ISSN 0265-0568 NPRRDF 5 1-1-1-74 (1996) Natural Product Reports A journal of current developments in bioorganic chemistry Volume 13 Indexes CONTENTS ... 111 Preliminary pages for Volume 13 1-1 Index of authors cited 1-37 Subject index ISSN 0265-0568 Coden NPRRDF Natural Product Reports A journal of current developments in bioorganic chemistry Volume 13 1996 The Royal Society of Chemistry Cambridge ~~ ~~~~~~~ Natural Product Reports (ISSN 0265-0568) @ The Royal Society of Chemistry 1997 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 13 1-468; 1-1-1-74 (1996) Natural Product Reports A journal of current developments in bioorganic chemistry Volume 13 CONTENTS 1 Modern Bioassays using Metal Chelates as Luminescent Probes Peter G. Sammes and Gokhan Yahioglu 29 The DAP Pathway to Lysine as a Target for Antimicrobial Agents Russell J. Cox Revietving the literature published up to September 1995 45 The Biosynthesis of Plant Alkaloids and Nitrogenous Microbial Metabolites Richard B. Herbert Reviewing the literature published in 1994 59 Diterpenoids James R. Hanson Reviewing the literature published in 1994 73 Book Reviews Anticancer Drugs from Animals Plants and Microorganisms by George R.Pettit Fiona H. Pierson and Cherry L. Herald (reviewed by John Mann); Oxidative Stress and Antioxidant Defenses in Biology ed. S. Ahmad (reviewed by David J. Robins); Advances in Nitrogen Heterocycles (Volume I) ed. C. J. Moody (reviewed by Joseph P. Michael) 75 Marine Natural Products D. John Faulkner Revierzing the literature published in 1994 127 P-Phenylethylamines and the Isoquinoline Alkaloids Kenneth W. Bentley Reviewing the literature published between July 1994 and June 1995 151 Triterpenoids Joseph D. Connolly and Robert A. Hill Reviewing the literature published in 1994 171 Amaryllidaceae and Sceletium Alkaloids John R. Lewis Revierving the literature published in I994 177 The Biosynthesis and Degradation of Thiamin (Vitamin B,) Tadhg P.Begley Reviewing the literature published between January 1986 and January 1996 187 Pyrrolizidine Alkaloids J. Richard Liddell Reviewing the literature published between July 1994 and June 1995 195 Monoterpenoids David H. Grayson Reviewing the literature published in 1991 1992 and part of 1993 227 Steroids Reactions and Partial Synthesis James R. Hanson Revieit'ing the literature published in 1994 24 1 Recent Progress in the Chemistry of Non-monoterpenoid Indole Alkaloids Masataka Ihara and Keiichiro Fukumoto Reviewing the literature published between July 1994 and June 1995 263 Book Review Enzyme Catalysis in Organic Synthesis A Comprehensive Handbook by K. Drauz and H. Waldmann (reviewed by David R. Kelly) 265 Dietary Antioxidants in Disease Prevention Michael H.Gordon 275 Recent Advances in Annonaceous Acetogenins Lu Zeng Qing Ye Nicholas H. Oberlies Guoen Shi Zhe-Ming Gu Kan He and Jerry L. McLaughlin Reviewing the literature published up to January 1996 307 Natural Sesquiterpenoids Braulio M. Fraga Reviewing the literature published in 1994 327 Recent Progress in the Chemistry of the Monoterpenoid Indole Alkaloids J. Edwin Saxton Reviewing the literature published between July 1994 and December 1995 365 Decanolides 1O-membered Lactones of Natural Origin Gerald Drager Andreas Kirschning Ralf Thiericke and Marion Zerlin Reviewing the literature published between 1975 and 1995 377 Natural Guanidine Derivatives Roberto G. S. Berlinck Reviewing the literature published in 1994 and 1995 41 1 Oligomeric Proanthocyanidins Naturally Occurring O-Heterocycles Daneel Ferreira and Riaan Bekker Reviewing the literature published between January 1992 and December 1995 435 Muscarine Imidazole Oxazole Thiazole and Peptide Alkaloids and Other Miscellaneous Alkaloids John R.Lewis Reviewing the literature published between July 1993 and June 1994 469 The Glycopeptide Story -How to Kill the Deadly ‘Superbugs’ Dudley H. Williams 479 Catalytic Antibodies -Reaching Adolescence? Neil R. Thomas Reviewing the literature published up to the end of February 1996 513 Pigments of Fungi (Macromycetes) Melvyn Gill Reviewing the literature published between September 1992 and February I996 529 The Sesterterpenoids James R.Hanson Reviewing the literature published between November 1991 and March 1996 Natural Product Reports EditoriaJ Board Professor T. J. Simpson (Chairman) University of Bristol Dr J. R. Hanson University of Sussex Dr R. B. Herbert University of Leeds Professor J. Mann University of Reading Professor D. J. Robins University of Glasgow Dr C. J. Schofield University of Oxford Dr D. A. Whiting University of Nottingham Editorial Staff Editorial Office Dr Sheila R. Buxton The Royal Society of Chemistry Managing Editor Thomas Graham House Dr Roxane M. Owen Science Park Deputy Editor Milton Road Miss Nicoila P. Coward Cambridge Produeti0n Editor UK CB4 4WF Dr Carmel M. McNamara Telephone +44 (0) 1223 420066 Technical Editor Facsimile +44 (0) 1223 420247 Ms Dawn J.Webb E-mail perkin@rsc.org Miss Karen L. White RSC Server http://c hem ist ry.rsc.or g /rsc/ Editorial Secretaries 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 0-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 commissioned by members of the Editorial Board or accepted by the Chairman for consideration at meetings of the Board. Contributors to Volume 13 Begley. Tadhg P. 177 Gordon Michael H. 265 Oberlies Nicholas H. 275 Bekker Riaan 41 1 Bentley Kenneth W. 127 Berlinck Roberto G. S. 377 Grayson David H. 195 Gu Zhe-Ming 275 Hanson James R. 59 227 529 Sammes Peter G. 1 Saxton J. Edwin 327 Shi Guoen 275 Connolly Joseph D. 151 Cox Russell J. 29 Drager Gerald 365 Faulkner D. John 75 Ferreira Daneel. 41 1 Fraga Braulio M. 307 Fukumoto Keiichiro 241 Gill Melvyn 513 He Kan 275 Herbert Richard B.45 Hill Robert A. 151 Ihara Masataka 241 Kirschning Andreas 365 Lewis John R. 171 435 Liddell J. Richard 187 McLaughlin Jerry L. 275 Thiericke Ralf 365 Thomas Neil R. 479 Williams Dudley H. 469 Yahioglu Gokhan 1 Ye Qing 275 Zeng Lu 275 Zerlin Marion 365 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 TUBMB and available from the publisher (59 Portland Place London W1N 3AJ UK). 4 Compendium of Chemical Terminology IUPAC Recornmendations 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 I979 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..I. 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 198l) 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. Biochenz. 1985 153 429-434. 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. Biochenz.. 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 433437. Nomenclature of glycoproteins glycopeptides and peptidoglycans (Recommendations 1985) Eur. J. Biochenz. 1986 159 1-6. Nomenclature and symbolism for amino acids and peptides (Recommendations I983) Pure Appl. Chenz. 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. Biochenz. 1983 131 9-15 (see also the Newsletter 1984 of NC-IUB and JCBN Eur. J. Biochrm. 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 oj Nomenclature of Bacteria and Statutes oj the Internatiorial Committee on Systematic Bacteriology (1989 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 (I 988) 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.