ISSN 0265-0568 NPRRDF 14 1-1-1-94 (1997) Natural Product Reports A journal of current developments in bioorganic chemistry Volume 14 Indexes CONTENTS ... 111 Preliminary pages for Volume 14 1-1 Subject index 1-47 Index of authors cited ISSN 0265-0568 Coden NPRRDF Natural Product Reports A journal of current developments in bioorganic chemistry Volume 14 1997 The Royal Society of Chemistry Cambridge Natural Product Reports (ISSN 0265-0568) 0 The Royal Society of Chemistry 1998 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.Printed in the UK by Henry Ling Ltd at the Dorset Press Dorchester Dorset ISSN 0265-0568 NPRRDF 14 1-1-1-94 (1997) Natural Product Reports A journal of current developments in bioorganic chemistry Volume 14 CONTENTS 1 Brassinosteroids Shozo Fujioka and Akira Sakurai 11 Quinoline quinazoline and acridone alkaloids Joseph P. Michael Reviewing the literature published between July 1994 and June 1995 21 Indolizidine and quinolizidine alkaloids Joseph P. Michael Reviewing the literature published between July 1994 and June 1995 43 Lignans neolignans and related compounds Robert S. Ward Reviewing the literature published between January 1994 and December 1995 75 Cyclopeptide alkaloids Dimitris C. Gournelis Gregory G. Laskaris and Robert Verpoorte Reviewing the literature published between January 1985 and December 1995 83 Recent advances in chemical ecology Jeffrey B.Harborne Reviewing the literature published between July 1992 and December 1995 99 The role of carbohydrates in biologically active natural products Alexander C. Weymouth-Wilson 111 The biosynthesis of C5-CZ5 terpenoid compounds Paul M. Dewick Reviewing the literature published between 1993 and 1995 145 Natural sesquiterpenoids Braulio M. Fraga Reviewing the literature published in 1995 163 Fatty acids fatty acid analogues and their derivatives Marcel S. F. Lie Ken Jie Mohammed Khysar Pasha and M. S. K. Syed-Rahmatullah Reviewing the literature published between 1988 and 1995 191 Diterpenoid and steroidal alkaloids Atta-ur-Rahman and M.Iqbal Choudhary Reviewing the literature between mid-1994and the beginning of 1996 205 Synthesis of amino acids incorporating stable isotopes Nicholas M. Kelly Andrew Sutherland and Christine Willis Reviewing the literature published between 1990 and mid 1996 221 The biosynthesis of the gibberellin plant hormones Jake MacMillan Reviewing the literature published up to September 1996 245 Diterpenoids James R. Hanson Reviewing the literature published in 1995 259 Marine natural products D. John Faulkner Reviewing the literature published in 1995 303 Amaryllidacae alkaloids John R. Lewis Reviewing the literature published in 1995 309 Chemistry and biosynthesis of clavulanic acid and other clavams Keith H.Baggaley Allan Brown and Christopher J. Schofield 335 Biosynthesis of fatty acids and related metabolites Bernard J. Rawlings Reviewing the literature published up to the end of 1994 359 Biosynthesis of plant alkaloids and nitrogenous microbial metabolites Richard B. Herbert Reviewing the literature published in 1995 373 Steroids reactions and partial synthesis James R. Hanson Reviewing the literature published in 1995 387 Phenethylamine and isoquinoline alkaloids Kenneth W. Bentley Reviewing the literature published between July 1995 and June 1996 413 Recent progress in the chemistry of non-monoterpenoid indole alkaloids Masataka Ihara and Keiichiro Fukumoto Reviewing the literature published between July 1995 and June 1996 43 1 Book review Analysis of steroids by L.John Gould and Toshihiro Akihisa (reviewed by James R. Hanson) 432 Corrigendum 433 