The Alkaloids Chemistry and Pharmacology 52

403 Pages·1998·14.89 MB·English

by  Geoffrey A. Cordell

THE ALKALOIDS
Chemistry and Biology
VOLUME 52
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THE ALKALOIDS
Chemistry and Biology
Edited by
Geoffrey A. Cordell
College of Pharmacy
University of Illinois at Chicago
Chicago, Illinois
VOLUME 52
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CONTRIBUTORS ............................................................ vii
PREFACE. ................................................................ ix
Alkaloids from Sri Lankan Flora
A. A. LESLIEG UNATILAKA
I. Introduction. ....................................................... 2
11. Surveys for Alkaloids.. .............................................. 5
111. Quinoline Alkaloids. ................................................ 7
IV. Acridone Alkaloids ................................................. 27
V. Isoquinoline Alkaloids. .............................................. 29
VI. Carbazole Alkaloids. ................................................ 41
VII. Monoterpene Indole Alkaloids ....................................... 46
VIII. Steroidal Alkaloids ................................................. 79
IX. Phenanthroindolizidine Alkaloids ..................................... 81
X. Ancistrocladus Alkaloids. ............................................ 82
XI. Colchicine and Related Alkaloids.. ................................... 82
XII. Quinazoline and Quinazolone Alkaloids ............................... 84
XIII. Miscellaneous Alkaloids ............................................. 84
XIV. Biological Activity .................................................. 85
XV. Summary and Conclusions ........................................... 88
References ......................................................... 97
The Sarpagine Group of Indole Alkaloids
MAURLI OUNASMARAR, JOH ANHINENA,N D MINNAW ESTERSUN(NDB EH ALONEN)
I. Introduction. ....................................................... 104
11. Occurrence.. ....................................................... 105
111. Syntheses. ......................................................... 137
IV. Reactions.. ........................................................ 145
V. Biosynthesis and Biogenesis .......................................... 148
VI. Spectroscopy ....................................................... 151
VII. Pharmacology ...................................................... 186
VIII. Perspectives. ....................................................... 186
References. ........................................................ 187
Pharmacology of Ibogaine and Ibogaine-Related Alkaloids
PIOTRP OPIKA ND PHILS KOLNICK
I. Introduction ........................................................ 197
11. Historical Overview.. ............................................... 198
V
vi CONTENTS
I11. Chemical Structure and Properties .................................... 199
IV . Pharmacokinetics ................................................... 201
V . General Pharmacological Actions ..................................... 202
VI . Lethality and Neurotoxic Effects ...................................... 211
VII . Effects on Specific Neurotransmitter Systems. .......................... 213
VIII . Conclusions ........................................................ 224
References ......................................................... 226
Chemistry and Biology of Steroidal Alkaloids from Marine Organisms
.
ATFA-UP-RA~EMANADW M IQBAL CHOUDHARY
I . Introduction ........................................................ 233
I1. Monomeric Steroidal Alkaloids ....................................... 234
111 . Dimeric Steroidal Alkaloids .......................................... 239
IV . Steroidal Amines from Marine Organisms ............................. 248
V . Synthetic Studies .................................................... 250
..................... ............................ 254
VII . Pharmacology ...................................................... 255
VnI. Spectroscopy ....................................................... 259
References ..................................................... 259
The Monoterpene Akaloids
GEOFFREAY . CORDELL
I . Introduction ........................................................ 261
. ....................................
I1 Isolation and Structure Elucidation 262
111 . Synthe-sis and Semisynthesis .......................................... 308
IV . Physical and Spectral Properties ...................................... 355
V . Biosynthesis and Biogenesis .......................................... 358
VI . Pharmacology ...................................................... 365
References ......................................................... 370
CUMULATIINVDEE XO FTITLE..S. ........................................... 377
INDEX.. ................................................................. 387
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
M. IQBALC HOUDHAR(2Y33 ), International Center for Chemical Sciences,
H.E.J. Research Institute of Chemistry, University of Karachi, Karachi
75270, Pakistan
GEOFFREAY. CORDEL(L2 61), Department of Medicinal Chemistry and
Pharmacognosy, College of Pharmacy, University of Illinois at Chicago,
Chicago, Illinois 60612-7230
A. A. LESLIEG UNARLAK(Al) , Bioresources Research Facility, Office of
Arid Lands Studies, University of Arizona, Tucson, Arizona 85706-6800
RRJOHA NHINE(1N0 3), Laboratory of Organic and Bioorganic Chemistry,
Technical University of Helsinki, Espoo, FIN-02150, Finland
MAURLI OUNASM(A1A03 ), Laboratory of Organic and Bioorganic Chemis-
try, Technical University of Helsinki, Espoo, FIN-02150, Finland
PIOTRP OPIK(1 97), Institute of Pharmacology, Polish Academy of Sciences,
31-343 Krakow, Poland
AITA-URR AHMAN(2 33), International Center for Chemical Sciences,
H.E.J. Research Institute of Chemistry, University of Karachi, Karachi
75270, Pakistan
PHIL SKOLNIC(K19 7), Neuroscience Discovery, Lilly Research Labora-
tories, Lilly Corporate Center, Indianapolis, Indiana 46285
MINNAW ESTERUN(1D0 3), Laboratory of Organic and Bioorganic Chemis-
try, Technical University of Helsinki, Espoo, FIN-02150, Finland
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PREFACE
During the preparation of this volume of The Alkaloids: Chemistry and
Biology, the death was announced of the Nobel Laureate, Sir Derek H. R.
Barton, at the age of 79. A consummately dedicated natural product chem-
ist, Barton contributed in many ways to the development of alkaloid chemis-
try. He was a founder of the concepts we now take for granted regarding
the conformational analysis of polycyclic ring systems. His ideas about
the biosynthesis of particular alkaloid groups, notably the importance of
phenolic coupling reactions in isoquinoline alkaloid biosynthesis, were fol-
lowed by some of the first biosynthetic experiments in plants testing his
hypotheses. Undoubtedly, his legendary creativity will stand the test of time.
In Chapter 1 of this volume, Gunatilaka, a former Ph.D. student of
Barton, reviews the work that has been conducted on the rich flora of Sri
Lanka for alkaloids. The chemical diversity of the alkaloids is profound
and is reflected in the biology associated with them.
In Chapter 2, Lounasmaa, Hanhinen, and Westersund present an exten-
sive review of the isolation, spectroscopic characterization, and syntheses
that have been conducted in the past 30 years on the sarpagine group of
alkaloids. Revised concepts regarding the biogenesis of these alkaloids
are discussed.
The recent substantial interest in ibogaine and its derivatives as potential
anti-addictive agents is reviewed in Chapter 3 by Popik and Skolnick from
the biochemical and pharmacological perspectives.
Chapter 4 offers an overview of the steroidal alkaloids from marine
organisms by Atta-ur-Rahman and Choudhary. In addition to their unique
sources and challenging structures, several of these alkaloids are currently
of substantial biological interest.
In the final chapter, an update is presented of a review that I prepared
almost 24 years ago on the substantial progress made regarding the isolation,
systhesis, and biological activities of the monoterpene alkaloids.
Geoffrey A. Cordell
University of Illinois at Chicago
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