusarium oxysporum f.sp.lycopersici 449 Fusarium roseum 337 Fusarium solani 450 453 454 Fusarium solani f.sp. mori 439 440 Fusarium solani fsp. phaseoli 450 451 Fusarium spp. 451 456 fusarubin 332 fusidic acid 550 futoene 206 Gaillardia aristata 158 Gaillardia pulchella 158 Galium mollugo 507 gallic acid biosynthesis 498 Gallus domesticus 538 ganoderic acids U-Z 1 Ganoderma applanatum 430 Ganoderma lucidurn 1 Gardenia jasminoides 499 502 5 15 520 gardenoside biosynthesis 5 15 gazaniaxanthin 37 1 geibalansine 396 geissoschizine 169 Gelsemium elegans 63 Genista pilosa 24 1 Genista spp.239 genistein 444 447 504 genistein 2’-hydroxy- 447 gent iopentaose 3’J4-di-( O-P-D- glucopyranosy1)- 452 456 geoporphyrins 575 gephyrotoxin 238 geranial 10-oxo- 515 geranyl diphosphate 527 geranyl diphosphate 2-fluoro 527 geranylgeranyl diphosphate 34 17 1 570 geranylgeranyl pyrophosphate 34 17 1 570 geranyltranstransferase 528 germacradiene 125 germacrane 133 150 germacranolides 133 151 152 germacranolides cis,cis- 152 germacrone 133 germichrysone 335 Gibberella jujikuroi 520 gibberellic acid 429 gibberellin A I 520 gibberellin A, 520 gibberellin A4 520 gibberellin A, 520 gibberellin A8 520 gibberellin A9 520 gibberellin A I aldehyde 5 19 gibberellin A I aldehyde 12cl-hydroxy- 520 gibberellin A ? 12a-hydroxy- 520 gibberellin A J 12cl-hydroxy- 520 gibberellin A 7 520 gibberellin A 19 520 gibberellin AZO 520 gibberellin 520 gibberellin A?<) 520 gibberellin 12cl-hydroxy- 520 gibberellin AS3,520 gibberellin Ass 520 gibberellins biosynthesis 5 19 gilvocarcin M biosynthesis 339 gilvocarcin V.biosynthesis 339 gindarine 84 Ginkgo biloba 376 377 glaucic acid 156 glaucine 3-hydroxy- 227 Glaucium corniculatum 82 86 90 228 229 Glaucium jimbrilligerum 84 228 229 glaufidine 228 NATURAL PRODUCT REPORTS 1985 Glediisia japonica 1 1 gleditsia saponins 11 Gliocladium deliquescens 173 Gliocladium virens 150 gliotoxin biosynthesis 173 globiferine 21 8 Glomerella cingulata 43 1 432 P-glucanases 45 1 glucan endo- 173-P-glucosidase 452 D-glucose 2-deoxy- 308 P-D-glucose 1-0-irans-cinnamoyl- 499 P-D-glucose 1-0-p-coumaroyl- 499 P-D-glucose 1,2-di-O-sinapoyl- 499 P-D-glucose 1-0-sinapoyl- 500 glucosinolate 4-hydroxy-3-methoxybenzyl- 247 glucosinolate indol-3-ylmethyl- 49 glucosinolate l-methoxyindol-3-ylmethyl- 49 glucosinolates 247 glutamate 1-semialdehyde 20 56 1 glutaric acid a-keto- 20 294 glutaric acid 2-0xo- 20 294 glutinosone 431 glycarpine 396 glyceollin I 444 449 glyceollin 11 444 glyceollin 111 444 449 glyceollins 442 454 glyceollins biosynthesis 504 glycerol 2,3-di-O-phytanyl-sn- 377 glycerol 2,3-di-O-sesterterpanyl-sn-, 377 glycerol 2-O-sesterterpanyl-3-0-phytanyl-sn- 377 glycine 173 177 glycine D-allyl- 303 glycine D-(4-hydroxyphenyl)- 304 glycine ~-(4-hydroxyphenyl)- 304 Glycine max 376 441 444 452 503 504 544 glycine N-(phosphonomethy1)- 3 12 496 glycinol 444 glycoalkaloids steroidal 433 glycobismine-A 398 glycofoline 397 glycolate oxidase 298 glycolic acid 298 glycomarine 82 glycophylone 394 glycosminine 396 Glycosmis citrijolia 393 397 398 Glycosmis cyanocarpa 396 Glycosmis pentaphylla 393 394 glycosylase I 452 glycosylases 45 1 glyoxylic acid 298 glyoxylic acid ( 1’R)-cyclohex-3’-enyl- 508 glyphosate 3 12 496 gmelanone 196 Gochnatia paniculata 148 157 gomaline 62 gomisin A 200 gomisin B 199 200 gomisin C 199 200 gomisin D 199 200 gomisin E 200 gomisin F 200 gomisin G 200 gomisin H 200 gomisin J 200 gomisin K 200 gomisin K, 200 gomisin K, 199 200 gomisin N 199 200 gomisin 0,200 gomisin P 200 gomisin Q 200 gomisin R 200 Gonyaulax polyedra 372 NATURAL PRODUCT REPORTS 1985 1-4 1 gorgosterol 472 554 gorgosterol 23-demethyl- 554 Gossypium hirsutum 528 Gossypium spp.429 gouregine 82 govanine (-)- 84 gramicidin S 293 gramine 5,7-dimethoxy- 49 gramine 7-methoxy- 49 Gramineae alkaloids 218 grandiflorine 87 grantaline 2 I8 grantianine 2 18 graucin A 6 graucin B 6 graucin C 6 graveolone 438 Grazielia serrata 152 grazielolide 152 gregatin B 406 griseofulvin 565 grossamide 205 guacolidine 228 guacoline 228 guadiscidine 228 guaiagrazielolide 157 guaiane 139 156 guaian-6~, 12-olides 157 guaianolides 157 guanidinium 3-iodoxybenzoate NNN‘N’-tetramethyl-N”-t-butyl- 470 guattegaumerine 83 Guatteria discolor 228 229 230 231 Guatteria gaumeri 83 Guatteria modesta 229 23 1 Guatteria ouregou 82 84 228 229 231 Guatteria scandms 84 Guettarda heterosepala 56 guettardine 56 170 guillauminine 76 Guillonea scabra 157 guillonein 157 gummadiol 196 gymnopilin 376 gymnopilin A<, 376 gymnopilin A 376 gymnopilin B ,,376 Gymnopilus spectabilis 376 gymnoprenol A 376 gymnoprenol B 376 377 gymnoprenol D 376 gymnoprenol E 376 Gynura segetum 2 18 haem 30 haem a 562 565 haem a biosynthesis 30 565 haem biosynthesis 19 561 haem d 565 haem d, 566 haem degradation 42 haem oxygenase 568 haem oxygenase (decyclizing) 566 haem synthase 30 haematoporphyrin derivative 42 577 Haliphthoros mi!fbrdensis 546 hallerin 15 1 hallerol 15 I Halobacterium halobium 37 1 375 halorhodopsin 372 hanegokedial 141 Hannoa klaineana 5 1 57 Hansenula anomala var.schneggii 77 Hansjordia puhinata 156 hapaltine acetate 393 haplocidine 18-0xo- 65 haplocidiphytine 76 haplophylline 394 Haplophyllum dauricum 196 393 Haplophyllum obtusijolium 393 Haplophyllum suaveolens 393 394 Haplophyllum vulcanicum 393 Haplophyton cimicidum 76 hardero’gen 28 Harpullia cupanioides 10 Hebeloma crustulinifbrme 1 Hebeloma sinapizans 2 Hebeloma vinosophyllum 2 hecogenin 10,7P-dihydroxy- 490 helenalin 158 Helenium puberulum 157 158 heliamine 1,2-didehydro- 81 heliangolides 15 1 152 helianthol A 148 Helianthus annuus 520 Helianthus tuberosus 148 5 13 Helichrysum bracteatum 195 Heliobacterium chlorum 57 1 heliocoromandaline 2 17 heliocurassavicine 21 7 heliocurassavine 21 7 heliocurassavinine 2 17 heliotridine 214 Heliotropium curassavicum 2 17 heliovinine 21 7 hellebrigenin 3-esters 487 Helminthosporium carbonum 446 448 449 Helmin t hospo rium sa tivum 26 3 hemigossypol 429 Hemileia vastatrix 434 hemiterpenoids biosynthesis 5 13 Heptacyclum zenkeri 84 heptaketides biosynthesis 332 heptaprenol [~-(trans)~-(cis)~]-, 377 heptaprenyl diphosphate 379 heptelidic acid 150 heptonic acid 7-phosphate 3-deoxy- 308 heptulosonic acid 7-phosphate 3-deoxy-D- arabino- 308 Herberta adunca 148 herbertane 148 herbertenediol (-)- 148 herbertenolide (-)- 148 herbolide D 152 hercynolactone 149 Hernandia guianensis 229 Hernandia ovigera 196 Hernandia peltata 83 heroin 88 90 89 herpes simplex virus 51 Herpetospermum caudigerum 202 herpetrione 202 Heterobasidion annosum (Fr.) Bref 424* Heterotheca sp.115 Heterotropa takaoi 207 208 heterotropan 208 heterotropanone 208 heterotropatrione 208 heteroyohimbine alkaloids 55 Hevea brasiliensis 527 hexaketides biosynthesis 330 hexanoic acid 3-hydroxy-3-methyl-6- phosphono- 527 hexaphyrins 576 Heynea trijuga 3 heynic acid 3 himachalane 118 125 150 0-himachalene 118 himalayine 87 himasecolone 118 hinesol 138 hinokinin 194 hircinol 437 506 hirsutane 129 hirsutene 128 129 132 hirsutic acid 129 hirsutinolide 152 histidine 171 hobartine (-)- 55 holochrome 34 Holothuria Jloridana 3 holothurin A 3 holothurin B, 3 homaline 245 Homarus americanus 370 375 Homarus gammarus 370 homoaromoline 83 homochelidonine (*)- 91 homocysteine S-adenosyl- 550 homogeranoic acid 367 homononactic acid 344 homospermidine I64 homotetrahydroberberines 85 hopane-l0,22-diol 30-acetoxy- 12 hopan-30-01 12 hopan-28,22-olide 17,24-dihydroxy- 12 hop-22(29)-en-3P-ol 12 Hordeum vulgare 503 561 HorsJeldia iryaghedhi I95 horsfieldin 195 hosenkol-A 13 533 Hovenia dulcis 6 hovenolactone 6 Hoya australis 10 huanshanine 230 Humata pectinata 12 humbertiol 148 humulane 125 150 humulene 125 126 128 133 517 humulene biosynthesis 5 17 humulen-13-oic acid 126 Humulus lupulus 158 hunnemanine 86 hybridalactone 322 hyderabadine 66 hydrasteine N-methyl- 86 P-hydrastine 86 hydrastine N-methyl- 86 hydrogenobyrinic acid 573 hydrohydrastinine 8 1 P-hydroxyacyl thioester dehydrase 322 hydroxycinnamate-CoA ligase 500 3-hydroxydecanoyl-[ ac yl-carrier-protein] dehydratase 321 0-hydroxydecanoyl thioester dehydrase 32 1 hydroxymethylbilane synthase 22* 563* (3S)-3-hydroxy-3-methylglutaryl-coenzyme A 525 hydroxymethylglutaryl-CoA lyase 429 hydroxymethylglutaryl-CoA reductase 5 13 525 hydroxymethylglutaryl-CoA reductase inhibitors 526 hydroxymethylglutaryl-CoA reductase (NADPH) 442 513 525 536 [hydroxymethylglutaryl-CoA reductase (NADPH)] kinase 526 [hydroxymethylglutaryl-CoA reductase (NADPH)]-phosphatase 526 hydroxymethylglutaryl-CoA synthase 525 hydroxymethylstylopine 84 hydroxynorlaudanosine 82 hydroxyrutacridone epoxide 440 hydroxyspheroidene 375 3(or 17)cc-hydroxysteroid dehydrogenase 541 3(or 17)S-hydroxysteroid dehydrogenase 538 2Ow-hydroxysteroid dehydrogenase 54 1 (R)-20-hydroxysteroid dehydrogenase 54 1 hyoscyamine biosynthesis 500 hypecorine 85 Hypecoum procumbens 85 hypercratine 182 hypersensitive response 431 433 454 Hypholoma fasciculare (Huds.ex Fr.) Kummer 2* Hypocrea citrina 4 1 6 ffypomyces semitranslucens 403 1-42 NATURAL PRODUCT REPORTS 1985 hypophyllanthin 197 ipomeamaronolide 429 isoflavans biosynthesis 505 Hypoxylon serpens 407 ipomeatetrahydrofuran 429 isoflavone 3’ 7-di hydroxy-4‘-me t hox y-,442 hypsorhodopsin 372 373 Ipomoea batatas 154 428 499 5 17 isoflavone 7-hydroxy-3’,4-methylenedioxy-, Hyptis suaveolens 8 iridodial 5 15 442 iridodial 8-epi- 5 15 isoflavone synthase 503 iridogermanal 353 isoflavone 2’,4‘,7-trihydroxy- 444 445 Ianthella basta 350 iridotrial 5 15 isoflavones isoprenylated 447 ibogamine alkaloids 7 1 iridotrial 8-epi- 5 15 isoflavonoids biosynthesis 503 icosa-5,8,11,14,17-pentaenoicacid 322 433 iriflorental 13 353 376 isofucosterol 544 547 551 552 ikarugamycin 408 a-irigermanal 353 isofucosterol 24,28-epoxides 552 ilicicolin H 334 335 41 1 y-irigermanal 353 isofutoquinol A 208 ilicicolin H biosynthesis 173 iripallidal 13 353 isofutoquinol B 208 illudane 150 iripallidol 376 isogeissoschizol 56 imidazole alkaloids 245 Irisflorentina 13 353 Impatiens balsamina 13 533 Iris germanica 353 isogeissoschizol 10-methoxy- 56 indanobenzazepines 87 Iris pallida 13 353 isogomisin 0 200 indole-3-acetic acid biosynthesis 499 Iris spp.376 isohardero’gen 29 indole 3-[2-(3-acetyl-N-piperidino)ethyl1-2-Iris versicoior 13 isohematinic acid 410 isoheterotropanone 208 ethyl- 65 iriversical 13 isoheterotropatrione 208 indole alkaloids monoterpenoid 54 a-irone 376 indole alkaloids terpenoid biosynthesis 168 a-irone (-)-(2S,6R)-cis- 353 i soindolobenzazepi nes 87 isoindoloisoquinolines 86 indole-3-carbaldehyde 499 a-irone (+)-(2S,6S)-trans- 353 isoiridogermanal 353 indole-3-carboxylic acid 499 P-irone 376 indole 3-dimethylaminoacetyl-5-methoxy- y-irone 376 isolanosterol (20s)- 2 50 isolariciresinol 4-methyl ether 197 isoliovil 195 indole-3-ethano1,499 y-irone cis- 366 Isolona pilosa 227 229 indole-3-methano1 499 y-irone trans- 366 Isoiona zenkeri 227 229 indole-3-pyruvic acid 498 Zryanthera grandis 197 isolubimin 432 433 infractine 5 1 ishwarane 138 139 infractine 6-hydroxy- 5 1 ishwaran-12-01 7,12-seco- 139 isolysergol (+)- 53 infractopicrine 5 1 islandic acid 404 isolysine 176 isomagnolol 207 integerrimine 2 16 isoantirhine 56 isomyomontanone 147 Inula helenium 152 isoasatone A 207 hula indica 15 1 isoasatone B 207 isoneopine 88 iso-obacunoic acid 3,10-1actone Inula racemosa 154 isoaustin 404 Inula royleana 152 isobacteriochlorin 37 38 1(1O+l9)abeo-7a-acetoxy-l0~-hydroxy-, 6 Inula sp.152 isobacteriochlorins 38 576 isopatchoul-3-ene 5 17 inundoside G 14 isobatatasin I 437 506 isopatchoulenol 5 17 inundoside G , 14 isobazzanene 148 isopavines 84 inuolide 15 1 isobisabolene 100 isopeltatin (+)- 199 a-ionol 368 isobornyl acetate (+)- 262 isopenicillin N 174 175 293 294 a-ionol 9-methyl- 367 isobornyl acetate 5-OXO- 262 isopenicillin N 2-demethyl- 302 a-ionol 3-OXO- 353 10-isobornyl sultone 279 isopenicillin-N synthetase 175 294 P-ionol 368 a’-is0 bu falin 48 7 isopentenyl diphosphate 171 527 isopentenyl diphosphate biosynthesis 529 P-ionol 5,6-epoxy-3-hydroxy-5,6-dihydro- isocadalene 4-methoxy- 117 353 isocalycinine 228 isopentenyl diphosphate 2,2-difluoro- 528 isopentenyl diphosphate 2-fluoro- 528 P-ionol (3S,5 R,6 R,9 R)-3,6-epoxy-5-hydroxy- isocalysterol 23H- 554 5,6-dihydro- 353 isocamphorquinone 279 isopentenyl-diphosphate A-isomerase 5 13 P-ionol 9-methyl- 367 isocaryophyllene 119 527 isopentenyl pyrophosphate 17 1 527 a-ionone 366 367 368 isocentratherin 152 a-ionone 7-methyl- 365 isochamaecydin 13 isophorone 365 isophytolaccinic acid A 10 P-ionone 366 368 371 isochanoclavine 53 P-ionone 4-acetoxy- 367 isocitrate dehydrogenase 3 16 isophytolaccogenin A 10 P-ionone 4-bromo- 368 isoclovane 119 isopimpinellin 438 isoplatydesmine 395 P-ionone 9-chloro- 368 isoclovene 120 P-ionone 3,4-didehydro- 368 isocochliodinol 74 isopluviatolide (-k)-,194 0-ionone (-)-(4R)-4-hydroxy- 354 isocodeine 88 isoprene 5 13 353 isocomane 12 1 isopropyl 1-thio-0-D-galactopyranoside, P-ionone 3-hydroxy-7,8-didehydro- 308 P-ionone (E)-7-methyl- 365 isocomene 12 1 isopulegol 1 16 P-ionone 4-propionyloxy- 367 isocomenic acid 121 isoquinoline alkaloids 8 1 y-ionone 366 isocorypalmine 84 isoquinoline alkaloids biosynthesis 166 P-ionones 5,6-epoxy-5,6-dihydro- 366 iso-a-curcumene 102 3-isorauniticine 57 a-ionylideneacetaldehyde,367 isocyclobazzanene 148 3-isorauniticine 14a-hydroxy- 60 P-ionylideneacetaldehyde,367 isodaurisoline 83 3-isorauniticine pseudoindoxyl 57 a-ionylideneacetic acid 366 isodehydrochelidonine 90 isorenieratene 3,3‘-dihydroxy- 350 a-ionylideneacetic acid (7E,9Z)- 376 isodendrolasin (4E)-1,6-dioxo- 429 isoreserpine 14a-benzoyloxy- 60 a-ionylideneacetic acid (9Z)- 366 isodendrolasin (42)-1,6-dioxo- 429 isoreserpine 14a-hydroxy- 60 P-ionylideneacetic acid (92)-5,6-epoxy-5,6- isodeoxypodophyllotoxin,( -t)- 199 isoretinol 360 dihydro- 366 isodictamnine 5,7-dimethoxy- 396 isoretronecanol 2 13 P-ionylideneacetic acid 5,6-epoxy-5,6-di- 3P-isodihydrocadambine 56 isoretulinal 75 hydro- 19-nor- 366 Isodon japonicus 53 1 isoretulinal 12-hydroxy- 75 a-ionylideneethanol (7E,92)- 376 isodrimeninol 100 isoretuline 18-acetoxy-N,-deacetyl-,64 ipalbidine 239 isoeburnamine (-)- 66 isosalicin biosynthesis 499 ipomeabisfuran 428 isoepicubenol 115 isosativan 446 ipomeabisfuran 10-hydroxy- 429 isoeugenol 501 isosativanone 446 ipomeamarone 428 428 isofenchone ( +)-9-bromo-6-endo-methyl- isosclerone 329 ipomeamarone (+)- 147 429 256 isosesquicarane 148 ipomeamarone biosynthesis 5 17 isofenchone 9-bromo-6-endo-methyl- 260 isosesquicarene 104 ipomeamarone 7,8-didehydro- 428 429 isofenchone syn-7,9-dibromo-6-endo-methyl- isosilerolide 155 ipomeamaronol 428 260 isositsirikine 16-epi-(Z)- 56 NATURAL PRODUCT REPORTS 1985 isositsirikine Nb-oxide 56 isositsirikine Nb-oxide 16-epi-,56 isosteganacin 199 isostegane ( -)- 202 isostrychnobiline 16,17-didehydro- 75 isothebaine O-methyl- 227 isotrilobine 83 83 isovallesiachotamine 56 isozeaxanthin 370 isozeaxanthin (4R,4’R)- 354 isozeaxanthin epoxides 357 izmirine 86 jaeschkeanadiol 149 janthitrems 50 Jasminum oficinale 52 1 jasmonic acid 433 Jatropha gossypijolia 193 jatrorrhizine 84 85 167 jinkoheremol 156 jinkohol 11 149 juglone 2-hydroxy- 329 julandine 239 Jungia stuebelii 156 157 158 jungistuebane 156 Juniperus spp.196 522 Justicia extensa 196 Justicia Jaca 196 Justicia prostrata 196 Justicia simplex 195 justicidin P 196 justicinol 196 justisolin 195 juvabione 148 juvabione threo- 102 juvenile hormone JH-111, 519 juziphine 82 Kadsura japonica 199 kadsurin 199 kaempferol 502 503 kaempferol 2,3-dihydro- 502 kaurene ent- 520 kaurene ent- biosynthesis 519 kaurenoic acid 520 kaur- 16-en- 19-oic acids 520 kayawongine 239 a-ketoglutaric acid 20 294 ketomycin biosynthesis 508 khusimone 114 kievitone 444 447 450 453 kievitone 5-deoxy- 447 kievitone 2,3-didehydro- 447 kievitone hydratase 450 451 kievitone hydrate 450 kievitone hydrate 5-deoxy- 448 kievitone 4’-O-methyl- 448 Kigeliu pinnutu 195 kigeliol 195 kijanimicin 334 kirrothricin 41 1 Klehsicdla pnwmoniae 31 1 312 3 13 496 Kluyiw-om?xs Iactis 522 Knrma attenuutu 197 Knightia strohilina 223 knightinol 223 knightinol acetyl- 223 Kokoona zeylanica I1 kombic acid.379 kopsamine 66 kopsane 10,22-dioxo- 69 kopsanone 69 Kopsia dasjwchis 186 247 Kopsia longiflora 66 Kopsia ofJicinalis.56 66 76 kopsilongine 66 kopsinal 3-OXO-l 4,15-seco- 66 kopsinaline ( -)-I 1,12-dimethoxy-N,-methoxycarbonyl- 66 kopsinaline (-)-12-methoxy- 66 latisodine 249 kopsinaline (-)-N,-methoxycarbonyl-1 1,12- latisoline 249 methylenedioxy- 66 lauformine 227 kopsinaline (-)-12-meth0~y-N~-lauformine N-methyl- 227 methoxycarbonyl- 66 laurane 148 148 kopsinaline (-)-I 1,12-methyIenedioxy- 66 laureacetal-D 149 kopsinine (-)- 76 laureacetal-E 149 kopsinine 3-oxohydroxy- 66 Laurelia novae-zelandiae 227 229 23 1 kopsirachine 186 247 Laurencia hybrida 322 kopsoffine (+)- 76 Laurencia nipponica 149 Krameria spp. 204 Laurencia obtusa 148 Laurencia okamurai 1 laurencial 149 laburnine 2 17 laurenobiolide 134 15 1 Laburnurn alpinum 166 laurycolactone A 8 Laburnum anagyroides 166 laurycolactone B 8 Laburnum spp.239 Lavandula angustijolia 52 1 lacinilene C 429 Leguminosae alkaloids 218 p-lactam antibiotics biosynthesis 293 lemnaphylla-7,21-diene 13 p-lactams biosynthesis 174 Lemnaphyllum microphyllum 6 6 1 3 13 Luctarius necator 150 lennoxamine 86 Lactarius vellereus 150 lennoxamine (-+)- 87 L-lactate dehydrogenase 3 13 Lepidoptera alkaloids 2 18 1,54actonase 527 lepiochlorin 407 laevulinic acid 21 Lepiota sp. 407 laevulinic acid 5-amino- 19 21 561 leptolepisol A 202 laevulinic acid 3-chloro- 21 laevulinic acid 5-chloro- 21 leptolepisol B 203 laevulinie acid &amino- 19 21 561 leptomycins 404 lagerenol 3 lespedamine 5I Lagerstroemia lancasteri 3 Lespedeza sericea 9 lanceol 101 Leucaena leucocephala 520 lancifolin A 204 Leucanthemopsis pulverulenta 152 lancifolin B 204 Leucoagaricus naucina 247 407 lancifolin C 204 leucocyanidin 502 lancifqlin D 204 leucoxylonine 229 lancifolin E 204 Liatris acidota 152 lancifolin F 204 Liatris aspera 152 lancilin 208 Liatris laevigata 154 lanosta-6,20(22)-dien-3~-ol,30-nor- 2 Liarris mucronata 152 lanost-8-ene-3,l Sdione (23S,24S)-17,23- Licaria armeniaca 206 206 epoxy-24,3 1-dihydroxy-27-nor- 2 Licaria rigida 208 lanosterol 530 533 534 536 537 544 545 lignans 192 546 lignans biosynthesis 203 501 lanosterol 3-epi- 533 lignans classification 19 1 lanosterol 24,25-dihydro- 534 537 lignans coumarino- 501 lanosterol 24,25-dihydro-27-nor- 537 lignans nomenclature 191 lanosterol 24,25-epoxy- 530 lignins biosynthesis 500 lanosterol 24P-methyl- 546 Ligularia dentata 2 17 545 ligularidine 2 17 lanosterol 24-methyIene-24,25-dihydro- 546 ligularinine 218 lanosterol synthase 530 536 ligularizine 21 8 lanosterol (20s)-tetranor- 530 Ligustrum japonicum 194 lansioside A 13 liliflodione 207 lansioside B 13 liliflol A 205 lansioside C 13 liliflol B 205 Lansium domesticum 13 liliflone 205 Lantana camara 10 limogine 87 Lantana tiliaejolia 12 limonene 522 lapiferin 149 limonene biosynthesis 515 lapiferinin 149 limousamine 82 lappaol A 202 203 linalyl acetate (-)-(I+ 429 lappa01 AL-D 202 Lindera glauca 156 lappaol AL-F 202 lindoldhamine 83 lappaol B 202 lindoldhamine NN-dimethyl- 83 lappaol C 202 203 lindoldhamine 7-O-methyl- 83 lappaol D 202 203 lindoldhamine 7’-O-methyl- 83 lappaol E 202 203 linifolin A 140 lappaol F 202 203 linoleic acid 435 lappaol H 202 203 linolenic acid 433 lariciresinol 194 lintetralin 197 lariciresinol monomethyl ether 194 lipoxygenase 433 433 Lark Ieptolepis 202 207 Lippia integrijolia 150 Laserpitium halleri 151 liquirit igenin 504 Laserpitium siler 154 155 lirinine 227 Lasiolaena morii 205 lirinine O-methyl- 227 lasubine I 242 liriodendrin 195 204 lasubine 11 242 Liriodendron spp.227 lathycarpin 448 Liriodendron tulipijera 152 157 195 198 Lathyrus sativus 448 449 204 1-44 NATURAL PRODUCT REPORTS 1985 lirionol 197 lithocholic acid Ia-hydroxy- 479 Lithospermum erythrorhizon 502 507 Litsea wightiana 229 LL-D253a biosynthesis 33 1 loganin 522 loganin biosynthesis 5 15 loline 2 18 loliolide 367 lolitrem A 50 lolitrem B 50 lolitrem C 50 lolitrem D 50 Lulium perenne 50 247 longibornane 125 150 longi bornane 2,4-dioxo-3,4-seco- 150 longibornane 2a,4a-endoperoxide 2p- hydroxy- 150 longiborn-3-en-2-al 2,3-seco- 150 longicaudatine 75 longicaudatine F 75 longicaudatine Y,75 longicornin A 153 longicornin B 153 longicornin C 153 longicornin D 153 longifolane 125 150 longifolene 1 18 longipinane 125 150 longipinane-2,7-dione cis- 150 longipinan-2-one 150 Loniceru morro wi 515 Lonicera tatarica 522 lophenol 24-methylene- 544 Luphocereus schottii 544 Lophophoru echinata 81 Lophophora williamsii 81 loroxanthin 350 lubimin 433 lubiminol 433 lucidin 3-O-primeveroside biosynthesis 507 ludovicin 1-epi- 155 Lufla aegyptica 11 lunularic acid 507 lupanine 166 440 lupanine 13-tigloyloxy- 440 lup-20(29)-ene-lp,3P,1 la-triol 8 lup-12-en-28-oic acid 3P-hydroxy- 8 lup-20(29)-en-27-oic acid 3P-hydroxy- 8 lupeolactone 8 lupinine 164 165 lupinine alkaloids 239 Lupinus alpinum 24 1 Lupinus luteus 165 241 Lupinus mutabilis 239 24 I Lupinus polyphyllus 440 lutein 358 370 371 374 375 luteolin 502 luteone 449 lychnocolumnic acid 126 Lychnophora salicifulia 1 50 lychnophorolide A 152 lychnosalicifolide I50 lychnosalicifolide 2-epi- 150 Lycium chinense 154 353 lycopene 351 375 lycopene 1,2-epoxy- 37 1 Lycopersicon esculentum 433 496 50 1 Lycopersicon peruliianum 5 18 lycoramine 25 1 lycorenine O-methyl- 25 1 lycorine-l-O-P-D-glucoside,249 Lycoris radiata 25 1 lysergene (?)- 53 lysergic acid 53 lysergine 53 lysine 164 176 a-lysine 176 0-lysine 176 lysine 6-pyridoxyl- 24 Lythraceae alkaloids 242 maackiain (+)- 443 444 449 maackiain (-)- 442 443 444 449 maackiain biosynthesis 504 maackiain (-)-4-methoxy- 449 Machilus japonica 194 Machilus zuihoensis 193 194 machilusin 194 Macleaya microcarpa 167 macommelins 402 macrocyclic pyrrolizidine alkaloids synthesis 2 16 macrolides biosynthesis 341 Macrophoma commelinae 402 macrophyllin B 207 macrostomine 82 macrostomine N-oxides 82 Mactra chinensis 349 mactraxanthin 349 magnesium chelatase 569 magnesium-protoporphyrin magnolenin-C 194 Magnolia denudata 205 207 Magnolia grandiflora 194 Magnolia hypoleuca Sieb.et Zucc.207* Magnolia IilifIora Desr. 205* 207* Magnolia ohovata Thunb. 207* Magnolia quinquepeta (Buc’hoz) Dandy Magnolia salicifolia I97 Magnolia stellata 194 Magnolia x soulangiana 152magnolol 204 magnoshinin 197 magnostellin A 194 magnostellin B 194 malekulatine 83 malic acid (-)-(S)-,429 malic enzyme 3 16 malloprenols 379 malonamyl-CoA 338 malonomicin 408 mamanine N-oxide (-)- 241 manassantin A 203 manassantin B 203 Manduca sexta 477 552 553 manicol 159 manicoline B 182 mansanone C 150 mansanone D 150 mansanone E 150 mansanone F 150 marasmane 150 Marchantia polymorpha 507 marmesin 440 marticin 332 maslinic acid 3-epi- 531 maslinic lactone 10 matairesinol dimethyl ether 194 matopensine 75 Matricaria chamomilla 522 matrine alkaloids 239 matrine ( +)-9~-hydroxy- 241 Matthiola incana 502 maysine 247 maytansine 247 maytenfolic acid 9 9 maytenfoliol 11 Maytenus diiiersijolia 9 11 Maytenus uariahilis 247 mearsine 183 Meconopsis villosa 87 Medicago rugosa 446 Medicago sativa 544 medicarpin (+)- 449 medicarpin (-)- 442 446 449 methyltransferase 32 569* 205* 207* medicarpin biosynthesis 504 medioresinol bis-p-D-glucoside (+)- 195 medioresinol mono-0-D-glucoside (+)- 195 megaphone 206 megastigmatrienone 367 mehranine 66 melampodin A 153 Melampodium longicorne 153 Melampodium rosei 152 I 53 melampolides 152 melanin biosynthesis 329 melcanthin A 153 melcanthin B 153 melcanthin C 153 meleagrin 52 Melia azedarach 6 7 meliatoxins 6 Melicope leptococca 50 393 397 Melilotus alba 11 melinonine-E 58 melinonine F 51 melitensin 134 melitensin 8-deoxy- 134 melitensin 1 1,12-didehydr0-8-deoxy-,134 mellein 328 mellein 4-hydroxy- 328 mellein 6-methoxy- 450 453 Melochia pyramidata 2 Melodinus guillauminii 57 66 76 Melodinus reticulatus 66 melrosin A 153 melrosin B 153 melrosin C 153 menadione 38 1 menaquinone-2 380 menaquinone-4 38 1 menaquinone-6 379 menaquinone-7 380 menaquinone-9 379 menaquinone-10 380 menaquinones 379 381 Menispermum dauricum 23 1 mensin 207 Mentha spicata 5 15 Mentha spp.522 menthol (-)- 515 menthyl acetate 5 15 meroterpenoids 404 mescaline 8 1 mesembrine 182 mesobiliverdin 568 42 2,3,15,16-tetrahydro- 42 mesohaem 568 575 mesohaemin 565 metalaxyl 456 Methanosarcina barkeri 574 550 methylations biosynthetic 576 methylpluviatilol (+)- 195 metocurine 84 mesobili verdin 3,3’ -didehydro-2,3-di hydro- mesobiliverdin 3,3’ 18’,18’-tetradehydro-methionine 36 177 methionine S-adenosyl- 32 36 38 39 295 methoxatin 393 methyl (1 32)-I 2-carboxyretinoate 363 methyl 4-dihydrotrisporate B 366 methyl retinoate 360 373 374 methyl trisporate B 424 methyl (7E,9Z)-trisporate B 366 methylcoenzyme M 574 methylenomycin A 41 7 methylenomycin B 41 7 Methylococcus capsulatus 533 4-methylsterol oxidase system 536 mevalonate kinase 5 13 527 mevalonic acid biosynthesis 525 mevalonic acid (R)-5-diphospho- 527 NATURAL PRODUCT REPORTS 1985 mevalonic acid 5-phospho- 527 mevalonolactone 537 mevalonolactone (RS)-,5 13 mevinolin 334 4 18 420 5 13 525 mevinolin (+)- 424 mexicanin I 140 miconazole 546 microbial metabolites butenolides 405 microbial metabolites cyclohexenes 424 microbial metabolites cyclopentenes 41 8 microbial metabolites met hylene- cyclopentanones 41 7 microbial metabolites olefinic 41 5 microbial metabolites piperidines 41 1 microbial metabolites pyran-pyranoid 401 microbial metabolites pyridines 41 1 microbial metabolites pyrones 402 microbial metabolites pyrroles 410 microbial metabolites pyrrolidines 41 0 Micrococcus luteus 375 38 1 Microplumeria anornula 66 Microsphaera alphitoidrs 376 Mikania goyazensis.152 milbemycin or? 343 milbemycin o(~,343 milbemycin D 343 milbemycins biosynthesis 343 minovincine 69 mirandin-A 205 mitomycins 3 13 Mitragyna parrifdia 57 ML-236B 525 modhephane. 122 modhephene 122 moenocinol 41 3 moenomycin 41 3 mollugin biosynthesis 507 Momordica churantia 5 momordicosides 5 monacolin K 525 monactin 344 Monascus ruhrr 420 monensin 329 Monilinia ,fructicolu 427 432 Monnieria trifolia 393 monocerin biosynthesis 332 monocrotaline 2 15 monocyclofarnesanes 100 I47 P-monocyclonerolidol 148 Monomorium pharaonis 98 monoterpenoids biosynthesis 5 14 Monotropa hjpopitjqs 424 Monlanou atriplieifblia 152 153 Montanoa ptoropotlu 1 5 1 morachalcone 439 moraprenol 378 morphine 85 88 morphine 6-O-acetyl- 88 morphine alkaloids 88 morphine 3-t-butyl ether 88 morphine 3,6-di-O-butyryl- 90 morphine N-oxide 88 morphinone I4(3-(bromoacetyl)amino- 88 morphinone 14-hydroxy- 89 Morus ah 439 Mostura hrunoni.v 58 mostueine 58 Mueor spp.490 mukaadial I48 mukolidine 49 mukoline 49 mukonal 49 mukonicine 49 multicolanic acid 405 multicolic acid 405 multicolosic acid 405 murrafoline 74 Murrayu euchrest(toliu 49 74 Murraya kounigii 49 murrayaquinone-B 49 Musa paradisiaca 2 3 Muscari comosum 2 muscarine 324 mutasterol 554 mutatochromes 357 mutatoxanthins 35 1 Mycobacterium spp.490 mycophenolic acid 98 416 mycorrhizin A 424 myodesmone 100 myomontanone (+)- 147 1-myoporol 428 6-myoporol 428 myoporone 428 myoporone (+)- 147 myoporone 6-deoxy-6,7-dihydroxy- 428 myoporone 4-hydroxy- 428 myoporone 7-hydroxy- 428 myoporone 4-hydroxy-7,8-didehydro-,428 myoporonol 4-hydroxy- 429 myoporonol ketal 4-hydroxy- 429 Myoporum montanum 147 myosmine 187 myrcene 522 myrcene biosynthesis 5 15 myricetin 503 myriocin 41 3 Myriococcum albomyces 4 13 Myristica .fragrans 204 207 Myrothecium roridum 149 Myrothecium tierrucaria 149 myrtine 242 myxalamide A 4 12 myxalamide B 4 12 myxalamide C 412 myxalamide D 412 My.~ococcus julvus 177 345 404 My.~ococcusvirescens 346 My.~ococcus xanthus 247 4 12 myxopyronin A biosynthesis 177 345 myxopyronins 404 myxovirescin A 2,3-didehydro- 247 myxovirescin A, 346 NADPH-cytochrome P-450 reductase 529 539 541 N ADPH-protochlorophyllide oxidoreductase 33 Naematoloma jasciculare (Fr.) Karst.2* nahagenin 12 nalbuphine 90 nalmefene 89 90 nalorphine 90 naloxone 89 90 naloxone hydrazone 90 naloxone methiodide 90 naloxone-6-spirohydantoin, 90 naltrexamine P-chloro- 90 naltrexone 89 90 Nandina domestica 229 naphthalene 1,8-dihydroxy- 329 naphthalene I ,3,6,8-tetrahydroxy- 329 naphthalene 1,3,8-trihydroxy- 329 330 2-naphthoic acid I ,4-dihydroxy- 507 2-naphthoic acid I ,4-dihydroxy-3-prenyl- 507 nap h t hoquinol 507 naphthoquinone 507 narcicrinine 249 Narcissus pseudonarcissus 439 508 or-narcotine 86 or-narcotinediol 86 nargenicin A I 334 nargenicin A I biosynthesis 335 naringenin 502 503 504 506 Nauclea diderrichii 56 nauclefine 59 neamine 176 necic acids biosynthesis 164 necic acids synthesis 2 16 necines synthesis 21 3 Nectandra miranda 205 Nectandra rigida I94 Nectandra sp.206 nectandrin A 194 nectandrin B 194 Nectria haematococca 449 450 45 1 Nectria spp.45 1 neoalatamine 154 Neochamaelea pulverulenta 6 7 neochromes 35 1 neocochliodinol 74 neoisostegane 199 neoliacine 152 neolignans 204 neolignans (3,3’)- 204 neolignans (8,l’)- 205 neolignans (8,3‘)- 204 neolignans (9,9’)- 204 neolignans (3-0-4)- 207 neolignans (8-0-4)- 207 neolignans (2,2’.5,1’)- 207 neolignans (8,1’.7,3’)- 206 neolignans (8,1’.7,9’)- 207 neolignans (8,5’.7,3’)- 207 neolignans (8-0-4.7-0-3’)- 208 neolignans classification 191 neolignans new types 208 neolignans nomenclature 191 neoligularidine 21 7 Neolitsea aciculata I52 neomenthol (+)- 515 neomycins biosynthesis 176 neo-olivil 194 neopine 6-O-mesyl- 88 neotokorogenin 550 neotriangularine 2 17 neoxanthin 375 Nepeta cataria 513 515 Nepeta hindostana 8 nepetalactone biosynthesis 5 I5 nepetidin 8 nepodin 330 neral IO-oxo- 5 15 netzahualcoyone 1 1 Neurospora crassa 3 12 375 546 566 neurosporene 35 1 372 375 neurosporen-4-oic acid ester ~-P-D-glucopyranosyloxy-4,4’-diapo-, 35 1 ngouniensine 64 ngouniensine 2O-epi- 64 Nicotiana debneyi 43 I Nicotiana rustica 159 43 1 Nicotiana silvestris 496 497 Nicotiana spp.353 431 449 Nicotiana tabacum 163 500 502 52 1 522 570 nicotine alkaloids 187 nidurufin 341 Nigrfla damascena 148 353 nissicarpin 448 Nissolia .fruticosa 448 nissolicarpin 448 nitrabirine 245 nitramine 185 Nitraria sibirica 245 nitrite reductases 566 Nocardia argentinensis 336 Nocardia sp.407 Nocardia spp. 304 Nocardia sulphurens 3 38 Nocardia unijbrmis subsp. tsuyamanensis 304 nocardicin A 304 nocardicinic acid ( -)-3-amino- 304 nocardicins 304 nocardicins biosynthesis 304 Nodulisoorium hinnuleum. 550 1-46 nodusmicin biosynthesis 335 nonactic acid 344 nonactin 344 nonaketides biosynthesis 335 non-tryptamine alkaloids 49 noracronycine 398 norapomorphine N-propyl- 88 noratropine oxalate 221 norbracteoline 228 norchelidonine 90 norchelidonine ( & )- 91 norcobyrinic acids 573 norcodeine 89 norcularicine 82 norcularidine 82 nordihydroguaiaretic acid 193 norfluorocurarine 18-acetoxy- 64 norfluorocurarine 18-hydroxy- 64 norisohaplophytine 76 norlaudanosine 82 norlaudanosine N-nitroso- 82 norlaudanosoline 166 norlaudanosoline synthase 166 normelinonine F 51 normorphine 90 nornicotyrine 187 nororipavine 6-demethoxy- 88 nororipavine N-propyl-6-demethoxy- 88 norpreocoteine 228 nor-reticuline 82 norrisane biosynthesis 5 19 nor-ruspolinone 163 norsanguinarine 90 norscopine 222 norscopinium bromide N-alkyl-O-(6,11 -di- hydrodi benzo[h,e]thiepin- 1 1 -yl)-N-methyl- 222 norsolorinic acid 340 nortropan-3-one N-isopropyl- 222 D-nOrValine 303 nudiflorine 186 nuevamine 87 nuevamine (*)- 86 obaberine 83 obacun-9( 1 I)-en-7cx-yl acetate 1 (1O-.19)abeo- 6 oblongine 82 obovatal 207 obovatol 207 obtusane (-)- 149 obtusifoliol 544 545 obtusifoliol 24,28-dihydro- 544 occidol 431 occidol acetate 43 I ochrobirine 87 Ochromonas malhamensis 548 549 ocimin 204 Ocimum americanum 204 Ocotea bucherii 227 Ocotea catharinensis 206 Ocotea sp.206 octadeca-9,l I 15-trienoic acid (92,I 1E 15Z)- I3-hydroxy- 435 octadeca-lO,12,15-trienoicacid (1OE,122,15Z)-9-hydroxy- 435 octaketides biosynthesis 334 octopamine 173 oestra-l,4-dien-l7P-ol 17a-ethynyl-1OP- hydroxy-3-oxo- 472 oestra-2,5( lO)-dien-l7P-01 3-methoxy- 483 17P-oestradio1 539 541 17P-oestradio1 7P-amino- 469 17P-oestradio1 7P-amino-2-hydroxy- 469 oestradiol 17P-dehydrogenase 541 17P-oestradio1 2,4-dimethoxy- 484 17P-oestradio1 2-hydroxy- 484 I7P-oestradio1 2-methoxy- 484 17P-oestradiol 4-methoxy- 484 8a,17P-oestradioIs 2-alkyl- 485 8a,17P-oestradioIs 16-alkyl- 485 oestranes syntheses 483 oestra-l,3,5( 10)-triene 3-methoxy-17- (methyletheny1idene)- 465 oestra-l,3-5( 10)-triene 3-methoxy-17- (phenyletheny1idene)- 465 oestra-l,3,5( 10)-trienes 3-methoxy-l,4- di(trimethylsily1)- 47 1 oestra-l,3,5( IO)-trien-l7p-01 12-chloro-3- methoxy-9-oxo-9,ll -seco-c-nor- 464 oestra-l,3,5( lO)-trien-3-01 17P-hydroxyl- amino- 470 oestra-l,3,5( lO)-trien-l7-01~ 17-ethenyl-3- methoxy- 470 oestr-4-en-3-one la-trimethylsilyl- 47 1 oestr-4-en-3-one 1P-trimethylsilyl- 47 1 oestr-5( 1O)-en-3-one 1a-trimethylsilyl- 47 1 oestr-5( 1O)-en-3-one 1P-trimethylsilyl- 47 1 oestr-5( lO)-en-3-ones 1Ip-aryl- 468 oestriol 484 oestriol 16-0-glucuronide 484 oestrogens 2-amino- 469 oestrogens biosynthesis 539 oestrogens 6-0xo- 485 oestrone 539 540 541 oestrone 2-hydroxy- 484 oestrone methyl ether 2-hydroxy- 484 oestrone methyl ether 4-hydroxy- 484 oestrone 2-nitro- 484 ohchinin 7 ohchinolal 7 Olea ajricana 197 Olea europaea 195 oleanane saponins 11 olean- 12-en-27-oic acid 3a,29-dihydroxy- 9 olean-18-en-28-oic acid 6P-hydroxy-3-oxo- 10 olean-12-en- 1-01 3,4-seco-3-nor- 10 oleanolic acid glycosides 544 oleic acid 322 333 olepupuane 147 148 olivacine 65 olivoretin A 52 olivoretin B 52 olivoretin C 52 olivoretin D 52 onoceranoxide 13 p-onocerine 530 oogoniol 550 oogoniol-I 550 oogoniol-2 550 ophiocarpine 84 ophiocarpine or-N-methyl- 87 oplopanane 149 a-oplopenone 150 oppositanes 154 orchinol 437 Orchis anatolica 437 Orchis italica 437 Orchis militaris 437 438 Orchis spp.437 507 orcinol 325 oricine 395 oriciopsin 6 Oriciopsis glaberrima 6 orientidine 228 orientine 227 orientinine 227 oripavine 88 oripavine 7or-amino-6,14-endo-etheno-, 88 oripavine 6-demethoxy- 88 ormosanine (-)- 242 Ormosia alkaloids 239 L-ornithine 163 orsellinic acid 325 417 orsellinic acid 3-dodecyl- 41 7 Orthopterygium huancuy 10 Orthosphenia mexicana 1 1 NATURAL PRODUCT REPORTS 1985 orthosphenic acid 11 Oryza sativa 435 oryzalexin A 435 oryzalexin B 435 oryzalexin C 435 osornine 83 Osteospermum auriculatum 150 Osteospermum barberiae 150 Osteospermum scariosum var.scariosum 150 Otanthus maritimus 157 otonecine 21 3 Oudemansieila mucida 4 16 oudemansin (-)- 416 oudemansin (+-)- 416 oudemansin A 4 16 oudemansin B 416 oureguattidine 228 ovalifolene 141 oxaline biosynthesis 17 1 oxindole-3-acetic acid 499 oxindole-3-acetic acid 7-hydroxy- 499 oxirapentyn 416 oxoaporphines 230 oxobuxifoline 230 oxocompostelline 82 oxocrinine 25 1 oxocularine 82 oxoisoaporphines 23 1 oxoisocalycinine 230 oxosanguinarine 90 oxosarcocapnidine 82 oxosparteine synthase 440 oxyacanthine 83 oxyhydrastinine 8 1 oxylubimin 433 oxytetracycline biosynthesis 337 oxyxanthin 45 350 oxyxanthin 58 350 pac hygonam ine 8 3 pachygonamine N-methyl- 83 Pachygone ovata 83 229 23 1 paliclavine (&)- 53 pallescensin I 100 pallescensin 2 100 pallescensin A 3P-hydroxy- 100 pallescensin F 100 pallescensin G 100 pallescensins 367 pallidine 88 pallidine (*)- 89 pallidinine (k)-@methyl- 89 palmatine 84 84 85 palmitic acid 322 333 palmitoleic acid 322 Panax ginseng 6 Panax japonicus 6 Panax notoginseng 6 Panax quinquejolium 6 Pancratium bgorum 249 pancuronium 84 paniculide A 103 104 paniculide B 104 paniculide B biosynthesis 517 paniculide C 104 paniculide D 104 pannarol 325 papakusterol 554 Papaver apokrinomenon 229 Papaver arenarium 82 84 Papaver bracteatum 8I 88 90 168 Papaver dubium var.glabrum 8 1 Papaver orientale 227 228 229 Papauer pilosum 227 229 Papaver somnuerum 88 168 Papaver triniifblium 82 84 88 227 229 papaverine 82 papaverine 3,4-dihydro- 82 parabactin 246 NATURAL PRODUCT REPORTS 1985 Paracentrotus licidus 245 Paracoccus denitriJicans 566 paraherquonin 405 paraquat 5 14 parfumidine 87 parfumine 87 parkeol 543 Parthenium spp.522 parvinolide 5 19 paspaclavine (+)- 53 Paspalum scrobiculatum 53 patchouli alcohol 141 Patrinia scabiosaefolia 1 1 patulin 325 401 paulownin 196 Pauridiantha lyallii 56 pauridianthoside 2 1-epi- 56 pavines 84 peduncularistine 54 Pegolettia senegalensis 15 1 152 153 154 pegolettiolide 8-hydroxy- 152 Pelecyphora asellijormis 81 penicillic acid 325 328 penicillin N 293 294 penicillin V 293 penicillins biosynthesis 174 293 Penicillium brejeldianum 332 333 Penicillium brecicompactum 4 16 420 Penicillium chrysogenum 175 293 294 300 Penicillium citreo-viride 326 404 Penicillium citrinum 327 420 Penicillium crustosum 171 Penicillium diversum 404 Penicillium expansum 41 5 Penicillium islandicum 404 Penicillium janthinellum 50 Penicillium kapuscinskii 53 Penicillium meleagrinum 52 Penicillium multicolor 405 Penicillium oxalicum 171 Penicillium paraherquei 405 Penicillium patulum 40 1 Penicillium puluillorum 404 Penicillium roquejorti 171 325 Penicillium spp.50 Penicillium verrucosum 404 Penicillium wortmannii 550 penitrem A 50 penitrem A biosynthesis 171 penitrem B 50 penitrem C 50 penitrem D 50 penitrem E 50 penitrem F 50 penlanfuran 148 Penstemon deustus 195 pentaketides biosynthesis 325 pentalenane 128 150 pentalenene 128 pentalenene biosynthesis 5 16 pentalenolactone E 128 pentalenolactone F 128 150 pentanol (3S)-3,4-dimethyl- 550 pentaphyrins 576 pentenomycin I (-)- 418 pentenomycin I (*)- 418 pentenomycin 11 418 pentenomycin 111 418 peptide alkaloids 245 Pergularia pallida 238 perhydrogephyrotoxin 238 perhydrohistrionicotoxin,185 perhydrohistrionicotoxin,depentyl- 185 Periandra dulcis 10 periandrin I 10 periandrin 111 10 pericathidine 77 Periconia macrospinosa 418 peridinin 372 375 Perilla jrutescens 5 17 52 1 perillaldehyde 136 Peripentadenia mearsii 183 periplanone-B 133 perloline 247 Perovska spp.522 Persea americana 353 pertic acid 152 Pertya glabrescens 152 Peschiera juchsiaejolia 62 7 1 76 Pestalotia junerea 437 Petasites jragrans 156 petasol 156 petroporphyrins mass spectroscopy 575 Petroselinum hortense 438 Petunia hybrida 503 Petunia spp. 501 Peumus boldus 227 228 229 Pjajia paniculata 9 pfafic acid 9 Phaeodactylum tricornutum 322 Phalaris aquatica 49 phaseic acid 518 phaseollidin 450 phaseollidin (-)-(6aR,llaR)- 445 phaseollidin (*)- 446 phaseollidin hydrate 450 phaseollin 453 phaseollin (-)- 444 445 phaseollin (+)- 446 phaseollinisoflavan 450 Phaseolus aureus 447 Phaseolus coccineus 520 Phaseolus mungo 447 Phaseolus vulgaris 441 442 444 445 449 451,453 456 520 pheantharine 83 phenalenones 9-phenyl- biosynthesis 509 phenanthrene phytoalexins 437 phenanthrenes 23 1 phenanthrenes biosynthesis 505 phenanthroindolizidine alkaloids 238 phenanthroindolizidine alkaloids biosynthesis 163 phenanthroquinolizidine alkaloids 238 phenazines biosynthesis 174 phenol 2-octaprenyl- 38 1 phenolic acids biosynthesis 498 phenols biosynthesis 498 phenols prenylated 5 14 phenoxyacetic acid 2,4-dichloro- 429 phenylacetic acids biosynthesis 500 phenylalanine ammonia-lyase 441 442 499 phenylalanine 2,5-dihydro- biosynthesis 509 phenylbenzofuran phytoalexins 438 439 phenylethanes biosynthesis 500 P-phenylethylamines 81 phenyl-lactic acid 499 phenylmethanes biosynthesis 500 phenylpropanes biosynthesis 500 phenylpropanoids biosynthesis 499 phenylpyruvate tautomerase 3 15 497 phenylpyruvic acid 3 16 498 phenylpyruvic acid p-hydroxy- 498 phenytoin 86 pheophorbides 34 pheophytins 34 pheromone 21 5 Phialophora lagerbergii 329 phillygenol 195 phillyrin 204 Phoebe jormosana 227 Phoebe molicella 228 229 23 1 pholipomycin 41 3 Phoma betae 334 Phoma exigua 432 Phoma pigmentivora 331 phomenone 13-deoxy- 156 Phomopsis leptostromiformis 247 phospho-2-dehydro-3-deoxyheptonate aldolase 308 495* phosphogluconate dehydrogenase 3 16 phosphomevalonate kinase 5 13 527 phosphonic acid 2-chloroethyl- 43 1 3-phosphoshikimate 1-carboxyvinyl-transferase 309* 496* 497 photocitral-A 515 phthalide-isoquinolines 86 phthalimidines azabicyclo[3.3.l]nonyl-,222 phycocyanin 568 phycocyanobilin 42 568 phycoerythrin 568 phycoerythrobilin 42 568 Phycomyces blakesleeanus 370 375 Phyllanthus niruri 197 phylloquinol biosynthesis 507 phylloquinone 38 1 phylloquinone biosynthesis 507 phylloquinone epoxide 380 phyltetralin 197 phyriaporphyrinogen 28 Physalis peruuiana 547 phytoalexin 147 150 154 phytoalexin elicitors abiotic 427 45 ,454 phytoalexin elicitors biotic 427 45 1 phytoalexin elicitors endogenous 45 ,454 phytoalexins acetylenic 436 453 phytoalexins alkaloids 440 phytoalexins analysis 449 phytoalexins benzofurans 438 phytoalexins benzoxazinones 440 phytoalexins bibenzyls 437 phitoalexins dihydrbphenanthrenes 437 phytoalexins flavans 439 phytoalexins fungal degradation 449 phytoalexins furocoumarins 438 phytoalexins isoflavonoid 441 phytoalexins isoflavonoid biosynthesis 44 1 phytoalexins phenanthrenes 437 phytoalexins phenylbenzofurans 438 439 phytoalexins polyacetylenic 436 phytoalexins stilbenes 437 phytoalexins terpenoid 428 phytochrome 568 569 phytoene 375 375 phytoene cis- 351 phytofluene 375 phytofluene cis- 351 phytol 34 Phytolacca acinosa 10 Phytolacca americana 204 208 phytolaccanol 10 Phytophthora cannabivora 437 Phytophthora capsici 431 432 Phytophthora infestans 427 432 433 452 45 3 Phytophthora megasperma 442 444 452 453 454 456 Phytophthora megasperma f.sp.glycinea 436 438 441 503 Phytophthora nicotiana 456 Phytophthora parasitica 43 1 440 phytosterols biosynthesis 544 phytosterols 29-fluoro- 552 phytuberin 431 phytuberol 431 phytyl diphosphate 34 570 phytyl pyrophosphate 34 570 Picea abies 424 Picea excelsa 506 piceatannol 506 picfeltarraegenin I 4 picfeltarraegenin 11 4 picfeltarraegenin 111 4 picfeltarraegenin V 4 picfeltarraegenin VI 4 picraline alkaloids 61 picralstonine 63 picrasinolide A 8 Picrasma ailanthoides 8 Picrasma quassioides 5 1 74 Picria fel-tarrae 4 picrohelenin 6-epi- 158 picropodophyllotoxone (*)- 198 picroroccellin 247 picrotoxane 149 picrotoxin 150 piericidin A, 41 1 piericidins 41 2 Pieris brassicae 553 pigments photoreceptor 375 a-pinene 521 522 (3-pinene 137 522 a-pinene biosynthesis 5 14 (3-pinene biosynthesis 5 14 pinguisane 141 pinidine 182 pinopalustrin 193 pinoresinol 195 pinoresinol bis-b-D-glucoside 195 pinoresinol 4’-O-P-D-glucoside (+)-1-acetoxy- 195 pinselin 335 Pinus pinaster 5 16 Pinus pinea 547 Pinus radiata 521 Pinus spp.5 14 Pinus sylvestris 499 Piper cfusii 195 Piper futokadsura 204 208 Piper fongum 182 Piper trichostachyon 181 piperidine alkaloids 182 piperidine alkaloids biosynthesis 163 piperine 182 piperitol (+)- 195 piperolongumine 182 piperonaline 182 piperundecalidine 182 piplartine 182 245 Piptocarpha opaca 152 Piptoporus australiensis 4 16 pisatin 451 pisatin (+)- 427 442 443 448 pisatin (-)- 444 449 pisatin 3-O-demethyl- 449 pisolactone 2 Pisolithus tinctorius 2 Pisum sativum 3 12 427 440 442 497 5 19 520 528 533 544 Pittosporum undulatum 10 11 plant tissue cultures 166 167 168 169 170 171 174 175 plasmid pATl53 3 12 Pfasmodiophora brassicae 49 plastoquinone-1 380 plastoquinone-9 380 38 1 Platismaria glauca 12 platydesmine 396 platynecine 2 14 platyphylline 21 8 plectaniaxanthin (2’s)- 354 pleiocarpamine 10-hydroxy- 62 pleiocarpamine 1 I -hydroxy- 62 pleurosine 77 plocamene D 514 Pluchea dioscoridis I54 Pluchea indica 154 Pluchea odorata 154 pluviatilol (+)- 195 pluviatolide ( f)- 194 podopetaline (-)- 242 Podopetafum ormondii 242 podophyllotoxin 196 204 podophyllotoxin biosynthesis 501 podophyllotoxin 4’-O-demethyl- 204 NATURAL PRODUCT REPORTS 1985 podophyllotoxin 4-O-demethyl- fluoro-16a-methyl-20-0~0-2’-phenyl-2’H- biosynthesis 501 464 podophyllotoxone 196 50 1 5P-pregnane-3a 17P-dio1 16aa-methyL~- podophyllotoxone (IR,2R,3R)- 196 homo- 483 Podophyllum emodi 204 pregnanes syntheses 483 Podophyffum hexandrum 196 204 50 1 pregnan-3-oic acid 5,20-dioxo-4-nor-4,5- Podophyllum peltatum 196 seco- 467 podorhizol ( & )- 199 pregnan-5a-01 3~-acetoxy-6~-azido-20-oxo-, podorhizone (-)- 202 470 podotoxin 195 5P-pregnan-3a-01 17P-chloro- 16aa-methyl-~- Pogostemon parviporus 5 I9 homo- 483 pollinastanol 544 5a 17a-pregnan-20-one 17g-hydroxy- 18-nor- polyacetylenes 436 468 Polyalthia cauliyora 228 pregna-4,8(9) 1 1,13(14)-tetraene-3,20-dione, Polyalthia caulijlora var.beccarii 229 230 18-nor-17-ambo- 483 23 1 pregna-2,4,6-trieno[3,2-c]pyrazole-1 lp 17a- Polyalthia nitidissima 83 229 23 1 21-trio1 21 -acetate 6-azid0-9a-fluoro-16a- polybeccarine 230 methyl-20-0~0-2’-phenyl-2’H-,465 polyether antibiotics 329 pregn-5-ene 3P-acetoxy- 18,20- polyether ionophores biosynthesis 344 diethoxyphosphinylimino-,489 polygalacturonase 44 1 pregn-4-ene-3,20-dione 17a-acetoxy-6P,7a-polygalacturonic acid 454 diazido- 470 polygodial 100 pregn-4-ene-3,6,20-trione, 17a-acetoxy-7a-Polygonum hydropiper 148 azido- 470 polyneuridine aldehyde 169 pregn-4-en-2 1-oic acids 17a-hydroxy-20-0~0- polyneuridine aldehyde esterase 169 AR? .