Natural products derived from unusual variants of the shikimate pathway Heinz G. Floss 453 Secondary metabolites from marine microorganisms bacteria protozoa algae and fungi Francesco Pietra 465 Coumarins Ana Estkvez-Braun and Antonio G. Gonzalez Reviewing the literature published between January 1995 and December 1996 477 Monoterpenoids David H. Grayson Reviewing the literature published in part of 1993 all of 1994 and part of 199.5 523 Biosynthesis of polyketides Bernard J. Rawlings Reviewing the literature published from mid 1993 to the end of 1994 557 Book review Biochemical aspects of marine pharmacology eds. P. Lazarovici M.E. Spira and E. Zlotkin (reviewed by John Mann) 558 Corrigendum 559 Recent progress in the chemistry of the monoterpenoid indole alkaloids J. Edwin Saxton Reviewing the literature published in 1996 591 Isopentenyl diphosphate isomerase a core enzyme in isoprenoid biosynthesis. A review of its biochemistry and function Ana C. Ramos-Valdivia Robert van der Heijden and Robert Verpoorte 605 Quinoline quinazoline and acridone alkaloids Joseph P. Michael Reviewing the literature published between July 1995 and June 1996 619 Indolizidine and quinolizidine alkaloids Joseph P. Michael Reviewing the literature published betweerz July 1995 and June 1996 637 Pyrrole pyrrolidine pyridine piperidine azepine and tropane alkaloids Reviewing the literature published between 1995 and 1996 653 Pyrrolizidine alkaloids J.Richard Liddell Reviewing the literature published in 1995 66 1 Triterpenoids Joseph D. Connolly and Robert A. Hill Reviewing the literature published between July 1995 and June 1996 David O’Hagan 681 Book review Phytochemical diversity. A source of new industrial products eds. S. Wrigley M. Hayes, R. Thomas and E. Chrystal (reviewed by David O’Hagan) The Royal Society of Chemistry Natural Product Reports Editorial Board International Advisory Board Professor T. J. Simpson (Bristol) Chair Dr S. J. Gould (Rahway NJ) Dr S. L. Flitsch (Edinburgh) Professor H. G. Floss (Washington OR) Dr J. R. Hanson (Sussex) Professor L. N. Mander (Canberra) Dr R. B. Herbert (Leeds) Professor K.Mori (Tokyo) Professor G. Hofle (GBF Germany) Professor J. Mann (Reading) Dr D. O’Hagan (Durham) Professor D. J. Robins (Glasgow) Dr C. J. Schofield (Oxford) Professor J. C. Vederas (Edmonton Canada) Dr D. A. Whiting (Nottingham) ~~~~~ Editorial Staff Publishing Editorial Staff Production Dr Sheila R. Buxton Managing Editor Miss Nicola P. Coward Editorial Production Dr Roxane M. Owen Deputy Editor Coordinator Mrs Dawn J. Webb Editorial Secretary Dr Camel M. McNamara Technical Editor Editorial Office The Royal Society of Chemistry Tel +44 (0) 1223 420066 Thomas Graham House Fax +44(0) 1223 420247 Science Park Cambridge E-mail perkin@rsc.org UK CB4 4WF RSC Server http://chemistry.rsc.org/rsc/ Advertisement sales Tel +44(0) 1223 432240.Fax +44 (0) 1223 426017 Information for Authors Natural Product Reports is a bimonthly journal of critical reviews. It aims to foster progress in the study of bioorganic chemistry by providing regular and comprehensive reviews of the relevant literature published during well-defined periods. Topics include the isolation structure biosynthesis biological activity and chemistry of the major groups of natural products -alkaloids terpenoids and steroids aliphatic aromatic and O-heterocyclic compounds. This is augmented by frequent reviews of the wider context of bioorganic chemistry including developments in enzymology nucleic acids genetics chemical ecology primary and secondary metabolism and isolation and analytical techniques which will be of