ISSN 0265-0568 NPRRDF 10 1-1-1-68 (1993) Natural Product Reports A journal of current developments in bio-organic chemistry Volume I0Indexes CONTENTS ... 111 Preliminary pages for Volume 10 1-1 Index of Authors Cited 1-39 Subject Index ISSN 0265-0568 Coden NPRRDF Natural Product Reports A journal of current developments in bio -organic chemistry Volume 10 1993 The Royal Society of Chemistry Cambridge Natural Product Reports (ISSN 0265-0568) @ The Royal Society of Chemistry 1994 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 Great Britain by the University Press Cambridge ISSN 0265-0568 NPRRDF 10 1-632 l-l-l-68(1993) Natural Product Reports A journal of current developments in bio -organic chemistry Volume 10 CONTENTS 1 Lignans Neolignans and Related Compounds R. S. Ward Reviewing the literature published between January 1989 and December 1991 29 Muscarine Oxazole Imidazole Thiazole and Peptide Alkaloids and Other Miscellaneous Alkaloids J. R. Lewis Reviewing the literature published between July 1990 and June 1991 51 Indolizidine and Quinolizidine Alkaloids J. P. Michael Reviewing the literature published between July 1990 and June 1991 71 Microbial Pyran-2-ones and Dihydropyran-2-ones J. M. Dickinson Reviewing the literature up to December 1991 99 Quinoline Quinazoline and Acridone Alkaloids J.P. Michael Reviewing the literature between July 1990 and June 1991 109 The Chemistry of Azadirachtin S. V. Ley A. A. Denholm and A. Wood 159 Diterpenoids J. R. Hanson Reviewing the literature published in 1991 175 Chemical and Biochemical Manipulations of Nucleic Acids 199 Tropane Alkaloids G. Fodor and R. Dharanipragada Reviewing the literature between January and December 1991 207 NMR of Proteins M. P. Williamson 233 The Biosynthesis of Shikimate Metabolites P. M. Dewick Reviewing the literature published during 1991 M. J. McPherson and J. H. Parish 265 Biological Variation of Microbial Metabolites by Precursor-directed Biosynthesis J. Rohr R. Thiericke and 29 1 Amaryllidaceae and Sceletium Alkaloids J.R. Lewis Reviewing the literature published during 1991 301 Stevioside and Related Sweet Diterpenoid Glycosides J. R. Hanson and B. H. De Oliveira Reviewing the literature published up to May 1992 311 Obituary David N. Kirk 1929-1992 313 Steroid Reactions and Partial Synthesis Reviewing the literature published in 1991 J. R. Hanson 327 Advances in Chemical Ecology J. B. Harborne Reviewing the literature published between January 1988 and June 1992 NATURAL PRODUCT REPORTS 1993 CONTENTS 349 Recent Progress in the Chemistry of Indole Alkaloids and Mould Metabolites J. E. Saxton Reviewing the literature published between July I991 and June I992 397 Natural Sesquiterpenoids B. M. Fraga Reviewing the literature published during 1991 421 Arsenic Compounds from Marine Organisms J.S. Edmonds K. A. Francesconi and R. V. Stick Reviewing the literature published up until October 1992 429 Macrocyclic Trichothecenes J. F. Grove Reviewing the literature published up to December 199I 449 P-Phenylethylamines and the Isoquinoline Alkaloids K. W. Bentley Reviewing the literature published between July 1991 and June 1992 471 Diterpenoid Alkaloids M. S. Yunusov Reviewing the literature published between December I989 and January 1992 487 Pyrrolizidine Alkaloids D. J. Robins Reviewing the literature published between July 1991 and June 1992 497 Marine Natural Products D. J. Faulkner Reviewing the literature published during 1991 541 HMG-CoA Reductase Inhibitors A.Endo and K. Hasumi Reviewing the literature published up to October 1992 551 A Survey of Natural Products which Abstract Hydrogen Atoms from Nucleic Acids J. A. Murphy and J. Griffiths 565 The Strobilurins Oudemansins and Myxothiazols Fungicidal Derivatives of P-Methoxyacrylic Acid J. M. Clough 575 The Biosynthesis of Plant Alkaloids and Nitrogenous Microbial Metabolites R. B. Herbert Reviewing the literature published between January and December 199I 593 Biosynthesis of Fatty Acid and Polyketide Metabolites D. O’Hagan Reviewing the