-polyneuridine-type alkaloids 169 pregn-4-en-6b-01 17a-acetoxy-7a-azido-3,20-a-polypodatetraene 13 dioxo- 470 y-polypodatetraene 13 pregnenolone 537 539 542 554 Polypodium fauriei 6 13 pregnenolone 21 -bromo- 483 Polypodium someyae 6 pregn-4-en-3-one 20a-hydroxy- 541 Polypodium vulgare 553 pregomisin I99 polysthicol 3 prelunularic acid 507 Polystichum aculeatum 4 prenylquinolinone alkaloids 394 Poiystichum ovato-pafeaceum 13 prenyltransferase 508 5 13 527 Polystichum polyblepharum 13 prephenate dehydratase 3 16 498 polyterpenoids 376 prephenate dehydrogenase 316 497 498 polyzonimine 182 Polyzonium rosalbum 182 prephenic acid 314 316 317 497 Poncirus x Citrus 6 prephytoene diphosphate 375 Populus x eurarnericana 500 presqualene diphosphate 528 529 porfiromycin 3 13 pretetramid 6-methyl- 337 poriferasterol 549 Primula elatior 11 poriferasterol biosynthesis 548 pristimerin 111 23-oxo- 11 poriferasterol 29-fluoro- 476 proaporphine alkaloid 166 porphobilinogen biosynthesis 21 562 proaporphines 227 porphobilinogen deaminase 22* 563* probenazole 435 porphobilinogen deaminase DNA procyanidins biosynthesis 502 sequences 564 progesterone 538 539 541 554 porphobilinogen deaminase mechanism 24 progesterone 19,21-dihYdroxY- 483 porphobilinogen synthase 21 * 562* progesterone 17a-hydroxy- 539 541 porphyria 27 29 42 577 progesterone 19-hydroxy- 483 porphyria acute intermittent 22 progesterone 21-hydroxy- 542 porphyria cutanea tarda 28 564 progesterone 1 1a-hydroxy- diazoacetate Porphyridium cruentum 568 48 3 porphyrin a 31 progesterone 21-hydroxy-1 9-nor- 483 porphyrin a dimethyl ester 565 progesterone 1 lp 19,21-trihydroxy- 483 porphyrinogen-3,7-dipropionicacid prohibitins 428 439 2,8,13,17-tetramethyl-12,18-divinyl- prolycopene 35 1 375 29 porphyrins h.p.l.c.574 propacin 501 porphyrins m.c.d. spectra 575 Propionibacterium freudenreichii subs p. Porpita sp. 370 shermanii 40 42 571* 573 prasinoxanthin 349 Propionibacterium shermanii 40 42 571 * pratorimine 249 573 pratosine 249 propionic acid 2-bromo-3-(5-imidazolyl)- preatroxigenin 9 563 precapnelladiene 128 propionic acid (3R)-3-dimethylamino-3- precapnellane 128 phenyl- biosynthesis 500 pregna-5,17-diene 3P-acetoxy-l6a-~hloro-~-Prostalidin A 196 homo- 489 prostalidin B 196 pregna-5,17-diene 3P-acetoxy- 16a-mesyloxy- prostalidin c,196 ’ D-homo- 489 Prosrhecochioris aestuarii 57 1 pregna-4,6-diene-3,2O-dione, 17a-acetoxy-6-protochlorophyllide 32 33 azido- 470 protochlorophyllide biosynthesis 569 pregna-4,6-diene-3,2O-dione, 1 7a-acetoxy-6-protochlorophyllide reductase 569 methyl- 468 proto’gen IX 28 29 564 pregna-1 ,4-dien-20-ones7 17a-acyloxy-2 1-proto’gen XIII 29 chloro- 483 protohaem ferro-lyase 30 pregna-2,4-dieno[3,2-c]pyrazole-l1 b 17or,21-protohaem oxidative ring-opening 566 trio1 2 1-acetate 6(-azido-7(-bromo-9a- protopine 86 167 NATURAL PRODUCT REPORTS 1985 protopine N-oxide 86 91 protopines 86 protoporphyrin biosynthesis 564 protoporphyrin dimethyl ester isomers 575 protoporphyrin IX 24 30 31 protoporphyrinatomagnesium(II) 32 33 569 protoporphyrinatomagnesium(II) 8',8'-di-hydro- 570 protoporphyrinatomagnesium(II) 133-U-methyl- 569 protoporphyrinogen biosynthesis 564 protoporphyrinogen IX 28 29 564 protoporphyrinogen XIII 29 protoporphyrinogen oxidase 29 564 protoporphyrins N-methylated 30 prunasin 503 Prunus laurocerasus 503 pseudoaspidospermidine 73 pseudoas pidosperm id i ne (20s)- 1 ,2-di-dehydro-20-hydroxy- 73 pseudocodeine 88 pseudocolumbamine 85 pseudoguaiane 139 I56 pseudoguaianolides 158 Psrui1oisochrj~si.s paradosa 554 pseudolycorine-1 -O-P-D-glucoside 249 Pseudomonas ueruginosa 308 566 Pseudomonus aurcw/uciens 17 I 174 3 14 Pseudomonas coronufaciens 4 1 3 Pseudomonus incognita 5 22 Pseudomonas luchrymans 4 3 1 Pseudomonas putida 262 Pseudomonas B-9004 335 Pseudomonas spp.440 539 Pseudomonas sjv-irigue 434 Pseudomona.r qv-ingae pv. tagetis 247 Pseudomonas tahuci 245 Pseudomonus trstosteroni 539 pseudomonic acid A 401 402 pseudomonic acid B 402 pseudomonic acid C 401 402 pseudomonic acid D 401 pseudo-oxynicotine 187 Pseudopa rmeliu tr.uana 1 2 Pseudotsuga mmziesii 50 1 502 pseudoyohimbine 14a-hydroxy- 60 psilostachynolide 158 Psolus jahricii 3 psoluthurin A 3 Pso ra leci corj-l!'foliu 5 09 psoralen 438 ptaquiloside I50 Pteritlium uyuilinum var. latiusculum 1 50 pterocarpan 3.9-dihydroxy- 444 445 pterocarpan (6aR I laR)-6a-hydroxy-3-met hoxy-8,9-me t h ylened iox y- 427 pterocarpans biosynthesis 505 Pri1osarcu.s gurnejsi 479 ptychanolide 141 143 158 Ptj,chanthus striutu.v 148 158 puberulin biosynthesis 50 I Puccinia c*oronutu 438 439 pulchelloid C 158 pulchrasterol 473 554 puleganolide 11 1 pulegone 11 1 pumiliotoxin A.238 pumiliotoxin 307A' 238 pumiliotoxin 307A" 238 pumiliotoxin B 138 punjabine 0-methyl- 83 purine N-benzylamino- 445 453 putrescine 163 164 Pjmunthus komho 379 pygeoresinol 197 pygeoside 197 Pygeum acuminatum 197 Pjrenochaeta terrestris 326 pyrenocine B 326 Pyrethrum parthenijolium 157 Pyricularia oryzae 329 435 pyridine alkaloids 186 pyridoxal phosphate 20 24 527 pyropheophorbide a I6' 17'-dinor-P,~- caroten- 18'-yl- 357 pyrrocorphin 576 pyrrocorphins 39 pyrrole alkaloids 181 pyrrole-2-carbaldehyde 5-n-nonyl- 181 pyrrolidine alkaloids 18 1 pyrrolidine alkaloids biosynthesis 163 pyrrolidin-2-one 4-hydroxy- 182 pyrrolizidine alkaloids biological studies 219 pyrrolizidine alkaloids biosynthesis 163 pyrrolizidine alkaloids pharmacological studies 219 pyrrolnitrin biosynthesis 171 a-pyrufuran 438 P-pyrufuran 438 y-pyrufuran 438 Pyrus communis 438 Pyrus serotina var.culta 41 3 pyruvic acid 3,4-dihydroxyphenyl- 166 qinghaosu 1 16 117 quadrane 123 quadrone 123 125 Quararibea $mebris 1 81 quassinoids 7 quassinoids synthesis 8 quebrachamine 69 quercetin 502 503 quercetin 2,3-dihydro- 502 quercetin 3-U-methyl- 503 quercetin 7-0-methyl- 503 quercilicoside A 12 Quercus ile.u 1 I 12 376 quinazoline alkaloids 396 quinic acid 499 quinic acid p-coumaroyl- 499 quinol ethers biosynthesis 503 quinoline alkaloids 77 393 quinoline alkaloids non-terpenoid 393 quinolizidine alkaloids biosynthesis 164 quinolizidine alkaloids genes associated with biosynthesis 166 quinols biosynthesis 507 quinones biosynthesis 507 quinones isoprenylated 379 radicinin biosynthesis 331 radicinol 33 1 Ram temporaria 372 randainal 204 SP-ranol 479 Raphanus satirus 499 526 raucaffricine 170 raucaffricine glycosidase 170 rauniticine 60 rauniticine I4cx-hydroxy- 57 59 rauniticine oxindole A 57 rauniticine pseudoindoxyl 57 Rauwolfia cajra 5 I 56 61 64 Rauwolfia serpentina 57 63 169 170 RaurvolJla spp.57 Rauwolfia romitoria 57 61 63 Ratlenia spectabilis 393 394 ravesilone 394 ravidomycin biosynthesis 338 reductiline 410 413 reductiomycin 410 413 reserpic acid 57 reserpine I4a-benzoyloxy- 60 resorcinol 2-n-hexyl-5-n-propyl- 335 resorcylic acid 6-pentyl- 405 resveratrol 506 reticuline 82 166 167 1-49 retinal 371 retinal 1I-cis-1 2-s-cis- 373 retinal (I 32)- 372 retinal (1 12,132)- 373 retinal (9Z,11 Z 132)- 373 retinal 4-acetoxy- 362 retinal 4-butyl- 360 retinal 3-diazoacetoxy- 365 retinal 3-diazoacetoxy-9-cis- 365 retinal 19-diazoacetoxy-9-cis- 365 retinal 7,8-didehydro- 360 retinal 19,20-dinor- 360 retinal 5,6-epoxy- 370 retinal 5,8-epoxy- 363 retinal 5,6-epoxy-5,6-d ih yd ro- 3 7 1 retinal 1 1,14-epoxy-20-nor- 360 retinal (72,92,11 E,13fl-I 2-fluoro- 360 retinal fluorophenyl- 374 retinal 4-hydroxy- 362 retinal 18-nor- 360 retinal 19-nor- 360 retinal 20-nor- 360 retinal 1 8-nor-7,8-didehydro- 360 retinal 4-OXO- 362 373 retinal,l6,17,18-trinor-, 360 retinal,l6,17,18-trinor,7,8-didehydro-, 360 retinamides 363 37 1 retinoic acid 373 376 retinoic acid (132)- 363 376 retinoic acid (1 32)-12-carbomethoxy- 363 retinoic acid (1 1E,13Z)-12-carboxy- 364 retinoic acid 4,4-difluoro- 362 retinoic acid (1 32)-12-(hydroxymethy1)- 363 retinoic acid 4-0x0- 376 retinoids 359 retinol 359 370 371 376 retinol (1 32)- 360 retinol 4-azido- 365 retinol (1 32)-12-carboxy- 363 retinol 3,4-didehydro- 375 retinol (1 32)-11,12-didehydro- 360 retinol 4,4-difluoro- 362 retinol 3-hydroxy- 375 retinol (1 32)-12-(hydroxymethy1)- 364 retinol 4-OXO- 376 retinonitrile 365 retinotaurine 376 retinoyl fluoride 363 retinyl acetate 360 373 374 retinyl acetate 4,4-difluoro- 376 retinyl palmitates 370 retinylnitrones 363 retronecine 2 14 retrorsine 163 164 retulinal 75 retulinal 12-hydroxy- 75 retuline N,-deacetyl- 75 retuline N,-deacetyl- 1,2-didehydro- 64 retuline 2,16-didehydro-23-hydroxy-, 64 reynosin I -epi- 155 rhamnogalacturonan I 454 rhazimol 62 Rhazya stricta 56 56 62 Rhizobium sp.351 Rhizopus stolonijer 453 454 454 rhodinose 408 rhodins 576 Rhododendron japonicum 12 Rhodomicrobium tlannielii 375 E-rhodomycinone 338 E-rhodomycinone 7-deoxy- 338 rhodopin 375 Rhodopseudomonas acidophila 3 75 Rhodopseudomonas gelatinosa 375 Rhodopseudomonas sphaeroides 19 20 2 I 22 24 25 27 29 30 33 35 40 42 375 555 564 569 570 571 573 rhodopsin 360 372 373 375 Rhodospirillum fultlum 35 1-50 NATURAL PRODUCT REPORTS 1985 Rhodospirillum rubrum 35 Rhodotorula glutinis 495 498 rhodoxanthin 375 rhoeadines 87 Rhus succedanea 499 ribaline (+)- 395 ribaline (&)- 395 ribalinidine (+)- 395 ribasine 87 riboflavin biosynthesis 42 ricinidine 186 Ricinus communis 454 riedelianine (+)- 395 rifamycin S 31 3 rishitin 431 432 433 rishitin P-sophoroside 156 rishitinone 139 432 roburic acid 4,23-dihydro- 12 Roccello fuc[fbrmis 247 rohituka substance 1 7 rohituka substance 2 7 rohituka substance 7 7 roquefortine biosynthesis 17 1 Rosa muhiflora 12 Rosa pomifera 35 1 310 rosamultin I2 roseadine 77 roseamine 77 rosibiline 64 Rosmarinus ofJlcinulis 522 rotenoids 505 rubixanthin 350 351 371 rubixanthin (1 5Z)-,357 Rubus .fruticosus 544 Rumex alpinus 330 Ruspoliu hypercrateriformis 163 182 Ruta graveolens 174 440 522 rutacridone 174 rutacridone epoxide 440 sarpagine-type alkaloids 169 sarracinic acid 21 7 Sassajras randaiense 207 Sassajras taiwanensis 204 sativane 114 sativene 118 saucerneol 203 Saururus cernuus 203 Saussurea ajinis 157 saussurea lactone 134 Saussurea lappa 157 saxoguattine 228 Sceletium alkaloids 182 Scenedesmus obliquus 570 Scheflera capitata 10 Schisandra chinensis 199 Schisandra henryi 194 199 Schisandra sp.3 194 Schisandra sphenanthera 199 schisanhenol 199 schisanlactone A 3 schisanlactone B 3 schisantherin A 199 schisantherin B 199 schisantherin C 199 schisantherin D 199 schisantherin E 199 Schistocerca gregaria 553 Sch istos t eph ium artem isiijolium 150 Schistostephiurn crataegijolium 147 Schistostephium crataegijoliurn 148 150 152 Schistostephiurn heptalobum 152 154 Schistostephium rotundijolium 154 schizandrin 199 200 Schizozygia CaJaeoides 66 schumannificine 247 schumannificine N-methyl- 247 Sch urnanniophyton rnagnificum 24I 154 Serratia marcescens 313 498 sesartin (+)- 195 sesbanimide 187 sesquicarane 100 sesquicarene 104 sesqui-a-ionone 356 sesqui-P-ionone 356 sesquilignans 202 sesquineolignan 208 sesquiterpene lactones 5 13 sesquiterpenoids biosynthesis 5 16 setoclavine 53 sevanine 82 seychellene 14 1 shairidin 157 shairidin desangeloyl- 157 shikimate dehydrogenase 309 496 shikimate metabolites biosynthesis 508 shikimate pathway enzymes 495 shikimate pathway in biosynthesis 306 shikimic acid 3-dehydro- 308 309 496 shikimic acid 3-phospho-4,5-dideoxy- 3 10 shikimic acid 5-enolpyruvyl-3-phospho- 309 shikonin 507 shi nj ud ilac tone 7 shinjulactone A 7 shinjulactone D 7 shinjulactone E 7 shiona-3,21-diene 13 sibirinone 403 sidnyaxanthin 349 Sidnyum argus 349 silphinane 122 silphinene 122 Simaba multifora 8 simplexoside 195 simplocosin 195 simsiolide 152 sinactine (+)- 84 Sabastiana pavoniana 10 Saccharomyces cereilisiae 322 38 1 5 545 546 550 561 565 Saccharopolyspora hirsuta 336 safynol 436 salicin biosynthesis 499 salicyl alcohol 499 salicylhydroxamic acid 433 salicylic acid 6-methyl- 325 Sa1i.u babylonica 500 Salix cupreu 503 Salmonella typhirnurium 31 5 Salsola micranthera 11 salutaridine I-bromo- 89 salutaridinol 1-bromo- 89 Salria lunata 12 Sahia oficinalis 5 14 5 15 5 16 5 17 Salria plebeia 192 sandaracopimaradiene 435 sanguinarine 86 90 91 santalane 104 p-santalene 104 106 p-santalol trans- 104 santamarine 138 santhogenol 2 santholin 2 Santolina oblongijolia 147 150 a-santonin 134 138 521 sclerosporal I 1S sclerosporin 1 I5 Sclerotinia jructicola 1 15 scopolamine biosynthesis 500 scopolamine pharmacology 223 scopoletin 501 scoulerine 84 85 167 Scytalium splendens 156 scytalone biosynthesis 329 sebiferine methiodide 88 secoberberines 85 secocepharan thine 8 3 secocitreoviridin 404 secodine 20,21 -didehydro-19-oxo- 69 secodine N,-methyl- 68 secoisolariciresinol 192 secolariciresinol 194 secologanin 168 170 522 secologanin biosynthesis 51 5 p-selinene 136 137 429 sendaverine 82 Senecio aureus 156 2 18 Senecio clevelandii 2 19 Senecio desfontainei 2 18 SenecioJilaginoides 156 Senecio jacobaea 2 19 Senecio microglossus 154 Senecio ochoanus 156 Senecio ouyodontus 132 sinactine N-methyl- 84 sinapyl alcohol 500 P-sinensal 98 sinomeneine ketone 1-bromo- 89 sinomenilic acid (-)-1-bromo- 89 sinomenilone (-)- 89 sinomenine 88 sinularane 114 sinularene 1 18 Sinularia capillosa 147 Sinularia jrma 147 siol acetate 149 sipholane triterpenoids 12 Siphonochalina siphonella 12 sirenin 104 sirohaem 36 sirohydrochlorin 36 37 38 39 571 574 si tost-4-ene-3,17-dione 6p 19-epoxy- 490 p-sitosterol 531 544 547 551 sitosterol 29-fluoro- 476 sitsirikine 10-methoxy- 56 sitsirikine 3,4,5,6-tetradehydro- 56 Sium latijolium 149 sodium monate A 401 solanapyrone A 404 solanapyrone B 404 solanapyrone C 404 solanascone 43 1 solanascone 2,3-didehydro- 156 a-santonin (-)- 522 Supindus mukorossi 11 Saprolegnia jerax 546 sarcocapnidine 82 Sarcocapnos crassijolia 82 87 Sarcocapnos enneaphylla 82 Sarcophaga bullata 553 Senecio pinnatus 156 Senecio spp.219 Senecio triangularis 2 17 senecionine 21 7 seneciphylline 21 8 senoxydane 132 senoxydene 132 133 solanascone P-sophoroside 3-hydroxy- 156 solanesol 378 Solanum aviculare 434 Solanum dernissurn 432 Solanum melongena 434 456 Solanum tuberosum 427 432 452 508 S~-solasodan-3-0ne 434 Sarcophyton glaucum 483 septicine 239 solasodenone 434 sarkomycin 417 septicine 13a-hydroxy- 239 solavetivone 431 432 sarpagine 169 serine 177 solavetivone /3-glucoside 3-hydroxy- 156 sarpagine alkaloids 61 serpenone 407 solavetivone 3-hydroxy- 431 NATURAL PRODUCT REPORTS 1985 1-5 1 solenopsin A 18p 2/ sonchucarpolide 156 Sonchus macrocarpus 154 Sophora chrysophylla 241 Sophora jranchetiana 242 Sophora japonica 241 449 Sophora macrocarpa 241 Sophora spp.239 sophoradiol 9 sorbicillin 41 7 Sorbus aucuparia 437 soyasapogenol A 9 soyasapogenol B 9 soyasapogenol E 9 sparteine 164 165 sparteine alkaloids 239 spathulin 158 spergulagenic acid A 10 spermidine 245 246 spermine 245 spheroidene 372 375 spheroidenone 372 Spinacia oleracea 500 507 508 a-spinasterol 547 548 spinescin ( +)- 195 spiniferin-1 100 spirilloxanthin 372 spirobenzylisoquinolines,87 spiro-broussonin 440 spironolactone 490 spiropiperidine alkaloids 185 spiropyrrolidine alkaloids 182 spirorenone 489 Spirulina geitleri 570 Spirulina platensis 56 1 Spodoptera exempta 153 squalene 528 536 537 542 544 546 squalene and sterol carrier protein 536 squalene biosynthesis 527 squalene cyclase 533 squalene 2,3 :22,23-diepoxide 530 squalene (1 227-1 2,13-didehydro- 528 squalene 2,3-dihydro-2,3-imino- 546 squalene epoxidase 529* 536 squalene 2,3-epoxide 530 533 544 squalene 2,3-epoxide (3RS)- 533 squalene 2,3-epoxide (3s)- 529 squalene 10,ll-epoxide (+)-(lOR,llR)- 1 squalene 2,3-epoxide 0-amyrin-cyclase 533 squalene 2,3-epoxide 18,19-dihydro- 530 squalene 2,3-epoxide (1 8Z)-tetranor- 530 squalene mono-oxygenase 529* 536 squalene synthetase 528 Slaphylococcus aureus 304 35 1 staphyloxanthin 351 stearic acid 333 steganacin (+)- 202 steganone 199 steganone (-)- 200 201 steganone ( k)- 202 Steganotaenia araliacea 199 Steiractinia mollis 1 54 Steiractinia spp.154 steiractinolides 154 155 stemphyloxin I 334 stephabenine 88 Stephania glabra 84 166 Stephania japonica 88 Stephania susakii 83 stercobilin 566 stercobilin 10,23-dihydro- 566 stercobilinogen 566 Stereum frustulosum 41 6 Stereum purpureum 5 17 sterigmatocystin 341 Sternbergia lutea 249 steroid 1,2-diacylglyceryI phosphates 470 steroid A-isomerase 538 539 steroid 16-methylene-l7-ketones,468 steroid a-methylene-lactones 468 steroidal glycoalkaloids 433 steroidal hormones biosynthesis in vertebrates 537 steroids biosynthesis in higher plants algae and fungi 543 steroids biosynthesis in invertebrates 551 steroids cyclopropano- syntheses 489 steroids Scr,6cr-epoxy-6P-hydroxymethyl- 462 steroids heterocyclic syntheses 488 steroids microbiological transformations 490 5a-steroids 6-0~0-3cr,5-cyclo- 489 steroids partial syntheses 472 steroids photochemical reactions 472 steroids reactions 461 steroids remote functionalization reactions 47 1 steroids unsaturated reactions 464 sterol-carrier protein 530 536 A24-~tero1 methyltransferase 550 sterols alkylation of side-chain 547 sterols biosynthesis in fungi 545 sterols biosynthesis in vertebrates 534 sterpurene-3,12,14-triol,517 sterpuric acid 517 Stevia achalensis 157 Stevia monardaejolia 152 stigmasta-5,28-dien-3P~l,(24R)- 473 stigmasta-5,28-dien-3P~l,(24S)- 473 stigmasta-8,24(28)-dien-3P-o1 546 stigmasterol 547 stigmasterol 29-fluoro- 476 stilbene phytoalexins 437 stilbene synthase 506 stilbene 3,3’,4,5’-tetrahydroxy-,506 stilbene 3,4’,5-trihydroxy- 438 stilbene 3,4,5-trihydroxy-3’-methoxy-, 506 stilbenes biosynthesis 505 streptazolin 41 1 Streptocarpus dunnii 507 Streptocarpus spp.502 streptolydigin 408 streptolydigin biosynthesis 334 Streptomyces aburaviensis 4 16 Streptomyces albus 379 Streptomyces amakusaensis 173 509 Streptomyces antibioticus 410 508 Streptomyces aureojaciens 313 3 14 4 15 Streptomyces cattleya 41 8 Streptomyces cinereocrocatus 522 Streptomyces cinnamomeus 4 1 1 Streptomyces clavuligerus 175 293 294 295 Streptomyces E/784 342 Streptomyces echinatus 171 Streptomyces echinosporus 41 3 Streptomyces erythraeus 342 Streptomyces erythrochromogenes 41 7 Streptomyces eurythermus 41 8 Streptomyces jimbriatus 4 15 Streptomyces flocculus 172 Streptomyces jradiae 116 342 Streptomyces gelaticus 415 Streptomyces gilvotanareus 339 Streptomyces griseorubiginosus 4 13 Streptomyces griseus 68 338 344 412 Streptomyces hagronensis 41 3 Streptomyces hydrogenans 541 Streptomyces hygroscopicus 343 41 5 Streptomyces lavendulae 41 1 Streptomyces lavenduligriseus 4 18 Streptomyces lydicus 334 408 Streptomyces mediolani 350 Streptomyces MG7-G 1 41 6 Streptomyces OM-674 407 Streptomyces orientalis 410 Streptomyces prunicolor 407 Streptomyces pulveraceus subsp.fostreus 404 Streptomyces rimosus 337 408 Streptomyces roseochromogenes 490 Streptomyces sp. 174 338 404 407 41 1 417 Streptomyces spp. 176 517 Streptomyces sviceus 3 12 Streptomyces threomyceticus 324 41 3 Streptomyces toyocaensis 247 Streptomyces triostinicus 171 Streptomyces UC53 19 150 Streptomyces verdensis 41 3 Streptomyces virginiae 177 344 Streptomyces viridochromogenes 41 1 Streptomyces xanthochromogenes 41 2 streptonigrin biosynthesis 172 streptothricin F biosynthesis 176 Streptoverticilliurn ehimense 49 Streptoverticillium eurocidicum 4 18 Strepto ver t icillium olivoret iculi 52 stress metabolites 428 striatene 148 striatol 148 strictamine 10-hydroxy- 62 strictamine 11-hydroxy- 62 strictamine 18-hydroxy- 63 strictosidine 168 169 strigol 367 strobamine 223 strobilurin A 416 strobilurin B 416 strobilurin C 416 strychnine alkaloids 64 strychnobiline 12’-hydroxy- 75 strychnobrasiline 14P-hydroxy- 64 Strychnos angolensis 61 Strychnos dinklagei 187 Strychnos henningsii 64 Strychnos kasengaensis 75 Strychnos longicaudata 56 64 75 Strychnos matopensis 75 Strychnos melinoniana 58 Strychnos ngouniensis 64 73 75 Strychnos soubrensis 64 Strychnos usambarensis 51 55 74 Strychnos variabilis 75 strychnosplendine N,-acetyl- 1 1-methoxy- 64 stylopine 84 Styrax oficinalis 196 styraxin 196 suaveoline 18,Na-didemethyl- 19-hydroxy-Nb- methyl- 61 subcosine I 242 Suberites sericeus 35 1 succinylacetone 22 Sulfolobus solfataricus 371* supinidine 21 3 swainsonine 236 sweet potato 154 428 499 517 Swietenia macrophylla 7 swietenidin-A 393 swietenine acetate 8cr,30cr-epoxy- 7 sylvamide 245 Symphytum ojicinale 2 17 Symplocos lucida 195 syncarpurea 247 Syncretocarpus sericeus 152 Synechococcus 6301 568 syringaresinol 204 syringyl alcohol 500 tabarin acetyl- 155 Tabernaemontana chippii 15 Tabernaemontana dichotoma 61 64 66 7 1 73 Tabernaemontana eglandulosa 64 66 72 73 tabersonine 69 tabersonine desethyl- 67 tabersonine (&)-11-methoxy- 71 tabtoxin 245 tacalciol 479 NATURAL PRODUCT REPORTS 1985 tacalciol (8s)- 1,2,3,4-tetradehydro-6,7,8,9-tetrahydro- 480 tacamine 72 tacamine 16-epi- 72 tacamine 16,17-didehydro- 72 tacamine (19S)-19-hydroxy- 72 tacamonine 72 tacamonine 17-hydroxy- 72 tachysterol, 479 tagetitoxin 247 tagitinin F 152 taiwanin C 3,4-dihydro- 197 talcamine 83 tanacetin 138 tanacetol A 150 tanacetol B 151 Tanacetum vulgare 150 151 154 taurin 156 taxine 500 Taxus baccata 500 503 Taxus wallichiana 195 tchibangensine 4' 17-dihydro-l7aH- 75 tchi bangensine 4' 17-dihydro- 17PH- 75 Teclea trichocarpa 397 tecomanine 183 Teichaxinella morchella 554 Telekia speciosa 152 teleocidin B 52 temisin 134 Tenebrio molitor 551 553 tenellin 41 1 tephrocarpin 449 Teph rosia bid willi 449 Terminalia alata 10 Terminalia arjuna 8 9 11 terminic acid 8 terminoic acid 9 terpenoids biotransformations 522 a-terpinene 514 a-terpineol 522 terretonin 405 testosterone 539 541 testosterone adducts 465 testosterone 14a 15a-ditritio-19-nor- 483 testosterone 16P-ethyl- 19-nor- 484 testosterone 19-nor- 485 testosterone 3-sulphinyl- 489 testosterone 3-thia- 489 testosterones 7a-alkyl- 484 Tethya amamensis 351 tetrachlorodibenzo-p-dioxin, 564 tetracycline 338 tetracycline 7-chloro- 338 tetraethylthiuram disulphide 433 tetrahydroalstonine 169 tetrahydroberberines 84 tetrahydrofolic acid 173 tetrahydropalmatine 84 tetrahydropalmatine (-+)- 85 tetrahydroprotoberberine alkaloids 166 tetrahydrorhombifoline 440 tetrahymanol 529 533 tetrahymanol 3-hydroxy- 533 Tetrahymena pyriformis 529 533 tetraketides biosynthesis 325 tetrandrine 83 84 tetraphylline 58 tetrapyrroles 575 tetrapyrroles biosynthesis 41 tetrapyrroles evolution of biosynthetic pathways 43 tetrapyrroles n.m.r.spectra 42 tetrapyrroles ,C n.m.r. 575 tetrocarcins 334 tetronic acids 405 tetronomycin 407 Teucrium marum 515 thalbaicaline 227 thaliblastine 84 thalictrine 86 Thalictrum baicalense 227 Thalictrum faberi 230 Thalictrum joetidum 229 23 1 Thalictrum foliolosum 84 229 Thalictrum javanicum 229 Thalictrum kuhistanicum 83 Thalictrum minus 229 231 Thalictrum minus var. majus 229 thalidastine 84 thalifabatine 230 thalifaberine 230 thalifabine 230 thalifarapine 230 thalifasine 230 thalifaurine 85 thalifendine 84 thalmidine 83 thalmine 83 thebaine 88 thebaine l-bromo- 89 thermoplasmaquinone-6 379 thermozymocidin (+)- 41 3 Thespesia populnea 150 thespesone 150 thespone 150 thiocamphor 270 thiolactomycin 407 thiotetromycin 407 Thuja occidentalis 522 thujone 134 Thymus longijlorus 194 thysanolactone 12 Tilapia nilotica 375 Tilia x europaea 150 430 Tiliacora dinklagei 82 Tinospora baenzigeri 84 Tinospora capillipes 229 Tinospora cordijolia 84 Tinospora crispa 84 Tinospora glabra 84 Tinospora merilliana 84 Tinospora sagittata 84 Tinospora sinensis 84 Tinospora smilacina 84 tirandamycic acid 408 tirandamycin 408 tirucalla-7,24-diene 6 tissue culture 520 tobacco mosaic virus 43 1 tokorogenin 550 tomaymycin 247 Torilis japonica 1 54 trachelanthamidine 21 3 Trachelospermum asiaticum 193 Trebouxia sp.548 trevoagenin A 5 trevoagenin B 5 triabunnine 54 triacetic acid lactone 324 335 triangularine 217 Trianthema portulacastrum 553 triarimol 546 Trichilia prieuriana 7 Trichoderma hamatum 415 Trichoderma viride 453 550 trichodermadiene 12,13-deoxy- 149 trichodesmine 164 21 8 trichodiene 107 tricholidic acid 2 Tricholoma sp. 2 trichonin 3 trichonine 18 1 trichophylline 67 Trichophyton mentagrophytes 529 Trichosanthes palmata 2 3 trichostatin A 415 trichothecane 106 148 trichothecene 149 trichoverrol B 108 109 tricyclazole 329 trideca-a-l,4-galacturonide, 454 tridemorph 544 545 546 Trifolium pratense 442 446 504 TriJolium repens 454 triketides biosynthesis 324 trinoranastraptene 157 triostin A biosynthesis 171 triparanol 537 Tripterygium hypoglaucum 9 Tripterygium wilfordii 9 trisporic acids 366 375 triterpenes pentacyclic 53 1 triterpenoids biosynthesis 529 triterpenoids biosynthesis in higher plants algae and fungi 543 triterpenoids biosynthesis in invertebrates 551 triterpenoids dammarane-euphane group 5 triterpenoids fusidane-lanostane group 1 triterpenoids hopane group 12 triterpenoids lupane group 8 triterpenoids miscellaneous 12 triterpenoids oleanane group 9 triterpenoids pentanor- 7 triterpenoids squalene group 1 triterpenoids tetranor- 6 triterpenoids ursane group 12 Triticum aestivum 526 Triticum compactum 499 Triticum sativum 3 75 Triticum spp.454 trixagol 367 Trogoderma granarium 552 trollichromes 35 1 tropane alkaloids analytical aspects 225 tropane alkaloids pharmacology 223 tropane alkaloids synthesis 221 laH,5aH-tropanium bromide benzilate 8- (2-fluoroet hyl)-3a-hydroxy- 224 tropic acid biosynthesis 500 tropolone alkaloids 168 tryptamine 499 tryptamine alkaloids isoprenoid 52 tryptamine alkaloids non-isoprenoid ,50 tryptophan 171 tryptophan alkaloids 52 tryptophan biosynthesis 498 tryptophan C-methyltransferase 172 tryptophan N-malonyltransferase 498 tsukushinamine-A (-)- 242 tsukushinamine-B (-)- 242 tuberin biosynthesis 173 509 tubocurarine 82 tubocurarine (+)- 84 tubotaiwinal 64 tubulosine biosynthesis 168 tulirinol 134 tunaxanthin A 350 tunaxanthin C 350 turmerone ar- 102 tylactone 341 tylohirsutine 13a-methyl- 238 tylohirsutinidine 13a-methyl- 239 tylolupenol A 9 tylolupenol B 9 Tylophora asthmatica 163 238 Tylophora hirsuta 238 Tylophora kerrii 9 tylophorine 163 239 tylophorinicine 238 tylosin 341 tyramine 173 tyrosine 166 168 173 tyrosine biosynthesis 498 tyrosine threo-p-hydroxy- 173 ubiquinols 380 38 1 ubiquinone-1 380 381 NATURAL PRODUCT REPORTS 1985 ubiquinone-3 380 ubiquinone-6 38 1 ubiquinone-8 38 1 ubiquinone-10 380 381 ubiquinone- 14 380 ubiquinones 379 380 ubiquinones biosynthesis 508 U DP-N-acetylglucosamine 1-carboxyvinyl-transferase 3 10 uleine alkaloids 64 uleine 20-epi- 65 Ulmus glahru 430 umbelliferone 501 umbellifolide 156 Umbellulariu callfornica 50 Uncaria ellipticu 57 Uncaria guianensis 57 Uncaria rhynchophylla 51 Uncaria sinensis 56 undecaprenyl diphosphate 379 Unio pictorum 370 Urbanodendron uerrucosum 194 206 u ro bilinogen 566 urobiliverdin 111 566 uro’gen decarboxylase 27 35 564* uro’gen I 22 564 uro’gen 111 36 563 564 571 uro’gen 111 decarboxylation 27 Uromyces phaseoli 453 546 550 uroporphyrinogen decarboxylase 27 35 564* uroporphyrinogen isomers 27 uroporphyrinogen I 22 564 uroporphyrinogen I biosynthesis 564 uroporphyrinogen 111 36 563 564 571 uroporphyrinogen 111 biosynthesis 22 563 564 urophyrinogen 111 decarboxylation 27 uroporphyrinogen-111 carboxy-lyase 22 35 564* uroporphyrinogen-111 synthase 22* 564* uroporphyrins 27 urs-18-en-28-oic acid 3P-hydroxy- 12 urs- 12-en-28-oic acid 24-hydroxy-3-oxo- 12 urs-12-en-28-oic acid 2c(,30( 19c(,24-tetra- hydroxy- 12 urs-12-en-28-oic acid 2c(,30(,24-trihydroxy- ursolic acid 531 ursolic acid 3-epi- 12 ursolic acid 2c(-hydroxy- 53 1 ursolic acid 6P-hydroxy- 12 usambarensine (1 7R)-N4~-carbomethoxy- 4’,5’,6’ 17-tetrahydro- 75 usambarensine N-oxide (17&)-4’,5’,6’ 17- tetrahydro- 75 Ustilago maydis 545 546 Utiariu ufielii 247 valdiviolide 100 valencane 138 valerane 138 valeranone 139 valerenal 14 1 valerenane 139 Valeriana oficinulis 158 valeric acid 4,5-dioxo- 20 561 valine 176 Valsa ceratospermu 330 vanillic acid 499 vanuatine 83 vateamine 83 vecuronium 84 velbanamine ( 14S,20R)- 73 Velella velellu 370 vellosimjne 169 vellosimine reductase 169 velutinal 150 velutinal (6-ketostearyl)- 150 velutinal stearyl- 150 venalstonidine 19p-hydroxy- 66 viridin 2-demethoxy- 550 venalstonidine ~-oxo- 66 Virola carinata 204 204 207 venalstonine 19P-hydroxy- 66 Virola pavonis 208 verafinin B 153 Virola sebifera 193 197 verbascenine (*)- 247 Virola spp.50 Verbascum pseudonobile 246 Virola surinamensis 207 verbaskine 246 virolin 207 Verbena hybrida 502 virustomycin A 247 Verbena spp.502 vitamin A, 376 Verbesina aff. coahuilensis 153 vitamin A, 375 376 Verbesina uirgatu 154 vitamin B,, 42 vermelone 329 vitamin Bl2 biosynthesis 36 571 vernodalin 1 1,13-dihydro- 153 vitamin D, 5,10-didehydro-6,19-epidioxy-Vernonia amygdalina 153 5,6,10,19-tetrahydro- 480 Vernonia glabra var. glabra 15 1 154 vitamin D2p-D-glucopyranoside 483 Vernonia neocorymbosa I48 vitamin D,,6-hydroperoxy-4,5-didehydro-Vernonia nudgora 152 5,6-dihydro- 480 Vernonia polyanthes 147 152 vitamin D acetate lOC,19,25-trihydroxy- Vernonia poskeana 152 10,19-dihydro- 481 vernopolyanthofuran 6,7-didehydro- 147 vitamin D3 5,IO-didehydro-6,19-epidioxy-verrol 149 5,6,10,19-tetrahydro- 480 verrucarin A 109 vitamin D3 1,25-dihydroxy- P-D-gIUCO- verrucarin E 325 pyranosides 483 verrucarin J 108 vitamin D3 P-D-glucopyranoside 483 verrucarinic acid 109 vitamin D3,6-hydroperoxy-4,5-didehydro-verrucarinolactone 110 1 1 1 5,6-dihydro- 480 verrucarol 107 108 vitamin D, l-hydroxy- p-D-gluco- verrucosidin 404 pyranosides 483 verrucosin 194 vitamin D3 25-hydroxy- p-D-glUC0- versicolorin A 341 pyranosides 483 versicolorin A 8-deoxy-6-U-methyl- 341 vitamin D3 lcr-hydroxy-25-methy1- 482 versicolorin C 341 vitamin K, biosynthesis 507 versiconal acetate 341 vitamins A 359 versiconol 341 vitamins D hydroxylated 477 versiconol acetate 341 vitamins D syntheses 479 Verticillium albo-atrum 429 vitamins K 379 381 Vitex negundo 156 Verticillium dahliae 429 vitexin 503 Verticillium intertextum 405 41 7 vitexin 2”-O-rhamnoside 503 Verticillium spp.456 Vitis vinrfera 437 vertinolide 405 Voacanga africana 77 171 vertinolide (-)- 405 voafrine A 77 171 vestitol 449 voafrine B 77 171 vestitol (-)- 446 vobasinol 62 75 vestitone ( f)- 446 vobparicine 75 vetispirane 138 156 432 Vochysia guianensis 182 or-vetispirene 138 vochysine 182 vetiver oil 149 vomifoliol 5 18 p-vetivone 138 vomifoliol acetate 369 Vicia faba 353 436 456 vomilenine 170 Vigna angularis 9 11 195 vomilenine 21 -acetyl-19,20-dihydro- 61 vinblastine 170 vomilenine 21-deoxy- 61 Vinca erecta 62 vincadifformine indolenine 16-hydroxy- 68 warburganal 100 148 vincadifformine (-)- 67 Warburgia stuhlmannii 148 vincamenine 1l-methoxy-A14- 66 Warburgia ugandensis 148 vincamine 68 --Wedelia hookeriana 154 vincamine (+)- 71 Wedelia scaberrima 11 vincamine 16-epi- 68 Wikstroemia indica 193 vincamine alkaloids 65 Wikstroemia spp.193 vincane 68 wikstromol 193 vincanol 1 l-methoxy-A14- 66 wilfofide A 9 vincatine 67 wilforlide A 9 vincoridine 17-hydroxymethyl- 63 wilforlide B 9 vindolicine 77 Winterstein’s acid biosynthesis 500 vindoline 170 wisanine 182 vindoline 16-O-acetyl- 68 withaferin A 12P-hydroxy- 490 vindoline 14-acetyl-17-U-deacetyl-3,14-withaferin A 15P-hydroxy- 490 didehydro-I4,15-dihydro-,68 withaperuvin C 463 vindolinine 16-epi-(19S)- 66 wodeshiol 195 vinorine 169 Wolinella succinogenes 379 vinorine synthase 169 wortmannin 550 vinoxine 58 WS-l228A 415 violacene 5 14 WS-I228B 415 202 violaxanthin (1 5Z)- 351 wuweizisu C (-t)- wyerone 436 virginiamycin M,,biosynthesis 177 344 viridicatumtoxin 41 5 viridifloric acid 216 Xanthium strumarium 376 5 I8 viridin 550 xanthocidin (+)- 417 1-54 xanthocidin (?)-4,5-didehydro-4,5-dideoxy- 417 xanthocillin biosynthesis 509 xanthocillin dimethyl ether biosynthesis 509 xanthocillin monomethyl ether biosynthesis 509 510 Xanthomonas campestris 44 1 Xanthomonas campestris pv.maluacearum 429 Xanthomonas campestris pv. oryzae 435 436 xanthophyll K 349 xanthotoxin 438 xanthoxylol 195 Xerula longipes 41 6 Xerula melanotricha 4 16 Xestospongia muta 554 Xylocarpus moluccensis 7 xyloccensin G 7 xyloccensin H 7 xylopine N-formyl- 228 xylopinine 84 xylopinine 10-0-demethyl- 84 yamogenin 550 yenhusomidine 87 yenhusomine 87 yohimbine 85 yohimbine (*)- 61 yohimbine alkaloids 55 yohimbine 14P-hydroxy- 60 a-yohimbine 19,20-didehydro- 56 a-yohimbine 10-methoxy- 56 P-yohimbine 3,4-didehydro- 56 P-yohimbine 19,20-didehydro- 56 P-yohimbine 10-methoxy- 56 0-yohimbine N,-oxide 56 0-yohimbine oxindole 56 P-yohimbine pseudoindoxyl 56 yuzirine 82 Zanthoxylum acanthopodium 195 Zanthoxylum coco 393 Zea mays 20 35 247 403 499 547 Zea spp.520 a-zearalenol 337 p-zearalenol 337 zearalenone. 337 NATURAL PRODUCT REPORTS 1985 zeaxanthin 351 358 370 371 374 375 zeylasteral 11 zeylasterone desmethyl- I 1 zinaflorin I 153 zinaflorin 11 153 zinaflorin IV 153 zinaflorin V 153 zingiberenol 100 Zinnia peruuiana I53 Zinnia spp.502 zinnolides 153 zizaane 11 1 149 zizaene 114 zizanone 2-epi-,149 Zizyphus nummularia 6 zonarene 1 15 zuihonin A 194 zuihonin B 194 zuihonin C 194 zuihonin D 192 zymosterol 546 550 zymosterol 4,4-dimethyl- 535 546 zymosterol 24-met hylene-24,25-d ihyd ro- 550
ISSN:0265-0568
DOI:10.1039/NP98502000I1
出版商:RSC
年代:1985
数据来源: RSC
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| 2. |
Contents pages |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 007-014
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ISSN 0265-0568 NPRRDF 2 1-1-1-54 (1985) Natural Product Reports A journal of current developments in bio-organic chemistry Volume 2 Indexes CONTENTS ... 111 Preliminary pages for Volume 2 1-1 Index of Authors Cited 1-31 Subject Index ISSN 0265-0568 Coden NPRRDF Natural Product Reports A journal of current developments in bio- organic chemistry Volume2 1985 The Royal Society of Chemistry London Natural Product Reports (ISSN 0265-0568) 0The Royal Society of Chemistry 1985 All Rights Reserved No part of this publication may be reproduced stored in a retrieval system or transmitted in any form or by any means electronic mechanical photographic recording or otherwise without the prior permission of the publishers.Computer typeset by SB Datagraphics. Printed in Great Britain by Spottiswoode Ballantyne Printers Ltd ISSN 0265-0568 NPRRDF 2 1-580 1-1-1-54 (1985) Natural Product Reports A journal of current developments in bio-organic chemistry Volume 2 CONTENTS 1 Triterpenoids J. D. Connolly and R. A. Hill Reviewing the literature published between October 1982 and December 1983 19 The Biosynthesis of Porphyrins Chlorophylls and Vitamin BI2 F. J. Leeper Reviewing the Literature published between January 1978 and December 1983 49 Recent Progress in the Chemistry of Indole Alkaloids and Mould Metabolites Reviewing the literature published between July 1983 and June 1984 81 P-Phenylethylamines and the Isoquinoline Alkaloids K. W. Bentley Reviewing the literature published between July 1983 and June 1984 97 Sesquiterpenoid Synthesis J.S. Roberts Reviewing the literature published during 1983 147 Natural Sesquiterpenoids B. M. Fraga Reviewing the literature published during 1983 163 The Biosynthesis of Plant Alkaloids and Nitrogenous Microbial Metabolites Reviewing the literature published between July 1983 and June 1984 181 Pyrrolidine Piperidine and Pyridine Alkaloids A. R. Pinder Reviewing the literature published between July 1983 and June 1984 J. E. Saxton R. B. Herbert 189 Book Review Dictionary of Organic Compounds (Fifth Edition) First and Second Supplements ed. J. Buckingham Reviewed by J. R. Hanson 189 Book Review The Chemistry of Natural Products ed. R. H.Thomson Reviewed by R. B. Herbert 190 Book Review Phytochemical Methods -A Guide to Modern Techniques of Plant Analysis (2nd edition) by J. B. Harborne Reviewed by J. R. Hanson 191 Lignans and Neolignans D. A. Whiting Reviewing the literature published from 1976 to December 1983 213 Pyrrolizidine Alkaloids D. J. Robins Reviewing the literature published between July 1983 and June 1984 221 Tropane Alkaloids G. Fodor and R. Dharanipragada Revie wing the literature published between July 1983 and June 1984 227 Aporphinoid Alkaloids M. Sharnrna and H. Guinaudeau Reviewing the literature published between July 1983 avzd June 1984 235 Indolizidine and Quinolizidine Alkaloids M. F. Grundon Reviewing the literature published between July 1983 and June 1984 NATURAL PRODUCT REPORTS 1985 CONTENTS 245 Muscarine Imidazole and Peptide Alkaloids and Other Miscellaneous Alkaloids J.R. Lewis Reviewing the literature published between July 1983 and June 1984 249 Amaryllidaceae Alkaloids M. F. Grundon Reviewing the literature published between July 1983 and June 1984 253 Camphor A Chiral Starting Material in Natural Product Synthesis T. Money 291 Book Review Natural Products and Drug Development ed. P. Krogsgaard-Larsen S. B. Christensen and H. Kofod Reviewed by P. M. Dewick 293 Enzymology in Biosynthesis Mechanistic and Stereochemical Studies of P-Lactam Biosynthesis and the Shikimate Pathway J. A. Robinson and D. Gani Reviewing the literature published to December I984 321 The Biosynthesis of Polyketides T.J. Simpson Reviewing the literature published between July 1983 and June 1984 349 Carotenoids and Polyterpenoids G. Britton Reviewing the literature published between September 1982 and August 1984 389 Book Review Metabolites and Metabolism -A Commentary on Secondary Metabolism by E. Haslam Reviewed by D. A. Whiting 391 Erratum to Pyrrolizidine Alkaloids D. J. Robins (Vol. 2 No. 3 p. 213) 393 Quinoline Quinazoline and Acridone Alkaloids M. F. Grundon Reviewing the literature published between July 1983 and June 1984 401 Olefinic Microbial Metabolites excluding Macrocyclic Compounds R. C. F. Jones Reviewing the literature published during I982 and 1983 427 Phytoalexins C. J. W. Brooks and D. G. Watson Reviewing the literature published between January 1982 and July 1984 461 Steroids Reactions and Partial Synthesis J.Elks Reviewing the literature published during I983 495 The Biosynthesis of Shikimate Metabolites P. M. Dewick Reviewing the literature published during 1984 513 The Biosynthesis of C5-C20 Terpenoid Compounds D. V. Banthorpe and S. A. Branch Reviewing the literature published during I984 525 The Biosynthesis of Triterpenoids and Steroids D. M. Harrison Reviewing the literature published during 1979 1980 1981 1982 and 1983 561 The Biosynthesis of Porphyrins Chlorophylls and Vitamin BI2 F. J. Leeper Reviewing the literature published during 1984 I-1 Index of Authors Cited 1-31 Subject Index Natural Product Reports Editorial Board Professor G.Pattenden (Chairman) U n iversi ty of Notting h am Dr. D. V. Banthorpe University College London Professor M. F. Grundon University of Ulster at Coleraine Professor F. D. Gunstone University of St. Andrews Dr. J. R. Hanson University of Sussex Dr. R. B. Herbert University of Leeds Dr. T. J. Simpson U n iversity of Edinburgh Natural Product Reports is a journal of critical reviews published bimonthly which is intended to foster progress in the study of natural products by providing reviews of the literature that has been published during well-defined periods. For any individual topic successive reviews will deal with consecutive periods and while the coverage that was provided by the Specialist Periodical Reports on 'Aliphatic and Related Natural Product Chemistry' 'The Alkaloids' 'Biosynthesis' and 'Terpenoids and Steroids' will be continued this will be supplemented by occasional reviews of areas of both general and specific interest to workers in these and in other fields.All articles in Natural Product Reports are commissioned by members of the Editorial Board. This journal includes reviews of books relating to natural products. Volumes for review should be sent to the editorial office for which the address is The Royal Society of Chemistry Burlington House London W1V OBN and marked for the attention of Mr. B. J. Starkey. Contributors to Volume 2 Banthorpe D. V. 513 Bentley K. W. 81 Branch S. A. 513 Gani D. 293 Grundon M. F. 235 249 393 Guinaudeau H. 227 Pinder A. R. 181 Roberts J. S. 97 Robins D.J. 213 391 Britton G.,' 349 Brooks C. J. W. 427 Hanson J. R. 189 190 Harrison D. M. 525 Robinson J. A. 293 Saxton J. E. 49 Connolly J. D. 1 Dewick P. M. 291 495 Dharanipragada R. 221 Elks J. 461 Fodor G. 221 Fraga B. M. 147 Herbert R. B. 163 189 Hill R. A. 1 Jones R. C. F. 401 Leeper F. J. 19 561 Lewis J. R. 245 Money T. 253 Shamma M. 227 Simpson T. J. 321 Watson D. G. 427 Whiting D. A. 191 389
ISSN:0265-0568
DOI:10.1039/NP98502FP007
出版商:RSC
年代:1985
数据来源: RSC
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| 3. |
Front cover |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 009-010
