Progress in the Chemist17 of Organie Natural Produets 63

Transcription

1

2 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

3 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 by Springer-Verlag/Wien Softcover reprint of the hardcover 1st edition 1994 Library of Congress Catalog Card Number AC Typesetting: Macmillan India Ltd., Bangalore-25 Printed on acid free and chlorine free bleached paper ISSN ISBN-13: e-isbn-13: DOl: /

4 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 Ultraviolet Absorption Spectra 2. Infrared Spectra Nuclear Magnetic Resonance Spectra (a) lh-nmr Spectra.. (b) 13C-NMR Spectra Mass Spectra 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 Minabeolides Withametelin, Isowithametelin, Secowithametelin and Withametelin B Daturataturins A and B Withasomniferin A and 5-Dehydroxywithanolide R 5. Daturametelins D, E, F and G. 6. Withacoagin Sominone and Sominolide 8. Withanolide Y.. 9. Withaperuvin H Physagulin C laborosalactol M and laborosalactone M 12. laboromagellone

5 VI Contents B. Ring A Aromatic Withanolides laborol laborosalactone Q.... C. Ring D Aromatic Withanolide Salpichrolide A.... D. Ixocarpalactones Trechonolide A laborosalactone P Taccalonolides A and B.... E. Physalins Physalins Land M.... F. Acnistins Tubocaposides A and B.... Addendum.... Structure Formulas.... References Clerodane Diterpenes in Labiatae. By L. RODRiGUEZ-HAHN, B. ESQUIVEL, and 1. CARDENAS.... I. Introduction.... II. Clerodane Diterpenes. 1. Ajuga Species Scutellaria Species Teucrium Species.... Absolute Stereochemistry of Clerodane Diterpenoids from Teucrium Species Salvia Species Leonurus and Stachys Species III. Biological Activity.... Acknowledgement.... Table I. Distribution of Clerodane Diterpenoids in Teucrium sp. Addendum.. References.... Author Index... Subject Index

6 List of Contributors CARDENAS, J., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, Mexico, D.F., Mexico. ESQUIVEL, B., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, Mexico, D.F., Mexico. GUPTA, Dr. M., Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi , India. RAY, Prof. A. B., Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi , India. RODRiGUEZ-HAHN, Prof. Dr. 1., Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, Mexico. D.F., Mexico.