Alkaloids: Chemical and Biological Perspectives

377 Pages·1992·6.53 MB·English

by  Norman G. Bisset (auth.)

Alkaloids: Chemical and
Biological Perspectives
S. William Pelletier
Editor
Alkaloids: ChelIlical and
Biological Perspectives
Volume 8
Springer-Verlag
New York Berlin Heidelberg London Paris
Tokyo Hong Kong Barcelona Budapest
S. William Pelletier
Institute for Natural Products Research
and
The School of Chemical Sciences
The University of Georgia
Athens, Georgia 30602, USA
Volumes 1-6 of Alkaloids: Chemical and Biological Perspectives were published by John Wiley
& Sons, New York, New York.
ISSN: 0735-8210
Printed on acid-free paper.
© 1992 Springer-Verlag New York Inc.
Softcover reprint of the hardcover 1st edition 1992
All rights reserved. This work may not be translated or copied in whole or in part without the
written permission of the publisher (Springer-Verlag New York, Inc., 175 Fifth Avenue, New
York, NY 10010, USA), except for brief excerpts in connection with reviews or scholarly analysis.
Use in connection with any form of information storage and retrieval, electronic adaptation,
computer software, or by similar or dissimilar methodology now known or hereafter developed
is forbidden.
The use of general descriptive names, trade names, trademakes, etc., in this publication, even if
the former are not especially identified, is not to be taken as a sign that such names, as understood
by the Trade Marks and Merchandise Marks Act, may accordingly be used freely by anyone.
Production coordinated by Chernow Editorial, Inc. and managed by Christin R. Ciresi; manu
facturing supervised by Jacqui Ashri.
Typeset by Asco Trade Typesetting Ltd., Hong Kong.
9 8 7 6 5 4 3 2 1
ISBN -13 :978-1-4612-7715-6 e-ISBN -13 :978-1-4612-2908-7
DOl: 10.1007/978-1-4612-2908-7
Dedicated to
Derek Harold Richard Barton
(1918- )
In 1953, Barton realized that on theoretical grounds the formula ofPummerer's
ketone, and hence the biosynthesis of morphine according to Robinson, must
be wrong. He then developed (with T. Cohen, 1957) a rational theory for the
biosynthesis of all phenolic alkaloids. Work in the greenhouse eventually
confirmed almost all the predictions starting with morphine [in association"
with W. Steglich (1963) and partly with A.R. Battersby (1965)], alkaloids,
sinomenine, Amaryllidaceae alkaloids, especially galantamine (G.W. Kirby,
1960-1963), proaporphine alkaloids like crotonosine (1963) and finally the
Erythrina alkaloids (1966 and 1968) where the simplest phenolate radical
coupling had to be replaced by a more complex one (1974). He was also the
author of the first paper on conformation analysis (1950) which applies to all
classes of molecules. In later life (1960-), he was mainly concerned with
the discovery and invention of new chemical reactions for use in synthesis,
including manipulation and synthesis of alkaloids.
Preface
Volume 8 of this series presents four timely reviews on alkaloids: Chapter 1
is a magnificent and monumental review of curare, "a group of dart and/or
arrow poisons varying in composition and featuring muscle relaxation as
their basic pharmacological action." The fascinating history of curare is
recounted, beginning with early encounters by the Spanish Conquistadores
through its use as arrow poisons by the forest tribes in hunting and warfare,
its chemistry, ethnography, botany and pharmacology. A terminal section of
this chapter treats the development of modern muscle relaxants. This chapter
thus traces how curare-initially only a crude plant extract-has given rise
to the widely used and very important neuromuscular blocking agents of
today.
The precise role of plant secondary metabolites and their interactions with
insect herbivores have been focal points for research by chemists, botanists and
entomologists for many years. Alkaloids and their glycosides are frequently
involved as feeding deterrents. Chapter 2 treats the relationships between the
chemistry of alkaloids in host plants and the effects that these compounds
may have on insect herbivores. Interestingly, an alkaloid produced by a plant
may manifest different effects on different insects.
Members of the yohimbine family of alkaloids exhibit a wide range of
medicinal properties. The diverse biological activity of these compounds
and their intriguing structures have stimulated the interest of synthetic or