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Natural Product Reports Editorial Board Professor G. Pattenden (Chairman) University of Nottingham Dr. D. V. Banthorpe University College London Professor M. F. Grundon University of Ulster at Coleraine Professor F. D. Gunstone University of St. Andrews Dr. J. R. Hanson University of Sussex Dr. R. B. Herbert University of Leeds Dr. T. J. Simpson University of Edinburgh Natural Product Reports is a journal of critical reviews published bimonthly which is intended to foster progress in the study of natural products by providing reviews of the literature that has been published during well-defined periods. For any individual topic successive reviews will deal with consecutive periods and while the coverage that was provided by the Specialist Periodical Reports on 'Aliphatic and Related Natural Product Chemistry' 'The Alkaloids' 'Biosynthesis' and 'Terpenoids and Steroids' will be continued this will be supplemented by occasional reviews of areas of both general and specific interest to workers in these and in other fields.Bimonthly publication allows greater flexibility than the annual or biennial publication of volumes of each of the series of Specialist Periodical Reports mentioned above in that individual reviews can be published as they become available. All articles in Natural Product Reports are commissioned by members of the Editorial Board. Natural Product Reports (ISSN 0265-0568) is published bimonthly by The Royal Society of Chemistry Burlington House London W 1V OBN England. 1985 Annual Subscription Price U.K.f125.00 Rest of World f131.00 USA. $242.00. Change of address and orders with payment in advance to The Royal Society of Chemistry The Distribution Centre Blackhorse Road Letchworth Herts. SG6 lHN England. Air Freight and mailing in the U.S. by Publications Expediting Service Inc. 200 Meacham Avenue Elmont NY 1 1003. U.S. Postmaster send address changes to Natural Product Reports Publications Expediting Service Inc. 200 Meacham Avenue Elmont NY 11003. Second-Class postage paid at Jamaica NY 11431-9998. All other despatches outside the U.K. are by Bulk Airmail within Europe and Accelerated Surface Post outside Europe. Printed in the U.K. 0The Royal Society of Chemistry 1985 All Rights Reserved No part of this publication may be reproduced stored in a retrieval system or transmitted in any form or by any means electronic mechanical photographic recording or otherwise without the prior permission of the publishers. Computer typeset by SB Datagraphics. Printed in Great Britain by Spottiswoode Ballantyne Printers Ltd Subscription rates for 1985 U.K. f125.00 Overseas f131.OO U.S.A. USS242.00 Subscription rates for 1986 are U.K. f130.00 Overseas f143.00 U.S.A. USS252.00 Subscription rates for back issues (1984) are U.K. f120.00 Overseas f126.00 U.S.A. USS240.00 Members of the Royal Society of Chemistry should order the journal from The Membership Officer The Royal Society of Chemistry 30 Russell Square LONDON WClB 5DT England
ISSN:0265-0568
DOI:10.1039/NP98502FX009
出版商:RSC
年代:1985
数据来源: RSC
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| 4. |
Back cover |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 011-012
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ISSN:0265-0568
DOI:10.1039/NP98502BX011
出版商:RSC
年代:1985
数据来源: RSC
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| 5. |
Back matter |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 015-016
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NewBooks from theRoyal Society ofChemistry Molecular Biology and Biotechnology Molecular Biology and Biotechnology Edited by J.M. Walker and E.B. Gingold I ' Special Publicution No.54(1986) Softcover 348pp ISBN 0 85186 985 8 Price €25.00 ($45.00) I Edited by J MWalker and E B Gingold I This book covers the recent advances made in the field of biotechnology and is aimed not at expert biotechnologists but at scientific workers with little or no previous experience in this field. The contributions in this book should thus be seen as primarily having a teaching function. The book should prove of interest both to undergraduates studying for biological or chemical qualifications and to scientific workers from other fields who need a basic introduction to this rapidly expanding area.Contents Products from Micro-organisms; An introduction to Genetic Engineering; The Expression of Foreign DNA in bcherichia coli; Cloning in Brewer's Yeast Succharomyces cerevisiae; Cloning in Mammalian Cells; The Genetic Manipulation of Crop Plants; The Application of Genetic Engineering to the Production of Pharmaceutical Compounds; Clinical Applications of Molecular Biology; Generation and Use of cDNA Clones for Studying Gene Expression; Enzyme Technology Towards Usable Catalysts; Applications or Biotechnology to Chemical Production; Enzyme Recovery and Purification Downstream Processing; Biosensors; Enzyme Engineering. ~-Ordering Orders should be sent to The Royal Society of Chemistry Distribution Centre Blackhorse Road Letchworth Herts SG6 1 HN U.K.Non-RSC Members and US$ pricesquoted.RSC Members are entitled to a discount on most RSC books and journals details available horn:Assistant Membership Officer The Royal Society of Chemistry 30 Russell Square London WC 1B 5DT. Pharmacokinetics of Cardiovascular Central Nervous System and Antimicrobial Drugs by P.G. Welling and F. L. S. Tse Hardcover 468pp JSBN 0 851 86 937 8 Price €39.00 ($7 1.OO) During the last 20 years the drug industry and the practice of medicine have expanded at an incredible rate. This has been due to the combined influences of a number of factors including rapid advances in pharmacology and pathology and accompanying advances in such diverse areas as pharmacodynamics pharmacokinetics and the developmentof sophisticated drug delivery systems.The last of these has been the focus of frenzied activity during the last ten years and is likely to continue for some time. More recent advances in immunopharmacology and the use of monoclonal antibodies have provided further impetus to the quest for new drugs in many therapeutic areas. Three major areas of drug research and development which have undergone considerable changes in recent years include cardiovascular agents drugs acting on the central nervous system (CNS) and antimicrobial agents. This book reviews developments which have taken place in these subjects from 1970 to the early 1980's. Contents Cardiovascular Drugs Cardiac Glycosides and Other Cardiotonic Agents; Antiarrhythmic and Antianginal Agents; Beta-Adrenergic Receptor Antagonists; Diuretics; Other Antihypertensive Agents; Anticoagulants.Drugs Acting on the Central Nervous System; Antidepressants; Antipsychotic Agents; Sedatives Hypnotics and Tranquilizers; Anticonvulsants. Antimicrobial Agents Penicillins; Cephalosporins and Cephamycins; Tetrecyclines; Aminoglycosides; Sulfonamides; Erythromycin Its Salts and Esters; Other Antimicrobial Agents. CompoundIndex ROYAL SOCIETYOF CHEMISTRY Information Services SPECIALIST PERIODICALREPORTS Copies of back issues of the Specialist Periodical Reports from which Natural Product Reports is derived are still available as follows Aliphatic and Related BiosynthesisVOID7 Natural Product Senior Reporters R.B.Herbert and T.J. Simpson A review of the literature published during 1979,1980 and 1981. Chemistry VOID3 Brief Contents The Biosynthesis of Polyketides; Phenolic Compounds Senior Reporter F.D. Gunstone Derived from Shikimate; The Biosynthesis of C5-C20 Terpeniod This third volume in theseries reviews the literature published Compounds; The Biosynthesis of Alkaloids. during 1980 and 1981. Hardcover232pp 0 851 86 553 4 Brief Contents Price €33.00 ($59.00) Natural Aceiylenic and Olefinic Compounds; Acyclic Still available Terpenoids; Insect Pheromones and Related Natural Vol.1 (1971) 0 851 86 503 8 €20.00 ($36.00) Products; Prostaglandins and Leukotrienes; Fatty Acids and V01.2(1972)0851865135 €21.00($38.00) Glycerides; Lipids; Olefinic Microbial Metabolites including Vo1.3 (1 973) 0 851 86 523 2 €21 .OO ($38.00) Macrocyclic Compounds.Vo1.4 (1 974) 0 851 86 533 X €24.00 ($43.00) Vo1.5 (1 975) 0 851 86 543 7 €32.00 ($57.00) Hardcover374pp 0 851 86 662 X Price €42.00 ($75.00) Vo1.6 (1 977-78) 0 851 86 990 4 €48.00 ($86.00) Stillavailable Special Package Price (Vols.1-7)S108.00 ($1 93.00) VOI 1 (1 976-77) 0 851 86 642 5 €35.00 ($63.00) VOI 2 (1 978-79) 0 851 86 652 5 €49.00 ($88.00) Special Package Price (Vols. 1-3)€79.00 ($1 41.OO) Terpenoids and The Alkaloids VOI. 13 Senior Reporter J.R. Hanson Senior Reporter M.F. Grundon This twelfth volume in the series covers the literature A review of the literature published between July 198 1 and published between September 1980 and August 1981.June 1982. Brief Contents Brief Contents Part I:Terpenoids Monoterpenoids; Sesquiterpenoids; Biosynthesis; Pyrrolidine Piperidine and Pyridine Alkaloids; Diterpenoids; Triterpenoids; Carotenoids Tropane Alkaloids; Pyrrolizidine Alkaloids; lndolizidine and Polyterpenoids. Alkaloids; Quinolizidine Alkaloids; Quinoline and Acridone Part II:Steroids Physical Methods Steroid Reactions and Alkaloids; O-Phenylethylamines and the lsoquinoline Pa rtia ISyntheses. Alkaloids; Aporphinoid Alkaloids; Amarylidaceae Alkaloids; Hardcover366pp 0 851 86 356 6 Erythrina and Related Alkaloids; lndole Alkaloids; Price€62.00 ($1 11.OO) fycopodiumAlkaloids; Diterpeniod Alkaloids; Steroidal Still available Alkaloids; Miscellaneous Alkaloids.Vol. 1 (1 969-70)0 851 86 256 X €26.00 ($47.00) Hardcover343p 0 85186 367 1 Vol. 2 (1 970-71) 0 85186 266 7 €23.00 ($41 .OO) Price €33.00 ($59.00) Vol. 3 (1 971 -72) 0 851 86 276 4 €26.00 ($47.00) still available VOI. 4 (1 972-73) 0 851 86 286 1 €30.00 ($54.00) VOI. 1 (1969-70) 0 851 86 257 8 €24.00 ($43.00) Vol. 5 (1 973-74)0 851 86 296 9 €31 .OO ($56.00) Vol. 2 (1970-71) 0 85186 267 5 €20.00 ($36.00) Vol. 6 (1 974-75) 0 851 86 306 X €31.OO ($56.00) Vol. 3(1971-72)085186277 2E21.00 ($38.00) Vol. 7 (1 975-76) 0 851 86 31 6 7 €36.00 ($65.00) VOI. 4 (1 972-73) 0 851 86 287 X €24.00 ($43.00) Vol. 8 (1 976-77) 0 851 86 326 4 €33.00 ($59.00) Vol. 5 (1 973-74) 0 851 86 297 7 €26.00 ($47.00) Vol.9 (1 977-78) 0 851 86 650 6 €40.00 ($72.00) Vol. 6 (1974-75) 0 851 86 307 8 €28.00 ($50.00) VOl.10 (1 978-79) 0 851 86 336 1 €54.00 ($97.00) Vol. 7 (1975-76) 0 851 86 31 7 5 €35.00 ($65.00) Vol. 1 1 (1 979-80)0 851 86 346 9 €54.00 ($97.00) Vol. 8 (1 976-77) 0 851 86 327 8 €34.00 ($61.OO) Special package price (Vols 1 -1 2) C254.00 ($453.00) Vol. 9 (1 977-78) 0 851 86 660 2 €38.00 ($68.00) VOl.10 (1 978-79) 0 851 86 337 X €61.OO ($1 09.00) Non-RSC Members and US$ prices quoted. RSC Members are VOl.11 (1979-80) 085186347 7 €61.00 ($109.00) entitled to a discount on most RSC books and journals. Details VOl.12 (1 980-81) 0 851 86 357 4 €67.00 ($1 20.00) available fr0m:TheAssistant Membership Officer The Royal Society Special package price (Vols 1-1 3) €229.00 ($409.00) of Chemistry,30 Russell Square London WC1 B 5DT. Ordering ROYAL SOCIETYOF Orders should be sent to CHEMISTRY The Royal Society of Chemistry Distribution Centre Information Blackhorse Road Letchworth Herts SG6 1HN U.K. Services
ISSN:0265-0568
DOI:10.1039/NP98502BP015
出版商:RSC
年代:1985
数据来源: RSC
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| 6. |
The biosynthesis of porphyrins, chlorophylls, and vitamin B12 |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 19-47
F. J. Leeper,
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摘要:
The Biosynthesis of Porphyrins Chlorophylls and Vitamin BIZ F. J. Leeper University Chemical Laboratory Lensfield Road Cambridge CB2 7 E W Reviewing the literature between December 1977 and December 1983 1 The Biosynthesis of Haem 1.1 6-Aminolaevulinic Acid Synthase 1.2 The Synthesis of 6-Aminolaevulinic Acid in Plants 1.3 6-Aminolaevulinic Acid Dehydratase (Porphobilinogen Synthase) 1.4 Formation of Uroporphyrinogen I11 Hydroxymethyl-bilane Synthase (Porphobilinogen 1 Deaminase) and Uroporphyrinogen I11 Synthase (Cosynthetase) 1.4.1 Proof that 1-Hydroxymethylbilane is the Intermediate 1.4.2 The Mechanism of Deaminase 1.4.3 The Mechanism of Cosynthetase 1.4.4 Determination of Ratios of Isomers of Uroporp h yrinogen 1.5 Uroporphyrinogen Decarboxylase (Uroporphyrinogen Car boxy -1yase) 1.6 Coproporphyrinogen Oxidase 1.7 Protoporphyrinogen Oxidase 1.8 Ferrochelatase (Haem Synthase Protohaem Ferro- lyase) 1.9 Cytoc hromes 2 The Biosynthesis of Chlorophylls 2.1 Chelation of Magnesium and Methylation 2.2 The Formation of Ring E 2.3 Reduction of the Vinyl Group 2.4 Reduction of Ring D 2.5 Esterification of Chlorophyllide a 2.6 The Formation of Chlorophyll b 2.7 Bac terioc hlorop hylls 2.8 Conclusion 3 The Biosynthesis of Vitamin B12 3.1 The Basic Precursors 3.2 Intermediates on the Pathway 3.2.1 Factor I 3.2.2 Factor 11 Sirohydrochlorin 3.2.3 Factor I11 3.2.4 The Synthesis of Isobacteriochlorins and Chlorins 3.3 Steps beyond Factor I11 3.3.1 Decarboxylation of the Acetate Group at C-12 3.3.2 Methylation Steps 3.3.3 Model Studies of the Methylation Steps 3.3.4 The Extrusion of C-20 3.3.5 Other Steps on the Path to Vitamin B12 3.4 Factor F-430 4 Topics Related to the Biosynthesis of Tetrapyrroles 4.1 The Biosynthesis of the Nucleotide Loop of Vitamin B12 4.2 N.M.R.Spectra and Other Properties of Tetrapyrroles 4.3 The Degradation of Haem 4.4 Medical Aspects 4.5 Evolution of the Biosynthetic Pathways 5 References The biosynthesis of tetrapyrroles has not been reviewed before in this series or in the series of Specialist Periodical Reports on Biosynthesis and so this review will give an overall picture of the field up to the end of 1983 but with particular reference to work published since the last review in Annual Reports on the Progress 0f’Chemistry.l In this time several excellent reviews have appeared in books including that of Akhtar and Jordan in ‘Comprehensive Organic Chemistry’,2 several chapters in Dolphin’s two major series ‘The Porphyrins’ (Vols.I-VII)3 and ‘B1 2’ (Vols. I and 11),4 and ‘Vitamin B1 Proceedings of the Third European Symposium on Vitamin B12 and Intrinsic Factor’ edited by Zagalak and Friedri~h.~ However developments continue apace ;particularly fasci- nating have been the results on the formation of uroporphyrino- gen I11 from four molecules of porphobilinogen and this area alone has been the subject of several reviews.6 Overall pathway.The pathways for the biosynthesis of haem chlorophylls and vitamin B (cyanocobalamin) appear to be essentially the same in all organisms in which they are found. All of them start with 6-aminolaevulinic acid (ALA) two molecules of which are condensed as shown in Scheme 1 to give porphobilinogen (PBG). Four molecules of PBG condense head-to-tail with elimination of ammonia to form a linear tetrapyrrole which is the unrearranged 1-hydroxymethylbi- lane. Cyclization of this unrearranged bilane proceeds enzymatically with a rearrangement of ring D to give the type I11 uroporphyrinogen (uro’gen 111).At this point the pathway to vitamin B12 diverges from that of haem and the chloro- phylls; it will be treated in full in Section 3. The route to haem however involves the decarboxylation of uro’gen I11 at all four acetate side-chains to give coproporphyr- inogen I11 (copro’gen 111). Two of the propionate groups of copro’gen I11 are oxidatively decarboxylated to give the vinyl groups of protoporphyrinogen IX. Oxidation of this porphyr- inogen to protoporphyrin IX (proto IX) and insertion of Fe2+ into the centre of the macrocycle gives haem which is found as such in haemoglobin myoglobin cytochromes b and P-450 peroxi- dases catalase and erythrocruorin. In a modified form haem is present in the a and c cytochromes. Introduction of a Mg2+ ion into the macrocycle on the other hand is the first step on the route to the chlorophylls details of which will be given in Section 2.First we will examine the biosynthesis of haem in more detail. 1 The Biosynthesis of Haem This pathway which is so central in the production of the tetrapyrroles that are vital to all organisms has been intensively studied over many years by chemists and biochem- ists alike so that for every step the enzymes have been isolated and at least partially purified and characterized. Therefore it is appropriate in this case to treat each enzyme in a separate section beginning with the synthesis of ALA. 1.1 6-Aminolaevulinic Acid Synthase (EC 2.3.1.37) The major pathway to ALA (1) in bacteria and animals but not in plants is by the reaction of glycine with succinyl-CoA as shown in Scheme 2.The enzyme that is responsible has been isolated and purified from many sources including Rhodo-pseudomonas sphaeroides,’ Euglena gracilis,s and the livers of rat9 and chicken embryos,1° and the enzyme from soybean callus has been immobilized on a Sepharose support’ (as well as several other enzymes of porphyrin biosynthesis). There appear to be several forms1° of the enzyme in some of these SOU~C~S~.~ and it has been suggested that the chicken embryo liver enzyme that is initially synthesized in the cytosol has a NATURAL PRODUCT REPORTS 1985 CO,H HO 1-Hydroxymethylbilane ALA PBG ICOzH \COzH Protoporphyrin IX Copro'gen II I Uro'gen 111 Vitamin B,? pathway Chlorophyll pathway Scheme I COzH NH NH O,H PLkNH pLpPH (1) (PLP = pyridoxal phosphate CoA = coenzyme A) Scheme 2 molecular mass of 74 000 but a portion is lost when this is trans- ported into the mitochondria to give an active form (of mol.wt 68 000). This transport is inhibited by haemin. 6-Aminolaevulinic acid synthase requires pyridoxal phos- phate which in the absence of substrate forms a Schiff's base with the amino-group of a lysine residue in the enzyme from R. sphaeroides as judged by the detection of pyridoxyl-lysine after hydrolysis of a sample of the enzyme that had been inactivated with NaBH4.1Z Glycine is incorporated into ALA with the loss of C-1 ; in principle the requisite anion of the glycine- pyridoxal phosphate Schiff's base could be formed by this decarboxylation but in fact the loss of 50% of the activity from [2-3H]glycine indicates that it is a deprotonation step which generates the anion.Experiments with [2R-3H]glycine and [2S- 3H]glycine have shown that it is exclusively the pro-R hydrogen which is removed. Reaction with succinyl-CoA is followed by the decarboxylation. It has been shown that the pro-S hydrogen at C-5 of ALA is the one that is derived from glycine thepro-R hydrogen coming from the medium. This was determined by chemical degrada- tion of a sample of porphobilinogen that had been derived from [2-3H]glycine back to [2S-3H]glycine.'4 Thus it appears either that the reaction with succinyl-CoA occurs with inversion at C-2 of glycine and the decarboxylation then occurs with reten- tion of configuration or vice versa.In the absence of succinyl-CoA ALA synthase catalyses the exchange of the pro-R hydrogen of glycine and the 5-pro-R hydrogen of ALA with solvent,I5 as would be expected from the mechanism. It is also reported to cause exchange of the carboxyl group of glycine with NaHITO only in the presence of suc~inyl-CoA.'~ This incorporation is increased by the addition of ALA and coenzyme A and indicates the reversibi- lity of the whole sequence. 1.2 The Synthesis of 6-Aminolaevulinic Acid in Plants It is now clear that plants do not in general use ALA synthase in the production of chlorophyll. Thus I4C-labelled glycine is poorly incorporated (if at all) into ALAI7,'* or chlorophyll;3 where some incorporation is seen both [1-l4C]glycine and [2- 14C]glycine are incorporated.'' It has been shown using I4C-and 13C-labelled precursors that all five carbon atoms of glutamic acid (2) are incorporated into ALA and thence into chlorophylls;*8.19however the order of the likely steps i.e.one reduction and two transaminations is not certain. Enzymes which will cause the transamination of 4,5-dioxovaleric acid (DOVA) (3) and alanine to ALA and pyruvic acid have been isolated from several sou~ces.~ A purified enzyme from cucumber seeds is the first to have been shown to be specific for this transformation only.20 The mammalian liver enzyme with this capability is more active as an alanine :glyoxylate transaminase.2 of cl-ketoglutarate (4)to DOVA has been partially purified from the leaves of Zea mays,22but different workers obtained a NADPH-requiring extract from plastids of the same organism which converted both glutamate (2) and its 1-semialdehyde (5) into ALA ( It seems that either or both of the routes to (3) that are shown in Scheme 3 may be followed.NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER / Ho2cY-co2H 0 Ho2CPco2H (4) NH (2) Scheme 3 The role of DOVA (3) in the biosynthesis of ALA has been questioned by two studies in the first24 it was found that a mutant of R. sphaeroides that requires ALA for its growth could not grow on DOVA instead despite the fact that the transaminase was active. In the second it was found that DOVA inhibited the formation of porphyrins in Clostri-dium tetanomorphum again despite the presence of the transaminase because of inhibition of ALA dehydratase.It has been suggested1 that (3) is an intermediate but that it generally remains enzyme-bound and this could provide an explanation for the above results. It has been found26 that in Euglena gracilis 14C-labelled glutamate but not glycine is incorporated into chlorophyll whereas 14C-labelled glycine is the better precursor of the haems. Under conditions where chloroplasts are absent (in a mutant or when the organism is grown in the dark) [14C]glutamate is not incorporated into porphyrins at all. The indication is that the five-carbon route to ALA (and thence to the tetrapyrroles) is exclusive to the plastids whereas the ALA synthase route only operates in the cytosol and in mitochondria.It is likely that the same situation exists in higher plants also. 1.3 6-Aminolaevulinic Acid Dehydratase (Porphobilinogen Synthase; EC 4.2.1.24) Condensation of two molecules of ALA (1) in a Knorr-type pyrrole synthesis to give porphobilinogen (PBG) (6) is catalysed by ALA dehydratase. The two best studied dehydra- tases are from Rhodopseudomonas sphaeroides and bovine liver. Both are inhibited by NaBH only if ALA or laevulinic acid (7) is present thus indicating that a Schiffs base is formed.27 On hydrolysis of a sample that had been inactivated by NaBH in the presence of [4-14C]ALA a radioactive spot was detected that was chromatographically identical to one for the lysine derivative (8).2s Laevulinic acid alone is not a substrate but if it is mixed with ALA it can be utilized by the enzyme of R.sphaeroides to form the methylpyrrole (9).29Thus it seems that (7) can occupy the A site of the enzyme (the ALA-binding site which provides the acetate side-chain of PBG) and it is assumed that this is the site of formation of a Schiffs base (though it has not been proved). Formation of an imine would facilitate deprotonation on C-3 of ALA to give the enamine and so the likely course of the reaction is as shown in Scheme 4. It is known that it is thepro-R hydrogen which is lost at C-2 of PBG because incorporation of [5S3H]ALA (derived from [2- 3H]glycine -see Section 1.1) occurs without loss of tritium.30 It had been assumed on the basis of the above results that the first molecule of ALA forms a Schiffs base in the A site and then the second molecule occupies the P site.However Seehra and Jordan in an elegant experiment3’ (modelled on experi- ments with PBG deaminase that are described in the next section) have shown that on exposure of the enzyme to 1 equivalent or less of labelled ALA for 0.1 s followed by an excess of unlabelled ALA it is the P site which contains the majority of the labelled ALA. Thus PBG that had been made in this way from [5-13C]ALA contained all of the detectable I3C at c-2. The bovine liver dehydratase is an octamer of molecular weight 285 000,” and it appears (in an electron micrograph) to have the subunits arranged at the corners of a cube.32 It requires four Zn2+ or Cd2+ ions for full activity33 though it can Scheme 4 CO H lo H (7) (9) bind eight Zn2+ ions.34 The ion Hg2+ replaces Zn2+ and inactivates the enzyme.By immobilization of bovine liver dehydratase on a Sepharose support the dissociation of the enzyme into partially active tetramers could be demon-~trated.~~ It is-claimed that a dimer is the minimal complex that retains and this is consistent with the apparent presence of only four active sites per ~ctarner.~’*~’,~~ The N-terminal sequence up to residue 44 has been quoted.39 The subunits are identical except that half of them have the terminal methionine residue acylated and the other half have a free N-terminus.It is thought that the active site of bovine dehydratase involves two thiol groups of cysteine residues and two imidazole moieties of histidine as well as the zinc The thiol groups are easily oxidized in air to a disulphide thus deactivating the enzyme but it can be re-activated by the presence of thiols in the medium. In addition to normal thiol- directed agents the enzyme is also inactivated by 3-and 5-chlorolaevulinic acids.37 These active-site-directed agents alkylate different cysteine residues (only on the reduced enzyme). The results suggest that 5-chlorolaevulinic acid forms a Schiffs base with the enzyme and reacts with a thiol in that NATURAL PRODUCT REPORTS 1985 site whereas the 3-chloro-isomer reacts with a thiol in the alternative site.The role of these thiols is not certain though one or both may be involved in binding the zinc ion -oxidation to the disulphide causes release of the meta1.34,40 There is also speculation about the role of the zinc ion; one possibility is that it acts as a Lewis acid to make the ketone in the P site more electrophilic and the eventual loss of OH-from the same carbon more facile. It has been claimed,40 though that the zinc ion is only necessary to prevent oxidation of the thiol groups. The dehydratase of R. sphaeroides may be a hexameel or an ~ctamer,~~ and unlike the bovine liver enzyme it requires K+ or Mg2+ for acti~ity.~~.~~ In other respects the enzymes from the two sources are similar.6-Aminolaevulinic acid dehydratases from all sources are inhibited by laevulinic acid which has often been used to cause accumulation of ALA in v~uo.~? l 7* *Succinylacetone is also an inhibitor of dehydrata~e~~ and is particularly interesting because it is produced in humans who are suffering from a hereditary disorder of their tyrosine metabolism in which the enzyme that hydrolyses fumarylacetoacetate is defective.44 As a result there is a build up of succinylacetone which inhibits ALA dehydratase and causes excretion of ALA and other symptoms of acute intermittent porphyria. 6-Aminolaevulinic acid dehydratase can be immobilized on a Sepharose support,’ 1935,42 and this produces a very stable system which can be used for long periods of time to produce gram quantities of PBG for studies with the next enzymes in the pathway.4s 1.4 Formation of Uroporphyrinogen 111 Hydroxymethylbilane Synthase (Porphobilinogen Deaminase; EC 4.3.1.8) and Uropor-phyrinogen 111 Synthase (Cosynthetase; EC 4.2.1.75) Until only a very few years ago this step in the biosynthesis of porphyrins remained quite ob~cure.~.~ However as a result of much detailed and painstaking work we now have a considerably clearer overall view of the process.It has been known for some time that two enzymes are involved. The first enzyme PBG deaminase forms a tetramer of PBG with elimination of NH3. The observed product of this enzyme was uroporphyrinogen I (uro’gen I) and so it has been referred to as uro’gen I synthetase but it is now known that uro’gen I is the PBG (6) result of a chemical rather than of enzymic cyclization and so this name for the enzyme is inappropriate.The second enzyme uro’gen I11 synthase (usually described as cosynthetase) in conjunction with deaminase produces uro’gen I11 (instead of the type I isomer) from PBG. It was shown that uro’gen I is not a substrate for cosynthetase and the lack of any other known substrate led to the assumption that cosynthetase binds to and in some way modifies the action of deaminase. The combina- tion of deaminase and cosynthetase is sometimes called porphobilinogenase. It is now generally accepted that the true course of events is as shown in Scheme 5. Four molecules of PBG (6) are initially con- densed head-to-tail by deaminase to form the hydroxymethyl- bilane (10).This intermediate is the substrate for cosynthe- tase which cyclizes it to uro’gen I11 (1 1) with rearrangement of ring D. In the absence of cosynthetase 1-hydroxymethylbilane (10) cyclizes chemically without any rearrangement to give uro’gen I (12). 1.4.1. Proof that 1-Hydroxymethylbilane is the Intermediate Since the discovery that PBG is the precursor of uro’gen 111 many different hypotheses for the steps that are involved have been proposed.46 These can be divided into categories depending on the stage at which the rearrangement occurs mono- di- tri- or tetra-pyrrole. Some of the hypotheses could be discounted by the results of experiments with 13C-labelled PBG. For example,47 (2,ll- 3C2)PBG(13) diluted with unlabelled PBG was incubated with the deaminase-cosynthetase system to give a sample of uro’gen I11 in which eight atoms were labelled.In the 13C n.m.r. spectrum of the labelled protoporphyrin IX (14) that was obtained from this uro’gen 111 the signals of three of the meso carbons were fine doublets (J = 5.5 Hz) owing to long-range coupling across a pyrrolic ring (C-20 to C-4 C-5 to C-9 and C-10 to C-14) but the signal of one meso carbon (C-15) was a widely spaced doublet (J = 72 Hz) owing to coupling with a directly adjacent 13C (at C-16) -see Scheme 6. The implication of this experiment is that only one rearrangement occurs and it must involve an intramolecular inversion of the pyrrole ring that is destined to become ring D of uro’gen 111,in the course of which C-11 of PBG migrates from C-5 to C-2.COzH HO NH HN2 1 W ‘zH H cosynthetase f 602H Uro’gen 111 (1 1) k02H Uro’gen I (12) Scheme 5 NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER In experiments to find out at what stage the rearrangement of ring D occurs no significant incorporations were obtained with isoporphobilinogen (1 5Y8 or with di- or tri-pyrrolic com-pounds. The results with the di- and tri-pyrrolic compounds were confused by non-enzymic condensations and fragmenta- tions which could give bilanes and porphyrinogens but in general the overall rate of formation of a porphyrinogen was not significantly increased by the presence of the enzyme^.^^^^ The first result pointing in the right direction was the discovery of the unrearranged bilanes (16)-( 18) as by-products that are formed from PBG by deaminase in the presence of the appropriate nucleophiles (NH3 NH20H or NH20Me).49*50 The aminomethylbilane (16) was chemically synthesized5 and was found to be converted into uro’gen I faster in the presence of deaminase than purely chemically; furthermore with added cosynthetase uro’gen I11 was formed.The rearrangement to form uro’gen I11 was shown to be intramolecular by double- labelling with l3C. However it was soon realised that (16) could not be a true intermediate52 because (i) it is converted into uro’gens by deaminase (or deaminase-cosynthetase) 15 times slower than PBG; (ii) it is not a substrate for cosynthetase alone but is converted by deaminase into a compound which is a substrate for cosynthetase; (iii) it is not detected as a normal product of deaminase except in the presence of a large concentration of ammonia.The presence of an enzyme-free intermediate between PBG and the uro’gens was deduced from the fact that the initial production of porphyrinogens by deaminase alone was much slower than the consumption of PBG.52 The intermediate that is involved was first observed by 3C n.m.r. spectroscopy of the HO? (,, 11 &2 H H2N (13) I3C at CO2H k02H HOg2H (14) Scbeme 6l 3C is at either 0 or 0 or~orl c o NH2 H (10) X = OH (16) X = NH2 (15) (17) X = NHOH (18) X = NHOMe 23 product of incubation of [1 1-13C]PBG with deamina~e.~~.~~ In addition to the expected signals around 6 24.4p.p.m.for the pyrrole-CH,-pyrrole methylenes a signal was seen at 6 57.1* p.~.m.~~ This compound was stable in alkali but at pH 8.5 and 37 “C it gave uro’gen I chemically with a half-life of 4 minutes. This intermediate proved to be an excellent substrate for cosynthetase which very rapidly converted it into uro’gen III.52-54 (See later for methods of analysis of porphyrin isomers.) Scott and co-~orkers~~ considered several possible structures for the intermediate and to help distinguish among them they incubated deaminase with [l l-13C,1-15N]PBG.55 In the 13C n.m.r. spectrum of the resulting intermediate they observed that the signal at 6 57.1 p.p.m.was broadened; this was interpreted as being a doublet for which J = 6 Hz arising from a one-bond sN-l 3C coupling. They therefore decided on structure (19) for the intermediate. Battersby and co-~orkers~~ also obtained a 13C n.m.r. spectrum of the intermediate that was derived from [11-I3C 1-l5N]PBG but observed a doublet at 6 57.1 p.p.m. with a coupling constant of only 2.4 Hz -consistent with a two-bond 5N-13C coupling. As a result they proposed the open-chain hydroxymethylbilane structure (10). Further proof has been obtained that (10) is indeed the true intermediate. First the 3C n.m.r. spectrum of the model compound (20) showed a doublet (J = 2.3 2 0.2 Hz) at 6 57.3 p.p.m. for the hydroxymethyl carbon,52 very similar to that of the enzymic intermediate.Secondly the 3C n.m.r. spectra of the model compounds (21)57 and (22)58 showed a much more widely spaced doublet of coupling constant 10-10.7 Hz at 6 41.5-42.0 p.p.m. for the 1-pyrrolylmethyl carbon -very different from that of the enzymic intermediate. Thirdly the hydroxymethylbilane (lo) synthe- sized as shown in Scheme 7 was shown to be identical to the enzymic intermediate in all respects including its reaction with c~synthetase.~~ Also very importantly the rate of cyclization of (10) by cosynthetase when deaminase was present was identical with that when deaminase was nor present.63 The only remaining objection to the role of the hydroxy- methylbilane as the true intermediate is that it may be in equili- brium withacompound which is theactualproductofdeaminase and the substrate of cosynthetase such as the azafulvene (23).However the extremely rapid reaction of cosynthetase with (10) makes involvement of such a chemical step seem unlikely. * These values are taken from ref. 52; the values in ref. 53 are 2.3 p.p.m. lower only because they are measured from a different standard. 2H HOzC (19) NATURAL PRODUCT REPORTS 1985 Mg MeOgco'Me+ ___+ MeO& several-steps MeowozMe But02C C02Bn Bu'02C C0,Bn OHC H AcO H H H H H // I (Bn = CH,Ph) I ji Reagents i TsOH CH2C12; ii NaBH,; iii AcOH CH,C12; iv NaOH Scheme 7 H H H H (23) Production of (23) at the active site of deaminase followed by its trapping by water or other available nucleophiles would account for the formation of bilanes (10) and (1 6)-( 18) but the non-enzymic reaction of (10) with NH3 or NH20H is reported to be very and so the formation of (23) is ruled out except when it is bound to an enzyme.In view of the above results the systematic name for PBG deaminase has been officially changed to hydroxymethylbilane synthase [EC 4.3.1.8].60 Similarly as cosynthetase does not in fact act in co-operation with deaminase but can function quite independently its name is also inappropriate and it should properly be uroporphyrinogen III synthase [EC 4.2.1.751. 1.4.2 The Mechanism of' Deaminase The order of assembly of the four PBG molecules to give the hydroxymethylbilane has been studied using pulse-labelling experiments (similar to that described earlier for 2 ALA - PBG).Unlabelled PBG (0.5 pmol) was added to deaminase (-0.25 pmol) that had been isolated from Euglena gracilis; this quantity of PBG was insufficient to allow formation of the biiane which was completed by addition of excess [ll-13C]PBG.59,61The resultant uro'gen I11 was chemically converted into coproporphyrin I11 tetramethyl ester and the relative proportions of 12C and 13C at the four meso positions were determined from the * H n.m.r. of the attached hydrogens in the presence of a shift reagent. It was quite clear that C-20 had the most 12C followed by C-5 C-10 and C-15 respectively. Thus the order of binding of the four pyrrolic rings is first ring A then ring B ring C and finally ring D.The ratios of '*C to 13C at the four sites were very close to the statistical distribution that would result if the rates of binding of each of the four successive PBG molecules were identical. The same order of assembly was found for deaminase that was isolated from Rhodopseudomonas sphaeroides. This ex per imen t em- ployed 14C-labelled PBG and the labelled sites were located by degradation of protoporphyrin IX.* Serious inconsistencies appear in the radioactivity measurements in this work; e.g.,degradation of samples of protoporphyrin IX showed that virtually all of the activity was in the two moles of ethylmethylmaleimide that were formed from rings A and B despite the fact that halfof the activity from [2,1 l-l4C2]PBG should be at the meso carbons which are lost in the degradation.Kinetic experiments on deaminase have shown that the first PBG molecule is covalently bound to the en~yrne~~.~~ with release of 1 mole of ammonia.63 Thus the necessary steps for the formation of the hydroxymethylbilane are as shown in Scheme 8. In this scheme the di- and tri-pyrrolic intermediates remain bound to the enzyme which explains why these types of intermediate cannot in general be detected or incorporated during conversion of PBG into Anderson and De~nick,~~ working with human deaminase observed four different forms of deaminase to which PBG was bound. These separated forms had 1 2 3 and 4 molecules of PBG bound per molecule of deaminase. Subsequently Jordan and co-workers66 have separated by gel electrophoresis three forms of deaminase with [3,5-l4C2]PBG bound to them.All three forms were able to complete the synthesis of 14C-labelled hydroxymethylbilane when excess unlabelled PBG was sup- plied. By subsequent conversion of the hydroxymethylbilane into protoporphyrin IX and degradation they were able to show that the three forms had respectively 1 2 and 3 molecules of PBG bound. There was no sign of a form with four PBG molecules bound in this experiment with deaminase from R. sphaeroides. In contrast Battersby et have found that the tetrapyrrolic hydroxymethylbilane (1 0) forms a relatively stable complex with deaminase from Euglena gracilis. The nature of the enzymic group X (see Scheme 8) to which the first PBG molecule becomes attached has not been rigorously established but there are indications that it might be an amino-group of a lysine residue.First,63 the enzyme having a molecule of [ 1 1-l 3C]PBG covalently bound to it was digested with proteolytic enzymes to obtain small peptide fragments with the pyrrole unit(s) attached. In the I3C n.m.r. spectrum signals appeared at 6 24.5 p.p.m. (attributed to pyrrole-CH,- pyrrole) and others were just visible at 6 42-43 p.p.m. attributed to peptide-NH-CH,-pyrrole. Se~ondly,~' deamin-ase is inhibited by pyridoxal phosphate. With NaBH this inhibition becomes irreversible indicating that a Schiffs base is formed between the pyridoxal phosphate and an amino- group at the active site. On hydrolysisof a sample of the enzyme that had been inactivated with pyridoxal phosphate and [3H]NaBH, E-pyridoxyl-lysine was positively identified by dilution analysis.It is conceivable however that the lysine residue that is thus modified is involved in some other role in the active site. One further interesting observation is that while 14C-labelled PBG remains covalently bound to deaminase even after denaturation treatment of the denatured complex with hydroxylamine does release the radi~activity.~~ As a denatured enzyme cannot catalyse the release of the substrate it may be that hydroxylamine causes SN2-type displacement of the enzymic group. The experiments that have been described in this section have been largely on deaminase that was isolated and purified NATURAL PRODUCT REPORTS 1985 -F.J. LEEPER 25 Enz-X’ \ CO?H C02H HOzC HecozH Enz-Xl HN+cozH HOzC Ho2:wcozH HOzC from either Rhodopseudomonas sphaeroides or Euglena gracilis though many other sources have been de~cribed.~ The enzyme has usually been found to have a molecular weight of about 40 00049.66.69 (but one report68 quotes 20 000). For the enzyme from E. gracilis the values of KMfor PBG depend on whether hydroxymethylbilane is present or absent. Under the best conditions a value of 105pmoldm-3 was obtained6j and a value for k,, of 0.27 s-l has been ~alculated.~~ As yet no sub- strate for deaminase other than PBG [and the aminomethyl- bilane (1 6) and some of its isomers5*] has been found. Similar pyrroles such as isoporphobilinogen (1 5) opsopyrroledicar-boxylic acid (24),and 2-aminomethylpyrrole-3,4-diaceticacid (25) are competitive inhibitors but are not used as substrates by the en~yme.~ Several questions about the action of deaminase remain unanswered.The stereochemistry of all of the steps is unknown and so is the mechanism by which the tetrapyrrole (but not the di- or tri-pyrrole) is released. It is however known that for the enzyme from Euglena gracilis release of the hydroxymethyl- bilane is slow except in the presence of PBG.63 In the biosynthesis of fatty acids and polyketides the condensations are thought to occur repeatedly at the same active site with the growing chain being attached to a long flexible pantotheine chain; the same principle is used in the enzymic synthesis of some oligopeptides e.g.gramicidin S. It is possible that deaminase uses a single catalytic site in a similar fashion though the alternative that there are four separate catalytic sites one for each PBG unit is just as likely. I .4.3 The Mechunism of’ Cosyntherase There have been very few studies on cosynthetase itself partly because a convenient was not available until its substrate was identified as (10). One plausible mechanism for HOzC C02H COzH (23) CO,H H2N rq n (24) the rearrangement,47 based on a proposal first put forward in 1961,73 is shown in Scheme 9. In this mechanism loss of water from the hydroxymethylbilane to give (23) is followed by cyclization onto the substituted a-position of ring D to give a spiro-compound (26).Fragmentation of (26) could give either (23) again or a different azafulvene (27) which would cyclize in the normal way to give uro’gen 111 (1 1). Another possible route from (26) to (11) would involve a series of [1,5] sigmatropic rearrangements. In a model study to test the feasibility of these rearrangement mechanisms the pyrrolenine (28) was ~ynthesized.’~ Under very mild acid conditions (28) rearranged to give (23) as the major product. The structure of this major product and other minor products shows that the fragmentation-recombination mechanism predominates over the sigmatropic rearrangement in this case. While the spiro mechanism is a highly plausible one another mechanism has been suggesteds7 which also fits the known facts; it is shown in Scheme 10.This scheme uses an enzyme- bound electrophile to hold ring D as it is detached from the other three pyrrole units turned around and re-attached. In principle the electrophile could be a proton but this would not provide covalent attachment to the enzyme. In Scheme 10 the electrophile is shown as an iminium ion. In this context it is interesting that two recent reports suggest that folic acid which is a likely source of such an iminium ion may be involved in the mechanism of cosyntheta~e.’