Fortsehritte der Chemie organiseher Naturstoffe Progress in the Chemist17 of Organie Natural Produets 63 Founded ~ L Zeehmeister Edited ~ W. Berz, O. W. Kir~, R. E. Moore, W. Steglieh, and Ch. ramm Authors: J. Cardenas, B. Esquivel, M. Gupta, A. B. Ray, L. Rodriguez-Sahn Springer-Verlag Men New York 1994
Prof. W. HERZ, Department of Chemistry, The Florida State University, Tallahassee, Florida, U.S.A. Prof. G. W. KIRBY, Chemistry Department, The University, Glasgow, Scotland Prof. R. E. MOORE, Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, U.S.A. Prof. Dr. W. STEGLICH, Institut fiir Organische Chemie der Universitiit Miinchen, Miinchen, Federal Republic of Germany Prof. Dr. CH. TAMM, Institut fiir Organische Chemie der Universitiit Basel, Basel, Switzerland 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 machines or similar means, and storage in data banks. 1994 by Springer-Verlag/Wien Softcover reprint of the hardcover 1st edition 1994 Library of Congress Catalog Card Number AC 39-1015 Typesetting: Macmillan India Ltd., Bangalore-25 Printed on acid free and chlorine free bleached paper ISSN 0071-7886 ISBN-13:978-3-7091-9283-2 e-isbn-13:978-3-7091-9281-8 DOl: 10.1007/978-3-7091-9281-8
Contents List of Contributors....................... VII Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones. By A.B. RAY and M. GUPTA. I. Introduction.... A. Features of Withasteroids and Their Classification. B. Distribution of Withasteroids II. Structure Elucidation Methods.... A. Physical Methods.... 1. Ultraviolet Absorption Spectra 2. Infrared Spectra......... 3. Nuclear Magnetic Resonance Spectra (a) lh-nmr Spectra.. (b) 13C-NMR Spectra.... 4. Mass Spectra.... 5. Circular Dichroism Spectra. 6. X-Ray Crystallographic Methods. B. Degradative Reactions... C. Chemical Transformations.... D. Synthesis of Withanolides.... III. Biogenesis and Biosynthesis of Withasteroids. IV. Chemotypes and Chemogenetics.. V. Biological Activity of Withasteroids VI. Chemistry of With asteroids A. Withanolides....... 1. Minabeolides.... 2. Withametelin, Isowithametelin, Secowithametelin and Withametelin B....... 3. Daturataturins A and B.... 4. Withasomniferin A and 5-Dehydroxywithanolide R 5. Daturametelins D, E, F and G. 6. Withacoagin....... 7. Sominone and Sominolide 8. Withanolide Y.. 9. Withaperuvin H....... 10. Physagulin C........ 11. laborosalactol M and laborosalactone M 12. laboromagellone.... 2 3 6 14 14 14 15 16 16 25 31 37 38 40 45 47 52 55 56 59 59 59 60 63 64 64 66 67 67 68 69 69 70
VI Contents B. Ring A Aromatic Withanolides... 1. laborol..... 2. laborosalactone Q.... C. Ring D Aromatic Withanolide.... 1. Salpichrolide A.... D. Ixocarpalactones.... 1. Trechonolide A...... 2. laborosalactone P.... 3. Taccalonolides A and B.... E. Physalins.... 1. Physalins Land M.... F. Acnistins.... 1. Tubocaposides A and B.... Addendum.... Structure Formulas.... References............................. 71 71 72 74 75 76 76 78 78 80 81 93 Clerodane Diterpenes in Labiatae. By L. RODRiGUEZ-HAHN, B. ESQUIVEL, and 1. CARDENAS.... I. Introduction.... II. Clerodane Diterpenes. 1. Ajuga Species.............. 2. Scutellaria Species................................ 3. Teucrium Species.... Absolute Stereochemistry of Clerodane Diterpenoids from Teucrium Species.... 4. Salvia Species.... 5. Leonurus and Stachys Species III. Biological Activity.... Acknowledgement.... Table I. Distribution of Clerodane Diterpenoids in Teucrium sp. Addendum.. References.... Author Index... Subject Index........ 107 107 112 112 118 121 138 141 157 161 162 163 179 184 197 205
List of Contributors CARDENAS, J., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, 04510 Mexico, D.F., Mexico. ESQUIVEL, B., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, 04510 Mexico, D.F., Mexico. GUPTA, Dr. M., Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221 005, India. RAY, Prof. A. B., Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221 005, India. RODRiGUEZ-HAHN, Prof. Dr. 1., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, 04510 Mexico. D.F., Mexico.