The Alkaloids: Chemistry and Pharmacology 25 PDF
Preview The Alkaloids: Chemistry and Pharmacology 25
THE ALKALOIDS Chemistry and Pharmacology Volume XXV This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Pharmacology Edited by Arnold Brossi National Institutes of Health Bethesda, Maryland VOLUME XXV 1985 ACADEMIC PRESS, INC. Hurcourt Bruce Jovunovich, Publishers Orlando San Diego New York London Toronto Montreal Sydney Tokyo COPYRIGHT o 198.5 BY ACADEMIC PRESS,I NC. 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 published by ACADEMIC PRESS INC. (LONDON) LTD. 24-28 Oval Road, London NWl 7DX LIBRARYO F CONGRESS CATALOG CARD NUMBER: 50-5522 ISBN: 0- 12-469525-6 PRINTED IN 'THE UNITED STATES OF AMERICA 8.5 xii 87 88 gn7fi543zi CONTENTS CONTRIBUTOR.S. ........................................................ vii PREFACE. ............................................................... ix CONTENTOSF PREVIOUVSO LUMES. ......................................... xi Chapter 1 . Antitumor Alkaloids MATTHEWS UFFNESSA ND GEOFFREYA . CORDELL I . Introduction ......... 3 I1 . Erythrophleum Alkaloids ............................................... 4 I11 . Tuxus Alkaloids ...................................................... 6 IV . Sesbaniu Alkaloids ................................................... 18 V . Pyrrolizidine Alkaloids ................................................ 21 VI . Acronycine .......................................................... 38 VII . Emetine and Related Alkaloids ........ ........................... 48 VIII . Cephuiotuxus Alkaloids ................................................ 51 IX . Colchicine .......................................................... 69 X . Camptothecine ....................................................... 73 XI . Ellipticine ........................................................... 89 XI1 . Maytansinoids ....................................................... 142 XI11 . Phenanthroindolizidine and Phenanthroquinolizidine Alkaloids ................ 156 XIV . Bisisoquinoline Alkaloids .............................................. 163 XV . Benzo[c]phenanthridine Alkaloids ....................................... 178 XVI . Protoberberine Alkaloids ............................................... 188 XVII . Amaryllidaceae Alkaloids .............................................. 198 XVIII . Miscellaneous Alkaloids ............................................... 212 References .......................................................... 223 Addendum .......................................................... 280 References ........................................................ 345 INDEX. .................................................................... 357 V This Page Intentionally Left Blank CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors’ contributions begin GEOFFREYA . CORDELL(I ), Program for Collaborative Research in the Phar- maceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612 MATTHEWS UFFNESS(l ), Natural Products Branch, Division of Cancer Treat- ment, National Cancer Institute, Bethesda, Maryland 20205 This Page Intentionally Left Blank PREFACE The use of dimeric “Vinca” alkaloids in cancer therapy together with the clinical evaluation of camptothecin and Cephalotaxus alkaloids in China mark alkaloids as an especially interesting class of natural products in which better antitumor agents may be found. To underline the importance of alkaloids in this respect, the chapter “Antitumor Alkaloids,” written by internationally known experts, became Volume XXV of The Alkaloids. ‘‘Antitumor Alkaloids, containing more than 2000 literature references, dis- ” cusses the biological properties of alkaloids isolated from 120,000 plant extracts representing over 6000 genera of plants in antitumor screenings and presents data on the therapeutic evaluation of interesting candidates in humans. The chapter does not discuss the therapeutically important group of dimeric Vinca alkaloids, which will be presented in similar detail in a future volume of The Alkaloids. Arnold Brossi
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