Chemistry and Biology

385 Pages·1999·15.01 MB·English

by  Geoffrey A. Cordell

THE ALKALOIDS
Chemistry and Biology
VOLUME 53
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THE ALKALOIDS
Chemistry and Biology
Edited by
Geoffrey A. Cordell
College of Pharmacy
University of Illinois at Chicago
Chicago, Illinois
VOLUME 53
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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
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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
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