~. 76 NATURAL PRODUCT REPORTS 1985 HO2* ZH HO2 W 2H NHHN 1 NHHN 1 Bu'02C&p -+a H H H CO~BU' .ozcW 2H H O 2 W O2H NH HN NHHN -*co2H \t/ u *co2H HO2C H02CH02C HOzC C02H d02H b02H C02H A* J H O 2 W 02H NHHN I \ H02C C02H COzH C02H Scheme 10 NATURAL PRODUCT REPORTS 1985 -F.J. LEEPER Cosynthetase from a number of different sources has been and the hydroxymethylbilane (10) is a substrate in all cases. The specificity of cosynthetase for various bilanes has been tested several times. In experiments with aminomethylbi- lanes deaminase must also be present to convert the aminomethylbilanes into hydroxymethylbilanes before these can act as substrates for cosyntheta~e.~~ This presents the added complication that the enzymic reaction may fail to give uro’gens faster than the non-enzymic cyclization because the aminomethylbilane does not interact with deaminase. A study of the isomer composition however gives some indication of the extent to which cosynthetase has been involved.Studies on the aminomethylbilanes (16) and (30)-(34) in Cambridge using enzymes of Euglena gracifi~,~~ and on (16) and (33)-(36) in Buenos Aires using enzymes from a variety of source^^^,^^ (Rhodopseudomonas sphaeroides wheat germ rat blood and rat spleen) have been published. Both groups find that the unrearranged bilane (16) is cyclized fastest but the results differ for different organisms on the extent of inversion of ring D that occurs for (16) and the other bilanes. The interpretation of the results is made difficult by the presence of two enzymes and by the high proportion of non-enzymic cyclization that occurs in most cases.More direct studies on the substrate specificity of the cosynthetase of E. gracilis have used hydroxymethylbilanes.80 As mentioned earlier the unrearranged hydroxymethylbilane (10) is a very good substrate and is almost completely rearranged. Bilanes in which the substituents on ring c(38) or on ring D (39) are reversed were cyclized by cosynthetase and underwent considerable inversion -45% for (39) 95% or more for (38). Compounds (37) and (40) were not found to be substrates at all. When bilanes (41) and (42) (from which a carboxyl group on ring D was missing) were incubated with cosynthetase,*l (42) was a good substrate -cyclization occurred at about 25% of the rate of that for (10) -but (41) was a poor substrate. Proton n.m.r. spectroscopy revealed that two isomers were formed from (42) in a ratio which indicated that enzymic cyclization proceeded with 65% inversion of ring D.In conclusion our knowledge about the mechanism of cosynthetase is still incomplete but any detailed hypothesis will have to take into account the fact shown in these studies that a type I bilane is rearranged almost completely to a type I11 porphyrinogen whereas a type I11 bilane (in which substituents on ring D are reversed) is rearranged to a considerable extent to a type I porphyrinogen. Obviously there is no common intermediate from these two bilanes. I .4.4 Determination oj’Ratios oj’Isomers of Uroporphyrinogen Much of the foregoing work on deaminase and cosynthetase was greatly helped by the ability to distinguish which uro’gen isomers are formed and to measure their ratios.This has been made very much easier and more accurate by the use of h.p.1.c. Ratios of uro’gen isomers are not determined directly; instead the uro’gen mixture is invariably oxidized to the much more stable uroporphyrins using iodine or benzoquinone. Uropor- phyrin isomers (see Table 1) have been separated by h.p.1.c. both as the free acids (on reverse-phase and as Y (16) NH2 (30) NH2 (31) NH2 (32) NH2 (33) NH2 (34) NH2 (35) NH2 (36) NH2 (10) OH (37) OH (38) OH (39) OH (40) OH (41) OH (42) OH R’ R2 R3 R4 R5 R6 R7 R8 A P A P A P A P A P A P A P P A A P A P P A A P A P P A A P A P P A A P A P A P P A P A P A A P P A A P P A A P P A P A P A P A A P A P A P A P A P P A A P A P A P A P P A A P A P A P A P P A P A P A P A A P A P A P A P MeP A P A P A P AEt (A = CH2C02H,P = CH2CH,C02H) Table 1 The positions of side-chains in the isomers of uroporp hyrin R’ R3 R’ R4 NH HN- R8 \ R7 Type CH,C02 H I R1 R3 R5 R7 I1 R’,R4 R5 R8 111 RI R3 R5 R8 IV R’ R3 R6 R8 R5 R6 CH2CH2COzH R2 R4 R6 R8 R’ R3 R6 R7 R2 R4 R6 R7 R2 R4 R5 R7 was later develo~ed.~~b Recently a separation of all four isomers as the free acids by reverse-phase h.p.l.c.eluting with MeCN/H20 that is buffered with NH,OAc and HOAc (elution occurred in the order I 111 IV 11) has been described.85 This latter technique effected the separation within 25 minutes; however in general reverse-phase h.p.1.c.has a lower capacity than the normal-phase procedure and so would not be suitable on a semi-preparative scale. The separation of uroporphyrin coproporphyrin and the hepta- hexa- and penta-carboxylated porphyrins that are intermediate between them is of considerable interest in clinical chemistry as these compounds are present in the urine of patients suffering from various porphyrias. Such a separa- tion is relatively easy by h.p.1.c. or t.l.c. but particularly impressive is a simultaneous separation of the types I and I11 isomers of coproporphyrin and uroporphyrin and of the penta- hexa- and hepta-carboxylic intermediates that has been reported recently.86 methods successfully separate uroporphyrins I 11 and 111 but uroporphyrin IV cannot be separated from uroporphyrin 111.The normal sequence of elution is I I11 + IV 11. Uroporphyrins can be decarboxylated to give coproporphyr- ins by heating in dilute HCl (at 180°C) or without solveqt. This technique has been employed by the Cambridge group in their studies on deaminase-cosynthetase because it is possible to separate all four isomers of coproporphyrin. The first separation of the four isomers relied on two successive h.p.1.c. runs. The first run separated types 11 I11 + IV and I in that order and the second run using a different solvent system then separated types I11 and IV after several recycles.84 A more effective separation of all four isomers in a single run as their zinc complexes (when the order of elution was I 11 111 IV) Both 1.5 Uroporphyrinogen Decarboxylase (Uroporphyrinogen Car- their methyl esters .(on normal-phase ~olumns).~~-~~,~~ boxy-lyase; EC 4.1.1.37) The next step on the route to haem is the four-fold decarboxylation of uro’gen I11 (1 1) to copro’gen I11 (46).It was thought that a single enzyme was responsible for all four decarboxylations but until recently the enzyme had not been purified and so this could not be verified. In 1983 four different groups all reported the purification of a single enzyme that is capable of the four decarboxylati~ns.~~-~~ The kinetics of the decarboxylation reactions are complicated by the existence of the hepta- hexa- and penta-carboxylic intermediates and by inhibition of the reactions by the products.It seems that the first decarboxylation to give a heptacarboxylic porphyrinogen is the fastest; this intermediate accumulates initially and then is converted into copro’gen I11 at a lower rate.89-91 The intermed jate hexa- and penta-carboxylic porphyrinogens can be detected but their concentrations are usually low. At high concentrations of uro’gen 111 the heptacarboxylic intermediate accumulates to a greater extent and the overall rate of formation of copro’gen 111 is red~ced.~~-~l It has been s~ggested~~-~’ that there are two (or more) catalytic sites one for the first decarboxylation and the other(s) for the remaining three decarboxylations.The evidence for this is not conclusive but does come from several different experiments. For example the decarboxylation of uro’gen Ill was inhibited by uro’gen I whereas decarboxylation of the intermediates was not inhibited by uro’gen I but was inhibited by intermediate type I porphyrin~gens.~~ Inhibition by polychlorinated biphenyls at low concentration leads to accumulation of the heptacarboxylic intermediate but at higher concentrations uro’gen I11 was hardly decarboxylated at all.89 The decarboxylase is also inhibited by bivalent metal ions such as Cu2+ ZnZ+ and Hg2+ and by thiol-directed reagent~.~~-~O All of the uro’gen isomers are decarboxylated by the enzyme to give the corresponding copro’gen isomers but reports on the relative rates vary.The majority of reports find that the first decarboxylation of uro’gen I11 is faster than for uro’gen I but that subsequent decarboxylations are at similar rates for the two isomeric series except that the pentacarboxylic intermedi- ate accumulates to a greater extent for uro’gen I than for uro’gen 111. For uro’gen 111 the order of the decarboxylations is not random; the first decarboxylation is specifically on ring D to give (43) (known as phyriaporphyrinogen) as the only major heptacarboxylic intermediate. 1,93 The hexa- and penta-car- boxylic porphyrinogens are not usually present in sufficient quantities for structure determination but the corresponding porphyrins are excreted in reasonable amounts by sufferers of porphyria cutanea tarda or by animals in which a porphyria has been induced by prolonged administration of hexachloro- benzene or other halogenated aromatics.Jackson eta/.isolated milligram quantities of the intermediate porphyrins from the faeces of rats that had been poisoned with hexachlorobenzene and showed by total synthe~is,~~.~~ that the porphyrins that were isolated corresponded to the porphyrinogens (43) (44) and (45).Thus it seems likely that the preferred order of decarboxylations is clockwise starting at ring D then A B and finally C. However it was found that the other isomers of the intermediate type I11 porphyrinogens can also be substrates for the decarboxylase and so the order of decarboxylations cannot be considered obligatory.In contrast to uro’gen 111 the decarboxylation of uro’gen I is relatively non-specific ;95 both of the possible hexacarboxylic isomers are formed in roughly equal amounts. Porphyrins of the type I series are excreted by sufferers of certain porphyrias in which uroporphyrinogen I11 synthase is deficient. CO,H \-f \ C02H CO,H R’ R’ R3 RJ (I1)A A A A (43) Me A A A (44) Me Me A A (45) Me Me Me A (46) Me Me Me Me (A =CHZCOZH) NATURAL PRODUCT REPORTS 1985 The most reasonable chemical mechanism for the decarbox- ylation of the acetate side-chains of uro’gen I11 is as shown in Scheme 11. Barnard and Akhta~-~~ have produced evidence in support of this mechanism and shown that the decarboxylation at all four positions proceeds with retention of configuration.Thus (2R)-[2-3H,2-2H]succinate (47) was incorporated into haem by a cell-free preparation from chicken erythrocytes. On degradation of the labelled haem (48) the methyl groups were obtained as acetic acid which was found to be chiral with the S configuration by the malate synthase-fumarase assay. This finding has been confirmed using different organisms in work that will be described later on bacteriochlorophyll aIg2and vitamin B,2.209 1.6 Coproporphyrinogen Oxidase (EC 1.3.3.3) The two oxidative decarboxylations of copro’gen 111 (46) to give proto’gen IX (52) are again catalysed by a single enzyme and in this case the indications are that only a single active site is The propionate on ring A is the first to be converted into a vinyl group ;thus the tricarboxylic porphyrino- gen (50) is the first intermediate which can be detected.This porphyrinogen named hardero’gen because the corresponding porphyrin can be isolated from the harderian gland of rats is a H J Scheme 1 H (47) (46) R’ =P R? =P (49) R’ =HP R’ =P (50) R’ =V R’ =P (51) R’ =P R’ =V (52) R’ =V R’ =V [P =CH2CHICOZH,V =CH=CH2 HP =CH(OH)CHZC02H] NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER much better substrate for the enzyme than its isomer isohardero'gen (51). Kinetic.experiments have shown9' that in the presence of excess copro'gen 111 the proto'gen IX that is produced is all derived directly from copro'gen without release of the intermediate hardero'gen (50).The proportion of (50) which does get released into the medium cannot compete successfully for the active site with the excess of copro'gen I11 that is present.In aerobic organisms oxygen is the electron acceptor in the oxidation but anaerobes have a different enzyme which uses a hydride acceptor as its oxidizing agent.98Rhodopseudomonas sphaeroides has both the aerobic and anaerobic forms depending on the conditions of growth and the existence of two pathways (one dioxygen-dependent one NADP-depen-dent) has been demonstrated in soybean root nodules.99 The mechanism for the aerobic enzyme has been suggestedloOto proceed via a hydroxylation to give (49)as the first intermedi-ate.Synthetic (49)was found to be a good substrate for the enzyme that was purified from bovine liver. However the enzyme did not have the properties that would be expected of a hydroxylation system (there was no requirement for any metal ion or cofactor) and so it is still doubtful whether hydroxylated species are true intermediate^.^^ An alternative mechanism shown in Scheme 12 would account for the involvement of (49).In this mechanism loss of a hydride ion from the p-position of a propionate side-chain would give an intermediate imine of the type (53),also available by dehydration of a hydroxypropionate side-chain. Loss of C02 from (53)would then generate the vinyl group. The stereochemistry of the oxidative decarboxylation has been shown to involve loss of thepro-S hydrogen atom that is p to the carboxyl group in the propionate side-chain in chicken reticulocytes,lO1in Euglena gracilis,'O*and recently in both the aerobic and the anaerobic enzyme of Rhodopseudomonas sphaer~ides.~~ The overall elimination of H and C02 has been shown to be trans in the aerobic enzyme from E.gracilis.loo Thus the stereospecifically labelled PBG (54) gave protopor-phyrin IX that was labelled as shown in structure (55). COZH COzH /-b0-H " \ (53) 1 Scheme 12 H02C-$ H2N H (54) (55) < COZH (56) R' = R' = CH 2CH'COzH (57) R' = CH=CH2 R2 = CHzCHzC02H (58) R' = R2 = CH=CH2 COZH / - (59) R = Me CH=CH, or H 60,H (45) R' = CHZCHICO'H R' = CH'C02H (60) R' = CH=CH2 R' = CH2C02H (50) R' = CH=CHZ R' = CH In eukaryotes coproporphyrinogen oxidase is mainly asso-ciated with the mitochondria and is thought to be located in the intermembrane space.Io3 The purified enzyme from bovine liverloois a monomer of molecular mass 71 600. The substrate specificity of the enzyme from various sources has been studied :97* O4 copro'gens I and I1 do not react but copro'gen IV (56) is a substrate and the product is proto'gen XI11 (2,8,13,17-tetramethyl-1 2,18-divinylporphyrinogen-3,7-dipropionic acid) (58).104.'05 In this conversion the tricarboxylic porphyrin (57) accumulates to a greater extent than from copro'gen III.'04 When all of the results of enzyme specificity are collected it appears that the propionate unit is best decarboxylated if it occurs in the middle of the series of substituents shown in part-structure (59).] O0,] O4 An alternative route to haem may be importantIo6 in porphyria patients in whom the pentacarboxylic porphyrino-gen (45)is not efficiently decarboxylated by uro'gen decarbox-ylase. This porphyrinogen can act as a substrate for copro'gen oxidase to give dehydroisocoproporphyrinogen (60). The propionate on ring B is not oxidatively decarboxylated but the remaining acetate side-chain on ring c can be decarboxylated by uro'gen decarboxylase to give hardero'gen (50),which is the normal intermediate of copro'gen oxidase. In humans who are not suffering from porphyria the concentrations of (45)are so low as to make this alternative pathway insignificant.1.7 Protoporphyrinogen Oxidase (EC 1.3.3.4) The enzyme which oxidizes proto'gen IX (52) to the corre-sponding porphyrin (61) has previously been isolated from R I (61) R = CH=CH, M = H,H (64) R = Et M = H,H (65) R = H M = H,H (66) R = CH=CH2 M = Fe f' \ CO2H CO2H yeast Escherichia coli and rat liver.Io7 As with copro'gen oxidase aerobic organisms use oxygen as the oxidant but it has been shown for E. coli and R. sphaeroides that are growing anaerobically that the enzyme is membrane-bound and the oxidation is linked with the electron-transport chain. lo8 Assay procedures for protoporphyrinogen oxidase have been pub- lishedlo9 but otherwise little work on the enzyme has been published recently.The oxidation involves removal of six hydrogen atoms one from each of the four meso positions and two from nitrogen atoms. It was known that removal of hydrogen from all of the meso positions is stereospecific' lo because the enzymic oxidation of stereorandomly tritiated proto'gen IX occurs with loss of 50% of the label whereas the chemical oxidation occurs with loss of only 4% of the label due to a large isotope effect. As yet it is not known which hydrogen is the one that is removed at any of the sites but the overall stereochemistry from PBG has been studied with interesting results.' [1 1 S3H]PBG was synthesized enzymically from [2-3H2]glycine and was incorpor- ated into protoporphyrin IX with retention of only 25% of the label.Degradation of this labelled protoporphyrin IX to the four isomeric biliverdins e.g. (62) was used to show that the tritium was all at position 10. As the stereochemistry of the various steps in the formation of uro'gen I11 from PBG is not known no conclusion about the stereochemistry of the oxidation of proto'gen can be drawn except that it differs at the various sites. It was suggested that loss of three of the meso hydrogens would be from the same side in the three successive oxidations while loss of the fourth meso hydrogen could be from a different side because it occurs during tautomerism of the resultant product e.g. (63) to the porphyrin. Proto'gen oxidase does not oxidize uro'gens or copro'gens though it is reported to oxidize proto'gen XI11 (58) hardero'gen (50) isohardero'gen (5l) and mesoporphyrinogen IX.lo4 It seems that non-polar groups on rings A and B are an important factor. 1.8 Ferrochelatase (Haem Synthase Protohaem Ferro-lyase; EC 4.99.1.1) The last step in the biosynthesis of haem (66) is the insertion of Fe2+ into the centre of the macrocycle. In eukaryotes the enzyme that catalyses this process is located on the inner face of NATURAL PRODUCT REPORTS 1985 the inner mitochondria1 membrane.' l2 The enzymes from rat liver,' 3 l4 bovine liver,' 5* ' and Rhodopseudomonas sphaer- oides1I7 have recently been solubilized and purified. A sensitive assay for ferrochelatase in tissues using 59Fe has been developed.j9 Kinetic studies' * are claimed to indicate an ordered mechanism in which binding of iron occurs prior to the binding of the porphyrin and then after insertion of the metal haem is released prior to the release of two protons. Ferrochelatase is specific for porphyrins with hydrophobic groups on rings A and B (ie. not uro- or copro-porphyrins) and with the substituents methyl propionate propionate and methyl on rings c and D. Both V,, and KMincrease in the series protoporphyrin IX (61) < mesoporphyrin IX (64) < deutero-porphyrin IX (65),' 14-' and the porphyrin with no substi- tuents on ring A or B is the best substrate that has been studied so far. One explanation that has been put forward' l8 is that release of the haem is the rate-determining step and protoporphyrin IX (which is bound most strongly) is also released most slowly.Other bivalent metals than iron can be inserted into porphyrins. In particular Zn2+ is reported' to be a better substrate even than Fez+; Co2+and Ni2+ can also be substrates. The ions Cuz+ Mnz+ Pb2+ and Hgz+ however are not substrates but inhibitors,' l4 as are thiol-directed reagents. Other inhibitors of ferrochelatase are N-methylated proto- porphyrins which occur in animals to which drugs such as 3,5- dicarbethoxy-l,4-dihydrocollidine or griseofulvin have been administered. The N-methyl derivatives arise by occasional methylation of the haem moiety of cytochrome P-450during metabolism of the drugs in the liver. l 2o The compounds 6v that are methylated on each of the four nitrogen atoms are almost equally good inhibitors' 2o (K = 7 nmol dm-3; ref.116). The N-methylated protoporphyrins that are produced in the liver are optically active but it has not been determined which face of the porphyrin has been methylated.120 1.9 Cytochromes As mentioned earlier unmodified haem (66) is the prosthetic group of several enzymes including the cytochromes b and P-450. The prosthetic group haem a (67) has been isolated from cytochrome oxidase.' There are very few studies on the biosynthesis of haem a and so the order of the steps is not known. It seems likely that protoporphyrin IX (61) is the precursor and that either the 18-formyl compound (68) or the 3- alkylated compound (69) is formed next.Both (68) and (69) have been synthesized. Results suggesting that mevalonate is the precursor of the side-chain have been obtained122 but otherwise no descriptions of incorporation experiments have been published. The likely mechanism for formation of the side-chain at C-3 using farnesyl pyrophosphate is shown in Scheme 13. The stereochemistry of the secondary alcohol of haem a is not known. 602H k02H (67) R = CHO M = Fe (69)R = Me M = H,H (70) R = CHO M = H,H NATURAL PRODUCT REPORTS 1985 F. J. LEEPER C02H k02H (61) R = Me (68) R = CHO J &' & Scheme 13 f \ C02H C02H f \ C02H C02H The last step in the biosynthesis is claimed to be the insertion of iron into porphyrin a (8l,82-dihydrocytoporphyrin)(70)'23 because in Candida utilis that has been grown in a medium that is deficient in copper ions an inactive form of the cytochrome is produced which has porphyrin a and not haem a bound to it.The other major class of cytochromes containing a modified haem is the cytochromes c. These have the vinyl groups attached to the thiol group of a cysteine residue of the enzyme. .-,,. I Scheme 14 In most cytochromes c both vinyl groups have reacted with two cysteine residues which are three residues apart in the peptide chain.' X-Ray crystal structures of the enzymes show that in all cases the new chiral centres are of S configuration as in (72). 24 Cytochrome c-558 from Euglena gracilis' 25 and a similar cytochrome from Crithidia oncopelti' 26 have been shown to have the haem attached by only one covalent link to the vinyl group at C-8 as in (71).The mechanism of formation of the thioether link is presumably that shown in Scheme 14. It would be interesting to determine whether the overall addition to the double-bond is cis or trans. Recently an enzyme has been implicated in the formation of the covalent links between haem and the apo- cytochrome c; it has been named cytochrome c synthetase. 27 2 The Biosynthesis of Chlorophylls The path to the chlorophylls diverges from that of the haems at the point of protoporphyrin IX; magnesium instead of iron is inserted in the centre of the porphyrin. There are marked differences in the type of reactions involved in this later part of the biosynthesis of chlorophylls.Whereas in the biosynthetic reactions considered so far the intermediates that have been described have for the most part been free in solution migrating from one enzyme to the next and many of the enzymes themselves have been in solution also the second part of the biosynthesis of the chlorophylls occurs only in chloroplasts and all of the enzymes are bound to membranes and are quite possibly associated with other enzymes of the pathway. The intermediates too become increasingly non-polar and insoluble in water and the later ones are largely protein- bound in the chloroplasts. As a result of these differences the study of the biosynthesis of chlorophylls is not as well advanced as that of the porphyrins.The enzymes that are involved usually cannot be solubilized and sometimes stop functioning when the chloro- plasts are disrupted. Often studies rely on absorption spectra for the identification of intermediates which can be unreliable. For example mono- and di-vinyl compounds cannot easily be distinguished and nor can various esters be distinguished from their parent acids. Furthermore one compound can show a number of different spectroscopic forms depending on its environment (free in solution or bound to different proteins monomeric or dimeric etc.). Lastly it seems that the difficulties in studying the biosynthesis of chlorophylls may be increased by the relative lack of specificity of the enzymes leading to a metabolic network and also by the existence of degradative enzymes that catalyse for example the hydrolysis of esters.These problems will become more apparent when we discuss the steps in more detail. Recent reviews include ones by Jones,' 28 Castelfranco and Beale,' 29 Rebeiz,I3O and Rebeiz and Lascelles. Overall pathway. The production of protoporphyrin IX for the biosynthesis of chlorophylls is thought to follow exactly the same route as for haem but it should be pointed out that the results with Euglenagracilist6 show that the two processes occur in separate compartments and it is quite possible that the enzymes in chloroplasts are substantially different from those in the cytosol or in mitochondria. The basic outline of the route to chlorophyll a is shown in Scheme 15.After insertion of magnesium into protoporphyrin IX the carboxyl group of the propionate that is attached to C-13 is converted into its methyl NATURAL PRODUCT REPORTS 1985 Protoporphyrin IX (61) Protoporphyrin IX Mg complex (73) 1 Divinyl protochlorophyllide (R = CH=CH2) Chlorophyllide a (R = 14) Monovinyl protochlorophyllide (R = Et) Chlorophyll a (R = phytyl) Scheme 15 'H=CH (or Et) d02H (75) R = CH=CHCO,Me (76) R = CH(OH)CH,C02Me (77) R = COCH2C0,Me ester (74). This is followed by an oxidation and cyclization of this side-chain to form ring E. The resulting protochlorophyl- lide (1 7,18-didehydrochlorophy11ide)is reduced in ring D by a light-dependent enzyme to give a chlorophyllide.Reduction of the 8-vinyl group to an ethyl group might it seems occur at any stage along this pathway. The final step to make chlorophyll is esterification of the free carboxyl to give the phytyl ester (phytyl = hexahydrogeranylgeranyl). 2.1 Chelation of Magnesium and Methylation For a long time it was not certain which of these steps came first. The evidence' 28 that chelation preceded methylation was that protoporphyrinatomagnesium(I1)(73)and its methyl ester (74) can be found in some mutants and in organisms that have been treated with inhibitors such as 8-hydroxyquinoline or phenanthroline. However the methyl ester of free protopor- phyrin IX has also been found and until recently the direct enzymic insertion of magnesium into protoporphyrin IX had not been observed.Two groups have now been able to observe the specific chelation of magnesium by preparations of 33 or lysed134 plastids from cucumber. Both groups found that ATP is required for the reaction. The enzyme which performs the methylation of the carboxyl group in the 13-propionate is more well-known;2~128 it uses S-adenosylmethionine (SAM) and protoporphyrinatomagne-sium(I1) is a much better substrate than free protoporphy- rin IX. The enzyme has been called S-adenosyl-L-methio- nine :magnesium protoporphyrin 0-methyltransferase (EC 2.1.1.11); it has been partially purified from barley135 and recently the enzymes from wheat seedlings' 37 and Euglena gracilis have been more highly purified by affinity chromato- graphy.The kinetics of the enzyme of E. gracilis are said to show a random Bi-Bi mechanism with two dead-end ternary complexes.136 The enzyme from wheat on the other hand (78) R = CH=CH2 (79) R = CHZCH3 shows a ping-pong mechanism with binding of protopor- phyrin IX to the enzyme only occurring in the presence of SAM. 37 The observation of magnesium-free protoporphyrin IX methyl ester may be due to non-enzymic demetallation during isolation or to enzymic demetallation which has been observed recently by Crawford and Wang13* in studies on mutants of Chlamydomonus reinhardti. They showed that protoporphyrin IX is not methylated but that the magnesium complex is. If the further metabolism of the methyl ester is blocked removal of the magnesium occurs in a process that is dependent on iron salts and oxygen.2.2 The Formation of Ring E The oxidation and cyclization of the propionate which forms ring E should involve several steps but very little is known about possible intermediates. Ellsworth and Ar~noff,'~~ in the late 1960's reported the isolation of postulated intermediates from mutants of a species of the genus Chorellu; they suggested that these were the divinyl and monovinyl forms of porphyrins with acrylate 0-hydroxypropionate and 0-ketopropionate side-chains which had lost the magnesium from the corre- sponding compounds (79 (76) and (77) during isolation. Since then there has been no confirmation that these are true intermediates on the normal path to the chlorophylls although intermediates from higher plants have been detected by fluorescence spectroscopy,140-14' which are thought to be (79 (76) and (77).131.'40 A likely mechanism2 for the ring-closure is shown in Scheme 16.Cell-free preparations that are capable of transforming (74) into (78) have been and the evidence from these studies and from studies with intact organisms is that the process requires dioxygen and ATP as well as NAD(P)/ NAD(P)H. The preparations also require SAM for maximum NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER NAD+ Scheme 16 efficiency (to reverse an enzymic hydrolysis of the methyl ester) and one report140 finds that coenzyme A (CoA) is important. It is not obvious why either CoA or ATP should be necessary.In whole organisms grown under conditions of iron deficiency (74) accumulates which suggests that an iron-dependent oxygenase may be involved.144 However the same group142 have failed to observe inhibition of the transformation in isolated chloroplasts by iron-sulphur-protein- or haem-directed inhibitors by chelators of copper ion or by peroxide scavengers; inhibition was observed with methyl viologen and similar compounds. 2.3 Reduction of the Vinyl Group The timing of the reduction of the vinyl group has been a matter of controversy for a long time. Earlier the more widely accepted view' 28 was that it occurred at the protochlorophyl- lide stage. Thus it was thought that the divinyl protochlorophyl- lide (78) (also known as magnesium divinylphaeoporphyrin us methyl ester) is reduced to the monovinyl compound (79).The evidence for this rested on the observations128 that (78) can be found in Rhodopseudomonus sphueroides and in cucumber seed coats and that it can be converted into chlorophyllide a by a cell-free system from barley. (The conversion of the protochlor- ophyllide into the chlorophyllide was believed to occur only at the monovinyl level.) However direct transformation of (78) into (79) was not demonstrated. This view is however at variance with the identification of mono- as well as di-vinyl intermediates prior to protochloro- phyllide in Chlorellu mutants that was mentioned earlier. 39 Furthermore Ellsworth and Hsing' 45 prepared a partially purified homogenate from etiolated wheat seedlings that was able to catalyse the reduction of the 8-vinyl group of protoporphyrinatomagnesium(I1) methyl ester by [3H]NADH (but not NADPH).They did not observe significant reduction of the divinyl protochlorophyllide with this preparation. Strong support for the view that reduction can first occur at a protoporphyrinatomagnesium stage is given in numerous papers by Rebeiz and co-workers130,1 31 in which they describe the identification of mono- and di-vinyl analogues of all of the intermediates i.e. protoporphyrinatomagnesium(I1) and its monoester,146 protochlorophyllide,147 chlorophyllide u,148and chlorophyll They also observed in uiuo the conversion of both mono-and di-vinyl protochlorophyllides into their corresponding chlorophyllides and chlorophylls.149Thus they have proposed that the monovinyl and divinyl paths branch at the stage of protoporphyrinatomagnesium(I1)(73) and remain separate until the chlorophyllide stage where reduction of the divinyl to the monovinyl compound can again be ob-served. The reduction of a vinyl group at the protochlor- ophyllide stage as well however has not yet been disproved. It is claimed' 51 that the main biosynthetic route is the divinyl oqe in normal greening tissues while the monovinyl route prevails only in etiolated tissues (of plants that were grown initially in the dark). Rebeiz's two pathways are each proposed152 to be further subdivided into a path having the 17-propionate as a free acid (as described above) and a path with this propionate esterified with a long-chain alkyl group (to be discussed later).In Rebeiz's investigations the various intermediates are separated by t.1.c. on silica gel and then mono- and di-vinyl forms are separated by a reversed-phase type of t.1.c. on polyethylene. The compounds are identified by fluorescence 33 spectra. Because fluorescence emission spectra can be recorded at any number of excitation frequencies (or excitation spectra at any number of emission frequencies) the technique is very useful for analysing mixtures of compounds and this allows Rebeiz and co-workers to identify mono- and di-vinyl species in intact tissue. The intermediates in this work have only been isolated in picomole quantities and this has precluded any characterization other than by spectrofluorometry.Further- more the samples remain contaminated with other non-fluorescent compounds. Full proof of the proposed pathways must await full characterization of the pure intermediates and the investigation of product-precursor relationships prefera- bly using labelled precursors. 2.4 Reduction of Ring D The reduction of a protochlorophyllide to a chlorophyllide involves the overall trans addition of hydrogen across the 17-1 8 double-bond to give the (1 7S,18s)-compound. In higher plants this process requires light; thus etiolated seedlings (grown in the dark) accumulate a form of protochlorophyllide which can be converted into a chlorophyllide by the briefest flash of light.In normal circumstances the level of protochlorophyllide does not continue to build up in the dark because the synthesis of ALA is shut off but if ALA is fed to the seedling the control point is apparently by-passed and protochlorophyllide does accumulate in relatively large quantities. 28 I 29 The course of the reaction in intact tissue has been followed spectroscopically in a number of studies,' 28*129and the results are not easy to reconcile because of all of the different conditions and techniques that have been employed. One reasonable overall view is summarized in Scheme 17. Free protochlorophyllide absorbing at around 635 nm binds to the reduced enzyme (or enzyme-NADPH complex) to give a chromophore absorbing at 650 nm which is the photoredu- cible form.Using a laser with a 5 ns pulse it was foundls3 that this fluorescent protochlorophyll was immediately converted into a non-fluorescent intermediate absorbing at 690 nm which decayed with a time constant of 3 ps to give a fluorescent chlorophyllide absorbing at about 678 nm. The photoconver- sion can occur at very low temperatures l 54 e.g. 4.2 K but the non-fluorescent intermediate is stable at this temperature and starts to decay if the temperature rises above 170K. The absorption spectrum of the chlorophyllide then undergoes a number of changes which can occur in the dark; it is thought that a shift in the absorption to 683 nm which takes about 30 seconds may reflect dissociation from the enzyme and that a later shift to 672 nm may reflect the phytylation step.l 28 Under conditions of lower light intensity where the phototransforma- tion is incomplete other absorption/emission bands appear and this has led to the suggestion that the phototransformable protochlorophyllide (650 nm) may be a dimeric species and that therefore two light reactions are required to reduce both molecules.128 After a flash of light the re-formation of the reduced enzyme-protochlorophyllide complex from oxidized enzyme NADPH and free protochlorophyllide may take up to 30 seconds.The enzyme that is responsible for this photoreduction NADPH :protochlorophyllide oxidoreductase (EC 1.6.99.l) has been isolated several times. 28. 29 Recent reports have hv Pchlide Pchlide. Emr, -Pchlide*- Enzred (635 nm) (690 nm) 'T* (650nm) Enzred 47 EI\ I NADPH Chlorophyll a c--Chlide Chlide -Enz, (672 nm) (683 nm) (678 nm) (Pchlide = protochlorophyllide Chlide = chlorophyllide) Scheme 17 agreed on a minimum molecular weight of 36000-37000.~55 Grifiths' 56 has studied the substrate specificity of the enzyme and found that protochlorophyllide esters' 56 are not substrates and nor are protoporphyrinatomagnesium derivatives; s7 ring E must be present with the correct substituents.However both mono-and di-vinyl protochlorophyllides are reduced. 57 Activity is still observed if magnesium is replaced by zinc but not if it is replaced by other metals or removed entirely.ls6 The purified enzyme-N ADPH-protochlorophyllide com-plex is called the holochrome.The values of molecular weight that have been determined for various holochrome prepara- tions have a very great range indicating that there is a considerable degree of aggregation. The holochrome undergoes similar changes in absorption to those that are observed in intact tissues but the initial absorbance of the protochlorophyl- lide complex is of somewhat shorter wavelength (638 nm). 28 Some algae and lower plants can synthesize chlorophylls in the dark and contain a second enzyme for the reduction of protochlorophyllide which is light-independent. Pine seedlings also have this capability but only for a short time after germination. One recent report' 58 claims that paradoxically barley that has grown in the light has the ability to synthesize chlorophyll when it is put in the dark but that dark-grown barley does not which would explain why the reduction of protochlorophyllide in the dark is not normally observed.2.5 Esterification of Chlorophyllide u Until recently the esterification of chlorophyllide a was thought to be catalysed by an enzyme named chlorophyllase (EC 3.1.1.14) which is found in all green leaves.' 28 However in uitro,this enzyme could only be shown to catalyse the reverse reaction i.e. hydrolysis to chlorophyllide a and phytol (in methanol or ethanol the methyl or the ethyl ester of chlorophyllide a is obtained). Also chlorophyllase has a broader range of substrates than the esterifying enzyme; in whole leaves phaeophorbides (magnesium-free chlorophyl- lides) are not converted into phaeophytins (magnesium-free chlorophylls) but chlorophyllase will catalyse the reverse reaction.59 Furthermore Akhtar and co-workers using ALA that was labelled with l80in the carboxyl group have shown that in the esterification the 0-phytyl bond of bacteriochloro- phyll a is the one that is formed. 160Thus when bacteriochloro- phyll a that had been biosynthesized from [1-l8O2]ALA was hydrolysed the phytol that was produced contained l80 with at least 90% retention of the label from ALA. If the ester had been formed by chlorophyllase by the reverse of the hydrolysis reaction (which presumably involves cleavage of an 0-acyl bond) then no l80 would be expected in the phytol. If chlorophyllase is not a synthetic enzyme then its role is presumably in the breakdown of chlorophylls that are no longer needed and it is only released when the chloroplast is ruptured.(81) R' = CZOH35 RZ = Et (82) R' = C2OH37 R2 = Et NATURAL PRODUCT REPORTS 1985 In 1977 Riidiger and co-workers showed that geranylgeranyl pyrophosphate rather than the free alcohol is the precursor of the phytyl chain161 and they also demonstrated162 the presence of esters of chlorophyllide a in which the esterifying group was geranylgeranyl (80),dihydrogeranylgeranyl (81) and tetrahy- drogeranylgeranyl(82) as well as chlorophyll a (83) with phytyl (hexahydrogeranylgeranyl) as the esterifying group. It is not known which double-bonds are reduced in the partially reduced intermediates.By following the levels of the various esters they showed that (80)was formed first followed by (81) (82) and then (83). The same conclusion was drawn from a time-course study of the incorporation of 4C-labelled precur- sors into these esters.163 It now seems however that the phytyl ester is produced by at least two different paths because (i) the esterifying enzyme termed chlorophyll synthetase can use phytyl pyrophosphate as well as geranylgeranyl pyrophosphate' 64 (and presumably intermediates between them also) and (ii) an enzyme causing the stepwise reduction of geranylgeranyl pyrophosphate to phytyl pyrophosphate has been detected in chloroplasts.165 The enzymes which reduce the geranylgeranyl-containingchloro-phyll and geranylgeranyl pyrophosphate both use NADPH as hydride donor.66 Chlorophyll synthetase has been located on the thylakoid membrane in the chloroplast.166*167 It appears to be specific for chlorophyllides a and b and simple derivatives of them; little or no reaction was observed with protochlorophyllide phaeophorbide a or bacteriochlorophyllide a.168 As mentioned earlier Rebeiz and co-workers have observed small pools of all of the metabolic intermediates that are esterified with various long-chain alcohols at the propionate group at C-17. 30 l 46-52 Rebeiz has provided evidence that 7 the pathway to these fully esterified intermediates diverges from that of the normal intermediates after protoporphyrinato- magnesiurn(~~)l 69 and that the pools of protochlorophyllide and esterified protochlorophyllide are not interconvertible.70 This is consistent with the observations that protochlorophyllide is not esterified by chlorophyll synthetase168 and nor are protochlorophyllide esters hydrolysed by chlorophyllase. 29 Belanger and Rebeiz observed photoconversion of pools of esters of both monovinyl and divinyl protochlorophyllide into chlorophylls149 but Shioi and Sasa concluded that this did not occur from their measurements of the levels of protochloro- phyllide esters that exist during the synthesis of chloro- phylls. The latter authors have identified the four esters of protochlorophyllide from geranylgeranyl to phytyl and have separated them by h.p.l.c.172 If the protochlorophyllide esters are converted into chloro- phylls then another reductase enzyme must exist because the known protochlorophyllide -reductase was found' 56 not to use the esters as substrates.On the other hand if they are not R2 = Et (84) R' = phytyl RZ = CH=CH2 NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER converted into chlorophylls it is difficult to see what else happens to them. Either way the fully esterified intermediates are much less abundant than the normal free acid interme- diates and constitute (at most) a minor pathway to the chlorophylls. Rebeiz et al. have detected several components in the chlorophyll a fraction from plants by their fluorescence and have partially purified them by h.p.1.