general interest to all workers in the area.Articles in Natural Product Reports are generally commissioned by members of the Editorial Board but the Society is always prepared to consider offers of articles for publication. In such cases a short synopsis rather than the completed article should be submitted to the Managing Editor ar the address given above. Contributors to Volume 14 Atta-ur-Rahman 191 Baggaley Keith H. 309 Bentley Kenneth J. 387 Brown Allan 309 Grayson David H. 477 Hanson James R. 245 373 431 Harborne Jeffrey B. 83 Herbert Richard B. 359 Pasha Mohammed Khyser 163 Pietra-Valdivia Ana C. 591 Rawlings Bernard J. 335 523 Sakurai Akira 1 Choudhary M. Iqbal 191 Connolly Joseph D. 661 Dewick Paul M. 111 EstCvez-Braun Ana 465 Faulkner D. John 259 Floss Heinz G. 433 Fraga Braulio M.145 Fujioka Shozo 1 Fukumoto Keiichiro 413 Hill Robert A. 6 Ihara Masataka 41 3 Kelly Nicholas M. 205 Laskaris Gregory G. 75 Lewis John R. 313 Liddell J. Richard 653 Lie Ken Jie Marcel S. F. 163 MacMillan Jake 22 1 Mann John 557 Saxton J. Edwin 559 Schofield Christopher J. 309 Sutherland Andrew 205 Syed-Rahmatullah M. S. K. 163 van der Heijden Robert 591 Verpoorte Robert 591 Ward Robert S. 43 Weymouth-Wilson Alexander C. 99 Willis Christine 205 Gonzalez Antonio G. 465 Gournelis Dimitris C. 75 Michael Joseph P. 11 21 605 619 O’Hagen David 637 681 Nomenclature It is the policy of The Royal Society of Chemistry to en- courage the use of IUPAC* and IUBMB* Recommendations on nomenclature. Many of the appropriate nomenclature documents are included in the following compilations.Compilations 1 Nomenclature of Organic Chemistry Sections A B C D E F and H 1979 edition a 550-page hardcover volume published in 1979 available from Pergamon Press Oxford. Section F of this volume covers general principles for the naming of natural products. 2 A guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993) a 182-page softcover volume published in 1993 available from Blackwell Scientific Publications Oxford to be used in conjunction with item 1. 3 Biochemical Nomenclature and Related Documents A Compendium 2nd edition 1992 a 348-page softcover manual published in 1992 by Portland Press Ltd for IUBMB and available from the publisher (59 Portland Place London W1N 3AJ UK). 4 Compendium of Chemical Terminology IUPAC Recommendations a 456-page volume published in 1987 available in hardcover and softcover from Blackwell Scientific Publications Oxford.Specific Recommendations A selection of specific recent recommendations [many of which are included in Biochemical Nomenclature and Related Documents see above] that will be of particular interest to those who investigate bioorganic chemistry or the chemistry occurrence or biosynthesis of natural products includes Extension of Rules A-1.1 and A-2.5 concerning numerical terms used in organic nomenclature (Recommendations 1986) Pure Appl. Chem. 1986 58 1693-1696. [The original versions of these Rules are in Nomenclature of Organic Chemistry 1979 edition see above] Nomenclature of steroids (Recommendations 1989) Eur.J. Biochem. 1989 186 429-458. Nomenclature of tetrapyrroles (Recommendations 1986) Pure Appl. Chem. 1987 59 779-832. Nomenclature and symbols for folic acid and related compounds (Recommendations 1986) Pure Appl. Chem. 1987 59 833-836; Eur. J. Biochem. 1987 168 251-253. Nomenclature of prenols (Recommendations 1986) Pure Appl. Chem. 1987 59 683-689; Eur. J. Biochem. 1987 167 181-184. Nomenclature of retinoids (Recommendations 198 l) Pure Appl. Chem. 1983 55 721-726; Eur. J. Biochem. 1982 129 1-5. Nomenclature of vitamin D (Recommendations 1981) Pure Appl. Chem. 1982 54 1511-1516; Eur. J. Biochem. 