167 Topics in Current Chemistry
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1 167 Topics in Current Chemistry
2 Marine Natural Products - Diversity and Biosynthesis Editor: Paul J. Scheuer With contributions by B. J. Baker, C.W J. Chang, G. Cimino, W H. Gerwick, R. G. Kerr, D. G. Nagle, F! J. Proteau, I? J. Scheuer, G. Sodano With 10 Figures and 7 Tables Springer-Verlag Berlin Heidelberg NewYork London Paris Tokyo Hong Kong Barcelona Budapest
3 This series presents critical reviews of the present position and future trends in modern chemical research. It is addressed to all research and industrial chemists who wish to keep abreast of advances in their subject. As a rule, contributions are specially commissioned. The editors and publishers will, however, always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics in Current Chemistry in English. ISBN Springer-Verlag Berlin Heidelberg New York ISBN O Springer-Verlag New York Berlin Heidelberg Library of Congress Catalog Card Number This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitations, broadcasting, reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions ofthe German Copyright Law, of September 9,1965, in its current version. and permission for use must always be obtained from Springer-Verlag. Violations are liable for prosecution under the German Copyright Law. ~1 Springer-Verlag Berlin Heidelberg 1993 Printed in Germany The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore for general use. Typesetting: Macmillan India Ltd., Bangalore- Printing: Saladruck, Berlin, Binding: Liideritr & Bauer, Berlin 51/ Printed on acid-free paper
4 Guest Editor Prof. Paul J. Scheuer Department of Chemistry University of Hawaii at Manoa Honolulu, HI USA Editorial Board Prof. Dr. Michael J. S. Demur Department of Chemistry, The University of Texas Austin, TX 78712, USA Prof. Dr. Jack D. Dunitz Laboratorium fiir Organische Chemie der Eidgendssischen Hochschule UniversitPtsstraBe 6/8, CH-8006 Ziirich Prof. Dr. Klaus Hafner Institut fiir Organ&he Chemie der TH Petersenst&e 15, Darmstadt, FRG Prof. Dr..?hB It6 Faculty of Pharmaceutical Sciences Tokushima Bunri University Tokushima 770/Japan Prof. Dr. Jean-Marie Lehn Institut de Chimie, Universitt de Strasbourg 1, rue Blaise Pascal, B. P. Z 296/R& F Strasbourg-Cedex Prof. Dr. Kenneth N. Raymond Department of Chemistry, University of California, Berkeley, California 94720, USA Prof. Dr. Charles W. Rees Hofmann Professor of Organic Chemistry, Department of Chemistry, Imperial College of Science and Technology, South Kensington, London SW7 2AY, England Prof, Dr. Joachim Thiem Institut fiir Organische Chemie, Universitlt Hamburg Martin-Luther-King-Platz 6,20146 Hamburg, FRG Prof. Dr. Fritz Viigtle Institut ftir Organische Chemie und Biochemie. der Universitxt, Gerhard-Domagk-Str. 1, Bonn, FRG
5 Preface Marine Natural Products - Diversity and Biosynthesis contains four chapters, which review some of the most lively research topics in the field, all written by active contributors. Steroid chemistry, the glamor area of natural product research in the years following World War II, was replaced by macrolides, alkaloids, and prostanoids. Sterol chemistry again became exciting when an unanticipated rich diversity of marine invertebrate sterols were isolated, notably from sponges. After pioneering research in Italy, the field was reborn in Carl Djerassi's laboratory at Stanford. As a result, we now have a better and more detailed knowledge of sterol biosynthesis than of any other class of marine natural products. The authors of Chapter 1 are Stanford alumni. Naturally occurring isocyano compounds are no longer an oddity since their frequent isolation from members of the class of Demospongiae. Their biogenesis has intrigued chemists ever since the first terrestrial isocyano compound (an amino-acid derivative) was described from a micro-organism. All known marine isocyano compounds are terpenoid and their biosynthesis continues to pose an unsolved problem, which is discussed in Chapter 2. Early natural product research with marine mollusks supported a conclusion that all secondary metabolites of mollusks are diet-derived, which proved to be premature. In fact, the biosynthetic capability of some marine mollusks covers a wide spectrum of chemical classes and substances. Much of this recent insight has resulted from work in the laboratories of the authors of Chapter 3. Oxylipin is a term that has not yet fully entered the scientific vocabulary. Indeed, a new word for oxidized fatty acid-derived compounds was needed, as the older terms - prostanoids, eicosanoids - proved to be too narrow for an ever-widening spectrum of discoveries. Much of this research has come from the laboratory of the authors of Chapter 4. Their account demonstrates the
6 Preface diversity and highlights some of the unique biosynthetic pathways of oxylipins. I should like to thank all authors for their contributions and Springer-Verlag for including the volume in their Topics in Current Chemistry series. Honolulu, April 1993 Paul J. Scheuer VIII
7 Table of Contents Biosynthesis of Marine Sterols B.J. Baker, R.G. Kerr... Marine Isocyano Compounds C.W.J. Chang, P.J. Scheuer... Biosynthesis of Secondary Metabolites in Marine Molluscs G. Cimino, G. Sodano... Oxylipins from Marine Invertebrates W.H. Gerwick, D.G. Nagle, P.J. Proteau... Author Index Volumes
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