ganic chemists. Several of these complex alkaloids, such as reserpine and
yohimbine, present challenging synthetic targets. Chapter 3 reviews de
velopments in the synthesis of yohimbine alkaloids over the past twelve
years, focusing particularly on the approaches used to synthesize target
molecules.
Chapter 4 summarizes available knowledge about the loline-type pyrrolizi
dine alkaloids. These alkaloids have been reported from only a few genera of
grasses (Poaceae). Their occurrence in grasses is closely associated with the
presence of endophytic fungi. The chapter treats isolation, characterization,
synthesis and the biological activities of these alkaloids.
vii
viii Preface
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 volumes in this series.
s.
William Pelletier
Athens, Georgia
August 1991
Contents
Preface vii
Contributors xi
Contents of Previous Volumes xiii
1. Curare 1
Norman G. Bisset
2. Alkaloid Chemistry and Feeding Specificity of Insect Herbivores 151
James A. Saunders, Nichole R. O'Neill, and John T. Romeo
3. Recent Advances in the Synthesis of Yohimbine Alkaloids 197
Ellen W. Baxter and Patrick S. Mariano
4. The Loline Group of Pyrrolizidine Alkaloids 320
Richard G. Powell and Rich(lrd J. Petroski
Subject Index 339
Organism Index 357
ix
Contributors
Ellen W. Baxter, The R.W. Johnson Pharmaceutical Research Institute,
Welsh and McKean Roads, Spring House, PA 19477-0776, USA
Norman G. Bisset, Pharmacognosy Research Laboratories, Chelsea Depart
ment of Pharmacy, King's College London, University of London,
Manresa Road, London SW3 6LX, England
Patrick S. Mariano, Department of Chemistry and Biochemistry, The Uni
versity of Maryland, College Park, MD 20742, USA
Nichole R. O'Neill, U.S. Department of Agriculture, Agricultural Research
Service, Beltsville, MD 20705, USA
Richard J. Petroski, National Center for Agricultural Utilization Research,
1815 North University Street, Peoria, IL 61604, USA
Richard G. Powell, National Center for Agricultural Utilization Research,
1815 North University Street, Peoria, IL 61604, USA
John T. Romeo, Biology Department, University of South Florida, Tampa,
FL 33620, USA
James A. Saunders, U.S. Department of Agriculture, Agricultural Research
Service, Beltsville, MD 20705, USA
xi
Contents of Previous Volumes
Volume 1
1. The Nature and Definition of an Alkaloid 1
S. William Pelletier
2. Arthropod Alkaloids: Distribution, Functions, and Chemistry 33
Tappey H. Jones and Murray S. Blum
3. Biosynthesis and Metabolism of the Tobacco Alkaloids 85
Edward Leete
4. The Toxicology and Pharmacology of Diterpenoid Alkaloids 153
M.H. Benn and John M. Jacyno
5. A Chemotaxonomic Investigation of the Plant Families of
Apocynaceae, Loganiaceae, and Rubiaceae by Their Indole
Alkaloid Content 211
M. Volkan Kisakiirek, Anthony J.M. Leeuwenberg, and
Manfred Hesse
Volume 2
1. Some Uses of X-ray Diffraction in Alkaloid Chemistry 1
Janet Finer-Moore, Edward Arnold, and Jon Clardy
2. The Imidazole Alkaloids 49
Richard K. Hill
3. Quinolizidine Alkaloids of the Leguminosae: Structural Types,
Analyses, Chemotaxonomy, and Biological Properties 105
A. Douglas Kinghorn and Manuel F. Balandrin
xiii
xiv Contents of Previous Volumes
4. Chemistry and Pharmacology of the Maytansinoid Alkaloids 149
Cecil R. Smith, Jr. and Richard G. Powell
5. 13C and Proton NMR Shift Assignments and Physical Constants
of CwDiterpenoid Alkaloids 205
S. William Pelletier, Naresh V. Mody, Balawant S. Joshi, and
Lee C. Schramm
Volume 3
1. The Pyridine and Piperidine Alkaloids:
Chemistry and Pharmacology 1
Gabor B. Fodor and Brenda Colasanti
2. The Indolosesquiterpene Alkaloids of the Annonaceae 91
Peter G. Waterman
3. Cyclopeptide Alkaloids 113
Madeleine M. Joullie and Ruth F. Nutt
4. Cannabis Alkaloids 169
Mahmoud A. EISohly
5. Synthesis of Lycopodium Alkaloids 185
Todd A. Blumenkopf and Clayton H. Heathcock
6. The Synthesis of Indolizidine and Quinolizidine Alkaloids of
Tylophora, Cryptocarya, Ipomoea, Elaeocarpus, and Related
Species 241
R.B. Herbert
7. Recent Advances in the Total Synthesis of Pentacyclic
Aspidosperma Alkaloids 275
Larry E. Overman and Michael Sworin
Volume 4
1. Amphibian Alkaloids: Chemistry, Pharmacology and Biology 1
John W. Daly and Thomas F. Spande
2. Marine Alkaloids and Related Compounds 275
William F enical