1982 124 223-227. Nomenclature of tocopherols and related compounds (Recommendations 1981) Pure Appl.Chem. 1982 54 1507-1510; Eur. J. Biochem. 1982 123 473-475. Recommendations for the presentation of thermodynamic and related data in biology (1985) Eur. J. Biochem. 1985 153 429434. Enzyme Nomenclature (Recommendations 1984) Supplement 1 Corrections and additions Eur. J. Biochem. 1986 157 1-26. Enzyme Nomenclature 1992 (Recommendations of the Nomenclature Committee of the International Union of Biochemistry on the nomenclature and classification of enzyme- catalysed reactions) Academic Press Orlando Florida 1992. Nomenclature for multienzymes (Recommendations 1989) Eur. J. Biochem. 1989 185 485-486. Symbolism and terminology in enzyme kinetics (Recommendations 1981) Eur. J. Biochem. 1982 128 281-291. Symbols for specifying the conformation of polysaccharide chains (Recommendations 1981) Pure Appl.Chem. 1983 55 1269-1272; Eur. J. Biochem. 1983 131 5-7. Polysaccharide nomenclature (Recommendations 1980) Pure Appl. Chem. 1982 54 1523-1526; Eur. J. Biochem. 1982 126 439-441. Abbreviated terminology of oligosaccharide chains (Recommendations 1980) Pure Appl. Chem. 1982 54 1517-1522; Eur. J. Biochem. 1982 126 433-437. Nomenclature of glycoproteins glycopeptides and peptidoglycans (Recommendations 1985) Eur. J. Biochem. 1986 159 1-6. Nomenclature and symbolism for amino acids and peptides (Recommendations 1983) Pure Appl. Chem. 1984 56 595-624; Eur. J. Biochem. 1984 138 9-37 (see also Eur. J. Biochem. 1985 152 1 and the Newsletter 1985 of NC-IUB and JCBN ibid.1985 146 pp. 238 and 239 and the Newsletter 1986 ibid. 1986 154 pp. 485 and 486). Nomenclature for incompletely specified bases in nucleic acid sequences (Recommendations 1984) Eur. J. Biochem. 1985 150 1-5 (see also Eur. J. Biochem. 1986 157 1). Abbreviations and symbols for the description of conformations of polynucleotide chains (Recommendations 1982) Pure Appl. Chem. 1983 55 1273-1280; Eur. J. Biochem. 1983 131 9-15 (see also the Newsletter 1984 of NC-IUB and JCBN Eur. J. Biochem. 1984 138 p. 7). A list of restriction endonucleases and their isoschizomers (updated annually) is given in R. J. Roberts and D. Macelis Nucleic Acids Res. 1991 19 2077-2109. Glossary for chemists of terms used in biotechnology Pure Appl. Chem.1992 64,143. Selection of terms symbols and units related to microbial processes Pure Appl. Chem. 1992 64 1047. Organism Nomenclature Recent codes of nomenclature for organisms include International Code of Nomenclature of Bacteria and Statutes of the International Committee on Systematic Bacteriology (I989 Revision) ed. P. H. A. Sneath V. B. D. Skerman and V. McGowan American Society for Microbiology Washington DC USA 1976. [Appendix 2 of this publication (Approved Lists of Bacterial Names) appeared in Int. J. Syst. Bacteriol. 1989 39.1 International Code of Botanical Nomenclature (1988) ed. W. Greuter H. M. Burdett W. G. Chaloner V. Demoulin R. Grolle D. L. Hawksworth D. H. Nicholson P. C. Silva F. A. Stafleu E. G. Voss and J. McNeill Koeltz Scientific Books Konigstein Germany 1988.International Code of Zoological Nomenclature 3rd edn ed. W. D. L. Ride C. W. Sabrosky G. Bernardi R. V. Melville J. 0. Corliss J. Forest K. H. L. Key and C.W. Wright International Trust for Zoological Nomenclature in association with the British Museum (Natural History) London UK and the California Press Berkeley and Los Angeles USA 1985. * IUPAC International Union of Pure and Applied Chemistry. IUBMB International Union of Biochemistry and Molecular Biology.