~'~~ Chlorophyll a (83) accounts for 80-90% of the fraction and the 81,82-didehydro- chlorophyll a (84) is present in very small amounts (<1%); the remainder is said to consist of three chlorophylls of unknown structure.The divinylated chlorophyll (84) accumulates to a large extent in a mutant of Zea mays and the structure has been well established by n.m.r. and mass spectroscopy. 174 2.6 The Formation of Chlorophyll b Chlorophyll b (86) differs from chlorophyll a (83) only in having the 7-methyl group oxidized to a formyl group. Earlier studies showed that label in (83) is incorporated into (86) and thus (83) was taken to be the immediate precursor of (86)' 28 However more recently a pool of chlorophyllide b (85) has been detected' 75 (along with 8' ,82-didehydrochlorophyllideb) and it was shown that this does not originate by hydrolysis of (86) during isolation.A study of the time course of incorporation of I4C into the various metabolic indicated that labelling of (85) precedes (86) suggesting that (85) is the precursor. It is known that chlorophyll synthetase will also esterify (85),163 and the four esters from chlorophyllide b geranylgeranyl ester to the phytyl ester have all been isolated and separated by h.p.l.~.'~~ Thus it seems that oxidation of chlorophyllide a is one route to chlorophyll b and there is a need for further study to determine whether direct oxidation of chlorophyll a is possible or whether it must first be hydrolysed to the chlorophyllide. 2.7 Bacteriochlorophylls Photosynthetic bacteria contain a number of 'bacteriochloro- phylls' instead of the normal chlorophylls.Bacteriochlorophyll a has the structure (87; R = phytyl). The intermediates of the normal biosynthesis have not been extensively investigated but on the basis of intermediates from mutants' 28v (mostly of Rhodopseudomonas sphaeroides) the most likely path is from chlorophyllide a by hydration of the 3-vinyl group followed by reduction of ring B to give 3-deacetyl-3-( 1-hydroxyethyl)bacter-iochlorophyllide a (88). Oxidation of the hydroxyethyl group then gives (87; R = H) and esterification gives the bacteriochlorophyll. Most of these intermediates have been detected in R. sphaeroides by their fluorescence emission and excitation spectral 78 and by optically detected magnetic resonance at zero field.' 79 Scholz and Ballschmiter180 have investigated minor components of bacteriochlorophyll a fractions by h.p.1.c.and concluded that the six minor compounds that they detected in addition to (87) are diastereoisomers. On the basis that oxidation of the mixture with DDQ gave a single chlorophyll derivative they decided that the components are epimers of (87) at C-7 and C-8 and in ring E; tentative structures have been assigned on the basis of chromatographic mobility. There is more variation in the long-chain ester in bacteria than in higher plants; in Rhodospirillum fulvum the normal phytyl ester of bacteriochlorophyllide a is found but in R. rubrum it is the geranylgeranyl ester. I8O The photosynthetic reaction centres of R.rubrum contain a mixture of this geranylgeranyl bacteriochlorophyllide and bacteriophaeophor- bide a (the magnesium-free compound) as its phytyZ ester. The stereochemistry of the reduction of the 8-vinyl group which occurs at some stage of chlorophyll biosynthesis after protoporphyrin IX has been studied in bacteriochlorophyll a in R. sphaeroides.*82Incorporation of ALA that had 2H and 3H isotopes in the S configuration at C-2 (89) led to the formation of a sample of (88) in which both of the methyl groups that are RO (85) R = H (86) R = phytyl -4Y I (87) XY = 0,R = geranylgeranyl or phytyl (88) X = OH Y = R = H (90) Scheme 18 attached to ring B are in the R configuration as in (90) (established by selective degradation to acetic acid and assay by the usual malate synthase-fumarase method).Thus it is shown that overall the new hydrogen atom at the end of the ethyl group at C-8 is added on the same side as that from which the carboxyl group had been lost. As the stereochemistry of the latter process is known for Euglena gracilis (see Section 1.6) it could be concluded that the addition of hydrogen is from the si-face as shown in Scheme 18. The stereochemistry of the methyl group at C-7 shows that for this organism also the uro'gen decarboxylase step occurs with retention of configuration (see Section 1S). Bacteriochlorophyll b has an exocyclic double-bond2 at C-8 which has now been shown to have the E configuration (91) by n.m.r.spectroscopy using the n.0.e. difference technique. 83 The stereochemistry at C-7 has not yet been determined. Members of the green sulphur bacteria produce a number of closely related pigments known as Chlorobiurn chlorophylls or bacteriochlorophylls c d and e. The structures have been deduced to be (92) for the c series184 and (93) for the d series;185,186 thee series is the same as the d series but with the methyl group at C-7 oxidized to formyl.2 Separation of the magnesium-free methyl ester analogues of these pigments has been achieved using reversed-phase h.p.l.~.,l~~ 87 and partial syntheses of the simplest of them in the c and d series from a derivative of chlorophyll a have been re~0rted.l~~. NATURAL PRODUCT REPORTS.1985 H2N0 H2 H R R' = Et Pr" Bu',or neopentyl R2 = Me or Et (92) R3 = Me (93) R3 = H Noteworthy features of these bacteriochlorophylls are (i) the esterifying alcohol is farnesol (ii) the side-chains at C-8 and at C-12 and the position C-20 bear extra methyl groups which have been found to be derived from methionine and (iii) the configuration of hydroxyethyl groups at C-3 is S when the substituent at C-8 is small (ethyl or propyl) and R when it is large (isobutyl or neopentyl).184,185 2.8 Conclusion The recent results that have been described in this section have shown that the biosynthesis of chlorophylls is not as straightfor- ward as had previously been thought. However much of this work is still very incomplete as many of the intermediates have only been characterized spectroscopically and chromatogra- phically.There is definitely a need for more chemistry to be undertaken in order to isolate purify characterize and synthesize larger quantities of some of the postulated interme- diates and also to perform more definitive experiments using specifically labelled compounds. 3 The Biosynthesis of Vitamin B, The biosynthesis of vitamin B1 (cyanocobalamin) has been covered quite recently in a comprehensive review by Bat- tersby.189 As a result this review will not detail all of the work which has been done but only the important results and those published since the beginning of 1981. 3.1 The Basic Precursors' 7 2 89 Early experiments by Shemin and co-workers established that the cobyrinic acid moiety (94) of vitamin B, (95) is like porphyrins derived from ALA (1) and that the additional methyl groups are provided by methionine.Initial experi- ments with PBG (6) or uro'gen 111 (11) failed to show incorporation of these precursors in intact cells but they are well incorporated in cell-free systems. From uro'gen I11 (1 I) the required steps to cobyrinic acid (94) which is a known precursor of vitamin B1 ,,can be seen to be (i) decarboxylation of the acetate group at C-12; (ii) extrusion of C-20; (iii) introduction of seven methyl groups; (iv) insertion of cobalt. Using 13C n.m.r. spectroscopy it was shown that all of the methyl groups of (94) are labelled by [Me-13C]methionine and that only seven carbons all of them sp2 hybridized are labelled by [5-l3C]ALA.Thus C-20 of uro'gen is lost altogether and does not become the methyl group at C-1 of cobyrinic acid. The possibility that either decarboxylation of the acetate at C-12or methylation at C-1 might occur as the next biosynthetic step after uro'gen I11 (1 1) was investigated using synthetic bilanes and porphyrinogens. The I-methylbilanes that were tested were not incorporated into cobyrinic acid and the incorporation of the decarboxylated uro'gen was very much less than that of uro'gen I11 itself. Therefore it was unlikely that either of these steps could come next. 3.2 intermediates on the Pathway Evidence for the next steps has come from the isolation of compounds that are related to the next three intermediates of the pathway.The structures of the compounds that have been isolated (96)-(98) shown in Scheme 19 are the result of much work by several different groups. Much of the published evidence for the finer details of these structures is biogeneti- cally based. The arrangement of the acetate and propionate side-chains was deduced from the fact that these compounds are derived from uro'gen 111. Once it was known which rings are methylated the position of methylation and its stereochemistry were deduced from the observation that these compounds could be converted into cobyrinic acid. As yet none of these compounds has been synthesized. The compounds (96)-(98) are thought not to be the true intermediates but oxidized forms of them.It has been shown that dihydro-(97) is a better precursor than (97) itself and that a reduced form of (96) is the true intermediate. 3.2.1 Fuctor I Compound (96) was first isolated as its octamethyl ester by and Muller and co-worker~~~~ called Factor I. It was recognized as a chlorin which had one C-methyl group. A sample of methyl-labelled (96) obtained on incorporation of [ Me-'T]SAM was not incorporated into cobyrinic acid unless it was first reduced with sodium amalgam.191 Degradation of the cobyrinic acid showed that the activity was virtually all in rings A + D and knowing the structure of the next intermediate (97) it could be deduced that the site of the methylation was ring A. The methylation of uro'gen I11 at C-2 would naturally lead to a tetrahydro-form of (96) such as (99) or a tautomer of it; see Scheme 19.It is likely that this is the true intermediate and is produced on reduction of (96) with sodium amalgam thus explaining the incorporation results. 3.2.2 Fuctor II Sirohydrochlorin1.2*89 Compound (97) was first isolated in the form of its iron complex as the prosthetic group of bacterial sulphite and nitrite reductases but its structure was not known until the connection with the intermediates of biosynthesis of vitamin B was made. The iron complex was termed sirohaem and the metal- NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER HOz -Methylate C-2 -Me HOz 60,H %-(94) tautomerize CO H C0,H COzH (99) (100) R = H ii 11 (101) iii R11 = Me i i HO?C CO H HOzC C02H (97) R = H (98) R = Me Reagents i air; ii Na analgam; iii H , catalyst or enzyme Scheme 19 ,C02 H HOzC COiH H( fi HOIC COzH C02H ( 102) (103) R = H free compound sirohydrochlorin.Oxidation of (97) can occur (104) R = Me while it is being isolated giving the lactones (102) and (103) Proton n.m.r. spectroscopy of the octamethyl ester of (97) and many of the early structural studies were performed on the showed that the signals of the four meso protons were in the methyl esters of these lactones. They can be reduced with zinc positions that would be expected for an isobacteriochlorin. to give (97) back again. Detailed analysis of the n.m.r. spectrum and biogenetic arguments taken together led to the conclusion that it is rings A and B that are reduced and so the structure is as shown.This was confirmed by incorporation experiments in two ways. First,lg2 sirohydrochlorin that had been labelled with 14Cin the methyl groups by incorporation of [Me-14C]methionine was incorporated into cobyrinic acid (94). Degradation of the heptamethyl ester (cobester) of this labelled compound showed that the methyl groups of ring B and either ring A or ring D were labelled. As it was known that adjacent rings of sirohydro- chlorin are methylated it follows that they must be rings A and B. In the second incorporation experiment lg3 [5-l 3C]ALA was incorporated into sirohydrochlorin. Because of the rearrange- ment of ring D C-14 C-15 and C-16 were all labelled and thus C-15 was immediately recognizable as a triplet in the 3C n.m.r.spectrum. This signal was the most downfield of those from the meso carbons and is due to the meso carbon between the two pyrrolic rings. Thus again it must be rings A and B which are the reduced ones. As with Factor I sirohydrochlorin (97) was thought to be an oxidized form of the true intermediate which on mechanistic grounds should be a dihydro-form (100). By working in rigorously anaerobic conditions Battersby et al. 94 have isolated the dihydrosirohydrochlorin as its methyl ester (101) and shown it to be identical to the product that was obtained by catalytic reduction of sirohydrochlorin ester which was proved to be the ester of (100).Furthermore this dihydro-compound was a better precursor of cobyrinic acid than sirohydrochlorin itself and so it is most likely to be the true intermediate. The incorporation of sirohydrochlorin must be due to a fortuitous enzymic reduction to (100) prior to the next methylation step. The enzyme system that is responsible for the first two methylations of uro’gen I11 to give dihydrosirohydrochlorin has been partially purified to a 50-fold enri~hment.~ It has a pH optimum of about 7 a value for the KM for SAM of 217 pmol dm-3 and a molecular weight of about 200 000. Using this enzyme system it was found that the isobacterio- chlorin chromophore is only generated if oxygen is present thus providing further evidence that the true intermediates are reduced forms of the isobacteriochlorins.As mentioned above the iron complex of (97) is well known. In addition a cobalt(m) complex of an isobacteriochlorin has been identified in the sulphite-reducing organisms Desulphoui- brio gigas and D. desulphuri~ans~~~ and it is likely that this is C0”’-(97). As well as the pigments already mentioned epimers at C-3 of (96)Ig6 and (97)’ 97 have been identified and epimers at C-3 and at C-8 were both obtained during the isolation of (100).lg4 It is not known whether these epimers are present in the incubation mixture or are produced in the early stages of isolation. 3.2.3 Factor III The third compound that is related to precursors of vitamin B was identified as a methylsirohydrochlorin. The early struc- tural work was on the bislactone (104) that is produced during isolation (the tentative structure that was proposed had the third methyl group misplaced).Shortly afterwards spectrosco- pic studies on the octamethyl ester of Factor I11 itself provided proof that the structure is (98). lg8 99 From a biogenetic point of view the position of the third methyl group on C-20 was surprising as C-20 is lost on the path NATURAL PRODUCT REPORTS 1985 to cobyrinic acid. Indeed when the trimethylisobacteriochlorin was biosynthetically labelled with 3H in the methyl groups (from [Me-3H]methionine) and 14C in the ring (from [4-I4C]- ALA),200 or vice uersa,lg9 it was found that incorporation into cobyrinic acid resulted in loss of one of the three methyl groups.Thus the possibility that the methyl group at C-20 of (98) migrates to C-1 is discounted. As with sirohydrochlorin it is assumed that (101) i.e. the dihydro-form of (98) is the true biosynthetic intermediate. 3.2.4 The Synthesis of’Isobacteriochlorins and Chlorins While much has been accomplished with the small quantities of Factors 1-111 that are available from natural sources there is still an urgent need for a synthetic route to these compounds for complete confirmation of their structures for further investiga- tion of their chemistry and for the production of isotopically labelled compounds for further biosynthetic studies. Syntheses of isobacteriochlorins with alkyl substituents have been reported which combine a corrinoid A-B half with a porphinoid C-D half either using a metal ion to act as a template20 or using Eschenmoser’s sulphur-contraction proce- dure.202,203 However attempts to repeat these syntheses with the natural acetate and propionate substituents have not been successful.A recent approach which has proved to be applicable to the natural substituents is Battersby’s photochemical cyclization. In this an A-D half is combined with a B-C half to give the seco- compound (105). Irradiation of (105) produces204 the model isobacteriochlorin (106) in 45% yield.205 Using this approach several model isobacteriochlorins204~206 have and chl~rins~~~ been synthesized including the dimethyl ester of ( +)-bonellin (107),208which is a pigment that has been isolated from a marine worm Bonellia viridis.The application of this approach to the synthesis of Factors 1-111 is currently being investigated. 3.3 Steps beyond Factor I11 Despite considerable efforts no intermediates have been detected beyond the trimethylisobacteriochlorin (98). Our knowledge of the later steps therefore relies on (a) some isotopic labelling studies (b) studies on the chemistry of model compounds and (c) mechanistic considerations. 3.3.1 Decarboxylation of’the Acetate Group at C-12 The mechanism of this decarboxylation is most probably the same as that for the decarboxylation of uro’gen I11 to copro’gen I11 which was discussed in Section 1.5. If this is the case it must occur before the methylation at C-12 while this carbon is still sp2hybridized.Apart from this no information is available on the timing of the step. It is known’ that the decarboxylated acetate group provides the pro-S methyl group at C-12 in (94). Recently it has been shown209 that for this methyl group incorporation of ALA having 2H and 3H in the S configuration at C-2 leads to a chiral methyl group of R configuration at C-12 of cobyrinic acid. Thus this decarboxylation occurs with retention of configuration (like that of uro’gen 111). I \ MeO,C C02Me kO,Me (105) NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER 3.3.2 Methylation Steps It has been mentioned earlier that all of the methyl groups that are introduced into (96)(including the one at C-20) are derived from S-adenosylmethionine (SAM).Furthermore using [Me-2H3]-or [Me-2H3,Me-’ 3C]-methionine intact incorporation of the CD3 group at every position has been demonstrated. Using methionine that carries a chiral C1H2H3H group Arigoni210 has shown that the methylations at C-5 C-7 C-12 and C-15 all occur with inversion of configuration of the chiral methyl as expected for a direct SN2 reaction. Information about the order of the methylations after (98) has been obtained2 in a ‘pulse-labelling’ experiment of the same kind as we have seen for PBG deaminase and ALA dehydratase (Sections 1.4.2 and 1.3). A cell-free system from Clostridium tetanomorphum that is capable of synthesizing cobyrinic acid was incubated with sirohydrochlorin and a deficiency of SAM. This was followed by an excess of [Me-’TISAM so that the methyl groups that are added later should contain more 13C than the earlier ones.In the 13C n.m.r. spectrum of the cobyrinic acid heptamethyl ester it could be seen that of the five enriched methyl groups that at C-17 had the least amount of 3C label and was therefore the first of the five to be introduced. In principle this type of experiment could reveal the order of all five methylations and work on this is in progress. Methylation of dihydro-20-methylsirohydrochlorin(101) at C-17 would be expected to furnish a pyrrocorphin (125; R = CH2C02H M =H,H) (Scheme 23) and this (or its 12- decarboxylated derivative) is presumed to be an intermediate on the pathway. Two groups2 have recently reported an efficient method of removing one or both of the methyl groups at C-5 and C-15 of the heptamethyl ester of cobyrinic acid.Nussbaumer and Arigoni used lead tetra-acetate to produce the hydroxymethyl derivatives followed by an acidic ion-exchange resin to remove the hydroxymethyl group. Eschenmoser’s group on the other hand found that heating cobester in the presence of propane- dithiol led to the bis-demethyl compound. These techniques should allow the production of labelled forms of the demethyl compounds in order to test whether they are intermediates in the biosynthesis. 3.3.3 Model Studies of’the Methylation Steps Eschenmoser and co-workers have described some very interesting results on the methylation of 15,23-dihydroisobac- teriochlorins (also called dipyrrocorphins) and pyrrocorphins.For example the pyrrocorphin (109) was obtained213 by tautomerization of octaethylporphyrinogen (108) with the MgI+ salt of triazabicyclo[4.4.0]dec-5-ene(TBD) (see Scheme 20). The magnesium (or zinc) complex of (109) was methylated with Me1 to give the corphin complex (1 lo) which could be further tautomerized to give the more stable pyrrocorphin (1 11) (after demetallation). Even more relevant to the biosynthesis of vitamin BI2 have been the results with 20-methylated tetrapyrroles2 (Scheme 21). When the metal-free dihydroisobacteriochlorin (1 12) reacted with Me1 the major product was the 12-methylated pyrrocorphin (1 13) along with a minor amount of (1 14). The zinc complex of (115) which is a pyrrocorphin that is very similar to (1 13) was methylated at C-17 by Me1 to give the corphin (1 16) (which cannot in this case tautomerize).The regioselectivity of methylations is slightly different from the biosynthetic sequence described in the previous section in which C-17 is methylated before C-12 but it was found that tautomerization of the dihydroisobacteriochlorin (1 12) to the more stable pyrrocorphin (1 17)203 gave a substrate whose magnesium complex is methylated chiefly at C-17 giving the pyrrocorphin (1 18) (after tautomerization of the corphin). Thus Eschenmoser has demonstrated that the required methylations at C-17 and C-12 are chemically possible and this type of bioeenetic svnthesis might also. in the lone run. provide I -E t ’\D N’ Et- Et / Et M Me Et I kt Scheme 20 (1 10) tautomerize - I + I R (113) R =Me (115) R =H4 Scheme 21 compounds with natural substituents for testing as interme- diates on the biosynthetic pathway.3.3.4 The Extrusion ojC-20 Early results on the extrusion of C-20 were claimed to show that this carbon is lost as formaldehyde.’ However this was made doubtful by the finding that C-20 becomes methylated. Re- investigation215 has shown that C-20 and its attached methyl grow are eliminated intact as an acetic acid unit. NATURAL PRODUCT REPORTS 1985 (1 19) \ iii [M= Nil' or CO"~] ii [M = Zn"] or \ TI [M= iv H] iii[M = Nilf] (122) (121) Reagents i heat or hv H+; ii hv; iii heat; iv H+; v OH-Scheme 22 The mechanism for the ring-contraction of a porphinoid to a corrinoid system and the reason for the puzzling methylation of C-20 have been suggested by some more elegant model chemistry from Eschenmoser's group.The nickel or cobalt complexes of the 20-methyl-20-hydroxydihydrocorphin(1 19) gave on melting (at 295°C and 260"C respectively) the corresponding metal complexes of the 19-acetylcorrin (12 (Scheme 22). This reaction may be a concerted migration or may involve ring-opening to a seco-compound followed by a re- closure to the corrin. The seco-compound (1 20; M = Zn") can be produced from (1 19; M = Zn") either by careful heating or photochemically in the presence of traces of acid,217 and it is also formed if (121;M = Zn") is demetallated in the presence of TFA at room temperature.Removal of the acetyl group from the nickel complex of (121) can be effected2I6 by treatment with 2M-KOH at 70 "Cto give the corrin (122) with release of acetic acid. With this precedent it seems most likely that the biosynthesis follows a similar course such as that illustrated in Scheme 23. The need for the methyl group on (2-20 was explained when the model analogous to (1 I9) but lacking this methyl group was synthesized. It was found that this compound tautomerized very readily to give the ketone (123) and no ring-contraction could be effected. 3.3.5 Other Steps on the Path to Vitamin B, The stage in the biosynthesis at which insertion of cobalt occurs has not been determined.On the one hand the identification of cobalt complexes of isobacteriochlorins that was mentioned earlier' 95 and the observation that the intermediate isobacter- iochlorins (97) and (98) are formed when Propionibacterium shermunii is grown in a cobalt-free medium suggest early insertion of the metal. However other organisms that have been grown in cobalt-free medium excrete cobalt-free corrins such as cobalt-free cobyrinic acid amides from Rhodopseudo-monos sphaeroides2 and cobalt-free cobalamin and cobyric acid from Chromatiurn ~inosurn.*'~ While it is not suggested that these compounds are precursors of vitamin B 2 their isolation nevertheless suggests a later rather than an earlier insertion of cobalt. On chemical incorporation of cobalt into the crude metal- free cobyrinic acid c-amide a small amount of the dehydrocobyrinic acid c-amide (124) was isolated,2 as its ester as well as the expected product.It was suggested that this might be an intermediate in the biosynthesis of cobyrinic acid (94). However this view has been contradicated by the finding2'0 that (1 24) is consistently formed as an artefact during handling of the corresponding corrin. Furthermore a very recent result2*' has indicated that the hydrogen atoms at C-18 and C- 19 of cobyrinic acid are derived from the medium rather than from a reduced nicotinamide coenzyme. When cobyrinic acid was biosynthesized from uro'gen I11 by the cell-free enzyme system in D20,deuterium was incorporated at both C-18 and C-19.This deuterium was not detected by deuterium n.m.r. as previous results222 had shown that the n.m.r. signals from deuterium that is attached to the heptamethyl ester of cobyrinic acid are extremely broad; instead the deuterium was detected by the isotopic shift of the n.m.r. signals of adjacent I3Cnuclei at C-19 and the methylene of the acetate group at (2-18 (derived from the appropriately labelled uro'gen 111). These results suggest that the hydrogen atoms at C-18 and C-19 arise through protonation at these positions rather than by reduction of an 18-19 double-bond. As shown in Scheme 23 the biosynthesis of vitamin B could follow a route which has no oxidations or reductions; in view of the fact that vitamin B plays an important role in primitive anaerobic bacteria such a route is extremely attractive.The biosynthesis of cobyrinic acid from the dihydrotrimeth- ylisobacteriochlorin (101) that is shown in Scheme 23 is purely hypothetical but it is as far as possible consistent with current knowledge on the biosynthesis and the chemistry of model systems. However there are many alternative schemes that could be proposed. Nature has provided us with several surprises in the biosynthesis of vitamin B,' and no doubt has one or two more that have still to be discovered. 3.4 Factor F-430 In the past few years a nickel complex of a new reduced porphyrin system has been identified in methanogenic bac- teria. It has been termed factor F-430 and is -apparently involved in the last step in the reduction of C1compounds to methane.The structure of its methyl ester has been eluci- as (126) by a combination of spectroscopic methods including the interpretation of the 3C n.m.r. spectra of samples of (126) that were obtained after incorporation of various 3C-labelled forms of ALA and [Me-13C]methionine. The similarity of structure (1 26) to that of sirohydrochlorin (97) and the mode of incorporation of ALA can leave no doubt that factor F-430 is related to intermediates of the biosynthesis of vitamin B and is probably derived from sirohydrochlorin. NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER k02H (125) R = CH,C0,HorCH3 M = H,H or CO"' HO,k k02H I 30,H y&/ H+ - I H02C COzH HOzd k0,H methylation at C-5 and C-I5 + (94) IHOzC \CO,H Scheme 23 Me02c R Some reports have appeared on the biochemistry of the production of factor F-430225 and on the chemistry of factor F-4302" and model systems.226 Bykhovskii et al.227have isolated several fractions of pigments (as yet unidentified) that are excreted from methane-producing organisms and which ap- pear to be precursors of factor F-430 that are related to sirohydrochlorin.4 Topics Related to the Biosynthesis of Tetrapyrroles The aim of this section is not to give a comprehensive coverage of any topic but rather to give the interested reader some recent leading references to areas which border on the biosynthesis of tetrapyrroles. 4.1 The Biosynthesis of the Nucleotide Loop of Vitamin B, The remainder of the biosynthesis of vitamin B12 after cobyrinic acid has not been covered in this review because it does not affect the tetrapyrrole nucleus.This part of the biosynthesis has been well reviewed re~ently.~,*'~ In the first step cobyrinic acid is amidated at all of the carboxyl groups except the propionate at C-17 giving cobyric acid. This is followed by amidation of the final carboxyl group with aminopropanol phosphorylation of the hydroxyl group attachment of a guanosine phosphate group and then replacement of this by a dimethylbenzimidazole nucleotide. Finally the extra phosphate group on the nucleotide is hydrolysed off to give the vitamin B itself. Forms of vitamin 42 NATURAL PRODUCT REPORTS 1985 (CHOH), I CHiOH Scheme 24 B1 with bases other than dimethylbenzimidazole do occur naturally.The dimethylbenzimidazole has been found to be derived from riboflavin229 as shown in Scheme 24. The biosynthesis of riboflavin is not yet fully understood but a recent paper230 on the incorporation of multiply 3C-labelled precursors has provided some useful information. 4.2 N.M.R.Spectra and Other Properties of Tetrapyrroies Very important in the study of biosynthesis are physical methods for structure determination and for locating isotopic labels. The most important method is undoubtedly n.m.r. spectroscopy and there is always a need for reliable n.m.r. data and assignments. Smith et have reported 13C and lH n.m.r. spectra of six ‘Type IX’ porphyrins as part of a whole series of papers on the n.m.r.spectra of porphyrins. The spectra of most tetrapyrroles are concentration-dependent and the 3C signals for a-pyrrolic positions (and sometimes p-also) can be very much broadened by slow tautomerism of the NH groups. It was found that both of these disadvantages are overcome in the n.m.r. spectra of zinc(I1) complexes of porphyrins in the presence of pyrrolidine. Useful spectroscopic data are also contained in the papers by Clezy and Fooke~,~~~ describing their syntheses of many diacetyl- divinyl- and diformyl- .~~~ porphyrins. Scott et ~1have reported the I3Cand 15Nn.m.r. spectra of uroporphyrinogens. In the chlorophyll field Wray et al.234 have made a comprehensive collection of 3C data of 15-substituted chlorin derivatives and 13Cassignments have also been published for chlorophyll u,235 chlorophyll b,236and bacteriochlorophyll a.237 The lH n.m.r.spectra of chlorophylls have been studied,238 often to obtain information about their aggregati0n.23~ The IH and 13C n.m.r. spectra of cobester have been analysed in and an almost complete assignment of the 13C n.m.r. spectrum of vitamin B12 has also been published recently.241 Also useful in biosynthetic studies may be an account242 of the Fast Atom Bombardment (FAB) mass spectra of several corrins and a collection243 of X-ray crystal data on corrins including cobester. Scott and co-worker~~~~ have used n.m.r. spectroscopy to follow the course of biosynthesis of porphyrins in intact organisms and have been able to observe the conversion of [5-l3C]ALA into PBG and thence into uro’gen and copro’gen.Using this non-invasive technique they have the factors which regulate the biosynthesis of porphyrins in Rhodopseudomonas sphaeroides and Propionibacterium sher- manii. Scott has reviewed his work on n.m.r. studies of metabolism.246 In order to perform isotopic labelling studies a researcher must be able to introduce the isotopic label into the desired precursor. In two recent papers,247 Smith and co-workers have described the introduction of 2H and I3C labels into porphyr- ins including protoporphyrin IX. This may in some cases provide an easier access to labelled precursors than the usual total synthesis. 4.3 The Degradation of Haem248 The pathway for the removal of unwanted haem in mammals involves as the first step the oxidative cleavage of the ring (127) (128) (R = Et Me or H;M = Ni or VO) with loss of C-5.The resulting linear tetrapyrrole biliverdin is then converted into a dihydro-form bilirubin and this is excreted as its conjugates with glucuronic acid. In plants and algae the same degradation of haem is used to make linear tetrapyrroles such as phycocyanobilin (3,3l- dide hydro-2,3-di hydromesobiliverdin) and p hycoerythrobilin (3,3],18l 1 82-tetradehydro-2,3 15,16-tetrahydromesobiliver-din) which when covalently bound to proteins play important functional roles as photoreceptors and photosynthetic light- harvesters. Recently a ‘Symposium-in-Print’ has been devoted to the subject of linear tetrapyrr~les~~~ and it includes papers on the mechanism of degradation of haem250 and the stereochemistry of biliprotein chrom~phores~~~ which both provide useful references.Also a book on the subject has recently been Another form of degradation of tetrapyrroles occurs when organisms die and decompose. The metalloporphyrins which can be found in oil shales marine sediments rocks etc. are for the most part the remnants of the chlorophylls of decayed plants and photosynthetic organisms. Porphyrins of the types (127) and (128) have been identified recently in oil hale^.^^^-^^^ It is most common that all of the side-chains have been reduced to alkyl groups and the magnesium in the centre of the macrocycle has been replaced by nickel or the vanadyl group (VO).Complete structure determination of these porphyrins as indeed of many of the natural products discussed earlier is greatly facilitated by the technique of nuclear Overhauser effect (n.0.e.) difference spectroscopy. 259 The rigid porphyrin macrocycle helps to produce good nuclear Overhauser effects between nearby hydrogen atoms and this allows reliable determination of the position of each of the peripheral substi tuents. 4.4 Medical Aspects One of the incentives for research into the biosynthesis of porphyrins has been the existence of disorders in the human biosynthesis of haem termed ‘porphyrias’. The several different forms of porphyria have now been correlated with biosynthesis to the extent that a defect in each enzyme of the pathway to haem is now known to give rise to a different porphyria.260*26 The effect of chemicals on the enzymes of the porphyrin pathway has been the subject of recent reviews.262 Much interest has been in Pb2+ which is known to inhibit several of the enzymes of the porphyrin pathway (see Section l) especially ALA dehydratase; the assay of this enzyme in the blood can be used as an early indication of lead poisoning.Another indicator which has proved reliable is the level of protoporphyrinatozinc in the blood which rises in parallel with the level of lead. An area of considerable medical interest at present is the use of porphyrins as photosensitizers to combat cancers. ‘Haemato- porphyrin derivative’ which is produced on treatment of haematoporphyrin (129) with acetic and sulphuric acids followed by mild aqueous alkali is absorbed preferentially by cancerous tissue; on irradiation with visible light the tissue is destroyed by the singlet oxygen that is produced by the photosensitizing porphyrin.Although the major components of the ‘haematoporphyrin derivative’ mixture have been identi- NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER OH fied,264 it seems that they are not the active ones. The structure of the active component(s) has yet to be elucidated but they may be dimeric or 01igomeric.~~~ A collection of papers on the subject has been published recently.266 While ‘haematopor- phyrin derivative’ is of considerable promise chlorins have proved better photo sensitizer^^^^ and also have the advantage that they absorb red light which is the colour that is best transmitted through human tissue.The use of chlorins looks particularly interesting especially if one can be found that can be localized in cancerous tissue. 4.5 Evolution of the Biosynthetic Pathways It was shown in the late 1960’s that porphyrins can be formed in a hydrogen-cyanide-producing prebiotic soup,268 and Eschen- moser has speculated that a vitamin-B ,-like corrin could result from the polymerization of hydrogen cyanide. 269 This specula- tion led him to investigate the tautomerization of porphyrino- gens under anaerobic conditions,270 which he has shown can lead to pyrrocorphins;212 this coupled to his experiments on non-enzymic ring-contraction,2 6+ lends a good deal of credence to the idea that corrins may have existed before life began.Vitamin B12 can be found in some of the most primitive of anaerobic organisms,271 which evolved in the reductive atmosphere of this planet before oxygen-producing plants arrived. It is significant then that no oxidation (or reduction) occurs in the biosynthetic pathway. The methylations which occur on the pathway using S-adenosylmethionine are thought to be a more recent type of reaction and so Eschenmoser considers that a ‘protocobyrinic acid’ having protons in place of the methyl groups may have been a predecessor of contemporary corrinoids. In the methylation steps also Eschenmoser has shown that the reactions are chemically very feasible and it would seem possible that Nature has taken pre- existing chemical reactions and improved them by the evolution of enzymes to cataiyse them.The biosynthesis of haem and the chlorophylls is thought to be a later development than that of because it involves oxidative steps that are not possible for primitive anaerobes (some of which still do not make haem) and because their use is in the production and utilization of oxygen. Therefore the development of this pathway is likely to have started only when some organisms began the first primitive form of photosynthesis. A recent review covers this area.273 The universal use of type I11 rather than type I porphyrins may be another case in which Nature has adapted a pre-existing chemical reaction because the tetramerization of four molecules of PBG in random orientation leads statistically (and in practice) to a preponderance of uroporphyrin 111.It may be that the application of evolutionary ideas will lead to fruitful insights into the mechanisms of the enzymes (such as PBG deaminase and cosynthetase) that have been developed to perfect the reactions and will provide the inspiration that is needed to solve the many remaining problems in the biosynthesis of tetrapyrroles which it is hoped this review has served to highlight. Acknowledgements I would like to thank Prof. A. R. Battersby and Dr C. Abell for proof-reading the manuscript and Dr D. G. Buckley for his collection of reprints.5 References 1 D. G. Buckley Annu. Rep. Prog. Chem. Sect. B 1978 74 392. 2 M. Akhtar and P. M. Jordan in ‘Comprehensive Organic Chemistry’ ed. D. H. R.Barton and W. D. Ollis Pergamon Press Oxford 1979 Vol. 5 p. 1121. 3 ‘The Porphyrins’ ed. D. Dolphin Academic Press New York 1979 Vol. 6 Ch. 1-4. 4 ‘B,?’ ed. D. Dolphin John Wiley New York 1982 Vol. 1 Ch. 4 and 5. 5 ‘Vitamin B Proceedings of the Third European Symposium on Vitamin B12 and Intrinsic Factor’ ed. B. J. Zagalak and W. Friedrich Walter de Gruyter and Co. Berlin 1979 Ch. 2. 6 A. R. Battersby C. J. R. Fookes G. W. J. Matcham and E. McDonald Nature (London) 1980,285,17;A. R. Battersby and E. McDonald Ace. Chem. Res. 1979 12 14. 7 R. C. Davies and A. Neuberger Biochem.J. 1979 177 649 and 661 ; Ref. 3 Ch. 4 and references therein. 8 V. Dzelzkalns T. Foley and S. I. Beale Arch. Biochem. Biophys. 1982 216 196. 9 A. Ohashi and G. Kikuchi J. Biochem. 1979 85 239. 10 G. Srivastava I. A. 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Biophys.Bioeng. 1981 10 151. 247 K. M. Smith E. M. Fujinari K. C. Langry D. W. Parish and H.D. Tabba J.Am. Chem. SOC., 1983,105,6638; K. M. Smithand K. C. Langry J. Chem. Soc. Perkin Trans. I 1983 439. 248 Reviewed by R. Schmid and A. F. McDonagh in ref. 3 Vol. 6 p. 258. 249 ‘Linear Tetrapyrroles’ ed. R. Bonnett Tetrahedron 1983 39 1839-1954 250 V. Rajananda and S. B. Brown Tetrahedron 1983 39 1927. 251 A. Gossauer Tetrahedron 1983 39 1933. 252 ‘Bilirubin Metabolism’ ed. K. P. M. Heirwegh and S. B. Brown CRC Press Florida 1982 Vol. 2. 253 C. J. R. Fookes J. Chem. Soc. Chem. Commun. 1983 1472 and 1474. 254 G. A. Wolff M. Murray J. R. Maxwell B. K. Hunter and J. K. M. Sanders J. Chem. Soc. Chem. Commun. 1983 922. 255 A. Ekstrom C. J.R. Fookes T. Hambley H. J. Loeh S. A. Miller and J. C. Taylor Nature (London) 1983 306,173. 256 J. Krane T. Skjetne N. Telnaes M. Bjoroy and H. Solli Tetrahedron 1983 39 4109. 257 J. F. Branthaver C. B. Storm and E. W. Baker Org. Geochem. 1983 4 121. 258 G. Habermehl and G. Springer Naturwissenschaften 1982 69 543. 259 K. N. Ganesh J. K. M. Sanders and J. C. Waterton J. Chem. Soc. Perkin Trans. 1 1982 1617; J. K. M. Sanders and J. D. Mersh Prog. Nucl. Magn. Reson. Spectrosc. 1983 15 353. 260 L. Bogorad in ref. 3 Vol. 6 p. 125; L. Eales ibid. p. 665. 261 S. W. Eubanks J. W. Patterson D. L. May and J. L. Aeling Int. J. Dermatol. 1983 22 337; G. H. Elder Br. J. Dermatol. 1983 108 729. NATURAL PRODUCT REPORTS 1985 -F. J. LEEPER 262 G.S. Marks D. T. Zelt and S. P. C. Cole Can. J. Physwl. Pharmacol. 1982,60 1017; G. S. Marks Trends Pharmacol. Sci. 1981 2 59. 263 See for example A. Fischbein J. C. Thornton L. Sarkozi S. Kon and S. Levin J. Appl. Toxicol. 1982,2,289; M.M. Joselow in 'Zinc in the Environment' ed. J. 0.Nriagu Wiley New York 1980 Vol. 2 p. 171. 264 P. S. Clezy T. T. Hai R.W. Henderson and Le van Thuc Aurt. J. Chem.,1980,33,585; R. Bonnett R. J. Ridge P. A. Scourides and M. C. Berenbaum J. Chem. Soc. Perkin Trans. I 1981 3135. 265 M. C. Berenbaum R. Bonnett and P.A. Scourides Br. J. Cancer 1982 45 571. 266 'Porphyrin Photosensitization' Ado. Exp. Med. Biol. 1983 Vol. 160 ed. D. Kessel and T. J. Dougherty. 267 L. Cariello M. de Nicola Giudici E. Tosti and L.Zanetti Gamete Res. 1982 5 161. 268 G. W. Hodgson and C. A. Ponnamperuma Proc. Natl. Acad. Sci. USA 1968 59 22. 269 A. Eschenmoser lecture given while Alexander Todd Visiting Professor University of Cambridge 20th May 1981. 270 A. Eschenmoser in ref. 5 p 89; Chem. Soc. Rev. 1976 5 377. 271 W. S. Beck in ref. 4 Vol. 2 p. 1. 272 N. H. Georgopapadakou and A. I. Scott J. Theor. Biol. 1977,69 381. 273 G. A. F.Hendry and 0.T. G. Jones J. Med. Genet. 1980,17 1.
