The Alkaloids: Chemistry and Pharmacology 38 PDF
Preview The Alkaloids: Chemistry and Pharmacology 38
THE ALKALOIDS Chemistry and Pharmacology VOLUME 38 This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Pharmacology Edited by Arnold Brossi National Institutes of Health Bethesda, Maryland VOLUME 38 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 1990 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. San Diego, California 92101 United Kingdom Edition published by ACADEMlC PRESS LIMITED 24-28 Oval Road. London NW 1 7DX LIBRARY OF CONGRESS CATALOG CARD NUMBER: 50-5522 ISBN 0-12-469538-8 (alk. paper) PRINTED IN THE UNITED STATES OF AMERICA 90 91 92 93 9 8 7 6 5 4 3 2 I CONTENTS CONTRIBUTOR..S.. ................................................................................... vii PREFACE. ............................................................................................... ix Chapter 1 . Ergot Alkaloids ICHlYA NINOMIYAAN D TOSHIKOK lGUCHl I . Introduction ..................................................................... 1 I1 . New Alkaloids ............................................................................... 2 111 . Synthesis ...................................................................................... 20 IV . Conformational Studies ............................................... 124 V . Biosynthesis .................................................................................. 130 VI . Pharmacological Properties of Related Compounds ............................... 142 References ................................................................ .... 148 Chapter 2 . Spirobenzylisoquinoline and Related Alkaloids GABORB LASK6 I . Introduction .................................................................................. 157 I1 . Occurrence and Structure Elucidation of Spirobenzylisoquinoline Alkaloids I59 I11 . Synthesis of Spirobenzylisoquinoline Alkaloids .................................... 184 IV . Synthesis of Indenobenzazepine Alkaloids .......................................... 203 V . Miscellaneous Transformation Reactions ............................... 206 V1 . Enzymatic Transformations .............................................................. 215 VII . Biosynthesis of Spirobenzylisoquinoline Alkaloids ................................ 218 References .................................................................................... 219 Chapter 3 . Purine Alkaloids ATTA-UR-RAHMAANN D MUHAMMAIDQ BAL CHOUDHARV I . Introduction ........ ................................................. 226 I1 . Occurrence. .............................................................. 227 111 . Isolation and Detection .................................................................... 228 IV . Purine Alkaloids from Plants ......................... 229 V . Purine Bases from Transfer RNAs of Plants and Animals ...................... 249 VI . Purine Alkaloids from Animals ... ............................................... 254 V vi CONTENTS V11. Nucleoside Antibiotics and Related Compounds from Microorganisms. 267 VIII. Synthesis of Purine Bases ................................................................ 280 IX. Spectral Properties of Purine Alkaloids ...................... ............... 304 X. Biological Activity of Purine Bases .......................................... 311 References .................................................................................... 313 CUMULATIVINED EX OF TITLES.. .............................................................. 325 INDEX ................................................................................................... 33 I CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors’ contributions begin. ICHIYAN INOMXY(AI) , Kobe Women’s College of Pharmacy, Kobe, Japan TOSHIKOK IGUCHI( I), Kobe Women’s College of Pharmacy, Kobe, Japan GABOR BLASKO (157), EGIS Pharmaceuticals, Budapest H-1106, Hungary ATTA-UR-RAHMA(2N2 5), H. E. J. Research Institute of Chemistry, Uni- versity of Karachi, Karachi-75270, Pakistan MUHAMMAIDQ BALC HOUDHAR(Y2 25), H. E. J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan vii This Page Intentionally Left Blank PREFACE Ergot alkaloids, because of their biological activities, represent an im- portant group of the indole alkaloids, and useful medical applications have been found for several of them. At the same time, LSD, also a mem- ber of this group of indole alkaloids, is one of the most potent hallucino- gens known. The first review on ergot alkaloids appeared in 1965 in Vol- ume 8 of this series; it was followed by a second review in 1975 in Volume 15. Both reviews focused on isolation and structure determination and included a discussion of pharmacological properties. The third review in this volume focuses heavily on synthesis, which has been mostly accom- plished since 1974. Included is a discussion of some novel drugs of this alkaloidal series. Spirobenzylisoquinoline alkaloids, when first discussed in 197 1 in Vol- ume 13 of this series, comprised seven alkaloids. In the meanwhile, this group of alkaloids has grown in number to 38, and these are presented here with structures and details of their synthesis. Purine alkaloids are not derived from amino acids and are for this reason often not included among the alkaloids. The most important representatives are coffein, the- ophylline, and theobromine from coffee, thea, and cacao, respectively, and are consumed in huge quantities. The chemistry of purine alkaloids, their spectral properties, and their pharmacological effects are discussed in this series for the first time. Once again, without the help of serious and devoted collaborators, this volume could not have been published. Arnold Brossi National Institutes of Health ix
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