The Alkaloids: Chemistry and Pharmacology 27 PDF
Preview The Alkaloids: Chemistry and Pharmacology 27
THE ALKALOIDS Chemistry and Pharmacology Volume 27 THE ALKALOIDS Chemistry and Pharmacology A list of contents of volumes in this treatise is available from the publisher on request. THE ALKALOIDS Chemistry and Pharmacology Edited by Arnold Brossi National Institutes of Health Bethesda, Maryland VOLUME 27 1986 ACADEMIC PRESS, INC. Harcouri Brace Jovanovich, Publishers Orlando San Dlego New York Ausb London Montreal Sydney Tokyo Toronto o COPYRIGHT 1986 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. Orlando, Florida 32887 United Kingdom Edition publishd by ACADEMIC PRESS INC. (LONDON) LTD. 24-28 Oval Road, London NWl 7DX LIBRARY OF CONGRESS CATALOG CARD NUMBER 50-5522 ISBN: 0-12-469527-2 (alk. paper) ISBN: 0-12-462652-1 (paperback) PRINTED IN THE UNITED mAm OF AMERICA 86878889 987654321 CONTENTS CONTRIBUTOR..S. ........................................................ vii PREFACE. ............................................................... ix Chapter 1. Alkaloids from Tabernaemontana BRUNOD ANIELAI ND GIOVANNPIA LMISAN0 I. Introduction ........................................................ 1 II. Taxonomy ......................................................... 2 In. Indole Alkaloids from Chemically Investigated Tubernuemonzana Species ..... 4 IV. Structure Elucidation and Chemistry .................................... 25 V. Pharmacology ...................................................... 120 References ......................................................... 124 Chapter 2. Corynantheine, Yohimbine, and Related Alkaloids CSABA SZANTAY, GABORB LASK6, KATALINH ONTYA, ND GABORM RNYEI I. Introduction ........................................................ 131 11. Structural Elucidations ............................................... 133 111. Synthesis .......................................................... 155 IV. Transformations, Reactions ........................................... 224 v. spectroscopy ....................................................... 236 VI. Pharmacology ...................................................... 25 1 References ......................................................... 257 Addendum ......................................................... 407 Chapter 3. Pyrrolidine Alkaloids GEORGESM ASSIOTA ND CLEMENTD ELAUDE I. Introduction ........................................................ 270 II. Hygrine and Hygroline ............................................... 270 III. Cuscohygrine and Dihydrocuscohygrine ................................. 272 IV. The Betaines: Stachydrine and Hydroxystachydrines ....................... 274 V. Occurrence of Pyrrolidine Alkaloids .................................... 277 V vi CONTENTS VI. Biosynthesis of Pyrrolidine Alkaloids ................................... 294 VII. Synthesis of Pyrrolidine Alkaloids ..................................... 298 VIII. Biological Activity of Pyrrolidine Alkaloids .............................. 310 IX. Addendum: Pyrrolidine Alkaloids from Black Pepper ...................... 312 References ......................................................... 316 Chapter 4. Metabolic Transformations of Alkaloids J. P. N. ROSAZZAA ND M. W. DUFFEL I. Introduction ........................................................ 323 11. Enzymes That Catalyze Alkaloid Transformations ......................... 33 1 111. Survey of Alkaloid Transformations .................................... 347 References ......................................................... 398 INDEX .................................................................. 41 1 CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors’ contributions begin. GABORB LASK(~13 1), Central Research Institute for Chemistry, Hungarian Academy of Sciences, 1025-Budapest, Hungary BRUNOD ANIEL(Il ), Dipartimento di Chimica Organica e Industriale, Facolth di Scienze, Universit2 degli Studi di Milano, Centro di Studio per le Sostanze Organiche Naturali del C.N.R., Milan, Italy CLEMENDT ELAUDE(*2 69), Facult6 de Pharmacie, Universit6 de Reims, 51096 Reims, France GABORD ~RNYE(1I3 1), Central Research Institute for Chemistry, Hungarian Academy of Sciences, 1025-Budapest, Hungary M. W. DUFFEL( 323), Division of Medicinal Chemistry and Natural Products, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242 KATALINH ONTY( 131), Institute of Organic Chemistry, Technical University, 11 1 1 - Budapest, Hungary GEORGEMS ASSIOT(2 69), Facult6 de Pharmacie, Universit6 de Reims, 51096 Reims, France GIOVANNPI ALMISANO(l ), Dipartimento di Chimica Organica e Industriale, Facolt2 di Scienze, Universith degli Studi di Milano, Centro di Studio per le Sostanze Organiche Naturali del C.N.R., Milan, Italy J. P. N. ROSAZZA(3 23), Division of Medicinal Chemistry and Natural Products, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242 CSABAS ZANTAY(1 3 l), Institute of Organic Chemistry, Technical University, 11 11 -Budapest, Hungary, and Central Research Institute for Chemistry, Hun- garian Academy of Sciences, 1025-Budapest, Hungary *Present address: Institut de Chimie, Universitk de Libge, Sart-Tilman, par 4000 Libge I, Belgium. vii This Page Intentionally Left Blank PREFACE Plants of the genus Tabernaemontana produce a great variety of indole al- kaloids, as discussed sporadically in earlier volumes under the appropriate class- es of indole alkaloids. The chapter ‘‘Alkaloids from Tabernaemontana” presented here is the first comprehensive review of the chemistry and phar- macology of the indole alkaloids produced by these plants. Indole alkaloids discussed in the chapter “Corynantheine, Yohimbine, and Related Alkaloids” were already reviewed in Volumes 8 and 11. In this updated chapter, besides structure elucidation, spectral properties, and pharmacological properties, great emphasis is given to synthesis of such alkaloids, a discipline much advanced by the Hungarian authors themselves. “Pyrrolidine Alkaloids,” discussed in Vol- umes 1 and 6 more than 20 years ago, are updated, and the chapter now includes discussion of biosynthesis and pharmacology. Properties of alkaloids from black pepper species, important as spices and flavoring agents, are discussed in an addendum. The chapter ‘‘Metabolic Transformations of Alkaloids” discusses enzymes involved in alkaloid transformations, and several examples of such reactions in several classes of alkaloids are presented. This topic was discussed in Volume 18 but is now updated and expanded. Arnold Brossi ix
The list of books you might like
