Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
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Progress in the Chemist~ of Organie Natural Produets
44 Founded by L. Zeehmeister Edited by W. Hen, H. Griseb"eh,G. W. Kirby
Authors: J. G. Buehanan, P. Crews, B. Epe, Fe J. EVllns, F. J. Hllnke, L. V. Milnes, A. Mondon, S. NII~lo.., s. E. Ta~lo..
Springer-Verlag Wien New York
198]
Dr. W. HERZ, Professor of Chemistry, Department of Chemistry, The Florida State University, Tallahassee, Florida, U. S. A. Pro!. Dr. H. GRISEBACH, Biologisches Institut II, Lehrstuhl fUr Biochemie der Pflanzen, Albert-Ludwigs-Universitat, Freiburg i. Br., Federal Republic of Germany G. W. KIRBY, Sc. D., Regius Professor of Chemistry, Chemistry Department, The University, Glasgow, Scotland
With 72 partly coloured Figures
This work is subject to copyright All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks
© 1983 by Springer-VerlagjWien Sorteover reprint or the hardcover 15t edition 1983 Library of Congress Catalog Card Number AC 39-1015
ISSN 0071-7886 ISBN 978-3-7091-8716-6 ISBN 978-3-7091-8714-2 (eBook) DOI 10.1007/978-3-7091-8714-2
Contents List of Contribntors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..
IX
Pro-Inflammatory, Tnmonr-Promoting and Anti-Tumour Diterpenes of the Plant Families Euphorbiaceae and Thymelaeaceae. By F. J. EVANS and S. E. TAYLOR ......... .
I. Introduction..........................................................
2
II. Classification of Structural Types. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3
III. Botanical Considerations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . I. The Family Euphorbiaceae . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. The Family Thymelaeaceae. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4 4 5
IV. Biosynthetic Relationships. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
6
V. Isolation of Diterpenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
9
VI. The Macrocyclic Diterpenes ............................................ 1. Casbane Type. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 2. J atrophane Type. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 3. Lathyrane Type .................................................... 4. Jatropholane and Crotofolane Types .................................. 5. Rhamnofolane .....................................................
13 13 13 16 25 26
VII. Tigliane Diterpenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 1. Phorbol and Its Esters. . .