The Alkaloids: Chemistry and Pharmacology 35 PDF
Preview The Alkaloids: Chemistry and Pharmacology 35
THE ALKALOIDS Chemistry and Pharmacology VOLUME 35 This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Pharmacology Edited by Arnold Brossi Natk~mlI nstitutes of Hdth &the&. Maryland VOLUME 35 Academic Press, Inc Harcourt Brace Jovanovich, Publishms San Diego New York Berkeley Boston London Sydney Tokyo Toronto COPYRIGHT 0 1989 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, 01 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 ACADEMIC PRESS LIMITED 24-28 Oval Road, London NW 1 7DX LIBRARY OF CONGRESS CATALOG CARD NUMBER: 50-5522 ISBN 0-12-469535-3 (alk. paper) PRINTED IN THE UNITED STATES OF AMERICA 89909192 9 8 7 6 5 4 3 2 1 IN MEMORY OF TETSUJI KAMETANI Dr. Tetsuji Kametani, who died on October 11, 1988, in Tokyo, Japan, was a giant in the field of chemistry of natural products. He had mastered total synthesis of most biologically active natural products, and his work has stimulated many working in the field. After his departure from the Pharma- ceutical Institute at Tohoku University in Sendai in 1980, his contributions to science did not diminish. On the contrary, they continued to flow and to be important despite his election to deanship and presidency at Hoshi College in Tokyo in 1981. The Japanese journal Hemvcycles, which is written in English and which he founded in 1973, became a prestigious journal for many working with heterocyclic compounds. Only time will tell how much the scientific communities in Japan and in the world have lost with his passing away. It is with admiration and thanks to my colleague and friend Dr. Rtsuji Kametani that I dedicate this volume of “The Alkaloids” to his lasting memory. Arnold Brossi This Page Intentionally Left Blank CONTENTS CONTRIBUT..~.R..S.. ........................ ;. ........................... ix PREFAC.E. .............................................................. xi Chapter 1. Alkaloids from Guuneria ANDIGC+ AV~M,I CH~LLE BOEUAFN,D BRUCEK. CASSELS ....................................................... I. Introduction 1 ............................................ 11. Botanical Considerations 2 ............... 111. Alkaloids from Chemically Investigated Guut&ria Species. 3 ................................ IV. Structure Elucidation and Chemistry.. 3 .............................................. V. Biogenetic Hypotheses 57 VI. Chemosystematics .................................................. 65 ..................................................... VII. Pharmacology. 69 VIII. Appendix .......................................................... 71 ......................................................... References 73 Chapter 2. 8-Phenethylamines and Ephedrines of Plant Origin JANL LJNDSTR~M ....................................................... I. Introduction 77 ........................................................ 11. Occurrence 77 ................. 111. Isolation, Identification, and Determination Procedures 131 IV. Synthesis .......................................................... 132 V. Biosynthesis ....................................................... 137 ................................................. VI. Biological Effects.. 142 ......................................................... References 144 Chapter 3. Lythraceous Alkaloids KAORU FUJI ....................................................... I. Introduction 155 .......................................................... 11. Synthesis 155 111. Occurrence and Biosynthesis ........- . ............................... 172 IV. Spectroscopic Studies ............................................... 173 References ......................................................... 175 vii viii CONTENTS Chapter 4. Dibenzazonine Alkaloids LUISC ASTEDOAN D DOMINGDOO MINGUEZ ....................................................... I. Introduction 177 ........................................ 11. Occurrence and Classification 179 ............................................. 111. Structure Determination 180 IV. Synthesis .......................................................... 183 V. Biosynthesis ....................................................... 205 VI. Pharmacological Properties .......................................... 209 .................................... VII. Related Alkaloids: Dibenzazecines 209 ......................................................... References 212 Chapter 5. Nuphar Alkaloids JACEKC YLIULASNKDI JERZYT . WROLIEL ....................................................... I. Introduction 215 11. Significance of Nuphar Species in the Aquatic Habitat .................. 216 ............................................ 111. New Nuphar Alkaloids.. 220 IV. Stereochemical 'Itansformations of Nuphar Alkaloids ................... 227 ........... V. Chemistry of Nuphar Alkaloids and Manifestation of Sulfur.. 232 VI. Synthesis of Nuphar Alkaloids ....................................... 239 VII. Spectroscopy of Nuphar Alkaloids.. .................................. 244 ..................................................... VIII. Pharmacology. 253 ......................................................... References 256 Chapter 6. Oxazole Alkaloids HELENM . JACOBASN D BASILA . BURKE I. Introduction ....................................................... 259 .......................................... 11. Oxazoles of the Gramineae 260 111. Oxazoles of the Rutaceae ............................................ 262 IV. Marine Oxazoles ................................................... 269 V. Bacterial Oxazoles .................................................. 27 1 VI. Biological Activity .................................................. 295 VII. Isolation and Spectral Characteristics ................................. 304 ......................................................... References 307 .......................................... CUMULATIINVDE EXOF TITLES 311 INDU( .............................................................. 317 CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors’ contributions begin. BASIL A. BURKE( 259), The Plant Cell Research Institute, Inc., Dublin, Cali- fornia 94568 BRUCEK . CASSEL(Sl ), Laboratoire de Pharmacognosie, UA 496 Centre National de la Recherche Scientifique (CNRS), Facultt de Pharmacie, Universitt de Paris-Sud, F-92296 Chiitenay-Malabry Cedex, France LUISC ASTEDO(1 77), Departamento de Quimica Orghica, Facultad de Quimica, Universidad de Santiago, 15706 Santiago de Compostela, Spain AND^ C A(l)~, La boratoire de Pharmacognosie, UA 4% Centre National de la Recherche Scientifique (CNRS), Facultt de Pharmacie, Universitt de Paris-Sud, F-92296 Chatenay-Malabry Cedex, France JACEKC YBULSK(2I1 5), Department of Chemistry, University of Warsaw, Warsaw, Poland DOMINGDOO MINGUE(1Z7 7), Departamento de Quimica Orghica, Facultad de Quimica, Universidad de Santiago, 15706 Santiago de Compostela, Spain KAoRU FUJI (155), Institute for Chemical Research, Kyoto University, Uji, Kyoto 61 1, Japan HELENM . JACOBS(2 59), Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica MICHELL EBOEUF( l), Laboratoire de Pharmacognosie, UA 4% Centre National de la Recherche Scientifique (CNRS), Facultt de Pharmacie, Universitt de Paris-Sud, F-92296 Chiitenay-Malabry Cedex, France JANL UNDSTR~(7M7), Department of Drug Metabolism, Astra Research Centre, S-151 85 Sodertalje, Sweden JERZYT . WR6BEL (215), Department of Chemistry, University of Warsaw, Warsaw, Poland ix
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