The Alkaloids: Chemistry and Pharmacology 34

421 Pages·1989·13.07 MB·English

by  Arnold Brossi (Eds.)

THE ALKALOIDS
Chemistry and Pharmacology
VOLUME 34
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THE ALKAL
Chemistry and Pharmacology
Edited by
Arnold Brossi
National Institutes of Health
Bethesda, Maryland
VOLUME 34
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CONTENTS
Contributors ............................................................ vii
Preface ................................................................. ix
Chapter 1. Chemistry and Reactions of Cyclic Tautomers
of Tryptamines and Tryptophans
TOHRUH INOA ND MASAKNOA KACAWA
I. Introduction ....................................................... 1
11. Cyclic Tautomers of Tryptamines and Tryptophans ...................... 4
III. Cyclic Tautomers of Tryptophan-Containing Dipeptides . . ... 17
IV. 3a-Hydroxypyrrolo[2,3-b]indoleD erivatives. ............................ 18
V. 3a-Bispyrrolo[2,3-b]indole Alkaloids: Dimeric, Trimeric,
Tetrameric, and Pentameric Tryptamines ............................... 41
VI. 3a-Prenylpyrrolo[2,3-b]indolesa nd Related Alkaloids .................... 49
VII. Other Pyrrolo[2,3-b]indoles .... 65
References ......................................................... 69
Chapter 2. Alkaloids in Cannabis saliva L.
RAPHAEMLE CHOULAM
I. Introduction ....................................................... 77
11. Quaternary Bases, Amides, and Arnines . . 79
III. Spermidine Alkaloids ............................................... 80
IV. Synthesis of Cannabinoid Spermidine Alkaloids ........................ 83
V. Pharmacology ...................................................... 91
........................... 92
Chapter 3. Aconitum Alkaloids
TAKASHAIM IYAAN D HIDEOB ANDO
....... .... ...... 95
s .................................... 96
111. Pharmacology ...................................................... 126
IV. Analytical Methodology ............................................. 132
V. Tabulation of New Diterpenoid Alkaloids. ............................. 133
References . . 174
V
vi CONTENTS
Chapter 4. Protopine Alkaloids
MASAYUOKNI DAA ND HIROSHTIA KAHASHI
I. Introduction ....................................................... 181
11. Occurrence ........................................................ 182
111. Structure .......................................................... 182
IV. Conformation and Spectroscopy. .. 190
V. Synthesis .......................................................... 194
VI. Transformation of Protopines to Related Alkaloids ..................... 198
VII. Biosynthesis ....................................................... 201
VIII. Callus Culture ..................................................... 202
IX. Pharmacology ...................................................... 203
Addendum ......................................................... 203
References ......................................................... 204
Chapter 5. African Sfrychnos Alkaloids
GEORCEMS ASSIOATN D CL~MENDTEL AUDE
I. Introduction ....................................................... 21 1
11. Ethnobotany ....................................................... 215
111. Chemical Scree ... 217
’
IV. Alkaloid Conte ......................... 218
V. Biosynthesis an ... 288
ion. ............................. 301
VII. Synthesis and Chemistry. ............................................ 305
VIII. Pharmacology. .... ........................................... 319
IX. Conclusion ........................................................ 321
References ......................................................... 322
Chapter 6. Cinchona Alkaloids
ROBERVT ERPOORTJEA, NS CHRIPSEMAAND, THEOV AN DER LEER
I. Introduction ....................................................... 332
11. Isolation ............ ........................................... 333
111. Synthesis .......................................................... 344
IV. Spectroscopy ....................................................... 358