ISSN:0265-0568
DOI:10.1039/NP9850200019
出版商:RSC
年代:1985
数据来源: RSC
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Recent progress in the chemistry of indole alkaloids and mould metabolites |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 49-80
J. E. Saxton,
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PDF (3455KB)
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摘要:
Recent Progress in the Chemistry of lndole Alkaloids and Mould Metabolites J. E. Saxton Department of Organic Chemistry The University of Leeds Leeds LS2 9JJ ~ ~~ ~ ~ ~~ Reviewing the literature published between July 1983 and June 1984 (Continuing the coverage of literature in Natural Products Reports 1984 Vol. 1 p. 2 1) 1 General 2 Simple Alkaloids 2.1 Non-t rypt amines 2.2 Non-isoprenoid Tryptamines 3 Isoprenoid Tryptamine and Tryptophan Derivatives 3.1 Ergot Alkaloids 4 Monoterpenoid A1 kaloids 4.1 Aristotelia Alkaloids 4.2 Corynantheine-Heteroyohimbine-YohimbineGroup and Related Oxindoles 4.3 Sarpagine-Ajmaline-Picraline Group 4.4 Strychnine Group 4.5 Ellipticine-Uleine-Apparicine Group 4.6 Aspidospermine-Vincamine Group 4.7 Catharanthine-Ibogamine Group 5 Bisindole Alkaloids 6 Biogenetically Related Quinoline Alkaloids 6.1 Cinchona Group 6.2 Camptothecin 7 References 1 General During the past twelve months a monograph on the monoterpenoid indole alkaloids'" and two further volumes in the series that was founded by Manske (now edited by A.Brossi) have been published.Ib Volume 21 in the Manske- Brossi series includes chapters on the evodiamine-rutaecarpine group and camptothecin and Volume 22contains references to indole alkaloids in chapters on (a)Ipecac alkaloids and their p-carboline congeners (b) the elucidation of alkaloid structures by X-ray diffraction and (c) the application of enamide cyclizations in alkaloid synthesis.Of general interest is a compilation of 13C n.m.r. spectral data for indole alkaloids in which substituent-induced chemi- cal shifts have been calculated for various types of ar-hydroxy- and methoxy-substituted indole alkaloids.* Me2NCONH2 + ClCOSCl -2 Simple Alkaloids 2.1 Non-tryptamines Evidence for the presence of 3-indolylmethylglucosinolateand its 1-methoxy-derivative in the roots of the horseradish (Armoracia rusticana P. Gartner B. Meyer et Scherb.) has been ~btained.~ An improved preparation of 1-methoxyindoleacetonitrile which has been isolated from Brassicu pekinensis Rupr. that is infected by Plasmodiophora brassicue Woronin has been reported. Dendrodoine (l) a metabolite of the marine tunicate Dendrodoa grossularia has been very simply synthesized by 1,3-dipolar cycloaddition of indole-3-carbonyl cyanide and NN-dimethylaminoformonitrileN-sulphide itself prepared by thermolysis of 5-(NN-dimethylamino)-1,3,4-oxathiazol-2-one (2)(Scheme l).5 7-Methoxygramine and 5,7-dimethoxygramine have been isolated from the roots of twelve-day-old seedlings of the pasture grass Phalaris aquatica L.;evidence for the presence of 5-methoxygramine was also obtained.'j None of these gramine derivatives has previously been found in Nature. New carbazole alkaloids continue to be found in species of the genus Murraya. Mukonicine isolated from the leaves of M. koenigii is a pyranocarbazole of structure (3),' and is therefore an isomer of koenigicine. The stem bark of the same plant has yielded mukonal (4);this is simply 3-formyl-2-hydroxycarba-zole a probable biogenetic precursor of the pyranocarbazoles found in the plant.* Mukoline and mukolidine which occurs in the roots are 6-hydroxymethyl-1 -methoxycarbazole (5) and 6-formyl-1-methoxycarbazole(6) respectively ;9 both structures were confirmed by synthesis.Murrayaquinone-B a new alkaloid from the root bark of Taiwanese M. euchrestijiolia Hayata has the structure (7) and is the first carbazole quinone to be isolated from natural sources.1o Another new carbazole derivative in which 0-methylation has blocked pyran ring- closure is clausenapin (8) a constituent of the leaves of Clausena heptaphylla.' The micro-organism that elaborates carbazomycins A and B,' 2o provisionally designated as strain H 1051-MY10 has now been identified as Streptoverticillium ehimense.OY-0 ?NANMe2 (2) Dendrodoine (1) Reagents i DMF at 145-150°C for a few minutes %heme I 50 NATURAL PRODUCT REPORTS 1985 H Mukonal (4) Mukonicine (3) 0 Mukoline (5) R=CH20H Mukolidine (6) RXHO Murrayaquinone-B (7) In a notable series of papers Steyn and his collaborators have given details of the structure eludication of the tremor- genic mycotoxins penitrems A-F;14 a correction to the relative stereochemistry of penitrems A B E and F compared with that reported initially,12b is now made and the absolute configuration of the penitrems has been determined. On the basis of nuclear Overhauser effects (n.0.e.) between the proton at C-24 and those at C-39 and between the proton at C-24 and H at C-21 rings H and I must be cis-fused and the complete relative configuration of penitrem A is as shown in (9).The absolute configuration again as expressed in structure (9) was determined by application of Horeau's partial resolution method involving esterification of the hydroxy-group at C-25 by means of (f)-a-phenylbutyric anhydride. Penitrems B (lo) E (13) and F (14) similarly have an a-epoxide function. The absolute configuration of penitrem D (12) was also determined by Horeau's method and the absolute configuration of the other penitrems (B C E and F) by detailed comparison of the n.m.r. spectra with those of penitrems A and D.14 The mass spectrum of penitrem A is discussed briefly in the first of these papers,14 but has been discussed in greater detail together with the mass spectra of penitrems B-E by other workers.15 The janthitrems are a related series of tremorgenic mycotox- ins that have been isolated from Penicillium janthinellum a micro-organism which with several other Penicilliumspecies is associated with ryegrass staggers [a neuromuscular disease which affects livestock that graze on pastures in which perennial ryegrass (Lolium perenne) is predominant].In another impressive and detailed n.m.r. study,16 the structures and relative stereochemistry of janthitrems E F and G [(15)-( 17)] were deduced with the exception of the configurations at C-22 and C-23. The absolute stereochemistry implied in structures (15)-( 17) has not yet been established.The penitrems and janthitrems show an obvious biosynthetic relationship the major difference between the two series being the structure of the monoterpenoid unit and its mode of attachment to the benzene ring. Lolitrems A B C and D form another series of tremorgens which have been isolated from toxic perennial ryegrass and which are also suspected of being responsible for ryegrass staggers in livestock. In lolitrem B (18) the monoterpenoid unit has yet another structure and mode of attachment to the benzene ring and the degraded diterpene component has been extended by the incorporation of an additional mevalonate unit with formation of the tenth ring (ring 1).17 Lolitrem C (a minor metabolite) appears to be the 40,41-dihydro-derivative of lolitrem B.The exact origin of the lolitrems has yet to be established but it is relevant to note that an endophytic fungus of the genus Acremonium which infects ryegrass has recently been shown to be associated with the production of the neurotoxins that cause ryegrass staggers. 2.2 Non-isoprenoid Tryptamines Bufotenine has been shown to be a constituent of the stem bark of Umbellulariu culifornica Nutt. the leaves of which provide OyJ OMe Clausenapin (8) Penitrem A (9) Ri=C1 RZ=OH Penitrem B (10) R1=R2=H Penitrem E (13) R1=H RZ=OH Penitrem F (14) R1=Cl R2=H Penitrem C (1 1) R=Cl Penitrem D (12) R=H Janthitrem E (15) R'=H R2=OH Janthitrem F (16) R1=Ac RZ=OH Janthitrem G (17) R1=Ac Rz=H U Lolitrem B (18) some of the components of laurel bay oi1.18 Whereas aporphine alkaloids are normally encountered in the family Lauraceae this is the first report of the presence of bufotenine.The 0-methyl ether of bufotenine has been shown to be the major base in the dart poison used by the YanoSma Indians of Brazil; this appears to confirm earlier reports that the poison is concocted from extracts of species of the genus vir~la.~~= The aerial parts of Melicope leptococca (Baill.) Guillaumin (a shrub endemic to New Caledonia) contain alkaloids belonging to the furoquinoline acridine and indole groups. The four indole bases isolated were shown to be 5-methoxy-NN-dimethyltryptamine and its N,-oxide 6-methoxy-2-methyl- tetrahydro-P-carboline and a hitherto unknown alkaloid 3- dimethylaminoacetyl-5-methoxyindole(19a) whose structure NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON MeooT?!!JMe2 H was confirmed by its reduction to 5-methoxy-NN-dimethyltryp-tamine and by synthesis. 9b An efficient five-stage synthesis of lespedamine (19b) from methyl 2-nitrophenylacetate has some unusual features but proceeds in 24% overall yield (Scheme 2).20 The I3C n.m.r. spectrum of physostigmine has been re- analysed with the aid of the high-resolution proton-coupled spectrum and selective proton-irradiation experiments.2 Norharman is the simplest of the eighteen alkaloids isolated from the leaves of Rauwolja caflra;22a this is claimed to be the first report of its occurrence in a member of this genus.Two of the three anhydronium bases extracted from the root bark of Strychnos usambarensisproved to be melinonine F (20a) and normelinonine F (20b); of these the latter has not previously been isolated from natural sources. 22b Melinonine F has been shown to exhibit cytotoxic activity at relatively high concentrations in normal cancer cells.22c 4,8-Dimethoxy- 1 -(2-met hoxyet hyl)-&car boline (~OC) 3- methylcanthine-2,6-dione(20d) 4,9-dimethoxy-l-vinyl-P-car-boline (20e) and two bis-P-carboline bases (4.v.) are new alkaloids that have been found in the wood of Picrasma quassioides Bennet together with the known bases 1-acetyl-P- carboline 1-e t hyl-4,8-dime thoxy-fl-carboline 1-e thyl-4-me th- oxy-P-carboline 4-methoxy-l-vinyl-~-carboline, 4,8-dimeth-oxy-1-vinyl-P-carboline,canthin-6-one and 5-methoxycan-thin-6-0ne.~~& In other hands extracts of the root stem twigs and bark of the same plant have yielded 4,8-dimethoxy- 1-vinyl-l)-carboline together with 1-carbomethoxy-P-carboline 4,5-dimethoxycanthin-6-one(methylnigakinone) and 5-hydroxy-4-methoxycanthin-6-one (nigakin~ne).~~ A number of bioactive P-carboline derivatives including four with the previously unreported oxathiazepine ring system have been isolated from the Caribbean tunicate Eudistoma olivaceum which is reported to exhibit activity against Herpes simplex Eudistomins C E K and L which show the most potent antiviral activity have structures (21)-(24) and presumably originate from tryptophan and ~ysteine.~~~ The remaining eleven eudistomins are relatively simple P-carboline deriva- tives with structures (25)-(35) and include five bases (eudistomins G H I P,and Q) which contain the previously unreported 1-(2-pyrrolinyl)-P-carboline ring system.In these metabolites C-1 and the pyrrole (or pyrroline) ring are assumed to be derived from glutamic acid. The structures of eudistomins D and N were confirmed by synthesis.25b Three new P-carboline derivatives have been isolated from the fruit bodies of the gilled agaric Cortinarius infractus (Pers. ex Fr.) Fr.26 Infractine (36) is l-(2-methoxycarbonylethyl)-~-carboline and the second alkaloid is its 6-hydroxy-derivative (37). The third alkaloid infractopicrine is quaternary and was isolated as its chloride (38); it is reported to be responsible for the bitter taste of this toadstool.Four new P-carboline derivatives have also been found together with 1-methoxycanthin-6-one and two monoterpenoid indole alkaloids in the roots of Hannoa klaineana Pierre et Engl. (a tree endemic to tropical Africa). Decoctions from the roots of this plant are used locally against fever and intestinal disorders. The new bases are ethyl P-carboline-1-propionate(39) [cf infractine (36)] and its N,-oxide and 1-ethyl-0-carboline and its N,-~xide.~' It remains to be proved unequivocally that these ethyl esters are present in the plant and are not artifacts derived from the corresponding acid during the extraction and isolation procedure.Indeed this acid has recently been bH OMe OMe bMe Lespedamine (19b) Reagents i Zn NH,Cl MeOH; ii CH2N2; iii BrCH2CH2Br NaH; iv Me2NH Me,NH.HCl H20 DMF; v LiAlH4; vi HCl H20 Scheme 2 (20a) R=Me (20b) R=H OMe D1 R1 R2 R3 Eudistomin C (21) H OH Br Eudistomin E (22) Br OH H Eudistomin K (23) H H Br Eudistomin L (24) H Br H R' R1 R2 R3 R4 Eudistomin A (25) H OH Br 2-pyrrolyl Eudistomin D (26) Br OH H H Eudistomin J (30) H OH Br H Eudistomin M (31) H OH H 2-pyrrolyi Eudistomin N (32) H Br H H Eudistomin 0 (33) H H Br H R1 R2 Dl D2 n~ Eudistomin G (27) H Br Infractine (36) H Me Eudistomin H (28) Br H 6-Hydroxyinfractine (37) OH Me EudistominI (29) Eudistomin P (34) OH Br (39) H Et Eudistomin Q (35) OH H NATURAL PRODUCT REPORTS 1985 c1-Y %' 0' Infractopicrine (38) (42) R' = H R2 = COCF3 (46) R' = Br R2 = C02Me isolated together with 1-carbamoyl9-carboline l-carbometh- oxy-fbcarboline and two new alkaloids in a re-investigation of the constituents of the root bark of Ailanthus altissimu Swingle.28 The new bases are l-(2-hydroxy-l-methoxyethyl)-4-(43) R1 = H R2 = COCF3 (47) R1= Br R2 = C02Me ii [on (43)] iv [on (47)) 1 (44) R = H (48) R = Br methoxy-p-carboline (40) and 5-hydroxymethylcanthin-6-one (41).Canthin-6-one and 1-methoxycanthin-6-one were ob-tained in an investigation into the production of cytotoxic canthin-6-one derivatives in callus and cell suspension cultures of A.alti~sima.~~ Bergman's synthesis of rutaecarpine' 2c has now been extended to the synthesis of evodiamine and 13b 14-dihydro- rutae~arpine,~~ but full details are not yet available. In connection with biosynthetic studies complete assign- ments of the I3C n.m.r. signals of eight naturally occurring chaetoglobosins have been made.31 3 lsoprenoid Tryptamine and Tryptophan Derivatives The occurrence of flustramine A and flustramine B in Flustru folipcea L. has again been noted and the alkaloid content of specimens from Danish and Swedish waters has been compared. * Syntheses of (+)-debromoflustramine B (45)33 and (+)-flustramine B (49)34 have recently been reported. The two syntheses followed broadly similar lines the crucial stage being bis-alkylation of suitably N,-protected tryptamine derivatives [(42)or (46)] at N,and position 3 with formation of the pyrrolo- indoles (43) or (47).Some difficulty was experienced in both syntheses with the removal of the Nb-protecting group to form (44) and (48) (Scheme 3). Since bromine could not be introduced directly into position 6 in tryptamine the starting material [6-bromo-Nb-methoxycarbonyltryptamine(46)] for the synthesis of flustramine was itself prepared by an indirect multi-stage route.34 Two syntheses of borrerine (50)have also been rep~rted.~~~~~ A Debromoflustramine B (45) R = H Flustramine B (49) R = Br Reagents i Me2C=CHCH2Br acetate buffer; ii NaBH,; iii CH20 NaBH3CN; iv 10% NaOH EtOH boil for 100 h; v MeI K2C03 MeCOMe Scheme 3 I __+ a-bMe N' Y Isoborrerine (51) 1ii 111 t Borrerine (50) vi Since the direct Pictet-Spengler synthesis from tryptamine and senecioic aldehyde failed the French group prepared borrerine by an indirect isomerization of isoborrerine (5l) previously synthesized3'0 (Scheme 4).A more direct synthesis was achieved by preparation of the borrerine precursor (52) by a modified Pictet-Spengler cyclization of the Schiff s base (53) by means of methyl chloroformate and pyridine (Scheme 4).36 The structure of meleagrin (54) a metabolite of Penicillium meleagrinum Biorge IF0 8143 obtained during the process of screening Penicillium species for antimicrobial metabolites has been determined by X-ray crystal structure analysis of its 9-0-p-bromobenzoate m~nohydrate.~~ Melea-grin thus appears to be the 9-0-demethyl derivative of oxaline (53 but although p-bromobenzoylation esterified the 9-hydroxy-group methylation gave only the 14-methyl derivative rather than oxaline.Four metabolites olivoretins A-D which exhibit pro-nounced vesicant activity have been isolated39 from the mycelia of Streptoverticillium olivoreticuli in addition to the derivatives of pimprinine recorded earlier.40u Olivoretin D (56) is identical with teleocidin B,40b and olivoretin A is its 0-Tryptamine Reagents i ButOCl;ii CF3C02H at 20 "C; iii NaBH, MeOH; iv Me2C=CHCH0 4A molecular sieves CH2C12; v ClCO,Me py CH2C12; vi LiAIH, THF Scheme 4 methyl ether (57).39 The structure and relative configuration of olivoretin D and its identity with teleocidin B were revealed by X-ray crystal structure analysis.The absolute configuration follows from comparisons of the c.d. spectrum of teleocidin B (56) with those of the model indole-lactam (58) and its NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON Me I Meleagrin (54) R Oxaline (55) R = H = Me Olivoretin D (56) R Olivoretin A (57) R (ZTeleocidin B) = H = Me (58) B-CHMe2 at C-14 (59) a-CHMe at (2-14 Agroclavine-I (60) &H i-iv - H 0 L Ts v-xd xi xii - H xiii-xv J 2Me xviii xvi xvii -L / II \ H Clavicipitic acid I (61) a-H Clavicipitic acid I1 (62) P-H Reagents i TsCI K,CO, MeCOEt; ii MeMgI; iii rn-chloroperbenzoic acid CH,CI,; iv NaN, dioxan H,O; v Me2C(OMe), TsOH; vi H, Pt; vii TsCI NEt, CICH2CH,Cl heat; viii BrCH2C02Me K,C03 DMF; ix KOH MeOH H20, DME; x CH,N2 MeOH Et,O; xi POCl, DMF Et20; xii DBU PhH heat; xiii 1% HC1 MeOH THF H,O; xiv S=CC12 DMAP CH2C12; xv P(OMe), heat; xvi NaBH, N, hu at -7O”C Na2C03 MeOH DME H20 xvii separation of diastereoisomeric racemates; xviii KOH MeOH H,O at r.t.Scheme 5 diastereoisomer (59).41 It should be noted that in previous communications the stereochemistry at C-16 and C-19 in teleocidin B was incorrectly ill~strated.~~ The correct relative and absolute configuration for this metabolite are as depicted in (56). 3.1 Ergot Alkaloids Fumigaclavine A has been shown43 to be the major alkaloid produced by a strain of Aspergillus tamarii Kita which was found as a contaminant of the seeds of Paspalum scrobiculatum L.This plant is cultivated in some parts of India and used as a staple food by the poor. However consumption of the grains is often associated with symptoms of mycotoxin poisoning characterized by nausea vomiting delirium and unconscious- ness. Fumigaclavine may well be responsible at least in part for this toxicity. A study44 of the appropriate coupling constants in the proton n.m.r. spectrum of agroclavine-I (60) a metabolite of Penicillium k~puscinskii,~~ has revealed that ring c must have an envelope conformation ;epoxyagroclavine-I is its P-epoxide. The first total synthesis of (+)-clavicipitic acid I (61) and clavicipitic acid I1 (62) follows a lengthy and largely unexcep- tional route (Scheme 5).46 However the product of reduction and detosylation of the unsaturated ester (63) gave a mixture of products from which the two diastereoisomeric esters (64)and (65) were separated.Saponification then gave (f)-clavicipitic acid I (61) and (+Aavicipitic acid I1 (62). The suffixes I and I1 are proposed to denote these diastereoisomers which have not previously been obtained pure (albeit racemic). Natural clavicipitic acid is a mixture of the optically active acids I and 11 ar.d a mixture of racemates was also the end-product of Kozikowski’s ~ynthesis.~5 A shorter synthesis of clavicipitic acid (stereochemistry unspecified) has been briefly reported but details are not yet a~ailable.~’ Details of Kozikowski’s synthesis4OC of (+)-paliclavine and (+)-paspaclavine have now been published.48 Also published in detail are Rebek’s synthese~~~~.~~ of setoclavine lysergine and lysergic acid,49 and Oppolzer’s syntheses’ 2d of chanocla- vine and iso~hanoclavine.~0 This last synthetic approach has been extended by making use of the previously synthesized’ 2d trans- and cis-aldehydes (66) and (67) to afford new syntheses of (+)-6,7-secoagroclavine (68) and ( f)-paliclavine (69) (Scheme 6) and of (f)-costaclavine (70) (Scheme 7).50 Synthesesof (f)-lysergene (71) (k)-agroclavine (72),51 (+)-isolysergol (73) and (i-)-elymoclavine (74)52 have been the subject of recent Japanese reports (Schemes 8 and 9).Both routes involve the construction of the required tetracyclic framework by photocyclization of an enamide and require no further comment except to note that these are the first reported syntheses of all four bases.Isomerization of ergoline-8@carboxylic acid esters (75) to the thermodynamically unfavoured 8a-epimers (76) can be achieved in good yield by formation of the corresponding lithium enolate by means of LiNPri in tetrahydrofuran followed by decomposition with water or dilute aqueous acid.53 This opens up a route to the pharmacologically active 8a- carboxylic esters and several such compounds have been prepared for pharmacological evaluation. 54 Other compounds that have been prepared for this purpose include a series of 6- methylergolin-8-ylpropionic acid derivatives; of these the cyano-amide (77) exhibits the most potent antihypertensive activity.55 NATURAL PRODUCT REPORTS 1985 CHO CO~BU' -@Me i + epimer HN (66) (67) J ii iii Me Me 1 I 1 C02Me $ # @ -q$Mec02Bu1 H O S iii iv MeC02Bu1 HMe + epimer \ \ HN I HN Paliclavine (69) 1ii HN Iv Costaclavine (70) 6,7-Secoagroclavine (68) Reagents i Me3SicMeC02Me; ii H2 Pd A1203; iii CF3C02H; iv Reagents i H,C=CMeMgBr; ii CF3C02H; iii Ph3P=CMe2 Me,AI; v LiAlH Scheme 6 Scheme 7 cH20H CH20H -H -@ + \ Me i.ii @e iv v MbsN MbsN MbsN Me Me I Me ... Vlll ix v viii f---4 MbsN Agroclavine (72) + Lysergene (71) epimer (Mbs = p-methoxybenzenesulphonyl) Reagents i MeNH,; ii furan-3-carbonyl chloride; iii hv NaBH, PhH MeOH; iv 03,CH2C12 at -60 "C; v LiAlH,; vi MesC1 py; vii KOBu DMSO; viii PhSeSePh; ix Birch reduction.Scheme 8 An improved preparation of the clinically useful prolactin deduced ;57 the absolute configuration implied in structure (78) inhibitor 2-bromo-a-ergocryptine which involves bromination follows from comparison of the c.d. spectra of (78) and of a-ergocryptine by means of pyrrolidone hydrotri bromide or aristoteline of known absolute configuration. piperidone hydrotribromide has been described ;56 the method Peduncularistine triabunnine and aristolarine are three is also applicable to other peptidic ergot alkaloids. new alkaloids that have been isolated from Tasmanian Aristotelia pedunculari~.~~ The structure and absolute confi- 4 Monoterpenoid Alkaloids guration of peduncularistine (79) follow from its spectral data 4.1 Aristotelirz Alkaloids (unconjugated indole carbonyl and Z configuration of X-Ray crystal structure analysis of aristoserratine (78) has disubstituted alkene groups) and its hydrogenation to aristoser-confirmed the structure and relative stereochemistry previously ratine.Triabunnine (80) is the related hydroxyindolenine and NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON 55 SH~OAC CH20H 1 ii-vi vii-ix 9PMe HN AcN Elymoclavine (74) Ivii xi xii CH20Ac CH2OH I xiii ix x viii ix -___) \ ~ &Me \ Me AcN AcN Lysergene (71) (major product) Isolysergol (73) Reagents i hv NaBH, PhH MeOH; ii 0,; iii LiAlH,; iv separation of epimers; v H2 Pd/C; vi Ac20 py at 0 "C; vii SOCl2 PhH heat; viii HCI MeOH (on minor product); ix PhSeSePh; x DBU; xi MesC1 py; xii base; xiii deacetylation Scheme 9 lv (77) qqHi OT-lH Me Me - Aristoserratine (78) Peduncularistine (79) lii Aristolarine (8 1) Triabunnine (80) Reagents i H2 Pd; ii 02,hv Rose Bengal MeOH HC104 at 0 "C Scheme 10 was prepared by photochemical oxidation of aristoserratine (78) (Scheme 10).Aristolarine is unique among Aristoteliu alkaloids in being yellow owing to the presence of an indolin-3-one chromophore. The molecule contains only two methyl groups the third one normally encountered in the Aristoteliu alkaloids being (+)-Aristoteline (86) (-)-Hobarthe (82) Reagents i Br, Et20; ii HN3 BF3.Et20 PhH; iii LiAlH,; iv indole-3-acetaldehyde PhH; v HC02H at r.t.; vi 20% HCI H20' Scheme 11 replaced by a primary alcohol function attached (as expected) to a fully substituted carbon atom.If the monoterpenoid residue has the usual Aristoteliu skeleton a possible structure for aristolarine is (81); this is consistent with all of the available evidence but cannot yet be regarded as being unequivocally established. If furthermore aristolarine arises by rearrange- ment of a 3P-hydroxyindolenine [cJ:(80)] the relative stereo- chemistry in structure (81) would also result.s8 A short and efficient synthesiss9 of (-)-hobartine (82) relies on a neat preparation of (S)-(p-menth-l-en-8-yl)amine (83) of high optical purity from (S)-wterpineo1(84).Condensation of (83) with 3-indolylacetaldehyde gave an imine (85) which was cyclized to (-)-hobartine (82) in 64% yield by means of formic acid (Scheme 11). This synthesis establishes the absolute configuration of (-)-hobartine previously unknown ; further confirmation was obtained by its cyclization to (+)-aristoteline (86). 4.2 Corynantheine-He tero yohimbineYohimbine Group and Related Oxindoles 5,6-Dihydroflavopereirineis one of three anhydronium bases that have been isolated from the root bark of Strychnos usurnburensis.22b Flavopereirine itself is the simplest of eleven alkaloids that have been extracted from the stem bark of S. longicaudata Gilg. from ZBire.60 A glucosidic alkaloid from the leaves of Pauridiantha lyallii Brem.proves to be 21-epi-pauridianthoside (87)f1 this is the first example of a naturally occurring epimer of secologanin and presumably arises by enzymic hydrolysis of the glucose unit followed by epimerization at C-21 in the hemiacetal thus released and re-formation of the glucosidic linkage. Desoxycordifolinic acid (88) the parent diacid related to desoxycordifoline was obtained as the major alkaloid of the heartwood of Nauclea diderrichii (De Wild.) Merr.;62 in the extractions the use of ammonia and strong acids was avoided in an attempt to reduce the possible production of artifacts. It is thus of interest to note that no alkaloids containing a pyridine ring were encountered. The dried legumes of Rhazya stricta from which the seeds had been removed have been shown to contain isovallesiachotamine.63 The Oriental drug 'chotoko' [the dried climbing hooks and stems of a species of the genus Uncaria (possibly U.sinensis Oliver)] is reputed to have sedative and hypotensive properties.A methanol extract of this drug did in fact elicit a strong long-lasting hypotension when injected into rats and on fractionation it yielded cadambine 3a-dihydrocadambine and 3P-i~odihydrocadarnbine.~~~ The pharmacological activity of the extract appears to be due mainly to the last two of these a1 kaloids. The presence of cadambine in the leaves of Anthocephalus chinensis (Lamk.) A. Rich. ex Walp. known in India as 'wild cinchona' has been confirmed,64b and the high-field proton and 13C n.m.r.spectra of this alkaloid have been recorded and analysed. Guettardine a new alkaloid from the bark of Guettarda heterosepala has the structure (89) which was established by correlation with dihydrocorynantheol(90) (Scheme 12).65 This alkaloid may well be a biogenetic intermediate in the conversion of b-carboline alkaloids into the cinchonamine 21 -epi-Pauridianthoside (87) Desoxycordifolinic acid (88) i ii __* 1 OH bH / Guettardine (89) OH Dihydrocorynantheol (90) Reagents i TsCl CH2C12 at 0 "C;ii DMF heat; iii LiAlH, THF heat Scheme 12 NATURAL PRODUCT REPORTS 1985 group a possibility which is underlined by the presence of Cinchona alkaloids in the same plant. If so it indicates that fission of the 4-5 bond in an intermediate of the corynan- theine-geissoschizine type probably precedes formation of the quinuclidine ring.-A new alkaloid isolated from the leaves of Catharanthus roseus and Rhazya stricta66 is tentatively formulated as 16-epi- (2)-isositsirikine (91). This base was not identical with either of the two (a-isomers that were obtained by reduction of geissoschizine but the n.m.r. data were certainly consistent with those of structure (91) which had been prepared earlier (together with its stereoisomers) by reduction of 4,21-di-de hydrogeissosc hizine hydrochloride. In an extensive investigation into the constituents of Guyanese Aspidosperma marcgravianum Woodson no fewer than 46 alkaloids were isolated from the stem bark leaves and root bark.68 This tree is apparently not used locally for medicinal purposes but its wood finds extensive use.Twelve of the alkaloids that were isolated are new; these include 16-epi- isositsirikine Nb-oxide isositsirikine Nb-oxide 18,19-dihydro- antirhine isogeissoschizol 10-methoxyisogeissoschizol isoantirhine and 3,4,5,6-tetradehydro-18,19-dihydrocory-nantheol from this group. In addition tetrahydroalstonine dihydrocorynantheol Nb-oxide antirhine deplancheine (1 6R)- 18,19-dihydrositsirikine (1 69-1 8,19-dihydrositsirikine and 16-decarbomethoxy-16,17-dihydro-17-hydroxy- 19-epi-ajmali-cine were isolated for the first time from any species of the genus Aspidosperma. Thirteen other alkaloids had already been encountered in this genus; these include dihydrocorynantheol aricine reserpiline reserpinine isoreserpiline isositsirikine 16-epi-isositsirikine geissoschizol 1 0-methoxygeissoschizol P-yohimbine yohimbine 0-acetylyohimbine and 10-methoxy- di hydrocorynantheol .68 A similarly thorough investigation has also been carried out on the seeds of Aspidosperma oblongum (A.DC.) Pichon the aerial parts having been examined on previous occasions.69 Like A.marcgrauianum this species is also endemic to Guyana; it appears to have no local medicinal use but is prized for its wood. In all 35 alkaloids were isolated from the seeds; these included thirteen new ones all of which belong to this group; these are 1O-methoxy- 17-epi-alloyohimbine 19,20-didehydr@- yohimbine 3,4-didehydro-P-yohimbine(as the perchlorate) p-yohimbine oxindole P-yohimbine pseudoindoxyl P-yohimbine N,,-oxide 1 0-met hox y-& yohim bine 1 0-me thox y-a-yo him bine 19,20-didehydro-a-yohimbine, aricine pseudoindoxyl an ar- methoxyantirhine 10-methoxysitsirikine and 3,4,5,6-tetrade- hydrositsirikine.One other alkaloid 17-epi-alloyohimbine had already been prepared by partial synthesis and has now been isolated from natural sources for the first time. In addition antirhine vallesiachotamine neo-oxygambirtannine alloyo- himbine corynanthine and 3,4,5,6-tetradehydro$-yohimbine are among those isolated from any species of the genus Aspidosperma for the first time and P-yohimbine yohimbine aricine tetrahydroalstonine a-yohimbine 10-methoxycory- nanthine isositsirikine 16-epi-isositsirikine (16R)-sitsirikine (16R)-18,19-dihydrositsirikine,(16R)-lO-methoxy-18,19-dihy-drositsirikine and 10-methoxyisositsirikine were already known in this genus.69 Sitsirikine has also been found in the leaves of Rauwolfia cafra22a and yohimbine a-yohimbine and alloyohimbine in the seeds.70 Tetrahydroalstonine occurs in roots of Kopsia o_tfcinalis7 and in Alstonia yunnanensis Diels the roots of which are used in Chinese folk medicine for the treatment of headaches fever and hyperten~ion.~~ I-r-Is A MeOzC l6 CH20H 16-epi-(Z)-isositsirikine (91) NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON During a search for antimicrobial alkaloids in the root bark of Aspidosperma excelsum Benth. a number of inactive alkaloids including aricine yohimbine and O-acetylyohim- bine were isolated.73 The investigation into the variability of Thai specimens of the leaves of Uncaria elliptica R.Br. ex G. Don. previously noted,40d has been extended.74 A total of six samples has now been examined; from these seven of the eight possible diastereoisomers of the pentacyclic heteroyohimbine alkaloids were isolated. Only akuammigine was absent. Other alkaloids identified were 14P-hydroxy-3-isorauniticine,*tetrahy-droalstonine N,-oxide mitraphylline and isomitraphylline uncarine A and uncarine B and the four new natural products rauniticine pseudoindoxyl akuammigine pseudoindoxyl raun- iticine oxindole A and 3-isorauniticine pseudoindoxyl. The roxburghine alkaloids previously isolated from U.elliptica were not detected and in general this species seems to show considerably greater chemotaxonomic variation than had previously been suspected. The use of proton n.m.r. spectra in the identification of ajmalicine and its stereoisomers is e~emplified.~~ A South American species of the genus Uncaria U.guianensis (Aubl.) Gmel. appears to contain only oxindole alkaloid^.^^ The leaves contain rhynchophylline and isorhynchophylline and the roots yielded pteropodine speciophylline and mitra- phylline. Rhynchophylline and isorhynchophylline are also the two oxindole bases in the roots of Hannoa klaineana.27 A quantitative analysis of the tertiary bases in various organs of Uncaria rhynchophylla Miq. has been reported.76 Isocorynox-eine isorhynchophylline corynoxeine and rhynchophylline predominate in the hooks small stems and leaves whereas hirsuteine and hirsutine constitute 96% of the alkaloid content of the root bark. Little alkaloid is present in the wood but the proportion of the relatively rare alkaloids corynantheine and dihydrocorynantheine is somewhat higher than in the other parts. In the course of extracting the major alkaloids mitraphylline and isomitraphylline from the leaves of Bengali Mitragyna parvifolia (Roxb.) Korth. the N,-oxide of speciophylline was also isolated.77 Reserpic acid has been shown for the first time to be a natural product since it was isolated during an examination of the acidic constituents of the roots of Congolese RauwolJia oornit~ria.~~ It was shown not to be an artifact since the ester alkaloids in the roots remained intact.Pleiocarpamine is one of fourteen alkaloids that have been isolated from the stem bark and aerial parts of Melodinus guillauminii from New Caled~nia,~~ and it has also been obtained from the leaves of Catharanthusroseus together with fluorocarpamine and fluorocarpamine Nb-oxide.80 Cell suspension cultures of RauwolJia serpentina result in the formation of twelve indole alkaloids of which reserpine yohimbine ajmalicine 3-isoajmalicine serpentine and alston- ine belong to this group.81 Finally the pattern of distribution of alkaloids in the leaves stems and roots of ten African species of the genus RauwolJia has been summarized and the interrelationships of the alkaloid types have been discussed.82 Almost all of the alkaloids in these species belong to this group or to the ajmaline group although traces of akuammicine and its relatives in the strychnine group have been reported.Tetraphylline (92) Now known to be 14a-hydroxyrauniticine; for structure revision see later (ref. 96). (93) Melinonine E (94) \-xii OTQMe Ts H' TMe H H** iv v Ixiii. xiv GCOMe vii viii - (96) 3SR 19RS Mostueine (95) 3SR 19RS (+ 19-epimer) Reagents [Ref. 851 i HCO,Et NaH; ii N,-methyltryptamine AcOH THF at r.t.; iii H2S04 THF at 0 "C then at r.t. for 24 h; iv PhH Bu4N+ HSO, PhSO,CI 50%NaOH-H,O at r.t.; v MeMgI PhH; vi NaBH,; vii MesC1 NEt, THF at -20 "C; viii KOBu' THF 18-crown-6 at -20 "C; [Ref.861 ix N,-methyltryptamine toluene TsOH heat; x HCI MeOH; xi TsCI KOH glyme; xii MeLi LiBr THF at -78 "C; xiii LiAIH4 THF at -98 "C; xiv 10% KOH MeOH heat; xv HC(OMe),NMe, toluene heat. Scheme 13 NATURAL PRODUCT REPORTS 1985 It has been pointed that the absolute configuration at C-3 in heteroyohimbine alkaloids cannot be deduced unequivo- cally from the c.d. spectra since interaction between the indole ring and the chromophore in ring E can reverse the expected sign of the Cotton effect. Since the absolute configuration of yohimbane derivatives can be securely established by this method the chromophore in ring E in the heteroyohimbine series must first be removed e.g. by hydration reduction of the ester to a primary alcohol function or decarboxylation and hydration with formation of a ring E hemiacetal.The sign of the Cotton effect in the 270-300 nm region can then be safely used to deduce the configuration at C-3. Confirmation of the configuration that had been deduced for tetraphylline (92) was obtained by X-ray crystal structure determinati~n.~~ Melinonine-E a quaternary alkaloid of Strychnos melinoniana Baill. for which the structure (93) was earlier [19571 proposed on the basis of very limited evidence has now been re-in~estigated.~~ Its molecular formula determined by mass spectrometry is C,,H2 N20+,and the presence of nineteen carbon atoms [rather than twenty as in (93)] is confirmed by its I3C n.m.r. spectrum. Complete analysis of its proton and I3C n.m.r.spectra reveals that the alkaloid has the structure and relative stereochemistry shown in (94); melinonine-E thus contains a new skeleton. Biogenetically it could arise from an alkaloid such as antirhine in which case (94) would also show the correct absolute configuration. Two very similar synthese~~~~~~ of mostueine (95) (Scheme 13) serve to confirm the gross structure of this base from Mostuea brunonis but the conclusions concerning the stereo- chemistry of mostueine that have emerged are at variance. The French workersg5 established the relative stereochemistry of their intermediate (96) by X-ray crystallography and this leads to the opposite configuration at C-19 to that shown in (95) for mostueine if the final ring-closure involves a direct SN2 displacement on the 19-mesylate following deprotection of N,.However the American worked6 noted nuclear Overhauser enhancement of the signal owing to the axial proton at C-14 in mostueine when the signal of the methyl group C-18 was presaturated and of the signals of the protons at C-12 and C-21 when the signal of the proton at C-19 was presaturated. These observations are only consistent with the stereochemistry for mostueine that is shown in structure (99 i.e. 3SR,19RS. It therefore seems probable that cyclization of the mesylate derived from (96) involves overall retention of configura- tion at C-19. This may well be so,since the first part of the sequence to mostueine from (96) involves reaction conditions similar to those prescribed for the formation of chlorides from benzylic-type alcohols.Hence the resulting chloride may be the substrate for cyclization and the overall process from (96) to mostueine (95) involves double inversion at C-19. The structure of vinoxine (97) (Scheme 14) has also been confirmed by synthesis,87 and again this has led to revision of the stereochemistry. In an earlier investigation vinoxine was depicted as (98) on the basis of the chemical shift of the proton at (2-16. However the availability of both vinoxine and 16-epi- vinoxine from the synthetic work allowed comparison of J15 ,6 in these two bases with the reported values for pleiocarpamine and 16-epi-pleiocarpamine from which it was deduced that vinoxine has the stereochemistry shown in structure (97).87 A considerable amount of effort continues to be expended on the total synthesis of the mainstream yohimbine and heteroyo- himbine alkaloids.A reviewg8 of the methods available for the elaboration of the ethylidene side-chain in the ring-E-seco alkaloids shows how much attention has already been paid to this one structural feature. A new four-stage synthesis of flavopereirine (99) via 5,6-dihydroflavopereirine (loo) is claimed to be the most efficient yet reported (Scheme 15).89 1 'C02Me \C02Me MeO,Cm &I Me02C N CH~CH~OAC \ C02Me Me Vinoxine (97) R'=H R2=C0,Me 16-epi-Vinoxine (98) Rl=CO,Me R2=H Reagents i LiNPr', THF at -30 "C; ii HCl PhH at pH 3.5-4; iii 4M-HCl (on either epimer); iv 1.5M-HCl MeOH at r.t.; v NaBH, MeOH at 0°C Scheme 14 i ..... CHOEt / /o 5,6-Dihydroflavopereirine(100) Flavopereirine (99) Reagents i r.t.; ii Huang-Minlon reduction; iii LiAlH, THF; iv DDQ AcOH at 100°C. Scheme 15 NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON Details of McLean's synthesis45 of the diastereoisomers of (+)-decarbomethoxynauclechine have now been published.g0 Wanner's synthetic route involving the addition of ester anions to nicotinium salts has been applied in a very brief synthesis of nauclefine (101) (Scheme 16).91 The synthesis of (&)-corynantheidol by Imanishi et al. previously reported in brief has been described in detail.92 A new synthesis93 of (+)-dihydrocorynantheol (102) in- volves as its critical stage the alkylation-cyclization of 3,4- dihydro-a-carboline with the (a-lactone (103) which gave the tetracyclic lactam (104) in good yield and with a very high degree of stereoselectivity.Removal of the 0x0-group from the lactam and stereospecific reduction of the 3-14 double-bond was achieved by a two-stage sequence in which the second stage which presumably involves reduction of a 3-Nb immonium grouping by means of sodium borohydride occurs specifically at the 01 face owing to co-ordination of reagent with the free hydroxy-group attached to C-18. Reductive removal of this hydroxy-group and release of the hydroxy-group at C-17 then completed the synthesis (Scheme 17).93 Although several syntheses of (f)-ajmalicine are on record only partial syntheses of (-)-ajmalicine (105) have hitherto been reported.A total synthesisg4 of (-)-ajmalicine (Scheme 18) is therefore of considerable interest since this alkaloid is prescribed in some countries for the treatment of cardiovascu- lar disease. Pictet-Spengler cyclization of (+)-tryptophan- + 0-p -i,ii "H NH,*HCl \+ c1-amide with 4-formyl-2,2-bis(phenylthio)butyratehad earlier95 been shown to lead stereospecifically to the tetrahydro-a- carbbline derivative (106) from which the redundant carbox- amide group was then removed. Protection of N (to avoid lactam formation) and introduction of a double-bond conjugated with the ester group then gave an intermediate (107) which on reaction with methyl vinyl ketone followed by cyclization gave the tetracyclic keto-ester (108).Reduction of (108) gave the known lactone (109) in 7.5% overall yield from (-)-tryptophan. Conversion of (109) into (-)-ajmalicine by van Tamelen's route was then accomplished in 50% yield. A new partial synthesis77 of (-)-ajmalicine from mitraphyl- line (1 10) simply involves the reaction of mitraphylline methiodide with triethyloxonium fluoroborate followed by reduction (by sodium borohydride in acid solution) of the imino-ether (111) thus produced (Scheme 19). By use of the quaternary salt in this procedure the fission of the 3-Nb bond to give a ring-c-seco base was avoided and the stereochemistry at C-3 was preserved. Finally (-)-ajmalicine (105) was prepared by pyrolysis of the methiodide (1 12).77 The application of two methods for the introduction of a hydroxy-group into position 14 of the heteroyohimbine bases has allowed the structure of an alkaloid from Uncaria attenuata to be established.Originally postulated to be 1@-hydroxy-3- isorauniticine,12e this alkaloid has now been shown to be 14a- hydroxyrauniticine (1 13) since it can be prepared by hydro- H HGswCHzPh / J vi c- N auclefine (101 ) Reagents i NEt, MeCN; ii PhCH2Br MeCN heat; iii C:)-CO2Et Na+ EtOH then xylene heat for 30 minutes; iv Raney nickel TMF heat; v Pd/C Hz EtOAc MeOH HCl; vi 40% HBr-AcOH at 40°C. Scheme 16 vi vii viii (or ix) -OH bThp Dihydrocorynantheol (102) (Thp =tetrahydropyran-2-yl) Reagents i PhH; ii DMF at 80 "C under Nz for 30h; iii chromatography on silica gel; iv LiAlH, THF; v NaBH,; vi o-02NC,H,SeCN Bu3P THF under Nz; vii TsOH pyridine EtOH; viii Ph,SnH PhMe heat; ix W-2 Raney nickel EtOH Scheme 17 60 NATURAL PRODUCT REPORTS 1985 0Tj20NH2 H ( + )-Tryp tophanamide ii iii ii iv-vi + i -H H'* -TH H H* -SPh I OHCCH2CH2F'CozMe PhSpPh "C0,Me 0,Me SPh vii 1 HH t t t Me H** \ Me0,C 0,Me ( -)-Ajmalicine (1 05) 0 ( 108) ( 109) Reagents i PhH remove water azeotropically then CF,C02H CH2C12; ii trifluoroacetic anhydride; iii KBH, MeOH heat; iv PhSH NaH; v rn-chloroperbenzoic acid then PhMe heat; vi NaBH ; vii H,C=CHCOMe; viii pyrrolidine THF Scheme 18 A (-)-Ajmalicine (105) +\ H H-* jii 0;s- H' Et *-Me Mitraphylline (1 10) (1 11) Me0,C (1 12) Reagents i MeI THF; ii Et,O+ BF, CH,Cl2 under N,; iii NaBH, AcOH; iv heat in vacuo Scheme 19 "";Ix -< **' Me i-iii 1401-Hydroxyrauniticine (1 13) Me0,C Rauniticine (1 15) Hd (1 16) Reagents i Bu'OCl; ii HCl DME; iii KOH MeOH; iv BH, THF; v 3M-NaOH 30% H,O,; vi (PhCO,),; vii MeOH HCl; viii NaBH,; ix NaOMe Scheme 20 boration-oxidation of the enamine (1 14) prepared from and 1401-hydroxypseudoyohimbine(118).The initial products rauniticine (1 15) (Scheme 20).96The 3P-epimer 1401-hydroxy- from reserpine were 14a-benzoyloxyisoreserpine(1 19) and 14a- 3-isorauniticine (1 16) was the product of oxidation of the benzoyloxyreserpine (1 20) and no P-hydroxy-compounds ap- enamine (1 14) (by dibenzoyl peroxide) followed by reduction pear to be produced.p-Nitrobenzoyl peroxide gave analogous (by sodium borohydride). This latter method can also be used to products and 1401-hydroxyisoreserpine (122) was obtained introduce a hydroxy-group into position 14 in yohimbine and from 1401-p-nitrobenzoyloxyisoreserpine(121) by treatment reserpine;97 however the reaction appears to be less specific. with sodium methoxide followed by selective acylation with Yohimbine gives a mixture of l@-hydroxy-yohimbine (1 17) 3,4,5- trimet hoxy benzoyl chloride (Scheme 21) NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON MeO,C'* 6H (117) R'=OH R2=H; 3~-H (118) R'=H R2=OH; 3Q-H (1 19) R=OCOPh; 3~-H (120) R=OCOPh; 3Q-H (121) R&COC,H,NO,; 3a-H 'lii 122) R=OH ; 3a-H Reagents i NaOMe MeOH at r.t.; ii 3,4,5-trimethoxybenzoyl chloride pyridine DMAP at r.t.Scheme 21 A new ~ynthesis9*$~~ of (&)-yohimbine (123) and (&)-alloyohimbine (1 24) makes use of the reductive photocyclization of enamides in the direct synthesis of the desired pentacyclic system. The unconjugated enone (1 23 thus prepared,98 readily isomerizes to the normal enone (1 26a) or the allo enone (1 26b). Acylation of the lithium enolate from (126a) with chloroformic ester gave a mixture of products but the magnesium enolate gave the desired keto-ester exclusively in 67% yield. Hydrogen- ation of the double-bond then gave (&)-yohimbinone which was reduced to (+)-yohimbine (123) by means of sodium borohydride. An exactly analogous sequence of reactions on the allo enone (126b) afforded (&)-alloyohimbine (124) (Scheme 22).Details of SzBntay's syntheses of deserpidine 3-epi-17-epi- raunescine and several related compounds with the normal stereochemistry previously reported in brief O0 have been published. lo1 Ninomiya's group have also completed a new synthesis of (+)-deserpidine (128) (Scheme 23) again by use of the route involving the reductive photocyclization of enamides. lo2 The pentacyclic lactam (129) prepared (together with a regio-isomer) in an analogous manner to that of (127) was reduced and hydrolysed to the unsaturated methoxy-ketone (1 30) ; again this was accompanied by the formation of an isomer. Introduction of the ester group at C-16 was achieved preferably by acylation of the lithium enolate of (1 30) by means of methyl cyanoformate (Mander's method).Unexceptional stages then led to the ester (131) which has previously been converted into ( & )-deserpidine by Szantay et al. O A new synthesislo3 of (+)-deoxytubulosine (132) takes advantage of an ingenious preparation of the dihydropyran ester (1 33) which is essentially an analogue of 3,4-dihydroseco- loganin aglucon. Condensation of (1 33) with 3-hydroxy-4-methoxyphenylethylamine under reducing conditions gave the intermediate (1 34) which it was discovered suffered Pictet-Spengler cyclization two decarbomethoxylations and epimerization at C-5 when boiled with propionic acid. The synthesis was then completed using conventional stages (Scheme 24).lo3 Finally the microbiological hydroxylation of the heteroyo- himbine isomers ajmalicine tetrahydroalstonine 3-isoajmali- cine and akuammigine by seven micro-organisms has been studied.lo4 In many cases hydroxylation at C-10 was observed but in others (notably with the micro-organism MRRS 10-IBI w OMe .. ... 11 111 J (127) (126a) (1 26b) v-ix Iv-ix i bH OH Yohimbine (1 23) Alloyohimbine (124) Reagents i hv MeCN MeOH NaBH,; ii LiAlH,; iii HCl H,O; iv tartaric acid dioxan at 80 "C; v LiNPr', THF at -78 "C; vi MgBr,; vii CICOIMe; viii Hz PtO,; ix NaBH,; x silica gel Scheme 22 isolated from the roots of RauwolJia uomitoria) hydroxylation of C-11 occurred. 4.3 Sarpagine-Ajmaline-Picraline Group This group has recently been comprehensively reviewed.lo50 Normacusine B has been isolated from the seeds of RauwolJia cagra7Oand vomilenine strictamine akuammidine perakine raucaffrinoline normacusine B peraksine dihydroperaksine sarpagine macrophylline and three new bases have been isolated from the leaves.2za The three new bases were tentatively suggested to be 21 -deoxyvomilenine 2 1-acetyl-19,20-dihydrovomilenine,and 18,Na-didemethyl-19-hydroxy-N,-methylsuaveoline (1 35). Normacusine B has also been found together with sarpagine perakine vellosimine and vinorine in the roots of Alstonia yunnanensis Diel~;~~ this is the first reported occurrence of these alkaloids in the genus A lstonia. The root and stem barks of Strychnos angolensis Gilg.contain 1 1-methoxymacusine A (136),Iosb which like many quaternary alkaloids exhibits muscle-relaxant activity. Peri- vine and vobasine are two of the four major alkaloids of the leaves of Tabernaemontana dichotoma Roxb. and isornethuenine is one of the minor bases.lo6 The four alkaloids previously NATURAL PRODUCT REPORTS 1985 HOH2C liii iv QT%oMe-v vi Q%oMe HOH,CvCO,Me Me0,C MeO OH 0 vii-xi R9 H\ Rhazimol (137) R=H (EDeacetylakuammiline o'I '~ I oc~Me EErcinaminine) Ercinamine (140) R=OH HYC0,Me 16 Me0,C \OMe bMe 0 -0Me 11 Deserpidine (1 28) Reagents i LiAIH,; ii 10% HCl MeOH at r.t.; iii LiNPri2 THF at -78 "C; iv CNC0,Me; v H2 PtO, MeOH; vi NaBH,; vii BBr, CH2C12 at 0°C; viii 2M-NaOMe MeOH; ix NaOMe MeOH "3 heat for 72 h; x 3,4,5-trimethoxybenzoyl chloride pyridine; xi \ R3 epimerization at C-3 R' R2 R3 Scheme 23 10-Hydroxystrictamine (1 38) OH H H 1 1-Hydroxystrictamine (1 39) H OH H Gomaline (141) H H OH EtCH,CH=CHCO,Me -+ Me0,C 'Et isolated from the fruit stem bark and root bark have not so far been found in the leaves.Perivine and 16-epi-affinine are Me02CI\C0,Me among the bases in the bark of Peschiera fuchsiaefolia (DC.) Miers. and the presence of voachalotine and affinisine previously noted has been confirmed.lo7 The 13Cn.m.r. data for 16-epi-affinine and vobasinol were also recorded and analysed in this communication. Aspidodasycarpine is the only representative of this group to be encountered among the 35 alkaloids of the seeds of Aspidosperma ~blongum.~~ New extractions of Catharanthus roseus have yieldedIo8" rhazimol (1 37) which was first isolated108b from Rhazya stricta ; since this alkaloid is simply deacetylakuammiline the introduction of a new name is unnecessary.Strictamine Nb-oxide has been isolated from the leaves of Rhazya stricta.lo9 The two bases that were isolated earlier from Vinca erecta' lo and claimed to be 10- and 1i-hydroxypleiocarpamine have iv v nowlll been shown to be 10- and 11-hydroxystrictamine [(138) and (139)]. Two other bases from the same source are ercinamine and ercinaminine ;the former has been formulated as 10-hydroxydeacetylakuammiline (140) and ercinaminine vi vii -(another superfluous name) is its deoxy-derivative i.e.deacetyl- akuammiline (1 37). Yet another base has been isolated from the leaves of Catharanthus roseus;' the number isolated from the various organs of this prolific plant appears to exceed ninety. Deoxytubulosine (1 32) Gomaline an amorphous base is an indolenine whose proton Reagents i (C02Me)? KOMe; ii CH2(C02Me)2 KOMe; iii 3- n.m.r. and mass spectra are consistent with the presence of a hydroxy-4-methoxyphenylethylamine NaBH,CN; iv EtC02H strictamine skeleton carrying a hydroxy-group at C-i 8. Since heat; v CH,N,; vi Bui2AIH; vii tryptamine H+/H20 the methyl of the carbomethoxy-group is not shielded by the Scheme 24 indolenine ring system gomaline (141) is concluded to have the NATURAL PRODUCT REPORTS,1985 -J.E.SAXTON same stereochemistry as strictamine and it is therefore considered to be 18-hydroxystrictamine. A report' on the alkaloids of Gelsemium elegans [humanten- mine (gelsenicine?) humantenine humantenidine and hu- mantenirine] appears to duplicate one mentioned last year.45 Vomilenine ajmaline 17-O-acetylajmaline 17-0-acetylnor- ajmaline vinorine and sarpagine have been shown to be produced in cell suspension cultures of Rauwolfia serpentina;* of these only ajmaline had previously been found in cultured cells of this plant. The distribution of alkaloids is quite different from that observed in intact plants; in particular vomilenine which is the major alkaloid has not been found in R. serpentina and the yield is estimated to be 51 times that reported from R.vomitoria. Some new interrelationships in the corymine series have recently been reported. l4 Treatment of desformocorymine (142) with trifluoroacetic acid at room temperature gives a mixture of C-2 epimers (143) which presumably arise by protonation of N,in (142) fission of the bond between C-2 and Nb,proton exchanges to give (144) and recyclization. Proof of the structure of (143) was provided by its reduction to 2-epi-16- epi-cathafoline (149 which was further reduced and acetylated to give the base (146) also obtainable from picralstonine (147) (Scheme 25). This sequence constitutes the first interconver- sion of the corymine skeleton into the akuammiline skeleton and it also incidentally proves that C-16 suffers epimerization in the deformylation of corymine to give desformocorymine (142) and in the formation of picralstonine (147) by loss of the intermediate (149) analogous to (144) forms the hemiacetal (150); the alternative cyclization possible in (149) leads to the second product a highly unstable lactam which exists as a hydrated form (151).Treatment of the hemiacetal (150) with aqueous base also gives (151). The reaction of (150) or (151) with sodium methoxide leads to the formation of an indole base (152) whose structure was established by X-ray crystal structure analysis of its p-bromobenzoate. The fission of the 7- 16 bond in (150) and (151) is essentially the reverse of the process that has been postulated to occur in the biogenesis of the akuammiline group of alkaloids.In the course of purifying the hydrated lactam (151) a by- product was obtained whose molecular formula indicated the loss of two hydrogen atoms from dihydrocorymine (148). Its structure also determined by X-ray crystallography was shown to be (1 53) i.e. 17-hydroxymethylvincoridine,and it is presumably formed by oxidation of dihydrocorymine (1 48) in the reaction medium. Acylation of the 17-hydroxy-group in dihydrocorymine obviously blocks the formation of the hemiacetal (150). Consequently when dihydrocorymine trifluoroacetate (1 54) is treated with trifluoroacetic acid the reversible formation of (155) allows the equilibration of (154) and its C-3 epimer. Hydrolysis of the resulting mixture then gives predominantly 3- epi-dihydrocorymine [the C-3 epimer of (148)]; this affords a much more direct correlation of these C-3 epimers than has hitherto been achieved.Il4 Details of Husson's synthesis37b of the ervitsine ring system acetoxymethyl group from picraline.