The Alkaloids: Chemistry and Pharmacology 32

465 Pages·1988·15.45 MB·English

by  Arnold Brossi (Eds.)

THE ALKALOIDS
Chemistry and Pharmacology
VOLUME 32
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THE ALKALOIDS
Chemistry and Pharmacology
Edited by
Arnold Brossi
National Institutes of Health
Bethesda, Maryland
VOLUME 32
Academic Press, Inc.
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CONTENTS
Contributors ............................................................ vii
Preface ................................................................. ix
Chapter 1. Forensic Chemistry of Alkaloids by Chromatographic Analysis
YOHEHI ASHIMOTKOA, ZUKOK AWANISAHNI,D MASATAKMAO RIYASU
1. Introduction ....................................................... 1
11. Extraction, Preparation, and Derivatization 3
111. Analytical Techniques ............................................... 8
IV. Analysis of Alkaloids 14
References ......................................................... 61
Chapter 2. Steroidal Alkaloids of Apocynaceae and Buxaceae
ATTA-UR-RAHMAANUN A NJUMM UZAFFAR
........................ 19
s of Apocynaceae.. ................................. 19
111. Steroidal Alkaloids of Buxaceae ...................................... 175
IV. Biosynthesis ... .... .......... ... 23 1
V. Pharmacology ...................................................... 232
References ......................................................... 233
Chapter 3. Distribution of Alkaloids in Traditional Chinese Medicinal Plants
Cui-Qiu HAN,Y A-YANC HENA,N D XIAO-TIALNI ANC
1. Introduction ....................................................... 241
11. Diterpene Alkaloids ................................................. 242
111. Stephania Alkaloids. ............... ... 252
IV. Tropane Alkaloids .................................................. 261
V. Miscellaneous Alkaloids ............................................. 263
References ......................................................... 268
V
v1 CONTENTS
Chapter 4. N-Acyliminium lons as Intermediates in Alkaloid Synthesis
w.
HANKH lEMSTRA AND NlCO SPECKAMP
I. Introduction ............................................... 27 1
11. Isoquinoline .............................................. 272
111. Indole Alkaloids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 290
IV. Pyrrolidine, Piperidine, and Tropane Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . 30 7
V. Izidine Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 318
References ............................... 344
Chapter 5. Quinoline Alkaloids Related to Anthranilic Acid
M. F. GRUNDON
I. Introduction . . . ..................... 341
e . . . . . . . . . . . . . . . . . . . 346
111. 3-Prenyl-2-quinolinones and Related Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . 350
IV. Tricyclic Alkaloids Derived by Oxidation of 3-Prenyl-2-quinolinones and
Related Compounds ................................................ 358
V. 2,2-DimethylpyranoquinoEnone Alkaloids of the Flindersine Group and
Related Compounds ................................................ 378
VI. Dimeric Quinolinone Alkaloids ............ ......... ............ 38 6
VII. 1 ,I-and 1,2-Dimethylallyl Alkal nd Related Geranylquinoliries . 395
VIII. Furoquinoline Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 401
IX. 2-Alkyl- and 2-Aryl-4-Quinolinones and Related Alkaloids 423
X. Pharmacology ...................................................... 430
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 433
Index. . . . . . . . . . . . . . . . . . . . . . . ...................... 44 1
Cumulative Index of Titles.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 449
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
YA-YANC HEN (241), School of Pharmaceutical Sciences, Beijing Medical
University, Beijing, Peoples Republic of China
M. F. GRUNDON( 341), Department of Chemistry, University of Ulster, Col-
eraine, Northern Ireland
GUI-QIUH AN (241), School of Pharmaceutical Sciences, Beijing Medical
University, Beijing, Peoples Republic of China
YOHEI HASHIMW (l), Kobe Women’s College of Pharmacy, Kobe, Japan
HENKH IEMSTRA( 271), Laboratory of Organic Chemistry, University of
Amsterdam, Amsterdam, The Netherlands
KAZUKOK AWANISHI (l), Kobe Women’s College of Pharmacy, Kobe, Japan
XIAO-TIANLI ANG (241), Institute of Materia Medica, Chinese Academy of
Medical Sciences, Beijing, Peoples Republic of China
MASATAKMAO RIYASU( l), Kobe Women’s College of Pharmacy, Kobe, Japan
ANJUMM UZAFFAR (79), H. E. J. Research Institute of Chemistry, Univer-
sity of Karachi, Karachi, Pakistan
ATTA-UR-RAHMAN(7 9), H. E. J. Research Institute of Chemistry, Univer-
sity of Karachi, Karachi, Pakistan
W. NICOS PECKAMP( 271), Laboratory of Organic Chemistry, University of
Amsterdam, Amsterdam, The Netherlands
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PREFACE
The forensic chemistry of habit-forming alkaloids, including opium, coca,
ergot, and khat alkiloids, is much more sophisticated today than in 1970,
when this topic was reviewed in Vol. 12 of this series. Interest in the field has
recently been renewed, with the focus of attention being chromatographic
separation techniques and sensitive methods for alkaloid detection. Presen-
tation of many novel steroidal alkaloids isolated from Apocyanaceae and Bux-
aceae plants, together with partial synthesis of representative alkaloids, make
this chapter a valuable supplement to those which appeared in Vols. 9 and
14 of this series. The medicinal plants still widely used in Chinese folk prac-
tices contain many different alkaloids. The structures and pharmacological
properties of those alkaloids which have appeared in the literature since 1980
are presented here and may hopefully stimulate the appetite of those who
are interested in total synthesis. Cyclization of N-acyliminium ion inter-
mediates is an important method for the total synthesis of many types of
alkaloids and is presented here with several examples. Quinoline alkaloids
other than Cinchona alkaloids were reviewed in Vols. 3, 7, 9, and 17 of this
series. Since the last report appeared 10 years ago, 80 new alkaloids were
isolated and are presented here with their structures and pharmacological pro-
perties.
Arnold Brossi
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