literature published between mid- 1991 and mid- I992 625 Cumulative Contents Volumes 1-10 Natural Product Reports Editorial Board Professor T. J. Simpson (Chairman) University of’ Bristol Dr C.Abell University of’ Cambridge Dr J. R. Hanson University of’ Sussex Dr R.B. Herbert University 01 ’ Leeds Professor J. Mann University of’ Reading Dr D. A. Whiting University 01 ’ Nottingham ~ ~~ Natural Product Reports is a bimonthly journal of critical reviews. It aims to foster progress in the study of bio-organic chemistry by providing regular and comprehensive reviews of the relevant literature published during well-defined periods. Topics include the isolation structure biosynthesis and chemistry of the major groups of natural products -alkaloids terpenoids and steroids aliphatic aromatic and 0-heterocyclic compounds. Many reviews provide details of biological activity and wider aspects of bio-organic chemistry including developments in enzymology genetics and structural spectroscopic and chromatographic methods of general interest to all workers in the area.Articles in Natural Product Reports are commissioned by members of the Editorial Board or accepted by the Chairman for consideration at meetings of the 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 Thomas Graham House Science Park Milton Road Cambridge CB4 4WF and marked for the attention of the Senior Editor Reviews. Contributors to Volume 10 Bentley K. W. 449 Fraga B. M. 397 Murphy J. A. 551 Clough J. M. 565 Francesconi K. A. 421 O’Hagan D. 593 Denholm A. A. 109 Griffiths J. 551 Parish J.H. 175 De Oliveira B. H. 301 Grove J. F. 429 Robins D. J. 487 Dewick P. M. 233 Hanson J. R. 159 301 313 Rohr J. 265 Dharanipragada R. 199 Harborne J. B. 327 Saxton J. E. 349 Dickinson J. M. 71 Hasumi K. 541 Stick R. V. 421 Edmonds J. S. 421 Herbert R. B. 575 Thiericke R. 265 Endo A. 541 Lewis J. R. 29 291 Ward R. S. 1 Faulkner D. J. 497 Ley S. V. 109 Williamson M. P. 207 Fodor G. 199 McPherson M. J. 175 Wood A. 109 Michael J. P. 51 99 Yunusov M. S. 471 Nomenclature It is the policy of The Royal Society of Chemistry to en-courage the use of IUPAC and IUB Recommendations on nomenclature. Although many of the appropriate nomen-clature documents are included in the new edition of the IUB publication ‘Biochemical Nomenclature and Related Documents ’ (published by The Biochemical Society London 1992) a selection of recent Recommendations that will be of particular interest to those who investigate 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 Sections A B C D E F and H’ 1979 Edition] 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 I) Pure Appl. Chem. 1983 55 721-726; Eur. J. Biochem. 1982 129 1-5. Nomenclature of vitamin D (Recommendations I98 I) Pure Appl. Chem. 1982 54 1511-1516; Eur. J. Biochem. 1982 124 223-227. Nomenclature of tocopherols and related compounds (Recommendations 1981) Pure Appf. 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 485486. 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 439441. Abbreviated terminology of oligosaccharide chains (Recommendations 1980) Pure Appf.Chem. 1982 54 1517-1522; Eur. J. Biochem. 1982 126 433437. 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 Appf.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). The most recent of the lists of restriction endonucleases and their isoschizomers (updated annually) is R. J. Roberts and D. Macelis Nucl. Acids Res. 1991 19 2077-2109. Recent codes of nomenclature for organisms include ‘International Code of Nomenclature of Bacteria and Statutes of the International Committee on Systematic Bacteriology (1 989 Revision)’ ed. P. H. A. Sneath V. B. D. Skerman and V. McGowan American Society for Microbiology Washington D.C. U.S.A. 1976. [Appendix 2 of this publication (Approved Lists of Bacterial Names) appeared in Int.J. Syst. Bucteriof. 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 Federal Republic of 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 U.K. and the California Press Berkeley and Los Angeles U.S.A. 1985.