-9have been published. The rearrangement of di hydrocorymine (1 48) under similar The pharmacology of echitamine has been studied in some conditions follows a different course (Scheme 26).l14 Here the detail. ROH,C-C02Me ROH2C,,C02Me i Me Desformocorymine (1 42) (144) Dihydrocorymine (148) R=H (149) R=H (1 54) R=COCF3 (155) R-COCF3 1 / ii c- 9 HO' 2-epi- 16-epi-Cathafoline (145) iii iv I / AcoH2CYH iii v iv Picralstonine (147) Reagents i CF3C02H at r.t. for 40 h; ii Et,SiH CF,C02H; iii, LiAIH,; ivyAc20 NEt, CH,Cl,; v CH20 AcOH then NaBH (152) 17-Hydroxymethylvincoridine(153) Reagents i CF3C02H at r.t.; ii NaOMe MeOH Scheme 25 Scheme 26 NATURAL PRODUCT REPORTS 1985 4.4 Strychnine Group Akuammicine its N,-oxide and its 19,20-dihydro-derivative are among the leaf alkaloids of RauwolJia caflra.22a Stemma-denine occurs in the seeds of Tubernaemontana dichotomal and vallesamine in the seeds of Aspidosperma oblong~m.~~ 11-Methoxytubotaiwine is one of the antimicrobial alkaloids of the root bark of Aspidosperma excelsum ; compactinervine which is inactive is also present.73 Two new alkaloids Na-formylechitamidine (1 56) and Na-formyl-12-methoxyechitamidine(1 57) have been isolated together with echitamidine (158) from the bark of Nigerian Alstonia boonei De Wild.which is widely used locally as an antipyretic and in external application for rheumatic pains. The stem bark of Strychnos longicauduta Gilg. contains three new alkaloids [I ,2-didehydrodeacetylretuline(1 59) 18-ace-toxy-Na-deacetylisoretuline (1 60) and 23-hydroxy-2,16-dide- hydroretuline (161)] together with the Wieland-Gumlich aldehyde diaboline and N,-deacetyl-l 8-hydroxyisoretuline [Wieland-Gumlich diol (162)] from this group.60 The Wie- land-Gumlich aldehyde was also present in the root bark. The stem bark of S. ngouniensis Pellegrin yielded norfluorocurarine (1 63) and three new alkaloids i.e. 18-hydroxynorfluorocurarine (164) 18-acetoxynorfluorocurarine (1 65) and tubotaiwinal (166); this last base also occurs in the root bark.60 Norfluoro- curarine has also been obtained together with tubotaiwine and twenty alkaloids from the pseudoaspidospermidine-cleav-amine group from the leaves of Tabernaemontana eglandulosa Stapf.The stem bark of Strychnossoubrensis Hutch. et Dalz. a West African liana which has not previously been investigated has been shown to contain strychnobrasiline (1 67a) strychnofend- lerine isosplendine and a new base 14P-hydroxystrychnobra- siline (167b) whose structure was confirmed by an as yet unpublished X-ray crystal structure determination. 2oa The root bark of S. henningsii Gilg. which is used by the Zulus to relieve rheumatic pains has yielded diaboline holstiine Na-acetylstrychnosplendine(1 68a) and a new alka- loid which proves to be Na-acetyl-1 1 -methoxystrychnosplen- dine (168b).120b The stereochemistry of echitamidine (1 58) isolated recently from Indonesian Alstonia angustiloba and A.pneumatophora has been deduced from its n.m.r. spectrum and confirmed by X- ray crystal structure analysis of its trifluoroacetate. 21 Both C- 19 and C-20 have the S configuration; hence echitamidine (158) is (19S 20S)-19-hydroxy-19,20-dihydroakuammicine. An isomer (169) obtained from the same source is epimeric at C- 20 but the configuration at C-19 has not been established. Two other isomers [(170) and (171)l isolated from A. angustiloba belong to the tubotaiwine group but again their stereoche- mistry has not been completely elucidated. An attempt to prepare them by the hydroboration-oxidation of tubotaiwine resulted in the formation of the tertiary alcohol (172) by an anomalous reaction that has previously been observed in the akuammicine series.The very high positive optical rotations of (170) and (171) indicate that they belong to the enantiomeric series compared with akuammicine and echitamidine. Carbon-13 n.m.r. data have been recorded and analysed for norfluorocurarine vincanidine akuammicine and vinervin- ine,' 22 and for strychnine its ar-hydroxy- and ar-methoxy- derivatives and for members of the vomicine-icajine group. 23 On the basis of their proton n.m.r. spectra and comparison with model compounds rosibiline (1 73) has a trans B/C ring junction and the Wieland-Gumlich glycol formal (1 74) has a cis B/C ring fusion.' 24 Details of Ban's synthetic approach40e to the Strychnos alkaloids have been published.' 25 4.5 Ellipticine-Uleine-Apparicine Group (-)-Apparicine has been isolated from the leaves of Tabernae-montana dichotomal O6 and N,,N,-dimethyltetrahydroellipticin-ium hydroxide from Aspzdosperma gilbertii.26 The isolation and structure determination of ngouniensine which is the major alkaloid of the stem-and root-bark of Strychnos ngouniensis Pellegrin were reported earlier in brief;45 the full paper60 records the separation of thirteen alkaloids which include ngouniensine (1 75) 20-epi-ngouniensine (1 76) and / \OH N,-Formylechitamidine (1 56) R'=H R2=CH0 N,-Formyl-1 2-methoxyechitamidine (1 57) R'=OMe R2=CH0 1,2-Didehydrodeacetylretuline (159) (160) R=Ac Echitamidine (1 58) R1=R2=H; 19s (162) R=H H OH Norfluorocurarine (1 63) R=H (167a) R=H 18-Hydroxynorfluorocurarine (1 64) R=OH Tubotaiwinal (166) (167b) R=OH (161) 18-Acetoxynorfluorocurarine (165) R=OAc C02Me k02Me Echitamidine (1 58) 19S 20s (168a) R=H (170) (171) R'=H R2==OH (169) 20R (168b) R=OMe (172) R1=OH R2=H NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON la I R Wieland-Gumlich glycol formal (174) R=OH; 16a-H Rosibiline (1 73) R=H ; 16P-H CH Ngouniensine (1 75) R=H ;20P-H 20-epi-Ngouniensine (1 76) R=H ; 2001-H Glucosylngouniensine (1 77) R=GlcO; 20P-H 20-epi-Glucosylngouniensine(1 78) R=GlcO; 20a-H their 10- (or 1 1-)glucosyloxy-derivatives(1 77) and (1 78).Owing to paucity of material the exact position of the aromatic substituent in (177) and (178) has not yet been determined. Details of the synthesis45 of derivatives of olivacine and of ellipticine by Wanner et al. have been p~blished.~~ Husson's synthesis' 2f of 20-epi-uleine (1 79) via 2-cyano-A3-piperideines has been modified and improved and 20-epi-uleine can now be prepared in four steps from the N-oxide (1 80) (Scheme 27). The latest synthesis of ellipticine (181) involves as its critical stage the intramolecular 1,4-addition of an ester anion on an unactivated pyridinium salt (Scheme 28).12' In previous syntheses of this type the pyridinium ring has been activated by carbonyl groups at position 3. A very neat and efficient synthesis of 17-oxoellipticine (182) takes advantage of the greater reactivity of the ketone carbonyl than the amide carbonyl group in (183) towards alkyl-lithium reagents.The reaction of (1 83) with 2-lithio-2-trimethylsilyl-1,3-dithian followed by methyl-lithium gave the pyridocarba- zole derivative (1 84) which was converted into 17-oxoellipti- cine (182) in 25% overall yield (Scheme 29).128a The various approaches to the synthesis of ellipticine and its relatives up to the end of 1982 have been reviewed.128b A clue to the possible mode of action in uivo of the antitumour alkaloid 10-hydroxy-N-methylellipticiniumacetate (185) has been provided by a study of its reaction with adenosine and with methanol. 29 The reaction with adenosine in the presence of hydrogen peroxide and horseradish peroxidase gave a ketal of structure and stereochemistry (186) (Scheme 30) ; this presumably originates from two successive oxidations of (185) to a quinone imine followed by nucleophilic addition of adenosine.The reaction with methanol in the presence of copper(1) chloride-pyridine and oxygen gives an exactly analogous keto-ketal. In uivo 1O-hydroxy-N-methyl-ellipticinium acetate may well react after oxidation with the terminal nucleotide of mRNA or tRNA and hence inhibit the early stages of protein biosynthesis.' 29 4.6 Aspidospermine-Vincamine Group There continues to be a considerable amount of activity in this large group of alkaloids. Several new extractions and the isolation of several new alkaloids have been reported and a number of synthetic approaches have come to fruition.Aspidosperma marcgravianum Woodson the most prolific of the species recently examined contains among its 46 alkaloids two new ones from this group 18-oxohaplocidine (1 87) and 2- ethyl-3-[2-(3-acetyl-N-piperidino)ethyl]indole ( 188). Aspido- carpine limapodine haplocidine (1 89) aspidolimidine (190) rhazinilam tetrahydrosecodine (191) and decarbomethoxy- tetrahydrosecodine (192) were also isolated.68 N,-Acetylaspido- spermidine and 0-demethylaspidospermine are two of the Me ,O-Me Me i ii 111 Et0-Et4) -Nc-Q CN Etd CN (180) iv/ vi or v\ 20-epi-Uleine (1 79) Reagents i trifluoroacetic anhydride CH,CI,; ii Et,AICN PhH; iii KCN CH2C12 H20; iv indole AgNO, AcOH HzO at 60 "C for 24 h; v MeLi Et,O under argon; vi TsOH CHCI, heat; vii camphorsulphonic acid CHCI, heat.Scheme 27 CH, II ii-v Me Me Ellipticine (1 81) Reagents i 3-Acetylpyridine HBr MeOH; ii H, Pd/C MeOH; iii MeI; iv NaOMe MeOH; v ethyl nicotinate methiodide; vi NaAl(OCHZCHZOMe)2H,, xylene at 130 "C; vii PhSNa DMSO Scheme 28 (1 83) (182) Reagents i THF at -100 "C; ii MeLi; iii NaBH, EtOH heat; iv AgN03 H,O acetone Scheme 29 AcO-Me li (186) Ade = adeninyl Reagents i H202 adenosine horseradish peroxidase Scheme 30 -. R* H 18-Oxohaplocidine (1 87) R'=OH R2=Ac R3=0 Haplocidine (1 89) R'=OH R2=Ac R3=H2 Aspidolimidine (190) R'=OMe R2=Ac R3=H2 uN?R' H (188) R'=H R2=AC (191) Ri=C02Me R2=Et (192) R'=H R'=Et antimicrobially inactive alkaloids of A.ex~elsum.~~ The seeds of Tabernaemontanu dichotoma Roxb. contain tabersonine voaphylline and voaphylline hydroxyindolenine,l but 12- methoxyvoaphylline is one of the major alkaloids in the NATURAL PRODUCT REPORTS 1985 (+)-isoeburnamine] (-)-12-methoxy-N,-methoxycarbonyl-kopsinaline (203) (-)-Na-methoxycarbonyl-1 1,12-methylene- dioxykopsinaline (204) (-)-11 12-dimethoxy-Na-methoxycar-bonylkopsinaline (205) (-)-11,12-methylenedioxykop-sinaline (206) and (-)-I 2-methoxykopsinaline (207). The bases (204) and (206) are rare examples of indole alkaloids containing a methylenedioxy-group ; the only other species in which this structural feature has been encountered is Schizozygia caflaeoides.It is possible that alkaloids (203) and (204) are identical with kopsilongine and kopsamine from Kopqia longflora Merril1,l3l but this identity has not yet been established. Vindolinine N-oxide and 16-epi-(19S)-vindolinine N-oxide have been isolated from the leaves of Catharanthus roseus under conditions which it is claimed could not result in the formation of N-oxide artifacts,80 and a rapid procedure for the isolation of vindoline catharanthine and vinblastine from this source has been described.132 Details of the isolation and oxidative fragmentation of I6-epi-(19S)-~indolinine~~ have been published.133 Hyderabadine a new base isolated134a from the leaves of Ervatamiu coronaria is formulated as the pentacyclic ether (208) (stereochemistry undefined) on the basis of its n.m.r.and mass spectra. This structure bears an obvious relationship to that of voaphylline which occurs in the same plant. Mehranine another new alkaloid from the same plant is regarded as the epoxide (209) (stereochemistry again unspecified). 34b Finally three new alkaloids have been extracted from the bark of Microplumeria anomala (M. Arg.) Mgf. from the banks of the Rio Negro that are closely related to aspidocarpine (210). Anomaline (21 1) is 1 Sa-hydroxyaspidocarpine,and the other two bases are demethoxyanomaline (212) and 12-0-methylanomaline (21 3). * 35 These structures were deduced leaves.Io6 Voaphylline is also one of the constituents of the leaves twigs and stem bark of T. eglandulosa.l9 Fourteen alkaloids have been found in the stem bark and aerial parts of Melodinus guilluuminii Boiteau ;79 these include four new ones [~-oxo-14,15-seco-kopsinal (193) 11-meth~xy-A~~-vincamenine (1 94) 1 1 -meth~xy-A~~-vincanol (199 and 3-oxohydroxykop- sinine] and eight known bases [l 1-hydroxytabersonine 11-methoxytabersonine venalstonine (1 96) venalstonidine (1 97) 3-oxovenalstonine (198) 3-oxohydroxykopsinine kopsinine (1 99) 15a-hydroxykopsinine and 19P-hydroxyvenalstonine (200)l. In the novel alkaloid 3-oxohydroxykopsinine the position of the hydroxy-group was not determined owing to lack of material. Hexacyclic alkaloids are also a feature of the constituents of Melodinus reticulatus Boiteau from New Caledonia. 30 Tabersonine and 1 1 -methoxytabersonine occur in the fruits; the stems and leaves contain tabersonine venalstonine (196) and its 3-0x0-derivative (198) venalstoni- dine (197) and kopsinine (199) together with the three new alkaloids 19P-hydroxyvenalstonine (200) 19P-hydroxyvenal- stonidine (201) and 3-oxovenalstonidine (202).Kopsiu officinalis Tsiang et P. T. Li enjoys a reputation in Chinese popular medicine for the alleviation of gout and rheumatism and as an analgesic in pharyngitis and tonsillitis. The roots of this species have yielded nine monomeric alkaloids from this group including kopsinine 5,22-dioxokopsane and (-)-q~ebrachamine,~l and six new alkaloids which were shown to be (-)-isoeburnamine [the enantiomer of the familiar kO,Me (194) R1=H; 16,17-didehydro (1 93) (195) R'=H R2=OH A C0,Me (196) R'=HI RLH; (197) R'=H2 RLH; 14,15-epoxy (198) R'4 RZ=H; AI4(l5) (199) R'=H2 R'=H (200) R'=H2 R2=OH; (201) R1=H2 RLOH; 14,15-epoxy (202) Rl=O RLH; 14,15-epoxy NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON Me Mehranine (209) Aspidocarpine (210) R'=R3=H R2=OMe Anomaline (21 1) R1=H R2=OMe R3=OH Demethoxyanomaline (21 2) R1=R2=H R3=OH 12-0-Methylanomaline (21 3) R1=Me R2=OMe R3=OH mainly by comparison of proton and 13C n.m.r. data with those of appropriate models; in this connection the 13C n.m.r. data of refractine and cylindrocarpine were reported and analysed. The absolute stereochemistry (7S,20R,21 S) that was deduced for vincatine last yeaP5 has been contradicted in a new investigation.36 The Italian authors agree with Pakrashi's group concerning the relative stereochemistry (from n.m.r. evidence) but on the sound basis of a partial synthesis (see Scheme 31) of vincatine (214) from (-)-vincadifforrnine (219 in which C-20 remains unaffected they conclude that vincatine has the absolute configuration 7R,20S,21R. In fact vincatine (214) and Pakrashi's base give enantiomeric c.d. curves. Because of the possibility of a reversible Mannich fission of the 7-21 bond in vincatine equilibration with its three diastereo- isomers is facile and all four bases were obtained in the partial synthesis from (-)-vincadifformine. This epimerization at C-7 and C-21 will even take place in chloroform solution at 35 "C; hence values of optical rotation for vincatine tend to be variable and any conclusions based on them are suspect.Trichophylline a novel alkaloid isolated (together with lochnerine) from the roots of Cutharanthus trichophyllus (Baker) Pichon has the structure (216) according to X-ray crystal structure analysis. Reduction of trichophylline with sodium borohydride gives an unsaturated lactone formulated as (217). 37 Oxidative fission of the C/D ring system in derivatives of vincadifformine has been previously observed ; hence trichophylline may arise by oxidation at C-21 of an appropriate precursor e.g. a 14,15-didehydrominovincinine(218) followed by fission of the 20-21 bond and simultaneous migration of C-18 (Scheme 32). The chromatographic behaviour of the enantiomers of a number of Aspidosperma alkaloids on a stationary phase composed of a polyether-type P-cyclodextrin bead polymer has been studied.38 In favourable circumstances resolution could be achieved; e.g. (f )-vincadifformine and ( f )-quebracha-mine were resolved in very good yield on a preparative scale simply by passing their weakly acidic solutions through the chromatographic column of polymer. A number of further rearrangements and transformations in this area have been reported. Deamination of 1,2-didehydro- aspidospermidine (21 9) affords the hemiacetal (220) (Scheme 33); this result is not exceptional and can be explained by any one of three simple mechanisms. 39 Desethyltabersonine (221) synthesized by the Kuehne rearranges in boiling acetic acid to a mixture of products which includes 3.4% of desethylcoronaridine (222); this presumably arises by reverse Diels-Alder fission of ring c in (221) followed by a 4n + 2n cycloaddition in an alternative sense (Scheme 34).The desired rearrangement product dese t hy lca t haran t hine could not be detected. The purely thermal rearrangement of some aspidospermi- dine derivatives can give rise to products containing the vincane ring system. Thus pyrolysis of (-)-I ,2-didehydroaspi- dospermidine (21 9) at 200 "C affords (-)-aspidospermidine ?-9-Me iii ( -)-Vincadifformine N-oxide (215) 1 ?-(-)-Vincatine (214) Reagents i 302,ButOK Bu'OH; ii Me2S0,; iii (Me0)2P(0)-CH2C02Me NaH DME; iv KOLCN=NC02K MeOH AcOH; v W-2 Raney nickel DME at r.t.Scheme 31 I __+ H C02Me c- II (217) Trichophylline (2 16) Reagents i oxidation; ii NaBH Scheme 32 Reagents i NaN02 SM-HCl at 0°C Scheme 33 Desethy Itabersonine (221 ) Ill a$-& Me02C Desethylcoronaridine (222) Reagents i AcOH under argon heat for 15 h Scheme 34 NATURAL PRODUCT REPORTS 1985 x2 __+ Q-pEt ' N' + O'N -pEt HH Scheme 35 Et Et (227) (223) and (-)-eburnamenine (224).141 This is not a simple intermolecular oxidation-reduction process but probably proceeds via a dimeric species (225) which undergoes two 1,5- sigmatropic shifts to form an intermediate (226); this frag- ments to (223) and (224) (Scheme 35). Et Under flow thermolysis conditions (580 "C),1,2-didehydro-k02Me aspidospermidine (2 19) gives vincane (227) again via two consecutive sigmatropic shifts.16-Hydroxyvincadifforine indolenine (228) on pyrolysis or I flow thermolysis rearranges to a mixture of vincamine (229) and 16-epi-vincamine (230) possibly via an obvious variant of the same mechanism (Scheme 36).I4I A new method for the introduction of a double-bond adjacent to a lactam carbonyl group has been devised;142 this may well prove valuable as an alternative route to the formation of Al4(ls) Aspidosperma alkaloids. The reaction of a ring D thiolactam [(231) or (232)] with an arylsulphinyl chloride (229) 16P-OH in the presence of base gives an unsaturated thiolactam [(233) (230) 1601-OH or (234)] which can then be desulphurized [+(235)] or Scheme 36 hydrolysed [-+(236)] (Schemes 37 and 38).This process is not considered to involve an a-phenylsulphoxide elimination since The microbiological oxidation of dihydrovindoline by means the conditions are too mild but it probably involves a of Streptomyces griseus UI 1158 gives four products which are sulphinylation on sulphur encouraged by the relative acidity of 3-oxodihydrovindoline 3-hydroxydihydrovindoline and the the protons at C-14,adjacent to the thiolactam function; phenol that is obtained by demethylation of its ll-methoxy- elimination of a proton from C-15 in the intermediate (237) group and 14-acetyl-l7-O-deacetyl-14,15-dihydro-3,14-didehy-so formed and the departure of an effective leaving group drovindoline (238e).143b (ArSO-) then gave the unsaturated thiolactam.142 Magnus and his collaborators have reviewed their highly The oxidation of 16-0-acetylvindoline (238a) by means of successful indole-2,3-quinodimethane strategy for alkaloid enzymic (laccase and human caeruloplasmin) microbiological and the synthesis of Hunteria alkaloids eburna- (Streptomyces griseus) or chemical (DDQ)reagents gives the 3- mine vincamine and their relatives has also been reviewed.14s Nbimmonium derivative (238b). Hydrolysis of the 16-0-acetyl A synthesis of desethylvincadifformine by the fJ-acylpyridine group in (238b) gives the dimer (238c) (previously identified45 reduction-yclization route has been described in detail. 146 as a product of the microbiological transformation of Several alkaloid syntheses previously reported in brief vindoline) presumably via the intermediate enamine communications have now been published in detail.These (2384). 43u include syntheses of N,-methylsecodine (N.B. the preliminary NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON AkO 1ii iii P S-SOAr S-SOAr a:$! \ I ArSO S iv v __+ Reagents i Lawesson's reagent (MeOC6H,P2S,C6H40Me) HMPA at 85 "C for 20 h; ii MeC6H,SOCl EtNPri at 0 "C; iii H20 AcOH; iv MeI THF at 50°C; v NaBH, MeOH at r.t. Scheme 37 1ii iii R R (236) (234) (R = p-MeOC&S02) Reagents i Lawesson's reagent toluene at 90 "C ;ii p-MeC,H,SOCl PriNEt2 CH2CI2 at 65°C; iii H20 AcOH; iv Et,O+ BF, CH2CI, at 25 "C; v KOH H20 THF at 25 "C Scheme 38 communication is not cited here) 47 a~pidospermidine,~~~ N,- acetylaspidospermidine and quebrachamine 25 taberson-10,22-dioxokopsane and kopsanone and eburnamonine.' s1 Kuehne's synthetic approach to the anilinoacrylate alkaloids has been applied to the first synthesis of minovincine (239).52a Two syntheses were in fact completed (Scheme 39). In the first AcO AcO (238a) (238b) J (238d) 1 OMe QNMe Me H I C02Me (238c) py-fcoMe H H (238e) of these the indolo-azepine (240) was condensed with the chloroaldehyde ketal (241) the end-product of the fragmenta- tion-recyclization reaction of the quaternary ammonium ior! (242) being minovincine ketal(243). Acid hydrolysis then gave minovincine (239).Since the original chloroaldehyde ketal (241) is not readily accessible and the final hydrolysis stage [(243)-+(239)] proceeds poorly an alternative route was sought. Two variants of the new route were eventually developed. The more efficient route involves the reaction of the indolo-azepine (240) with the sodium salt of formylacetone which gave a vinylogous amide (244). Cyclization was achieved in a separate stage and benzylation of the product (245) followed by fragmentation and recyclization gave (246). The remaining stages are unexceptional (Scheme 39). The immediate biogenetic precursor of minovincine could be 20,21-didehydro-19-oxosecodine(247) and the synthesis of such a base is therefore of considerable interest. Yet another application of Kuehne's synthesis has resulted in the prepara- tion of (247); this constitutes the first example of a stabilized secodine intermediate and it affords another synthesis of minovincine (Scheme 40).l 52b Basically the route follows that illustrated in Scheme 39 and proceeds via the vinylogous amide (248) and (249) [cf (244) and (245)].Quaternization and fragmentation of (249) gave 20,21-didehydro-l9-oxosecodine (247) which is a stable base of m.pt. 155-156 "C.Subsequent NATURAL PRODUCT REPORTS 1985 HI C02Me QyQA H Me CO,Me eOzMe (243) CH,COMe 1 iii viii ix a-$l +\ \ %OMe NCHzPh xii xiii COtMe / -COMe Minovincine (239) C0,Me Reagents i THF heat; ii NEt, MeCN heat for 24 h; iii 20%H2S0, HzO MeOH for 18h at r.t.; iv NaOCH=CHCOMe HCl Et,O THF (or HCECCOMe MeCN); v HCl THF; vi Cl[CHzJ31 THF for 48 h at r.t.; vii NEt, PhMe heat for 26 h; viii NaI MeCOMe; ix KOBu' at r.t.; x PhCH2Br THF; xi NEt, MeOH heat for 2 h; xii Hz Pd/C AcOH; xiii Cl[CH,],I KzC03 PhH heat for 7 h Scheme 39 Ll iv-vi 0 \ viii -H CO,Me ___* 1 I ,COMe %OMe \ c1-H H C0,Me H COzMe COzMe (247) Minovincine (239) Reagents i 20% HCl EtzO MeOH for 4 h; ii TsOH PhH for 2 h remove water azeotropically; iii PhSH NEt, CHCI, at 0 "C; iv N-chlorosuccinimide CCl, at O "C; v NEt, CHC13 heat for 1.5 h; vi NaIO, MeOH HzO; vii K2C03 THF at 20 "C for 4 days; viii THF HCl; ix THF for 48 h; x NEt, MeOH at 67 "C for 45 minutes; xi xylene heat for 24 h Scheme 40 NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON thermal cyclization then afforded minovincine (239) in 77% yield. A total synthesis of (k)-l 1-methoxytabersonine (250) fol- lows an ingenious and conceptually original approach to the construction of the pentacyclic aspidospermine framework which makes use of an aza-Cope rearrangement in its critical stage.153 Thus the intermediate (251) which contains the desired cis ring-junction reacts with paraformaldehyde to give an oxazolidine (252) which rearranges thermally without added acid and subsequently cyclizes to 11-methoxy-1,2,14,15-tetradehydroaspidospermidine (253) in a very high-yielding completely stereospecific process. It is suggested that traces of formic acid in the reaction mixture catalyse the formation from the oxazolidine (252) of (254); this undergoes an aza- Cope rearrangement with formation of an enol-immonium ion (255) which is ideally set up for an intramolecular Mannich reaction.Imine formation completes the sequence of reactions to the observed product (253). Finally methoxycarbonylation with LiNPrj? and methyl chloroformate gives 1l-methoxytaber-sonine (250) (Scheme 41).l 53 An extension of earlier work by Szhntay and his collabora- tors has resulted in two further stereoselective syntheses of vincamine and related alkaloids. l 549 55 In both routes C-16 and C-17 originate from methylenemalonic ester which is added to an appropriate enamine. In the first of these syntheses the substrate was Wenkert's enamine [the base corresponding to (256)] and the cis Michael adduct (257) was elaborated as far as the oximino-ester (258) which was then resolved.Trans- esterification followed by hydrolysis and cyclization then gave (+)-vincamine (259) and (+)-apovincamine (260) (Scheme 42).154 By means of X-ray crystal structure analysis the (-)-oximino-ester (258) was shown to exist in the oxime form as illustrated rather than the cyclic form which is preferred in the corresponding keto-esters e.g. vincamine. V ___t 71 In the second synthesis,' 55 stereochemical control was achieved by use of an enamine [the base from (261)] that is related to Wenkert's enamine but derived from L-tryptophan. Addition of methylenemalonic ester was almost completely stereospecific; hydrolysis and decarboxylation then gave an immonium salt (262) which lost the carboxyl group from the tryptophan moiety comparatively readily.Further elaboration of the product gave the pentacyclic lactam (263) which has previously been converted into (+)-vincamine (259) and apovincamine (260). 55 For this last transformation an improved procedure has been developed (Scheme 42). 56 Three new preparations of Oppolzer's aldehyde (264) constitute three more formal syntheses of vincamine. 57 58 Two of these syntheses have been contributed by Langlois et al. and one of them is summarized in Scheme 43. Here the important lactam (265) is neatly obtained by a regiospecific photochemical rearrangement of a spiro-oxaziridine (266) prepared by oxidation of the imine derived from tryptamine and the simple keto-ester (267).57 4.7 Catharanthine-Ibogamine Group Voacangine hydroxyindolenine has been isolated from the ground bark of Peschiera fuchsiaefolia (DC.) Miers and the presence of voacangine has been confirmed. O7 Voacristine hydroxyindolenine occurs in Anacampta angulata (Mart.) Mgf. which is a species whose botanical classification seems to be in dispute.lS9 However the presence of this alkaloid is not inconsistent with its inclusion in the tribe Tabernaemontaneae of the family Apocynaceae. Examination of the leaves of Tabernaemontana dichotoma has revealed the presence of 19-epi- iboxygaine and 19-epi-voacristine ;lo6 the seeds of this species contain coronaridine ibogamine and voacangine.vi -SMe Et -SOPh + vii-ix ONHCoBu' OMe doSiMe3 NHCOBu' x xi 1 0"". OMe (251) xii xiii t t- ONH2 OMe (252) \ (253) 0,Me (250) Reagents i PhSCHCICH2CH2Cl ZnBr2 CH2C12 at 25°C; ii NaI MeCOEt under argon heat; iii NH, CHCl, at r.t. for 2 days; iv CIC02Me PhNEt, PhMe; v rn-chloroperbenzoic acid CHCl,; vi o-C6H4Cl2 CaC03 at 165 "C; vii BuLi THF at -78 "C; viii HCl H20 Et20( at 0 "C; ix Li80H MeOH at r.t.; x Ph,PMe+ Br- BuLi THF; xi 40%KOH MeOH heat for 8 h; xii (CH20), PhMe Na2S04; xiii heat for 6 h; xiv LiNPr'* ClC0,Me; THF at -78 "C. Scheme 41 NATURAL PRODUCT REPORTS 1985 (257) iv v I +- H H ( + )-Apovincamine (260) EtO,C-C-CH 11NOH i kt (261) (258) ii viii ix vi vii 1 C-3 epimer Reagents i H,C=C(CO,Et), KOBu' CH,CI,; ii H2 10% Pd/C DMF; iii KOH H,O EtOH at r.t.; iv NaNO, AcOH; v D-dibenzoyltartaric acid CH,CI,; vi NaOMe MeOH under nitrogen heat for 4 h; vii 5% H2S04 AcOH H20 heat for 2 h; viii 10% HCI H,O EtOH heat for 24 h; ix NaOH EtOH H20 at r.t.; x decalin at 16&170 "C for 30 minutes; xi P0Cl3 at r.t.for 2-3 days; xii Bu'ONO Bu'OK PhMe under nitrogen; xiii TsOH AcOH (CH,O), heat for 5 h; xiv ButOK MeOH at r.t. for 2 h Scheme 42 i ii &:,Me -(266) Tacamonine (272) R=H 17-Hydroxytacamonine (273) R4H 1iii iv -viii .'Et OH Et C02Me H H (264) (265) 16,17-Didehydrotacamine (274) Reagents i Tryptamine PhMe 4A molecular sieves at 40 "C; ii M-chloroperbenzoic acid at 0°C; iii hv MeCN at r.t.; iv POCl, MeCN; v NaBH, MeOH at -70 "C; vi chromatographic separation; vii LiAIH, THF; viii SO3 pyridine NEt, DMSO under argon Scheme 43 1.(276) R'=H R2=Et (277) R'=Et R2=H (279) R=H (278) R'=Et R2=OH (280) R=OH 18 The presence of tacamine (268) in the leaves of Tabernaemon-tana egfandufosa Stapf has previously been noted.45 The full R3 paper' l9 records the isolation of a total of 22 alkaloids from the leaves twigs and stem bark of which twenty (including twelve Tacamine (268) R1=CO,Me R2=OH R3=H new ones) belong to this group. Seven of these new alkaloids 16-epi-Tacamine (269) R1=OH R2=C0,Me R3=H belong to the tacamine (pseudovincamine) sub-group and have (270) R'=OH R2=R3=H (271) R1=R3=H R2=OH structures (269)-(275). Three cleavamine derivatives were also (19S)-19-Hydroxytacamine (275) R1=CO,Me R2=R3=OH encountered; these are the known compounds (+)-(20R)- NATURAL PRODUCT REPORTS 1985 -J.E. SAXTON H H It H Dichomine (281) I (14S 20R)-Velbanamine (282) Scheme 44 15,2O-dihydrocleavamine (276) and (-)-(2OS)-l5,20-dihydro-cleavamine (277) and a new base tentatively identified as (14S,20R)-velbanamine (278). The pseudoaspidospermidine group was represented by (+)-(20R)-1,2-didehydropseudoaspi-dospermidine (279) and (208-20-hydroxy- lY2-didehydropseu- doaspidospermidine (280) (both new) and (20R)- and (2051- pseudovincadifformine. An iboga alkaloid of novel type whose structure was divulged later (see below) was also isolated and the list is completed by the known bases coronaridine 11- hydroxycoronaridine and ibogamine.The isolation of eight bases of the tacamine group in this study poses an interesting chemotaxonomic problem since they have not been found in previous extractions of this species nor in any other species of the genus Tabernaernontana.The reasons for this are not clear but it is suggested that the plant material that was used from Cameroun may belong to a different race from the Nigerian and Tanzanian plants that had previously been investigated or it may be that during twenty years of cultivation in the Netherlands the climatic conditions and different nature of the soil had induced some subtle changes in the biosynthesis of secondary metabolites. l9 The novel iboga alkaloid from Tabernaernontanaeglandulosa has also been found and in somewhat greater amount in the leaves of T.dichotorna and has been named dichomine.160 A complete analysis of its proton and 13C n.m.r. spectra reveals that it has the structure (281); this structure together with the relative stereochemistry shown here was confirmed by the coupling constants of all of the signals in the 300 MHz proton n.m.r. spectrum and by comparison with expected values derived with the aid of a Dreiding model. The absolute configuration was assumed to be 14s since all known Tabernaernontanaalkaloids have this configuration. Proof was obtained by reduction of dichomine (281) with lithium aluminium hydride which gave (14S,20R)-velbanamine (282) presumably by the mechanism shown in Scheme 44.The rather strained ring system in dichomine (281) may well originate from an alkaloid such as (20R)- 1,2-didehydr0-20-hydroxypseu-doaspidospermidine (283) [the epimer of (280)] by a series of simple Mannich processes and prototropic shifts as outlined in Scheme 44.6o A new alkaloid from Strychnos ngouniensis has been shown by X-ray crystal structure determination of its p-bromoben- zoate to be (+)-16-hydroxyalloibogamine(284) and is the first CHO Ngouniensine (175) (285) -n VY HO 16-Hydroxyalloibogamine (284) (286) Scheme 45 natural iboga alkaloid of the a110 series to be discovered;161 furthermore it is remarkable in being racemic. One possibility for its biogenetic origin is that it could be derived from ngouniensine (175) which is the major alkaloid of this plant.Oxidation of ngouniensine (1 75) could generate the aldehyde (285) in which both C-3 and C-16 are epimerizable. Oxidation of (285) to the enamine (286) followed by cyclization and reduction then gives 16-hydroxyalloibogamine (284) (Scheme 45).’6’ The oxidation of coronaridine (287) by a variety of oxidizing agents has been examined. 16* Oxidation with potassium permanganate proceeds rapidly and gives a mixture of six compounds namely 5-hydroxy-6-oxocoronaridine(288) 3-oxocoronaridine (289) 5-oxocoronaridine (290) coronaridine hydroxyindolenine (291) and its 3-0x0-derivative (292) and a neutral compound (lacking an indole ring) which was postulated to be (293). Oxidation with manganese dioxide is much slower and gives four products which are (288) and (292) and two bisindole bases identified as (294) and (295).Oxidation with iodine gave a mixture of (289) (290) and 3-hydroxycoronaridine (296) and selenium dioxide gave only 6- oxocoronaridine (297). Oxidation with hydrogen peroxide or NATURAL PRODUCT REPORTS 1985 R3 uR2 Coronaridine (287) R' = R2 = R3 = H2 (288) R' = H2 R2 = H,OH R3 = 0 (289) R' = 0 R2 = R3 = H (290) R' = R3 = H1 R2 = 0 (296) R' = H,OH R2 = R3 = H2 (297) R' = R2 = HZ,R3 = 0 Et H MeOX (291) R = H2 (292) R = 0 -(293) with rn-chloroperbenzoic acid gave the same three products which were shown to be coronaridine hydroxyindolenine (291) coronaridine N,-oxide and coronaridine hydroxyindolenine N,-oxide.62 The synthesis of cleavamine by Imanishi et al. has been described in detail149 and a new synthesis of desethylcathar- anthine has been reported.163 5 Bisindole Alkaloids The first bis-carbazole alkaloids to be isolated have been found in Murraya euchrestijolia Hayata. 64-65Murrafoline from the root bark is a racemic alkaloid of structure (298) which was determined by X-ray crystal structure analysis. Murrafoline is clearly composed of a girinimbine unit attached to cycloma- hanimbine two monomeric carbazoles that occur in the same plant. 64 Bismurrayafoline-A (299) and bismurrayafoline-B (300) are dimeric species derived from the monomers murrayafoline-A (301) and murrayafoline-B (302); these monomers also occur in M.euchrestijolia. Bismurrayafoline-A has an unsymmetrical structure which is cleaved by hydrogenolysis (Pd/C-H2 in MeOH/HC02H) to give solely murrayafoline-A (301). Bismur- rayafoline-B (300) is a symmetrical dimer. 165 In a search for mycotoxins in species of the genus Chaetomium three isomeric bisindolylbenzoquinones have been isolated. The structure of cochliodinol (303) from C. cochliodes Palliser and C. elatum Kunze ex. Fr. was elucidated earlier and it has now been shown that isocochliodinol from C. murorum Corda has the isomeric 6,6'-disubstituted structure (304) and that neocochliodinol from C. amygdalisporum Udagawa et Muroi is the 7,7'-disubstituted isomer (305). 166 Murrafoline (298) QJ-DMe I OMe CH, / Bismurrayafoline-A (299) A Bismurrayafoline-B (300) OH Cochliodinol (303) R' = CH2CH=CMe2 R' = R3 = H Isocochliodinol (304) R' = R3 = H R2 = CH2CH=CMe2 Neocochliodinol (305) R' = R2 = H R3 = CH2CH=CMe2 Two alkaloids that are found in the wood of Picrasma quassioides Bennet prove to be dimeric P-carboline bases and are the first to be encountered from natural sources.The structures were shown to be (306)23a and (307),23b mainly on the basis of a detailed analysis of their n.m.r. spectra and by comparison with those of monomeric P-carbolines found in the same plant. New extractions of the leaves of Strvchnos usambarensis have resulted in the isolation of two novel quaternary alkaloids,16' which were separated and purified by the technique of droplet countercurrent chromatography for polar compounds.These two alkaloids were identified from their spectra and by comparison with authentic samples as the N,-methyl quater- nary derivatives (308) and (309) of 10-and 11-hydroxy-usam barine. NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON OMe OMe (307) (306) (308) R' = OH,R2 = H (309) R' = H,R2 = OH Several bases of the usambarensine group have been found among the 46 alkaloids of Aspidosperma marcgravianum.68 (17R)-4',5',6,17-Tetrahydrousambarensine N-oxide (3 10) and (17R)-N4'-carbomethoxy-4',5',6' 17-tetrahydrousambarensine (311) and the corresponding ethyl ester (312) are new and usambarensine (1 7R)-4,5',6' 17-tetrahydrousambarensine (3 13) (1 7S)-4',5',6',17-tetrahydrousambarensine (3 14) 5',6'-dihydrousambarensine (3 13 and ochrolifuanine A were found in the genus Aspidosperma for the first time.68 The root and stem barks of Strychnos longicaudata Gilg.and S. ngouniensis Pellegr. contain a number of Corynanthe+-carboline Strychnos-Corynanthe and bis-strychninoid alka- loids. The presence of longicaudatine in these and several other species of the genus Strychnos was recorded earlier ;45 recently eight other bisindole bases have been found four in each of these species.60 The alkaloids of S. ngouniensis are the two epimers 4',17-dihydro-l7PH-tchibangensine (3 13) and 4',17- dihydro-l7aH-tchibangensine(3 14) together with their 10'- hydroxy-derivatives [(3 16) and (3 17)]. Those from S. longicau-data are longicaudatine Y (3 18) and longicaudatine F (3 19) (which are new) nordihydrotoxiferine (320) and bisnor C- alkaloid H (321).60 Matopensine (322) (a new alkaloid from S.matopensis S. Moore and S. kusengaensis De Wild from Zaire) is a symmetrical dimer presumably resulting from the formation of a bis-carbinolamine from two molecules of the desoxy-Wieland-Gumlich aldehyde followed by dehydration. 16* Com-plete decoupling experiments and the identification of J values for the protons in the central oxygen-containing rings reveal that the configurations of the atoms in these rings are 2P-H 16P-H 2'P-H 16'P-H 17S and 17's. The molecule possesses a C2 axis of symmetry; the presence of a centre or plane of symmetry is excluded by the optical rotation [aID +lo5 O (MeOH).Matopensine is obviously very closely related to bisnordihydrotoxiferine (320) which also occurs in these Strychnos species. However it has not so far proved possible to interconvert these alkaloids ;prolonged treatment of matopen- sine (322) with an acid not surprisingly gives desoxy- Wieland-Gumlich aldehyde. 168 Acetylation of N in one of the molecules of desoxy- Wieland-Gumlich aldehyde would of necessity prevent the formation of a second N,-C-17 bond. Formation of a carbinolamine followed by dehydration would then give (323) which is the structure that has been deduced for a new alkaloid isolated from the root bark of S. variabilis de Wild. also from (310)R' = R2 = H; 17R;N,t-oxide (311) R1 = CO,Me R2 = H; 17R (312) R' = C02Et R2 = H; 17R (313) R' = R2 = H; 17R (314)R' = R2 = H; 17s (315) R2 = H;4',17-didehydro Longicaudatine Y (318)R = H (316) R' = H R2 = OH; 17R Longicaudatine F (319)R = OH (317)R' = H R2 = OH; 17s Nordihydrotoxiferine (320)R = H Bisnor C-alkaloid H (321)R = OH Matopensine (322) 16,17-Didehydroisostrychnobiline (323) Zaire.169a On the basis of a detailed lH n.m.r.analysis the configuration that has been deduced for 16,17-didehydroiso-strychnobiline (323) is 16'R,17'S. As expected from this formulation acid hydrolysis gives retulinal (324) and isoretu- linal (its C-16 epimer) together with their deacetyl derivatives. 12'-Hydroxystrychnobiline(325) is a new alkaloid from the same plant which is hydrolysed to deacetylretuline (326) and a mixture of 12-hydroxyretulinal and 12-hydroxyisoretulinal.69b Clearly C-16 has the Sconfiguration in 12'-hydroxystrychnobi- line; the configuration at the other centres deduced from the proton n.m.r. spectrum is 16S,17'R. A new type of bisindole alkaloid is represented by vobparicine (327) a minor constituent of the root bark of Tabernuemontanu chippii (Stapf) Pichon. 70 This molecule arises by union of apparicine (328) with vobasinol(329) and a partial synthesis by this route was carried out as proof of its structure (Scheme 46). The configuration at C-22 follows from the observation of nuclear Overhauser effects between the proton at C-22 and that at N,' and between the proton at C-3' and that at N,; no n.0.e. was observed between the proton at C-3' and 14a-H as would be expected on the basis of the structure and stereochemistry shown in structure (327).Fl H+yN* H Ac H \NW Deacetylretuline (326) 12'-Hydroxystrychnobiline (325) Vobasinol (329) r-i Apparicine (328) Reagents i 1.5% HCI MeOH under nitrogen heat for 2 h Scheme 46 Five of the six antimicrobial alkaloids of Aspidosperma excelsum are bisindole bases and were identified as ochro- lifuanine A tetrahydrosecamine 16-decarbomethoxytetrahy-drosecamine 16-hydroxytetrahydrosecamine,and 16-hydroxy- 16-decarbomethoxytetrahydrosecamine.73 The bark of Peschieru fuchsiuefoliu contains decarbomethoxy- voacamine demethylvoacamine and voacamidine and the presence of voacamine has been confirmed.107 Three new alkaloids have been isolated from the alkali- soluble fraction of extracts of Huplophyton cimicidum.17 Cimilophytine (330) represents a new type of bisindole alkaloid in which a dehydrocimicidine unit is attached to an unrear- ranged canthiphytine component.' la In norisohaplophytine (33 1) and haplocidiphytine (332) the dehydrocimicidine unit is attached to a rearranged canthiphytine unit as in haplophytine itself.lb Norisohaplophytine differs from haplophytine only in the absence of the N,-methyl group and in the position of the isolated double-bond in the Aspidospermu unit. Haplocidiphy- tine is the counterpart of cimilophytine in the rearranged haplophytine group the two bases exhibiting the same substitution pattern in the Aspidospermu unit.The stereoche- mistry of these alkaloids has not yet been fully elucidated; that depicted here is based on the stereochemistry of the other alkaloids of the Aspidospermu-canthinone group. 71b A new alkaloid (+)-kopsoffine from the roots of Kopsiu oficirzulis has the structure (333) and was partially synthesized by condensation of (+)-eburnamine (334) (contaminated with 16-isoeburnamine) and (-)-kopsinine in the presence of acid (Scheme 47).172 As in the case of vobparicine the monomers involved in this partial synthesis co-occur with the bisindole alkaloid in the plant; however the condensation conditions are such that in both cases it is considered extremely unlikely that the bisindole bases are artifacts. It should be noted that the eburnane component in (+> kopsoffine has the opposite configuration to that in (-> pleiomutine.172 NATURAL PRODUCT REPORTS 1985 Me HO' MeO\ \ HO rh COEt nR' Norisohaplophytine (331) R' = R2 = Me R3 = H Haplocidiphytine (332) R1 = R2 = H R3 = COEt (+)-Eburnamine (334) I H+V+d ,/' it ___+ + H H E02Me 60,Me (-)-Kopsinine (335) (+)-Kopsoffine (333) Reagents i 2% HCl MeOH heat for 4 h Scheme 47 %C02Me "p Me0 H u Callishiline (336) Guillauminine (C40H48N402) is a bisindole alkaloid of Melodinus guilluuminii which very probably belongs to the Aspidospermu-Eburneu group but its structure has not yet been elucidated.79 The structure of callichiline (336) which was first isolated in 1959 from Cullichiliu subsessilis Stapf has at last been revealed by X-ray crystal structure analysis; its 13Cn.m.r.spectrum has also been studied in detail and all of the signals have been assigned.173 Callichiline may well arise in the plant from a bisindole base derived from beninine and 1 l-demethoxy-vandrikine by rearrangement of the beninine-derived unit to the andrangine-like component of (336).l 73 NATURAL PRODUCT REPORTS 1985 -J. E. SAXTON Although plant cell suspension cultures are an excellent source of monomeric monoterpenoid alkaloids the formation of bisindole alkaloids in cultured cells appears not yet to have been uniquivocally established. The isolation of voafrine A (337) and voafrine B (338) from the cell suspension culture of Voacanga africana Stapf is therefore of considerable interest.74 These bases are 3’-epimers and are probably biosynthesized from tabersonine via the coupling of the isomeric A3(14)-enamine with the corresponding immonium salt. In passing it may be noted that a dimer of tabersonine was isolated from the root bark of Crioceras dipladeniiJorus in 1973,175 but nothing is known of its structure beyond the fact that the union of the tabersonine components appears not to involve aromatic positions. It is possible that this ditabersonine is identical with one of the voafrine epimers but this remains to be proved. -/ H *‘Et \/ ‘ N‘ H &O,Me Voafrine A (337) 3’a-H Voafrine B (338) 3’b-H H‘ Roseadine (339) (V = 10-vindolinyl) Reagents i 40% H2S0, H20 at r.t.for 30 minutes Scheme 48 CICO[CH,],C02Me Me3SiC-CCO[CH2],C0,Me I ii-v A rapid procedure for the extraction of vinblastine from the leaves of Catharanthus roseus has been described. 32 Three new alkaloids of the vinblastine group have been isolated from the leaves of C. roseu~.~~~ Roseadine (339) however is not an entirely new compound since it had been prepared earlier by Wenkert and his collaborators1 77 by rearrangement of leurosine (340) with aqueous sulphuric acid (Scheme 48). The structure that was proposed by Wenkert et al. has been confirmed mainly on the basis of a detailed analysis of the mass and n.m.r. spectra of roseadine but the 2 configuration of the double-bond as depicted in (339) is now preferred.76 Similarly on the basis of a detailed examination of the 13Cn.m.r. spectra the structures of pleurosine (leurosine N,’-oxide) and vindolicine were also confirmed. The structures of the other two alkaloids that were isolated in this study i.e. roseamine and pericathidine have not yet been divulged. The cytotoxic activity of pleurosine was assayed in several anti-cancer test systems and it was shown to be particularly active in two systems in vivo these being P-388 lymphocytic leukaemia and B-16 melanocarcinoma. Roseadine was also active in the P-388 test system but was not tested further. 76 A detailed study of the proton n.m.r. spectra of (20S)-20’-deoxyvinblastine and its N,’-borane complex has also been published.’ 78 6 Biogenetically Related Quinoline Alkaloids 6.1 Cinchona Group Quinidine and dihydroquinidine are among the 46 alkaloids of Aspidosperma marcgravianum;68 although these alkaloids are demonstrably monoterpenoid in origin it appears to be the first time that they have been found co-occurring with typical monoterpenoid alkaloids.Quinidine one of the minor constituents of the bark of Cinchona ledgeriana which is used in the treatment of cardiac ailments can be prepared in 50% yield by the microbiological reduction of quininone using Hansenula anomala var. schneg-gii. 79 Only two organisms out of 450 that were tested were able to achieve this conversion; of these the Hansenula species gave the better conversion. 6.2 Camptothecin Details of Kametani’s synthesis45 of ( f)-camptothecin by the double enamine annelation route have been published.180 The latest formal synthesis of ( & )-camptothecin (341) was developed during an exercise to demonstrate the utility of an ingenious new route to indolizin-5-ones (Scheme 49). l8 This GN*iMe 0 0 (344) VIII ix 1.. Camptothecin (341) (345) Reagents i Me3SiC-CSiMe3 AICl, CH2C12 at 0 “C,ii HOCH2CH20H,TsOH PhH heat; iii NaOH H20 MeOH; iv (COCI), PhH DMF at r.t.; v NaN, MeCN heat for 0.5 h; vi Me,SiC-CCHzCH2Me (343) CpCo(CO), rn-xylene hv heat for 3-5 h; vii Et,CO, KH PhMe; viii (CO,H), EtOH H,O; ix o-H2NC6H4CH=NC6H4Me-p TsOH PhMe Scheme 49 18 NATURAL PRODUCT REPORTS 1985 involves the [2 + 2 + 21 cycloaddition of a 5-isocyanatoalkyne 26 W.Steglich L. Kopanski M. Wolf M. Moser and G. Tegtmeyer (342) to disubstituted alkynes e.g. (343) catalysed by cyclopen- Tetrahedron Lett. 1984 25 2341. tadienylcobalt dicarbonyl. The product in this particular 27 L. Lumonadio and M. Vanhaelen Phytochemistry 1984 23 453. reaction consisted of 68%of the indolizinone (344) and only 5% 28 T. Ohmoto and K. Koike Chem. Pharm. Bull. 1984 32 170. of its regio-isomer in which the propyl and trimethylsilyl groups 29 L. A. Anderson A. Harris and J. D. Phillipson J. Nut. Prod. 1983 46 374. are reversed. The orientation observed in structure 30 J. Bergman Heterocycles 1984 21 404. (349 with the trimethylsilyl group a to the amide linkage was 31 S. Sekita K. Yoshihira and S. Natori Chem. Pharm. Bull. 1983, preferred in all of the reactions that were investigated even 31 490.when the other alkyne substituent was the sterically demanding 32 T. Sjoblom L. Bohlin and C. Christophersen Acfa Pharm. Suec. tertiary butyl group; this appears to point to the operation of a 1983 20 415. stereoelectronic effect that is peculiar to silicon. Elaboration of 33 P. Muthusubramanian J. S. CarlC and C. Christophersen Acta (344) by unexceptional methods then gave the tetracyclic Chem. Scand. Ser. B. 1983 37 803. pyridone (349 which is a pivotal intermediate in several 34 T. Hino T. Tanaka K. Matsuki and M. Nakagawa Chem. earlier syntheses of camptothecin (341).’* Pharm. Bull. 1983 31 1806. 35 M. D& de Maindreville J. Levy F. Tillequin and M. Koch J. Nut. Prod. 1983 46 310.7 References 36 E. Yamanaka N. 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Marini-Bettolo Gazz. Chim. Ital. 1983 113 773. 121 M. Ztches T. Ravao B. Richard G. Massiot L. Le Men-Olivier J. Guilhem and C. Pascard Tetrahedron Lett. 1984 25 659. 122 M. R. Yagudaev Khim. Prir. Soedin. 1983 210. 123 R. Verpoorte T. A. van Beek R. L. M. Riegman P. J. Hylands and N. G. Bisset Org. Magn. Reson. 1984 22 345. 124 T. A. Crabb and J. Rouse Org.Magn. Reson. 1983 21 683. 125 Y. Ban K. Yoshida J. Goto T. Oishi and E. Takeda Tetrahedron 1983 39 3657. 126 A. P. Duarte and E. C. Miranda An. Acad. Bras. Cienc. 1983,55 189 (Chem. Abstr. 1984 100 6911). 127 D. D. Weller and D. W. Ford Tetrahedron Lett. 1984 25 2105. 128 (a)M. G. Saulnier and G.W. Gribble Tetrahedron Lett. 1983,24 3831;(b)M. J. E. Hewlins A. M. Oliveira-Campos and P. V. R. Shannon Synthesis 1984 289. 129 V. K. Kansal S. Funakoshi P. Mangeney P. Potier B. Gillet E. Guittet and J. Y. Lallemand Tetrahedron Lett. 1984 25 2351. 130 H. Mehri C. Rochat S. Baassou T. Sevenet and M. Plat Planta Med. 1983 48 72. 131 W. D. 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Soc. 1983,105,6525. 143 (a) F. S. Sariaslani F. M. Eckenrode J. M. Beale and J. P. Rosazza J. Med. Chem. 1984,27 749; (b) M. E. Eckenrode and J. P. Rosazza J. Nut. Prod. 1982 45 226; 1983 46 884. 144 P. Magnus J. Gallagher P. Brown and P. Pappalardo Acc. Chem. Res. 1984 17 35. 145 Atta-ur-Rahman and M. Sultana Heterocycles 1984 22 841. 146 E. Wenkert K. Orito D. P. Simmons N. Kunesch J. Ardisson and J. Poisson Tetrahedron 1983 39 3719; J. Org. Chem. 1983 48 5006. 147 Atta-ur-Rahman M. Sultana I. Hassan and N. M. Hasan J. Chem. Soc. Perkin Trans. I 1983 2093. 148 C. Exon T. Gallagher and P. Magnus J. Am. Chem.Soc. 1983 105,4739; T. Gallagher P. Magnus and J. C. Huffman ibid. p. 9750. 149 T. Imanishi H. Shin N. Yagi A. Nakai and M. Hanaoka Chem. Pharm. Bull. 1983 31 1183. 150 P. Magnus T. Gallagher P. Brown and J. C. Huffman J. Am. Chem. Soc. 1984 106 2105. 151 T. Imanishi K. Miyashita A. Nakai M. Inoue and M. Hanaoka Chem. Pharm. Bull. 1983 31 1191. 152 M. E. Kuehne and W. G. Earley Tetrahedron 1983 39 (a) p. 3707; (b) p. 3715. 153 L. E. Overman M. Sworin and R. M. Burk J. Org. Chem. 1983 48 2685. 154 L. Szabo J. Sapi G. Kalaus G. Argay A. Kalmin E. Baitz-Gacs J. Tamas and Cs. Szantay Tetrahedron 1983 39 3737. 155 L. Szabb J. %pi K. Nogradi G. Kalaus and Cs. Szantay Tetrahedron 1983 39 3749. 156 L. Szab6 G. Kalaus and Cs. Szantay Arch.Pharm. (Weinheim Ger.) 1983 316 629. 157 Y.Langlois A. Pouilhes D. GCnin R. 2. Andriamialisoa and N. Langlois Tetrahedron 1983 39 3755. 158 T. R. Govindachari and S. Rajeswari Indian J. Chem. Sect. B 1983 22 531. 159 J. Gamier J. Mahuteau and C. Moretti J. Nut. Prod. 1984,47 191. 160 P. Perera T. A. van Beek and R. Verpoorte PIanta Med. 1983 49 232. 161 G. Massiot M. J. Jacquier P. Thepenier J. LCvy L. Le Men- Olivier C. Delaude J. Guilhem and C. Pascard J. Chem. Soc. Chem. Commun. 1983 1018. 162 K. Rastogi R. S. Kapil and S. P. Popli Heterocycles 1983 20 2001. 163 Cs. Szantay T. Keve H. Bolcskei and T. Acs Tetrahedron Lett. 1983 24 5539. NATURAL PRODUCT REPORTS. 1985 164 A. T. McPhail T. S. Wu T. Ohta and H. Furukawa Tetrahedron Lett 1983 24 5377.165 H. Furukawa T. S. Wu and T. Ohta Chem. Pharm. Bull. 1983 31 4202. 166 S. Sekita Chem. Pharm. Bull. 1983 31 2998. 167 M. Caprasse D. Tavernier and L. Angenot J.Pharm. Belg. 1983 38,211. 168 J. Massiot B. Massoussa P. Thepenier M. J. Jacquier L. Le Men-Olivier and C. Delaude Heterocycles 1983 20 2339. 169 M. Tits L. Angenot and D. Tavernier (a)J.Pharm. Belg. 1983 38,241; (b) J. Nut. Prod. 1983 46 638. 170 T. A. van Beek R. Verpoorte and A. B. Svendsen Tetrahedron ' Lett. 1984 25 2057. 171 (a)A. A. Adesomoju V. H. Rawal M. V. Lakshmikantham and M. P. Cava J. Org. Chem. 1983,48 3015; (b) A. A. Adesomoju M. V. Lakshmikantham and M. P. Cava Heterocycles 1983,20 1511. 172 X.Z. Feng C. Kan H.-P. Husson P. Potier S.K. Kan and M. Lounasmaa J. Nut. Prod. 1984 47 117. 173 A. T. McPhail E. W. Hagaman N. Kunesch E. Wenkert and J. Poisson Tetrahedron 1983 39 3629. 174 J. Stiickigt K. H. Pawelka T. Tanahashi B. Danieli and W. E. Hull Helv. Chim. Acta 1983 66 2525. 175 J. Bruneton A. Bouquet and A. Cavk Phytochemistry 1973 12 1475. 176 A. El-Sayed G. A. Handy and G. A. Cordell J.Nut. Prod. 1983 46 517. 177 E. Wenkert E. W. Hagaman B. Lal G. E. Gutowski A. S. Katner J. C. Miller and N. Neuss Helv. Chim. Acta 1975 58 1560. 178 A. de Bruyn J. Sleeckx J. P. de Jonghe and J. Hannart Bull. Soc. Chim. Belg. 1983 92 485. 179 L. Ray C. Das Gupta and S. K. Majumdar Appl. Environ. Microbiol. 1983 45 1935. 180 M. Ihara K. Noguchi T. Ohsawa K. Fukumoto and T. Kametani J.Org. Chem. 1983 48 3150. 181 R. A. Earl and K. P. C. Vollhardt J. Am. Chem. Soc. 1983 105 6991.