V. Chromatography . . ............ 37 1
VI. Biological Activities ................................................. 376
VII. Metabolism 378
VIII. Biosynthesis ....................................................... 382
IX. Biotechnology ........................... 38 9
References ......................................................... 391
Cumulative Index of Titles.. .............................................. 399
Index ................................................................... 405
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
TAKASHAIM IYA( 99, Hokkaido Institute of Pharmaceutical Sciences, 7-1
Katsuraoka-cho, Otaru, 047-02, Hokkaido, Japan
HIDEOB ANDO( 99, Hokkaido Institute of Pharmaceutical Sciences, 7-1
Katsuraoka-cho, Otaru, 047-02, Hokkaido, Japan
CLAMENDT ELAUD(E21 l), Faculte de Pharmacie, Universite de Reims, Reims,
France
TOHRUH INO( l), Faculty of Pharmaceutical Sciences, Chiba University
Yayoi-cho, Chiba-shi 260, Japan
GEORGEMSA SSIOT(2 1 I), Faculte de Pharmacie, Universite de Reims, Reims,
France
RAPHAELM ECHOULA(M77 ), Department of Natural Products, Faculty of
Medicine, Hebrew University, Jerusalem 91 120, Israel
MASAKON AKAGAW(Al) , Faculty of Pharmaceutical Sciences, Chiba Uni-
versity, Yayoi-cho, Chiba-shi 260, Japan
MASAYUKOI NDA( 1 81), School of Pharmaceutical Sciences, Kitasato Uni-
versity, Tokyo, Japan
JAN SCHRIPSEM(A33 l), Department of Pharmacology, Center for Bio-
Pharmaceutical Sciences, Gorlaeus Laboratories, University of Leiden,
2300RA Leiden, The Netherlands
HIROSHTI AKAHASH(1I8 1), School of Pharmaceutical Sciences, Kitasato
University, Tokyo, Japan
THEOV AN DER LEER( 331), Department of Pharmacology, Center for Bio-
Pharmaceutical Sciences, Gorlaeus Laboratories, University of Leiden,
2300RA Leiden, The Netherlands
ROBERTV ERPOORTE( 33 l), Department of Pharmacology, Center for Bio-
Pharmaceutical Sciences, Gorlaeus Laboratories, University of Leiden,
2300RA Leiden, The Netherlands
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PREFACE
Indole alkaloids represent a major class and were reviewed in a general
fashion in Vols. 2 (1952) and 7 (1960) of this treatise, before they were broken
up into subgroups. The chapter on “Chemistry and Reactions of Cyclic
Tautomers of Tryptamines and Tryptophans” (not including physostigmines)
discusses in detail the chemistry of the tricyclic alkaloids derived from
biologically important indole precursors, which occur in plants, fungi, and
mammals. “Alkaloids from Cannabis sutivu L.,” the source of the cannabi-
noids present in hashish, are minor constituents of little-known pharma-
cological actions and are presented here for the first time. The chapter on
‘2conitumA lkaloids” updates information already collected in Vols. 4 (1954),
7 (1960), 17 (1979), and 18 (1981) of this work and summarizes pharmacological
and toxicological data on these alkaloids used in herbal compositions in Japan
and in China. “Protopine Alkaloids” were first presented in Vol. 4 (1954) and
later repeatedly referred to under the title “Papaveraceae Alkaloids” in Vols. 10
(1967), 12 (1970), 15 (1975), and 18 (1981). The information collected here
updates the material presented in earlier reviews. More than 240 alkaloids
isolated by the end of 1987 from African Strychnos are listed in the chapter
on “African Strychnos Alkaloids,” which reviews the biochemistry, chemistry,
and pharmacology of these interesting indole alkaloids. This chapter updates
material discussed in Vols. 5 (1955), 8 (1965), and 11 (1968) of this treatise.
The medically important group of “Cinchona Alkaloids” presented in Vols. 3
(1953) and 14 (1973) is again reviewed here. In addition to chemistry, the
chapter discusses important analytical details and brings the pharmacology
of these alkaloids up to par.
It is pleasing to note that this volume continues to benefit from material
collected and presented by an international group of collaborators. Such
collaboration is vital in keeping this treatise moving.
Arnold Brossi
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