Alkaloids: Chemical and Biological Perspectives, Vol. 10

447 Pages·1996·14.43 MB·English

by  S. William Pelletier (Ed.)

Alkaloids" Chemical
and Biological
Perspectives
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Major Reference Works
Comprehensive Heterocyclic Chemistry II
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* In preparation
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ALKALOIDS: CHEMICAL
AND BIOLOGICAL
PERSPECTIVES
Volume Ten
Edited by
S. WILLIAM PELLETIER
Institute for Natural Products Research
and
The Department of Chemistry
University of Georgia, Athens
PERGAMON
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Copyright (cid:14)9 1996 Elsevier Science Ltd
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First Edition 1996
Library of Congress Cataloging in Publication Data
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Library of Congress
British Library Cataloging in Publication Data
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ISBN 0 08 042791 X
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Dedicated to
the memory of
Hans Eduard Schmid
(1917-1976)
His scientific interest centered on the chemistry of organic natural products as well as
on the mechanistic aspects of organic reactions. Important contributions in the field of
alkaloids began in 1945 (together with Paul Karrer) when he investigated Calabash
curare of the South American Indians. This muscle relaxant drug is a dark brownish
mixture of more than 60 alkaloids. He separated this water-soluble mixture with newly
developed methodology (cellulose column, two dimensional paper chromatography) and
characterized the individual alkaloids mainly by their UV spectra and color reactions
with Ce(IV) sulfate. Several observations facilitated structure elucidation of the hith-
erto unknown compounds. Alkaloids isolated from certain Strychnos species proved to
be identical with some of the curare alkaloids. Other curare alkaloids could be prepared
from Strychnos alkaloids by photochemical oxidation (e.g. curarine, calebassine). A
sophisticated methylation experiment (1958) demonstrated that the most important
(toxic) curare alkaloids are dimeric. In 1958 he discovered that the Weiland-Gumlich
aldehyde, a well known degradation product of strychnine, can be dimerized to give the
curare alkaloid dihyrotoxiferine. Subsequently, the structures of most of the curare al-
kaloids were elucidated.
When NMR and mass spectrometry became available, a large number of alkaloids from
various apocynaceous plants were investigated (e.g. species of the genera Alstonia,
Aspidosperma, Conopharyngia, Gabunia, Hunteria, lboga, Oncinotis, Rauwolfia,
Vinca). Villalstonine was the first bisindole alkaloid whose structure was elucidated by
mass spectral analysis.
One of his special interests was the correlation of compounds by partial syntheses,
including the determination of the absolute configuration of these natural products.
During structural investigation of the spermidine alkaloid oncinotine, he observed a
ring enlargement known as the Zip reaction.
Manfred Hesse
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Contributors
Raymond J. Andersen, Department of Chemistry and Oceanography, University of British
Columbia, Vancouver, B.C., Canada V6T 1Z1
Bill J. Baker, Department of Chemistry, Florida Institute of Technology, Melbourne,
Florida 32901, U.S.A.
I.R.C. Bick, Department of Chemistry, University of Tasmania, Hobart, Tasmania,
Australia 7001
Fangming Kong, Department of Chemistry and Oceanography, University of British
Columbia, Vancouver, B.C., Canada V6T 1Z1
Rob W. M. Van Soest, Department of Coelenterates and Porifera, Institute for Systematics
and Population Biology (Zoologisch Museum), University of Amsterdam, P. O. Box
94766, 1090 AT Amsterdam, The Netherlands
Marilyn J. Schneider, Department of Chemistry, Lafayette College, Easton, Pennsylvania
18042-1782, U.S.A.
vii
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Preface
Volume l0 of this series presents four timely reviews. Chapter 1 is a monumental survey of
"Alkaloids from Australian Flora" by I. R. C. Bick of the University of Tasmania. This chapter
provides a fascinating account of the history of alkaloid discovery in Australia beginning with the
isolation of the first alkaloid from an Australian plant, the Tasmanian sassafras (Atherosperma
moschatum), by Zeyer in 1861. Also included is a comprehensive survey of alkaloid-bearing
plants, and a section dealing with detection, estimation, extraction, and work-up procedures for al-
kaloids.
Chapter 2 by Marilyn Schneider of Lafayette College provides a comprehensive up date to the
chapter on "Pyridine and Piperidine Alkaloids" which appeared in volume 3 of this series. The fo-
cus of this chapter is on new alkaloids isolated, biosynthesis, and biological properties.
Chapter 3 by Raymond J. Andersen, Rob W. M. Van Soest and Fangming Kong of the
University of British Columbia and the University of Amsterdam, treats "3-Alkylpiperidine
Alkaloids Isolated from Marine Sponges in the Order Haplosclerida". Marine sponges occur in all
the world's oceans a~d are frequently one of the dominant life forms on tropical coral reefs and
under the Antarctic ice cap. Studies over the past thirty years have shown that sponges are a rich
source of alkaloids. Many of these sponge alkaloids are related to each other by the presence of a
3-alkylpiperidine moiety in their structures. It happens that the sponges that have been reported to
contain 3-alkylpiperidine alkaloids are all in the order Haplosclerida.
Chapter 4 by Bill J. Baker of the Florida Institute of Technology reviews "13-Carboline and
Isoquinoline Alkaloids from Marine Organisms". [~-Carbolinc and isoquinoline alkaloids are some
of the pharmacologically most significant marine natural products. This chapter treats the isolation,
structure elucidation, synthesis, biosynthesis, and pharmacological activity of these alkaloids.
Each chapter in this volume has been reviewed by at least one expert in the field. Indexes for
both subjects and organisms are provided.
The editor invites prospective contributors to write him about topics for review in future vol-
umes in this series.
S. William Pelletier
Athens, Georgia
October 1995