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This volume is part of a series which provides coverage of the chemotaxonomy, structure elucidation, synthesis, biosynthesis and biology of all classes of alkaloids, from higher and lower plants to marine sources and various terrestial animals. Each volume provides up to date and detailed coverage of particular classes or sources of alkaloids. The series should be a useful reference for all natural product chemists and biologists who have an interest in alkaloids, their diversity and their unique biological profiles.
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THE ALKALOIDS Chemistry and Pharmacology VOLUME 43 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 43 Academic Press, Inc. Harcourt Brace Jovanovich, Publishers San Diego New York Boston London Sydney Tokyo Toronto This book is printed on acid-free paper. @ Copyright 0 1993 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. 1250 Sixth Avenue, San Diego, California92101-4311 United Kingdom Edition published by ACADEMIC PRESS LIMITED 24-28 Oval Road, London NWI 7DX Library of Congress Catalog Number: 50-5522 International Standard Book Number: 0- 12-469543-4 PRINTED IN T I E UNITED STA'IES OF AMERICA 9 3 9 4 9 5 9 6 9 1 QW 9 8 7 6 5 4 3 2 1 CONTENTS CONTRIBUTORS ......................................................... PREFACE............................................................... vii ix Chapter 1 . Allelochemical Properties or the Raison d'Etre of Alkaloids MICHAELWINK I . Introduction ...................................................... I1 . Allelochemical Properties of Alkaloids ............................... 111. Raison d'Etre of Alkaloids ......................................... IV . Conclusions ...................................................... References ....................................................... I 5 86 I03 104 Chapter 2. Mammalian Alkaloids I1 ARNOLDBROSSI 1. Introduction ...................................................... I1 . Mammalian Indole Alkaloids ....................................... 111. Mammalian Isoquinoline Alkaloids .................................. IV . Mammalian Morphine ............................................. V . Alkaloid Formation in Mammals as a Therapeutic Concept ............. VI . Addendum ....................................................... VII . Conclusions ...................................................... References ....................................................... Chapter 3. Amphibian Alkaloids JOHNW . DALY.H . MARTINGARRAFFO.A N D THOMASF. SPANDE I . Introduction ...................................................... I1 . Steroidal Alkaloids ................................................ 111. Bicyclic Alkaloids ................................................. IV . Tricyclic Alkaloids ................................................ V . Monocyclic Alkaloids .............................................. .................................... VI . Pyridine Alkaloids ........ VII . Indole Alkaloids .............................................. VIII . Imidazole Alkaloids ............................................... IX . Morphine ........................................................ X . Guanidinium Alkaloids ............................................. V 186 187 199 242 251 255 257 263 263 264