ISSN:0265-0568
DOI:10.1039/NP9850200049
出版商:RSC
年代:1985
数据来源: RSC
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β-Phenylethylamines and the isoquinoline alkaloids |
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Natural Product Reports,
Volume 2,
Issue 1,
1985,
Page 81-96
K. W. Bentley,
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摘要:
P-Phenylethylamines and the lsoquinoline Alkaloids K. W. Bentley Department of Chemistry Loughborough University of Technology Loughborough Leicestershire LE 7 7 3TU ~~~ Reviewing the literature published between July 1983 and June 1984 (Continuing the coverage of literature in Natural Product Reports 1984 Vol. 1 p. 355) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 p-P henyle thy lamines Isoquinolines Benzylisoquinolines Cularines Bisbenzylisoquinolines Pavines and Isopavines Berberines and Tetrahydroberberines been synthesized.” Homotetrahydroberberines Secoberberines Protopines OH Phthalide-isoquinolines Isoindoloisoquinolines &NHMe Isoindolobenzazepines Indanobenzazepines Rhoeadines Spi ro benz y1isoqu ino1 ines Emetine and Related Bases Morphine Alkaloids Benzophenanthridines Colchicine References ethyl chloroformate yields the urethane (lo) which reacts with water to yield the urethane (1 1 ;R = COzEt); reduction of this with lithium aluminium hydride yields (+)-carnegine (1 1 ;R = Me).” In a similar manner starting from the 6,7-methylene- dioxy-analogue of (7) and using sodium hydride in place of methyl-lithium in the first step hydrohydrastinine (12) has 1 ‘1 OMe Me M Me0 O\ D e (4) “‘“PNMe HO \ (6) 1 AlBu! I CmNMe 1 P-Phenylethylamines (3) Mescaline has been isolated from Lophophora willianrsii,1,2 from Lophophora echinata and from Pelecyphora asellformis; 0-methylcandicine chloride and (+)-coryphanthine chloride have been isolated from Coryphantha greenwoodii and both of Ephedrine (1) has been shown to Me0dNMe these have been ~ynthesized.~ 0 react with spiro(cyc1ohexane- 1,3’-oxaziridine) to give the spiro- base (2).5 The 13C n.m.r.spectra of isoephedrine and J/-isoephedrine have been studied.6 Mescaline in body fluids has (5) been determined by gas chromatography/mass spectrometry using a,a,-dideuteriomescaline as an internal standard,’ and analytical studies have identified by-products in the synthesis of mescaline.8 The effects of mescaline on behaviour9 and the mutagenic effects of N-nitrosoephedrinelO have been studied. (7) 2 lsoquinolines Oxyhydrastinine has been isolated from Argemone mexicana and Papauer dubium var.glabrum ; corypalline and O-methylcory- palline have been isolated from Papauer bracteaturn’ and corypalline and N-methylcorypalline chloride have been AlBui isolated from Corydalis stricta ; 1,2-didehydroheliamine has I been isolated from Carnegiea gigantea. j4 N-Methylcorydaldine has been isolated from Fumaria ~aillantii.~ X-Ray crystallographic studies have resulted in the determin- ation of the absolute configurations of ancistrocladidine (3) and ancistrocladisine (4). Corypalline has been oxidized to the acetoxy-dienone (5) by lead tetra-acetate and this dienone has been made to react with corypalline in trifluoroacetic acid to give 8,8’-dicorypalline (6); similar reactions have been achieved between the dienone (5) and veratrole and between (5) and 1,2,3-trimetho~yb:nzene.~~ The isoquinolinium salt (7) has been shown to react with methyl-lithium to give the enamine (S) which reacts with di- isobutylaluminium hydride to give (9).Treatment of (9) with Benzylamines have been shown to react with styrene oxides to give P-hydroxy-&phenylethylamines and the amine (1 3) (prepared in this way) has been cyclized in acid to give the alkaloid cherylline ( 14).18 The I3C n.m.r. spectra of several isoquinoline alkaloids that have been obtained from cacti have been studiedI9 and a method of determination of salsolinol by gas-liquid chromato- graphy has been reported.20 3 Benzylisoquinol ines Alkaloids of this group have been isolated from the following Corydalis claviculata ‘ crassifoline (19 (+)-reticuline Corydalis stricta ‘ N-methylcoclaurine juziphine reticuline Fumaria vaillantii4 (+)-juziphine (-)-norjuziphine Glaucium corniculatum2 reticuline Papaver arenarium arenine glycomarine sevanine macrostomine and two macrostomine N-oxides Papaver triniijolium papaverine Sarcocapnos crassijolia crassifoline Tiliacora dinklageP oblongine (1 6) Of these (15) is the postulated precursor of the cularine alkaloids isolated for the first time and it is accompanied by two bases of the cularine group in C.claviculata and S. crussijolia. Oblongine is also a new alkaloid; its structure has been confirmed by synthesis.26 Asymmetric reduction of 3,4-dihydropapaverine to a sample of noriaudanosine in which there is 60% excess of the (S)-isomer (as determined by optical rotation) has been achieved by the use of reagents of structure (17) where R is Me Ph OCH2Ph or OCMe3.27 In contrast with the behaviour of ephedrine mentioned above hydroxynorlaudanosine reacts with spiro(cyclohexane-l,3’-oxaziridine)only with formation of an N-N bond and the product is unstable in acid undergoing cleavage of a carbon-carbon bond and bond migration to give the salt ( 18).5 Photolytic cleavage of N-acetyl-laudanosine chloride and N-nitrosonorlaudanosine to give veratric aldehyde together with 6,7-dimethoxy-2-methyltetra-hydroisoquinoline and 6,7-dimethoxytetrahydroisoquinoline respectively has been achieved.The aldehyde is assumed to be formed by oxidation of initially formed dimethoxybenzyl radicals or cations.28 The kinetics and products of the Pictet-Spengler cyclization of norlaudanosoline with formaldehyde to give tetrahydroxy- berbine have been studied.29 A patent covering the preparation of nor-reticuline from 3,4-dihydropapaverine has been published. 30 Corgoine (20; R = H) and sendaverine (20; R = Me) have been synthesized by cyclizing the appropriate bases (19; R = OH OH NATURAL PRODUCT REPORTS 1985 CH2Ph) and (19; R = Me) with polyphosphoric acid and debenzylating the products. The bases (19) were prepared by condensing 3-benzyloxy-4-methoxybenzaldehydewith amino- ethanol reducing the Schiff base and treating the product with the appropriately substituted benzyl chloride.31 Corgoine has also been synthesized from the amide (21) by cyclization with carbon monoxide in the presence of tributylamine palladium(I1) acetate and triphenylphosphine followed by reduction of the amide carbonyl and deben~ylation.~~ The detection of papaverine by t.1.c.has been described.33 The metabolism34 and mode of spasmolytic action35 of papaverine have been studied as have the relaxant effects36 of the alkaloid and its effects on blood on the heart,38 on the vascular system,39 and on the uptake of calcium The effects of N-methylpapaverine methylsulphate on synaptic transmi~sion~~ and of higenamine on the heart44.45 and the neuromuscular blocking action of ( +)-coclaurine ( +)-reticu-line ( -)-N-methylcoclaurine and yuzirine (obtained from the drug ‘Shin-I’)46 have been studied.The pharmacological properties of atracurium have been compared with those of (+)-tubocurarine and other neuromus- cular blocking agent^^'-^^ and revie~ed,~~.~ and analogues of atracurium have been prepared ;s2 methods of estimating atracurium in body fluids by g.1.c. have been des~ribed.~~?~~ 4 Cularines Alkaloids of the cularine group have been isolated from the following those marked by an asterisk being new Corydalis clavi~ulata”~~~~~~ cularine oxocularine (22; R = Me)* cularicine 0-methylcularicine* norcularicine* cularidine norcularid ine* culacorine (23)* claviculine (24; R = H)* sarcocapnidine (24; R = Me)* and limousamine (25)* Guatteria ouregou gouregine Sarcocapnos crassifblia2s sarcocapnidine oxosarcocapnidine (26)* and claviculine Sarcocapnos ennea~hylla~~ oxocompostelline (22; RR = CH2)* Claviculine and sarcocapnidine are methylated by diazometh- ane to sarcocapnine.25 Oxocularine and oxocompostelline have been synthesized from (27; R = Me) and (27; RR = CH2) respectively by processes involving a benzyne intermediate.55 Sarcocapnine sarcocapnidine oxosarcocapnidine and clavi- culine all have the orientation of oxygen substituents that is found in the cularine-morphine alkaloid cancentrine. Me0 mNMe2 ‘I-NaBH \ OH 1 1 COR 3 ’0OH (17) NATURAL PRODUCT REPORTS 1985 -K. W.BENTLEY HO Me0 Me0 qN\ RO6OR M H e N e ! p e 5 Bisbenzyl isoquinol ines \ OMe / Bisbenzylisoquinoline alkaloids have been isolated from the following those marked with an asterisk being new; Albertisia papuanabo aromoline homoaromoline coscoline 0-methylcoscoline* cosculine daphnoline dehydrotelobine isotrilobine lindoldhamine obaberine and Berberis buxijolia b1 oxyacanthine chillanamine (28)* curacutine (29; R = CHO)* osornine Guatteria gaumerib2 Hernandia peltata Pachygone ovatab4 (30)* and talcamine (29; R = C02Me)* lindoldhamine) (31 ;R =H)* R2 = OMe)* vateamine (32; R1 = OMe R2 = H) and malekulatine (33)* pachygonamine (34; R = H)* guattegaumerine (NN-dimethyl- vanuatine (32; R1 = H M H e N g \ OMe ’lR1 R2 o Me0 g /\ / e Polyalthia nit idissirnab Thalictrum kuhisranicumb6 and N-methylpachygonamine (34; R = Me)* (31 ; R = H) isodaurisoline (31 ; R = Me)* 7-0-methyl- lindoldhamine (35; R1 = Me R2 = H)* and 7’-0-methyl- lindoldhamine (35; R1 = H R2 = Me)* NN’-dimethyl-lindoldhamine thalmine thalmidine (32) The alkaloids that have been obtained from Hernandia peltata (33) are the first recorded dimers of reticuline.Pachygonamine and N-methylpachygonamine have both been converted into N-methyltiliamo~ine.~~Curacutine has been prepared by the oxidation of calafatine which has also been reduced by sodium in liquid ammonia to (-)-N-methylcoclaurine.61 Four bases (B C J and K) previously obtained from Stephania sasakii have been identified. Base K is 0-methylpunjabine (36; R = CHO) obtained by controlled oxidation of isotrilobine which on Wolff-Kishner reduction OH gives Base C (36; R = CH3); Base J is secocepharanthine (37; R = CHO) obtained by controlled oxidation of cepharanthine and is converted into Base K (37; R = CH20H) by reduction with sodium borohydride.The structure of pheantharine has been revised to (38)68 and (34) this has been confirmed by synthesis from the Reissert compound (39) and the dibromide (40) followed by elimination and N-methylati~n.~~.~~ Tetrandrine has been converted into two isomeric monomethiodides by partial methylation with methyl iodide’l and has been shown to be metabolized in rats to an 0-desmethyl base and to the N-2’-0xide.~~ Berbamine has NATURAL PRODUCT REPORTS 1985 6Me (37) I-I-OMe (39) (40) been unspecifically tritiated73 and the lH n.m.r. spectrum of repanduline has been examined in detail using long-range nuclear Overhauser effect difference spectro~copy.~~ The biological activities of a number of bisbenzylisoquino- line alkaloids have been reviewed.75 The distribution and pharmacological actions of (+)-tubocurarine have been exam- ined,76 as have the effects of the alkaloid on the neuromuscular j~nction,~~~~~ on the coagulation of blood,79 on the release of histamine,48 on dopaminergicsO and cholinergics recep-tors and on acetylcholinesterase activity.82 The properties of (+)-tubocurarine have been compared with those of atracu- pan~uronium,~~ hexamethoni~m,~~ and vecuro-ni~m.~~ The effects of tetrandrine on levels of cyclic AMP,84 on silic~sis,~~-~~ on the rat uterus,88 on action potential^,^^ and on calcium metabolismg0 and the effects of cepharanthine on the leucopaenia that is induced by anti-cancer drugsg1 and on the sickling of blood cells,92 of thaliblastine on diploid cells from human of dauricine on the heart,94.95 and of cepharanthine on plateletsg6 have been studied.The general pharmacology of berbamine has been reviewedg7 and the pharmacokinetics of dauri~ine,~~ and (&)-di-cycleanir~e,~~ methylcurineIo0 have been examined. A high-performance liquid-chromatographic technique for the estimation of tubo-curarine and metocurine in plasma has been described.Io1 6 Pavines and lsopavines Bisnorargemonine has been isolated from Chasrnanthera dependens' n2 and californidine and eschscholtzine have been isolated from Eschscholtzia caltfornica.lo3 The chemistry of the alkaloids of this group has been reviewed.Io4 7 Berberines and Tetrahydroberberines The following alkaloids of this group have been isolated from the sources cited; those marked by asterisks are new alkaloids Chasmanthera dependens I O coreximine (-)-govanine Coptis deltoides' O5 berberine coptisine jatrrorhizine and tetrahydropalmatine.Corydalis meifolia I O6 (+)-cavidine apocavidine dehydrocavidine* cheilanthifoline (+)-sinactine and stylopine Corydalis stricta' cheilanthifoline coreximine isocorypalmine scoulerine and hydkoxymethylstylopine Fumaria densiflora' O7 coptisine palmatine and ( )-sinactine Fumaria gaillardotii' O8 (-)-stylopine Fumaria ojjkinalis' O9 N-methylsinactine Fumaria vaillantii4 (-)-cheilanthifoline (-)-scoulerine and (+)-stylopine Glaucium fimbrilligerum 'O9 columbamine hydroxymethylstylopine Guatteria our ego^^^ coreximine 10-0-demethyl- xylopinine Guatteria scandens I I O discretine xylopinine Heptacyclum zenkeri' I dehydrodiscretine Papaver arenarium cheilanthifoline Papaver triniifoli~m~~ cheilanthifoline scoulerine and sinactine Stephania glabra' gindarine [(-)-tetrahydro-palmatine] Thalictrum foliolosum' I berberine columbamine dehydrodiscretamine jatrrorhizine palmatine thalidastine and thalifendine Tinospora baenzigeri I I berberine jatrrorhizine Tinospora crispa ' berberine jatrrorhizine and palmatine Tinospora cordifolia I palmatine Tinospora glabra ' berberine jatrrorhizine and palmatine Tinospora merilliana' I berberine jatrrorhizine and palmatine Tinospora sagittata' palmatine Tinospora sinensis' l4 palmatine Tinospora smilacina ' berberine The following have also been isolated from cell tissue cultures of the plants cited the yield from Coptisjaponica being much higher than from plants Argemone mexicana ' berberine Coptis japonica I berberine Dioscoreophyllum cumminsii' jatrrorhizine The mass spectra of some tetrahydroberberinesl and the crystal structure of tetrahydropalmatinel have been studied.00-Diacetylcoreximine has been converted (by the action of ethyl chloroformate) into the urethane (41) which has been reduced by lithium aluminium hydride to 6'-methylreticuline and by catalytic hydrogenation followed by hydrolysis to 6-methylnor-reticuline.2o A similar ring-fission of tetrahydro- berberine with ethyl chloroformate afforded the compounds (42)and (43) as minor products; the major product an analogue of (41) has been converted into canadaline (44) by hydrolysis N-methylation and oxidation and into the hydroxymethyl- compound (45) by hydrolysis and cyclization with formalde- hyde. 21 The unsensitized photo-oxidation of berberine has been shown to be catalysed by bases such as triethylamine methoxide ion ethoxide ion azide ion and mercaptide ion; the aldehydes (46; R = OEt) and (46; R = S[CH,],Me) have been prepared in this way. 22 The methoxyberberine betaine (48) which was obtained from the sensitized photo-oxidation product (47) by heating has been found to give (*)-ophiocarpine together with a small amount of (+_)-epiophiocar-pine on reduction with sodium borohydride.23 Ophiocarpine methiodide has been shown to be converted into 13-oxoallo- cryptopine and the indano-benzazepine (49) by callus cell cultures of Corydalis ophiocarpa ; epiophiocarpine behaves similarly but gives in addition 13-hydroxyallocryptopine.24 * NATURAL PRODUCT REPORTS 1985 -K. W. BENTLEY B M OMee OMe (47) (45) R'O / OMe (49) OR4 Me0 \ MeoqNTo R/ 0 (54) Me0 / SWN, CHI \ CF c\ c%" Meo%ph w\. %Me3 (57) (58) A synthesis of (+)-tetrahydropalmatine by Bischler-Napier- alsky cyclization of the amide (50),followed by reduction has been achieved.125 Cyclization of the amide (51; R = H) followed by reduction Mannich reaction with formaldehyde and further reduction afforded (+)-coreximine; the same processes starting from the amide (51 ;R = Br) yielded (+)-scoulerine.I 26 Similar processes using unbrominated interme- diates with final dehydrogenation have resulted in syntheses of dehydrodiscretine (52; R1 = R3 = R4 = Me R2 = H) pseudocolumbamine (52; R* = H R2 = R3 = R4 = Me) thalifaurine (52; R' = Me R2 = H R3R4 = CH,) and dehydrocheilanthifoline (52; R1 = H,R2 = Me R3R4 = CH,)."' The anion of m-meconine has been shown to react with 3,4-di hydro-6,7-dimet hoxy- and 3,4-di hydro-6,7-met hy- lenedioxy-isoquinoline to give the 13-hydroxy-8-oxoberberines (53; R = Me) and (53; RR = CH,); these have been reduced to the corresponding 13P-hydroxytetrahydroberberines.28 Photocyclization of the enamide (54; R = H) to the amide (55) has been accomplished in the presence of the quinine- lithium aluminium hydride complex;129 the enamide (54; R = OMe) however gives the reduced compound (56).130 The reaction of the acetylenic compound (57) with acetylene in the presence of cyclopentadienyl cobalt dicarbonyl has yielded 2,3- dimethoxy-10,ll-di(trimethylsilyl)tetrahydroberberbine and benzonitrile reacts with (57)under the same conditions to give the azatetrahydroberberine (58).1 31 The effects of berberine on smooth vascular muscle132 and the anti-secretory effects of the alkaloid alone and in combination with morphine clonidine yohimbine and ephe- drine133 have been examined as have the antihypoxic effects of berberine 13-methyIberberine jatrrorhizine and palma- tine,' 34 the effects of tetrahydroberberine on regioselective 0-methylation in brain,' 35 on levels of acetylcholine,' 36 and on the action of reverse tran~criptase,'~~ of coptisine columba- mine and jatrrorhizine on the activity of butylcholinester- ase 38 of tetrahydropalmatine on the behaviour of cats'39 and as a sedative,'2S.'J0 and ofdehydrocorydaline iodide as an anti- ulcer agent.I5l 8 Homotetrahydroberberines A new alkaloid (which has not been named) that has been isolated from Berheris actinacantha has been identified by X-ray diffractometry as the homotetrahydroberberine (59).14' 9 Secoberberines (-)-Corydalisol has been isolated from Hypecoum procum-The base (60) which was obtained by the pyrolysis of protopine N-oxide has been reduced catalytically and with zinc and acetic acid to corydalisol (61) and hypecorine (62).144*'45 The conversion of tetrahydroberberine into canadaline is NATURAL PRODUCT REPORTS 1985 0-J (62) described in Section 7 and of (-)-fumaricine into secoberber- ines in Section 16.10 Protopines Alkaloids of this group have been isolated from the following Bocconia cordata 46 protopine N-oxide Corydalis meijolia O6 protopine Corydalis stricta‘ protopine Eschscholtzia calijornica I O3 protopine allocryptopine Fumaria densijlora I O7 protopine cryptopine Fumaria gaillardotii’ O8 protopine Fumaria parvijlora 47 izmirine (63) Fumaria vaillantii4 protopine Glaucium corniculatum2 protopine allocryptopine Izmirine is a new base and the first protopine alkaloid to be found with a hydroxyl group at C-3.I4’ The I3Cn.m.r.spectra of salts of protopine allocryptopine 1-methoxyallocryptopine hunnemanine and thalictrine in deuteriotrifluoroacetic acid show that the cis protopinium salt predominates over the trans in all cases except with thalictrine where the trans salt predominates. 14* The pyrolysis of protopine N-oxide has been found to give in addition to the base (60) that is mentioned in Section 9 the base (64) and the nitrogen-free product (65); photolysis of the N-oxide gives (60) and sanguinarine (66). Similar reactions have been observed with allocryptopine N-oxide.4s 11 P ht ha1 ide- isoqui no1 i nes Alkaloids of this group have been isolated as follows from the sources cited where an asterisk denotes a new alkaloid Corjdulis meifolia O6 corlumine Corjdulis stricta adlumine bicuculline and 0-hydrastine Fumaria densijlora O’ adlumidiceine Fumaria gaillardotii’ O8 ( f)-bicuculline N-methyl hydrastine Fumaria r.aillantii4. (-)-adlumine adlumidiceine (+)-bicuculline (-)-capnoidine (-)-codedine (a-fumaramine (67)* (Z)-fumaramine fumaramidine N-methylhydrasteine and egenine (68)* Egenine is the first phthalide-isoquinoline hemiacetal to be isolated from natural sources. a-Narcotine and p-hydrastine and their diol reduction products have been shown to react with diborane at the nitrogen atom.or-Narcotinediol on heating with potassium t- butoxide and benzophenone has been found to give the base (69) rat her than the an hyd ro-diol without racemization at the benzylic centre. I 50 14-Methoxy-8,13-dioxocanadine(70) on pyrolysis has been found to give 35% of the ester (71) and 15% of the lactone (72) which has been N-methylated and reduced to (+-)-a-and (+)-p-hydrastine.IS1 P-Alkoxyphenylethylamines have been shown to react with (dimethylaminomethy1ene)phthalides to give phthalide-iso- quinolines which may be N-methylated; in this way (*)-CH2OH OMe QOMe OMe OMe x -, (73) cordrastine corlumine and adlumine have been synthe-sized.1s2 Phthalide anions have been allowed to react with 3,4-di hydroisoquinolines to give mixtures of erythro-and threo-phthalide-isoquinolines;or-and p-cordrastine and or-and p-isocordrastine have been synthesized in this way.’ 53 Methods for the determination of narcotine by high-performance liquid chromatography have been report-ed.1s4.1ss The effect of bicuculline on the binding of phenytoin to protein has been studied.Is6 12 I soi ndo loisoqu inoI ines The first alkaloid of this type (+)-nuevamine (73) which is a lower ring homologue of the isoindolo-benzazepine lennox- amine (74) has been isolated from Berberisdarwinii.Its structure was determined by spectroscopic methods and by its identity with material that had previously been prepared by fission of NATURAL PRODUCT REPORTS 1985 -K. W. BENTLEY chilenine (75) to a carboxylic acid by methanolic potassium hydroxide followed by cyclization in acid with loss of carbon dioxide.57 13 lsoindolobenzazepines This group of alkaloids discovered during the period of the last review (Nat. Prod. Rep. 1984 1 359 has been extended by the isolation of (*)-lennoxamine (74) which is a ring homologue of nuevamine from Berberis darwinii. 57 Chilenine (73 the previously identified alkaloid of the group has been found to be a minor product (7%) of the thermal rearrangement of the canadine derivative (70) (see Section 1l).ls1 14 lndanobenzazepines Two structural types of indanobenzazepines alkaloid have now been identified. In the group that had previously been recognized the 8,14-cycloberberine (76) has been stereoselecti- vely cleaved to a secondary base that gave the tertiary base (77; R = OH) and the methanesulphonyl ester of this base yielded (+)-fumaritrine (77; R = H) on reduction with sodium borohydride.58* 59 The cycloberberine (78) which was ob- tained from a synthetic berberine has been rearranged in aqueous acid and N-methylated to produce the tertiary base (79; R = PhCH2) which on hydrogenolysis gave fumarofine; this has been methylated by diazomethane to O-methylfumaro- fine (79; R = Me).' 589160 The conversion of a-N-methylophio- carpine into the indanobenzazepine (49) is covered in Section 7. The new group of indanobenzazepines discovered during the period of this review are derived from a 3,4-benzazepine rather than a 4,5-benzazepine system.Two such bases have been discovered namely himalayine isolated from Mecornpsis uillosa,16' and one base that has been assigned the names ribasine16* and limogine16' (each isolated from Corydalis claviculata) and grandiflorine (isolated from Argemone grandi- flora subsp. grandflora). 63 The definitive determination of structure is an X-ray-crystallographic study of ribasine,162 revealing the absolute configuration (80; R = H); other studies (75) (79) suggested the antipodal configuration. The identity of grandiflorine with ribasine was established. 163 Since the position of the hydroxyl group in himalayine which is a hydroxylimogine has been determined,16 its structure must be (80; R = OH). Ribasine has also been isolated from Sarcocapnos crassifolia .15 Rhoeadines A review of the alkaloids of the rhoeadine group has been published. I 64 16 Spirobenzyl isoqui no1 ines Spirobenzylisoquinolineshave been isolated from the follow- ing where an asterisk denotes a new alkaloid Corydalis meifolia 'Ob yenhusomine yenhusomidine Fumaria densifolia 'O' densiflorine (8 1)* Fumaria gaillardotii' Oa fumaricine (85) fumaritine Fumaria ojjicinalis I O9 epidihydrofumariline (82)* Fumaria vaillantii4 fumariline parfumine and parfumidine The n.m.r. spectrum and circular dichroism of O-methylfumaro- phycine have been studied and confirm the structure (83) for this base.165 Ochrobirine (84) has been prepared by the rearrangement of an 8,14-cycloberberine. 58 (-)-Fumaricine (85) has been subjected to oxidative photolysis to give the secoberberine hemiacetal (86) in low yield and this has been reduced at the carbonyl group by sodium borohydride.66 17 Emetine and Related Bases Alangicine (88) has been synthesized from the ester (87) by conversion into the corresponding P-(3-benzyloxy-4-methoxy-phenyl)ethylamide followed by Bischler-Napieralsky ring- closure and debenzylation. 167-169 The effects of emetine on the synthesis of proteins' 70 and on induced cardiomyopathy in rabbits' have been studied. (77) OH 18 Morphine Alkaloids Oripavine has been isolated from Papauer somniferum,' 72 amurine and salutaridine from Papauer triniif~lium,~~ pallidine from Chasmanthera dependens O2 and stephabenine (89) a new hasubanan alkaloid from Stephania japonica.73 Thebaine has been isolated from tissue cell cultures of Papauer bracteaturn.174The effect of climate on the yield of morphine from Papauer somnijerum has been studied. 75* 76 The structure of stephabenine was deduced from its hydrolysis to benzoic acid and 0,N-dimethylstephine. 73 X-Ray crystallographic determinations of the structures of bromocodide 77 sinomenine 78 and sebiferine methiodide (0-methylpallidine methiodide)' 79 have been accomplished and confirm the accepted structures of these compounds. The 13C n.m.r. spectrum of crystalline morphine has been studied. lg0 The structure of a zwitterion complex of morphine and platinum trichloride formed from morphine hydrochloride and potassium chloroplatinate has been determined by X-ray crystallography1 and the conformational and kinetic features of the binding between morphine and Mn2+ ions have been studied using Fourier-transform n.m.r.techniques. 82 [1,7,8-3H,]Morphine has been prepared in good yield. 83 Morphine 3-t-butyl ether has been prepared by the action of dimethylformamide t-butyl acetal on 6-0-acetylmorphine followed by hydrolysis of the resulting 3-0-t-butyl-6-0-dimeth- ylaminoacrylylmorphine. 84 Isocodeine $-codeine and allo-$- codeine have been N-demethylated by conventional methods using cyanogen bromide and ethyl azodicarboxylate,' 85 86 and quaternary salts of morphine codeine and thebaine with alkyl halides have been N-demethylated to N-alkyl nor-bases by sodium thiophenate ;l 873,6-diacetyl-l6,17-didehydromorphine which was identified as an impurity in illicit heroin has been prepared by the action of acetyl chloride on morphine N-oxide; it is protonated to the iminium salt.188 6-0-Mesylneopine has been converted into 6-demethoxyoripavine which was trans- formed into 6-demethoxynororipavine N-propyl 6-demeth- oxynororipavine apomorphine and N-propylnorapomor-phine.89 An adduct of thebaine with mercuric nitrate has been reduced to isoneopine. 190 f-? COCHzPh (90) OMe (89) NHCOCH(OEt)2 (93) (94) NATURAL PRODUCT REPORTS 1985 Thebaine has been treated with N-phenylacetylhydroxyl- amine and tetraethylammonium periodate to give the Diels- Alder adduct. (90) which has been hydrolysed to 14-(N-phenylacetylhydroxy1amino)codeinone; this and (90) have been rearranged presumably through the aziridinone (91) to the 14-aminocodeinone derivative (92) by sodium methoxide in methanol.N-Pivalylnorthebaine gives a similar adduct with N-chloroacetylhydroxylamine and this has been converted into (93).I9l The Diels-Alder adduct of thebaine and l-chloro-l- nitrosocyclohexane has been reduced in methanol to 14P-aminocodeinone and its dimethyl ketal and these have been converted into 14~-(bromoacetyl)amino-morphinoneand -morphine for receptor-binding studies. 192 Thebaine has been converted into buprenorphine (94) by conventional methods' 93 and buprenorphine has been rearranged in acid solution with results194 that are in conformity with those that have previously been described for the 0,N-dimethyl analogue.95 Diels-Alder addition of methyl vinyl ketone to P-dihydrothebaine 4-phenyl ether has been shown by an X-ray crystallographic to give the 6,14-exo-etheno-compound(95) in contrast to the behaviour of thebaine and P-dihydrothebaine. The half ester amide (96) and the isothiocyanate (97) derived from 7a-amino- 6,14-endo-etheno-oripavine, have been prepared for receptor- binding studies.197 The ketones (98; R = Me) and (98; R = Bun) have been converted into (99; R = Me) and (99; R = Bun) by treatment with the anion of thioanisole. These bases on treatment with trimethyloxonium tetrafluoroborate followed by sodium hydroxide gave the epoxides (loo) which were mixtures of diastereoisomers.The epoxides on treatment with boron trifluoride etherate gave the aldehydes (101) which were reduced to the primary alcohols (102). The mesyl esters of these alcohols on reduction with lithium triethylborohydride gave the methyl compounds (103) (obtained in better yield with lithium aluminium hydride) and the oxonium salts (104); thy salts (1 04) were hydrolysed to the tetrahydrofuran derivatives with loss of the 0-methyl group. The aldehyde (101 ;R = Me) was converted into the secondary alcohol (105) by propylmag- nesium bromide. The ketones (98; R = Me) and (98; R = Bun) have been reduced to secondary alcohols the mesyl esters of 'OMe (92) 0 (95) (96) Me0 \ Me Me Me0 I HO'L'C H SPh 89 NATURAL PRODUCT REPORTS 1985 -K.W. BENTLEY Me0 \ Me0 \ Me0 \ '@kMe Me0 g k M e Me @kMe Me0 ' I I Me Meo@kMe9 HO-' o% 0 Me\ Me OMe OMeMeo6 Me Me 0 which on treatment with dibutyl cuprate gave only the olefins (106; R = Me) and (106; R = Bun). The 3-0-demethyl analogues of the bases (1 02; R = Me) (1 03 ; R = Me) (1 03 ; R = Bun) and the tetrahydrofuran corresponding to the oxonium salt (104; R = Bun) have been prepared. The implications of the properties of these bases for theories of binding to opiate receptors have been considered. 98 8-Methyldihydrocodeinone 8-(3-hydroxypropyl)dihydro-codeinone and the base (107) have been prepared from codeinone.' 99 Dihydrocodeinone has been brominated to 1,7,7- tribromodihydrocodeinone hydrolysis of which in sodium hydroxide is accompanied by benzilic acid rearrangement to give (-)-1-bromosinomenilic acid (l08) which has been further transformed into ( -)-sinomenilone (109).200These reactions have been observed with 1-bromosinomeneine ketone which is the antipode of 1-bromo-7-oxodihydrocodein-one,201 and have previously been achieved in the dihydroco- deine series.202 The series of bases of general structure (1 10) in which R is CHO [CH=CH],Ph and [CH2I4Ph and their C-6 epimers (described in the previous review) has been extended by the preparation of N-cyclopropylmethyl and N-cyclobutyl analogues and by the reduction of the bases (1 11) to the alcohols (1 12) by lithium aluminium hydride; oxidation of the alcohols (1 12) to the ketones has also been achieved.*03 Hydrazones of 14-hydroxycodeinone and 14-hydroxymorphinone have been prepared204 and patents have been published for the prepara- tion of 14-hydroxy-N-(2-methoxyethyl)nordihydromorphin-of 14-hydroxy-N-ethoxycarbonylnordihydrocode~n-one,2o6 of derivatives of 14-fluorodihydrocodeine,207and of azines that are derived from I4-hydroxydihydromorphinone naloxone and naltrexone.208 The n.m.r.spectra of the epimeric 6-amino-14-hydroxydihydrodeoxymorphines209 and the meta- bolism of codeine210,21 and of 14-hydroxydihydromorphin-l one2I2 have been studied. A synthesis of codeine has been achieved by the oxidation of (-)-(R)-6'-bromo-N-trifluoroacetylnor-reticuline with aryl-iodoso-compoundsto 1-bromosalutaridine which wasconverted Meo& 0 Me0 successively into 1 -bromosalutaridinol 1-bromothebaine 1-bromocodeinone and codeine ;21 N-formyl- and N-ethoxy- carbonyl-nor-reticulines and their 6'-bromo-analogues have been oxidized by manganese and vanadium acetylacetonates to N-acyl-norisosalutaridines,214~2~ reduction of the N-substitu- ent of which gave (?)-~allidine.~*~ Patents have also been published for the oxidation of N-acyl-nor-reticulines to salutari- dine derivatives.216-218 Following principles of synthesis that were discussed in the previous report the iminium salt (1 13) has been allowed to react with diazomethane to give the ketone (114) which was converted (by conventional processes) into the dithioketal(ll5); hydrolysis of this gave a diketone which was converted into the enol ether ( -t)-0-methylpallidinine(1 16).219 Methods of detection and estimation of morphine,32*220-227 codeine,32.220.224-230 ethylmorp hine 26.30 norcodeine 29 heroin,226.23 1-238 3-and 6-0-a~etylmorphine,~~~ dihydro-nal~xone,~~~ m~rphinone,~~~ and nalmefene240 have been reported and the interference of pholcodine in the immuno- assay of opiates in urine has been The analgesic proper tie^,^^?-'^^ receptor binding,248 phar- haemodynami~s,~~~, mac~kinetics,~~~ 25 and teratogeni-of morphine and the use of the alkaloid in anaesthe- sia253. 254 have been studied as have the effects of morphine on beha~iour,~~~ on the central nervous -267 on the brain,268-271 on the activity of neurone~,~~~-~~~ on the cardiovascular ~y~tem,~~~.~~~*~~~ on the gastro-intestinal on re~piration,~~~*'~~-'~~tempera-tra~t,~~~-~~~ on body tUre,259.293.294 on the intake of food and water295 and the production of urine,296 on evoked potentials,297 on somatosym- pathetic reflexes,298 on locomotor activity,299 on the oestrus cycle,300 on ovulation,301 on hormonal regulation,302 on the production of pr~lactin~~~ and of luteinizing hormone releasing hormone,304 oxyt~cin,~~~ on the uptake of and vasopre~sin,3~~ calcium ions by synaptos~mes~~,~~ and mast cells,306 on dogs,307on the eye,308.309 on memory,267 on the production of cat echo la mine^^^^ and the turnover of n~radrenalin,~' on levels of corticosterone in plasma313 and of cyclic AMP,314 adenyl~yclase,~ somatostatin,316 and cytochrome P-45O3I in on tissues,314 on platelets,318 on T-lymph~cytes,~~~the pancreas,320 on the synthesis of proteins,321 on responses to phencyclidine322 and meth~trimeprazine,~~~ and on survival after hypo~ia.~~~ The narcotic antagonist properties3 25 and receptor bind- ing248*326 of naloxone and the use of this compound in \o (117) anaesthetics327 have been studied as have the effects of the compound on behavio~r,~~~*~~~.~~~-~~~ on endotoxin shoc k,3 8-343 haemorrhagic shock 344 34 and anap hyllacti~~~~ shock on temperature,294 on intake of food347,348 and of on the production of urine,296 on the heart,351 the brain,352.353 the cerebrospinal the eye,355 and the 1iver,356,357 on exercise on memory,358 on respirati~n,~~~?~~~ performance,361on platelets3 189362 and T-lymph~cytes,~’~ on neurone~,~~~ on gastric ulcer models,365 on the bar~reflex,~~~ on hyperglycaemia,366 on haem~rrhage,~~~ and on levels of mel~tonin,~~~ luteinizing hormone,369 growth hormone,370 and pr~lactin;~~~.~~ * the aphrodisiac effects of a combination of naloxone and N-propylnorapomorphine have also been The pharmacological and physiological effects of the following have also been studied her~in,~~~-~~~-~~~ 3,6-di-0-b~tyrylmorphine,~~~ codeine,247 other 3-0- n~rmorphine,~~~ nal~rphine,~ a1 kyl-morphine~,~~~ 5,379 naloxone methio-dide,350-380 naloxone hydraz~ne,~~~?~~~ naloxone-6-spiro-hydant~in,~~~ nalb~phine,~~’ fl-chl~ronaltrexamine,~~~~~~~~~~~ fl-f~naltrexamine,~~~,~~~,~~~ amides of N-allyl-6~-amino-14-hydroxydihydrodeoxynormor-phi ne 39 N-c ycloprop ylme t h y1-14- h ydrox y-6-met hylenedi hy- drodeoxynormorphine (nalmefene),392 dipren~rphine,~~~ and 7,s-dihydro- bupren~rphine,~~~,~~~-~~~ 5’,6’-dimethylcyclohex-5-eno[1’,2’ :8,14]~odeinone.~~~ 19 Benzophenanthridines Benzophenanthridine alkaloids have been isolated from the following Corydalis meijolia O6 di hydrosanguinarine Corydalis stricta I sanguinarine di hydrosanguinarine Fumaria uaillantiP norsanguinarine oxosanguinarine dihydrosanguinarine 8-acetonyldi hydrosanguinarine and 8-methoxy- di hydrosanguinarine Glaucium corniculatum” sanguinarine Papauer bracteatum sanguinarine (cell culture)”.‘ The chemistry of the alkaloids of this group has been revie~ed.~~~.~~~ The influence of pH on the ultraviolet absorption and fluorescence of sanguinarine has been stu- died.407 Norchelidonine (1 17; R = H) has been shown to give dehydronorchelidonine (1 18) on oxidation with Fremy’s salt and this on reductive alkylation with formaldehyde and sodium borohydride gives presumably through the iminium salt (1 19) only 3% of chelidonine (1 17; R = Me) the major product being the cyclic carbinolamine ether isodehydrocheli- donine (120).408 A patent has been published covering the preparation of benzophenanthridine epoxides as potential antitumour agents;409 for example sanguinarine on treatment with bromine followed by perchloric acid and sodium hydroxide gave the epoxides (1 21) and (1 22).The treatment of chelilutine with thiophosphoric acid thiaziridide has been reported to give the compound (1 23) which with analogues has been claimed to have antitumour activity.410 In extension of work covered in the previous review the compound (1 24) which was obtained from berberine has been oxidized by dichlorodicyanobenzoquinone to the quinone imine (125) and the amine (126) both of which have been NATURAL PRODUCT REPORTS 1985 Lo (118) NPh Me0 -NHPh I APh fl N Me Me0 \ Me0 NHPh I -H Me0 Me Me0 converted into the corresponding quinone which has been reduced to cis and trans forms of the diol (129) by sodium borohydride. Oxidation of (1 24) in methanol affords (127) which can be reduced in stages to cis and trans forms of ( 128).41 A synthesis of fagaronine has been achieved from the ketone (130) which was converted into the cyano-compound (131); this was hydrolysed reduced and cyclized to the ketone (1 32).Treatment of this ketone with methylamine followed by reduction afforded an amine which with chloral gave the formamide (133); this was dehydrogenated and treated with concentrated sulphuric acid or with boron trichloride (to cleave the isopropyl ether) to give a phenol which was cyclized to NATURAL PRODUCT REPORTS 1985 -K. W. BENTLEY C1-NMe ( 1 34) (135) ,R n (139) 0 fagaronine ( 134).4 2,3-Methylenedioxy-c~-methylhomop htha-lic anhydride has been condensed with the imine (135) to give the acid (136; R = C02H) and its diastereoisomer both of which were decarboxylated (by heating in dimethyl sulphoxide) to the same mixture of diastereoisomeric nitriles.The nitrile (136; R = H) was converted into the methyl ester which was reduced in good yield (on treatment with phosphorus oxychlor- ide followed by sodium borohydride) to the methyl ester (137) of corydalic 6-Bromomethyl-3,4-methylenedioxystyrene has been con-densed with the benzocyclobutene (138) to give (1 39; R = Br) which was then converted into (139; R = NO2) by iodine and silver nitrite. This nitro-compound cyclized at 120 “Cto (140) which on treatment with sodium methoxide and titanium trichloride gave the ketone (141). The ketone was reduced to ( +)-chelidonine (142; R = Me) by aluminium hydride and converted into (+)-norchelidonine (142; R = H) by sodium borohydride followed by hydrolysis.414 Following preliminary work on less substituted the amide (143) was photo-cyclized to a mixture of the lactams (144) and (145) of which (144) was oxidized to the acetoxy-compound (146) with lead tetra-acetate.The acetoxy-compound was hydrolysed and oxidized to the quinone (147) which was reduced with lithium aluminium hydride and catalytically to the diol(148; R1= R2 = H). This was converted successively into (148; R1 = MeSO, R2 = H) and (148; R1= MeS02 R2 = Ac) and the last of these was converted (by potassium hydroxide in methanol) into (149; R = OMe) which gave (+)-homocheli- donine (149; R = H) on hydrogen~lysis.~~~ Improvements in 91 C02Me I ‘Me Ld (1 37) \ri ‘Me (145) P I MeO&A:e Me0 methods of preparation of intermediates for the synthesis of bases of this group have been p~blished.~l~*~l~ The conver- sions of protopine N-oxide into sanguinarine and of allocrypto- pine N-oxide into chelerythrine are discussed in Section 10.20 Colchicine N-Acetoacetyl-N-deacetylcolchicinehas been isolated from Colchicum ~utumnale.~~ has been [ l-rne~ho~y-~~C]Colchicine prepared.420 N-Deacetyl-N-formylcolchicinehas been con-verted (by treatment with ammonium hydroxide) into N-deacetyl-N-formylcolchiceinamide,which has been found to have anti-tumour activity.42 Several analogues of colchicine have been prepared and tested as antileukaemic agents.422 The products of interaction of deacetylcolchicine and of colchifo- line with diacetyldihydrofluorescein have been found to be useful in producing coloured products with other compounds and this is useful in t.1.c.for the detection of these other compounds. 24 The neurotoxicity of colchicine has been as have the effects of the alkaloid on the eye,424v425 on ocular diseases,426 on the retention of on the effects of mutagens,428 on lymphocytotoxic functions,429 on the activity of pho~phatase,~~~ on the formation of peritoneal adhesions,431 on the hypothalamus,432 on on odontoblast and on amyloid~sis.~~~ The carcinogenic action of ~olchemid~~~ and the use of colchemid in an assay for mitotic poisons437 have also been studied.92 21 References I G. 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ISSN:0265-0568
DOI:10.1039/NP9850200081
出版商:RSC
年代:1985
数据来源: RSC
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