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THE ALKALOIDS Chemistry and Biology VOLUME 53 This Page Intentionally Left Blank THE ALKALOIDS Chemistry and Biology Edited by Geoffrey A. Cordell College of Pharmacy University of Illinois at Chicago Chicago, Illinois VOLUME 53 Academic Press San Diego London Boston New York Sydney Tokyo Toronto @ This book is printed on acid-free paper. Copyright 0 2000 by ACADEMIC PRESS All Rights Reserved. No part of this publication may be reproduced or transmitted in -.J iorm or by any means, electronic or mechanical. including photocopy, recording, or any information storage and retrieval system, without permission in writing from the Publisher. The appearance of the code at the bottom of the first page of a chapter in this book indicates the Publisher's consent that copies of the chapter may be made for personal or internal use of specific clients. This consent is given on the condition. however, that the copier pay the stated per copy fee through the Copyright Clearance Center, Inc. (222 Rosewood Drive. Danvers, Massachusetts 01923). for copying beyond that permitted by Sections 107 or 108 of the US.C opyright Law. This consent does not extend to other kinds of copying, such as copying for general distribution, for advertising or promotional purposes, for creating new collective works, or for resale. Copy fees for pre-2OOO chapters are as shown on the title pages. If no fee code appears on the title page, the copy fee is the same ils for current chapters. 0099-9598/00 $30.00 Explicit permission from Academic Press is not required to reproduce a maximum of two figures or tables from an Academic Press chapter in another scientific or research publication provided that the material has not been credited to another source and that full credit to the Academic Press chapter is given. Academic Press A Hnrcourt Science nnd Technology Compnny 525 B Street. Suite 1900, San Diego, California 92101-4495, U.S.A. http://www.apnet.com Academic Press 24-28 Oval Road, London NWI 7DX, UK http://www. hbuk.co.uk/ap/ International Standard Book Number: 0-12-469553- I PRINTED IN THE UNITED STATES OF AMERICA 99 0001 02 03 0 4 B B 9 8 7 6 5 4 3 2 1 CONTENTS CONTRIBUTOR..S. ....................................................... vii PREFACE ............................................................... ix Alkaloids as Chirality Transmitters in Asymmetric Catalysis CHOONGE Ul SONG I. Introduction ....................................................... 2 11. Enantioselective Carbon-Hydrogen Bond Formation ..................... 3 111. Asymmetric Oxidation ... ............................ 12 IV. Enantioselective Carbon-C 28 V. Enantioselective Carbon-Heteroatom Bond Formation .................... 46 VI. Conclusion .......................... .................... 50 References ................................................. 50 Biological Aspects of Aporphinoid Alkaloids Jos6 LUISR ios, SALVADOMRA fim, ROSAM . GINERA, ND M.C ARMENR ECIO 1. Introduction .................................... 58 ................................. 60 111. Pharmacology ........................... ................ 74 109 References ............ ....................... 110 Alkaloids Containing an Isoquinolinequinone Unit TURAONZ TURK I. Introduction ..... 11. Aza-anthraquinone 111. Saframycin Type Alkaloids ................ ................. IV. Isoquinolinequinone Type Alkaloids ...................... V. Naphthyridinomycin Type Alkaloids ........................... 204 VI. Summary.. .............................. ............. 230 References ........ Nitrogen-Containing Metabolites from Marine Bacteria WILLIAMH. GERWICKAN D NAMTHIPSI TACHIII'A I. Introduction ................................................. 239 11. Alkaloidal Chemistry of the Eubacteria ........................... 24 1 V vi CONTENTS Ill. Conclusions ....................................................... 219 References ......................................................... 28 1 The Pharmacology and Therapeutic Aspects of Colchicine CLAIRLEE HELLO I. History of Colchicine ............................ ... 288 11. Chemistry ......................................................... 289 Ill. Pharmacokinetics ......................................... 289 IV. Mechanisms of Action ............................................... 290 V. Side Effects and Toxicity ............................................. 29 I VI. Intoxication ..... 294 VII. Indications of Col 295 VIII. Colchicine Indications in Other Specialties .............................. 318 IX. Conclusion ............................................ 335 Acknowledgment ................................................... 335 References. ..... .... ........................ 336 .................................... 353 .................................................. 363 CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors' conrributions begin. WILLIAMG ERWICK(2 39), College of Pharmacy, Oregon State University, Corvallis, Oregon 9733 1-3507 ROSA M. GINER( 57), Department de Farmacologia, Facultat de Farmacia, Universitat de Valencia, 46 100 Burjassot, Valencia, Spain CLAIREL E HELLO( 287), Unite de Medecine Interne, Centre Hospitalier, Universitaire de Caen, 14000 Caen Cedex, France SALVADOMRA REZ( 57), Department de Farmacologia, Facultat de Farma- cia, Universitat de Valencia, 46 100 Burjassot, Valencia, Spain TURANO ZTURK(1 19), Chemical Laboratory, University of Kent at Canter- bury, Canterbury, Kent, United Kingdom M. CARMENRE CIO( 57), Department de Farmacologia, Facultat de Farma- cia, Universitat de Valencia, 46 100 Burjassot, Valencia, Spain JosB-LUISR ios (57), Department de Farmacologia, Facultat de Farmacia, Universitat de Valencia, 46 100 Burjassot, Valencia, Spain NAMTHIPS ITACHITT(A2 39), College of Pharmacy, Oregon State Univer- sity, Corvallis, Oregon 9733 1-3507 CHOONGE UI SONG( l), Division of Applied Science, Korea Institute of Science and Technology, Cheongryang, Seoul 130-650, Republic of Korea vii This Page Intentionally Left Blank PREFACE Several transformative changes occur with this volume of The Alkaloids: Chemistry and Biology. The first is that the authors have prepared their re- spective chapters in camera-ready format in order to accelerate the publica- tion process. Thanks to the fine cooperation of these authors, I believe that the excellent quality of the presentation of the series has been maintained. The second transformation is an attempt to continue to broaden the cover- age of the series. This has been done in this volume through several chapters. The first is a chapter by Song on the use of alkaloids as chiral transmitters in stereoselective synthesis. This area has developed very rapidly in recent years and some of the achievements have been spectacular. The second chapter reviews the alkaloids from marine organisms by compound class, reflecting this broadening of scope. This is now necessary as the number of interesting metabolites from marine sources has grown and the associated efforts of synthesis and biological investigation have burgeoned. Thus, Ozturk pro- vides a detailed discussion of the isoquinolinequinone alkaloids. The chapter by Gerwick and Sutachitta on the alkaloids from marine bacteria also reflects the increasing attention being paid to this area of the marine biome. Finally, Le Hello reviews in-depth the diverse clinical aspects of colchicine, an alka- loid that is finding many new therapeutic uses. Chapters on the clinical as- pects of alkaloids are rare in this series, and it is hoped that in the next few years the principal alkaloids used therapeutically can be covered. Geoffrey A. Cordell University of Illinois at Chicago ix
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