The Alkaloids: Chemistry and Pharmacology 47 PDF
Preview The Alkaloids: Chemistry and Pharmacology 47
THE ALKALOIDS Chemistry and Pharmacology VOLUME 47 This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Pharmacology Edited by Geoffrey A. Cordell College of Pharmacy University of Illinois at Chicago Chicago, Illinois VOLUME 47 ACADEMIC PRESS San Diego New York Boston London Sydney Tokyo Toronto @ This book is printed on acid-free paper. Copyright 0 1995 by ACADEMIC PRESS, INC. All Rights Reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the publisher. Academic Press, Inc. A Division of Harcourt Brace & Company 525 B Street, Suite 1900, San Diego, California 92101-4495 United Kingdom Edition published by Academic Press Limited 24-28 Oval Road. London NW 1 7DX International Standard Serial Number: 0099-9598 International Standard Book Number: 0- 12-469547-7 PRINTED IN THE UNITED STATES OF AMERICA 95 96 9798 99 0 0 B B 9 8 7 6 5 4 3 2 1 CONTENTS CONTRIBUTO....R....S.... ................................ ........ ..... ... ... ....... ................................. ....... ...... ...... ............ .. ..... .. ........ vii PREFAC..E.... ........................................................................................................ .. . . . . .. . . . . . . . . . . . . . . . . . . . ....... ........ .... .. ix Lupine Alkaloids SHIGEROUH MIYAK,A ZUKIS AITOA, ND ISAMUM URAKOSHI I. Introduction ................... 2 11. Occurrence. .................... 3 111. Spectroscopy. ....... 3 IV. Common Lupine .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56 78 .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . 92 98 VIII. Biological Activity 100 100 105 Biosynthesis in Rauwolfia serpentina Modern Aspects of an Old Medicinal Plant JOACHIMS TOCKIGT I. Introduction ... 116 116 119 123 143 VI. Biotransformation with R. serpentina Cell Suspensions .................................... 150 VII. The Phytochemistry of a Rauwolfia “Hairy-Root’’ System 161 VIII. Hybrid Cell Cultures Generated by Fusion of Rauwolfia and Rhazya Protoplasts ..................... 163 165 166 XI. Conclusions and Future Prospects. ....................................... 167 References ...................... .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168 V vi CONTENTS Noniridoid Bisindole Alkaloids J . SAPIA ND G . MASSIOT I . Introduction ..................................................................... 173 I1. Bisindoles from the Marine Environment ................................................... 174 111. Bisindales from Microorganisms .................................................................. 186 IV . Alkaloids of Plant Origin ............ .......... 216 ................................................................................................ 221 The Ecological Activity of Alkaloids KEITHS . BROWNJR. . AND Jos6 ROBERTOT RIGO I . Introduction: Ecological Activities of Alkaloid Classes .................................... 227 I1 . Alkaloids as Mediators in Two-Trophic-Level Ecological Interactions .......... 268 I11 . Alkaloids as Mediators in Three- or Four-Trophic-Level Ecological Interactions .................................................................................. 295 IV . Nontrophic Ecological Interactions ........... ....................................... 311 V . Evolutionary Patterns of Alkaloids in Nature ............................. 316 VI . Final Remarks ......... .................. ....................................... 337 References ................................................. ....................................... 338 CUMULATIVINED EXO F TITLE.S.. ........................................................................................ 355 INDEX... .................................................................................................................................. 363 CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors' contributions begin. KEITHS . BROWNJ,R '. (227), Laboratbrio de Ecologia Quimica, Departa- mento de Zoologia, Instituto de Biologia, UNICAMP, 13083-970 Campinas, SP, Brazil G. MASSIOT(1 73), URA CNRS 492, UniversitC de Reims-Champagne- Ardenne, FacultC de Pharmacie, F-51096 Reims, France ISAMMU URAKOSH(lI) , Department of Plant Chemistry and Pharmacog- nosy, Faculty of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Chiba 263, Japan SHIGERUO HMIYA(l ), Faculty of Pharmaceutical Sciences, Hoshi Univer- sity, Tokyo, Japan KAZUKSIA ITO( l), Faculty of Pharmaceutical Sciences, Chiba University, Chiba 263, Japan J. SAPI (173), URA CNRS 492, UniversitC de Reims-Champagne- Ardenne, FacultC de Pharmacie, F-51096 Reims, France JOACHISMT OCKIG(T1 15), Department of Pharmaceutical Biology, Insti- tute of Pharmacy, Johannes Gutenberg-Universitat, Mainz, Germany JosB ROBERTOT RIGO(2 27), Laboratbrio de Ecologia Quimica, Depart- amento de Zoologia, Instituto de Biologia, UNICAMP, 13083-970 Cam- pinas, SP, Brazil vii This Page Intentionally Left Blank PREFACE Although there are no prescription products containing a lupine alkaloid available on the American market, these alkaloids continue to provoke great interest, in part because of their diverse biology, their toxicity to grazing animals, and, as a result, the possibility of the alkaloids entering the human food chain. They also provide significant challenges in terms of structure elucidation and spectroscopic assignment, and more recently, several new skeleta have been isolated. All of these aspects are reviewed by Ohmiya, Saito, and Murakoshi. The biosynthesis of monoterpenoid indole alkaloids has been a very exciting area of research ever since the initial suggestions that all of the diverse skeleta came from a single precursor. Stockigt reviews the progress that has been made on characterizing the enzymes that are involved in the biosynthesis on the sarpagine-ajmaline class of alkaloids in Rauwolfia ser- pentina. There are many alkaloids with an indole nucleus other than those com- prising an iridoid unit, and Sapi and Massiot present a review of the many fascinating bisindole alkaloids in this series derived from marine, microbial, and plant sources. Finally, Brown and Trigo discuss the ecological significance of alkaloids, through the studies that have been made of various trophic level interac- tions, such as those between the plant, a herbivore, and a parasitoid. They also examine the evolutionary patterns of alkaloids in nature. The conclu- sion is clearly that alkaloids are not waste products of secondary metabo- lism, but have evolved over time as important metabolites which possess a myriad of biological activities, many of which allow the host system to survive and inhibit predation or some other form of exogenous influence. Geoffrey A. Cordell University of Illinois at Chicago ix
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