The Alkaloids: Chemistry and Pharmacology 42

325 Pages·1992·9.91 MB·English

by  Geoffrey A. Cordell (Eds.)

THE ALKALOIDS
Chemistry and Pharmacology
VOLUME 42
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THE ALKALOIDS
Chemistry and Pharmacology
Edited by
Geoffrey A. Cordell
College of Pharmacy
University of Illinois at Chicago
Chicago, Illinois
VOLUME 42
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CONTENTS
CONTRIBUTOR.S . . . . . . . . . . , . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii
PREFACE. .............................................................. ix
Chapter I. Eburnamine-Vincamine Alkaloids
MAURIL OUNASMAAAN D AUTOT OLVANEN
I. Introduction . . . . . . . . . . . . . . . . . . . . . . . .................. 2
11. Occurrence . . ............................ ............ 3
111. Syntheses . . . .......................... 3
IV. Reactions ...................................... 81
V. Biosynthesis . . ........................... 83
VI. Spectroscopy . . . . . . . . . . . . . . . . . . . . . . .................. 85
VII. Pharmacology ........................................ 94
VIII. Perspectives . . . . . . . . . . . . . . . . . . . . . . . .................. 104
IX. Addendum ..................................... 104
References .......................... 105
Chapter 2. Antifungal Alkaloids
ALICEM . CLARKA ND CHARLEDS . HUFFORD
I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 I7
11. Antifungal Alkaloids from Higher P .................. 120
111. Antifungal Alkaloids from Microo 141
IV. Antifungal Alkaloids from Marine s ......................... 144
. . . . . . . . . . . . . . . . . . . . . . . 145
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 146
Chapter 3. Chemistry of the Diterpenoid Alkaloids
FENG-PENWG ANGA ND XIAO-TIALNI ANG
I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 152
11. Norditerpenoid Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153
111. Diterpenoid Alkaloids . . . . . . . . . . . . . . , . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189
IV. Skeletal Conversions of Diterpenoid Alkaloids . . . . , . . . . . . . . . . . . . . . . . . . 240
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 242
V
vi CONTENTS
Chapter 4. Sulfur-Containing Alkaloids
JERZY T. WROBELA ND KRYSTYNWA OJTASIEW~CZ
I. Introduction ...... ..................... 249
11. Alkaloids with One ............ 250
111. Alkaloids with One Sulfur Atom in the Ring .......................... 257
IV. Alkaloids with More Than One Sulfur Atom ............... 27 I
V. Sulfur-Containing Alkaloids with a Peptide Structure ............... 282
VI. Pharmacology ............................... 292
References ................................... 294
CUMULATIVINED EX OF TITLES. .......................................... 299
INDEX ................................................................. 307
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
ALICEM . CLARK(I 17), Department of Pharmacognosy, School of Phar-
macy, The University of Mississippi, University, Mississippi 38677
CHARLEDS. HUFFORD(1 17), Department of Pharmacognosy, School of
Pharmacy, The University of Mississippi, University, Mississippi 38677
XIAO-TIANL IANG(1 51), Institute of Materia Medica, Chinese Academy of
Medical Sciences, Beijing 100050, People’s Republic of China
MAURIL OUNASMA(IA), Laboratory for Organic and Bioorganic Chem-
istry, Technical University of Helsinki, SF-02150 Espoo, Finland
ARTO TOLVANE(Nl) , Laboratory for Organic and Bioorganic Chemistry,
Technical University of Helsinki, SF-02 150 Espoo, Finland
FENG-PENWGA NG(1 51), Department of Chemistry of Medicinal Natural
Products, College of Pharmacy, West China University of Medical Sci-
ences, Chengdu, Sichuan 610041, People’s Republic of China
KRYSTYNWAO JTASIEWI(C24Z9 ), Department of Chemistry, University of
Warsaw, Warsaw, Poland
JERZYT . WROBE(L2 49), Department of Chemistry, University of Warsaw,
Warsaw, Poland
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PREFACE
With this, Volume 42 of the series “The Alkaloids, Chemistry and
Pharmacology,” the editorship formally is transferred. As the new editor
of this long-running series, let me first of all thank profusely, Dr. Arnold
Brossi, who, over the course of the period 1982-1991 did such a wonder-
ful job of not only maintaining the series, but enhancing both the quality of
the reviews and the rate of publication. As a result, the reputation of the
series is now finer than ever. Arnold, we wish you well in your “semi-
retirement” !
The goals for the future of the series are to maintain the outstanding
quality of the reviews, to provide such reviews in a timely manner as the
interest in various aspects of alkaloid chemistry and biology ebbs and
flows, and to examine this broad and diverse group of natural products
from some different perspectives. In the past few years we have seen
tremendous increases in the level of interest in natural products chemistry
in general, and in the field of alkaloid chemistry and biology in particular.
While plans are already in hand for the next few volumes, I would be very
willing to entertain proposals for future chapters for this series.
This volume deals for the most part, with the current status of four
groups of alkaloids of substantial biological relevance. Chapter 1 by Lou-
nasmaa and Tolvanen, focuses on the “Eburnamine-Vincamine Alka-
loids,” and discusses the new alkaloids, and the extensive synthetic and
pharmacologic work that has been conducted since the last review in 1981.
Clark and Hufford present a review which focuses on the “Antifungal
Alkaloids,” especially those compounds that might be important as lead
structures for the development of agents useful in treating the opportunis-
tic infections associated with AIDS. Wang and Liang bring up-to-date the
area of the diterpenoid alkaloids from a chemical perspective. Over the
years this large group of alkaloids has produced a fascinating array of
molecular gyrations. Finally, Wrobel and Wojtasiewicz revisit the topic of
“Sulfur-Containing Alkaloids” (which was last covered in Volume 26)
from a chemical and biological perspective.
Geoffrey A. Cordell
University of Illinois at Chicugo
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