The Alkaloids: Chemistry and Pharmacology 49

417 Pages·1997·16.27 MB·English

by  Geoffrey A. Cordell (Eds.)

THE ALKALOIDS
Chemistry and Pharmacology
VOLUME 49
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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 49
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CONTENTS
CONTRIBUTO. .R . .S . .. . .. . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . .. . . .. . . . . . . . vii
PREFAC. .E . . . . . . . . . . . . .. , . . . . . . .. . . .. . . . . . . . .. . . . . . . .. . . . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . ix
Gelsernium Alkaloids
HIROMITSTUA KAYAAMNAD SHIN-ICHISRAOK AI
.................................... 1
11. Sarpagine-Type Alkaloids. .. . . .. . . . .. . . . .. . . .. . . . .. . .. .. . . . .. . . . . . .. .. . . . . .. . , . . 2
. .. . . . . . . . . . . . . .. . . . . . . . . 17
IV. Humantenine-Type Alkaloids. . .. . . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . 21
V. Gelsedine-Type Alkaloids. . . . . .. . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . .. . . .. .. . . . . .. . . .. 33
VI. Gelsemine-Type Alkaloids.. . .. . . . . .. . .. . . . . .. . .. . . . . .. . . . . . . . .. . . . . .. . . . . . . . . . . 49
References . . .. . .. . . .. .. . . . . . . . .. .. . ................................... 75
Alkaloids Containing Quinolinequinone and Quinolinequinoneimine Units
TURANO ZTURK
I. Introduction.. . . . . . . . . . .. . . .. . . . .. . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . 79
11. Alkaloids Containing a Quinolinequinone Unit . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80
111. Alkaloids Containing a 143
IV. Summary.. . . . . . . . . . . . . . . 212
References . .. . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . .. . . . . . .. . , . . . . . , . .. . . .. . . . .. . . . . . . . 213
Biosynthesis of Terpenoid Indole Alkaloids in Cutharunthus roseus Cells
ROBERVTE RWORTREO, BERVTA N DER HEIJDENAN, D PAULOR. H. MORENO
I. Introduction.. . . . . . .. . . . .. . . ... . .. ... .. . . . . . . . .. . . . . .. . . . . . . . .. . . . . . . . . . . .. . . . . . .. 222
11. Biological Function of Alkaloids .. . .. . . . .. . .. .. . . ., . . . .. . . . . . . . . . . , 225
111. Pathway Leading to Terpenoid Indole Alkaloids: Intermediates and
Enzymes. . .. . .. . . . .. . .. . . . .. . . . .. . . . .. . . .. . . . . . . . . . . . . . .. . . . .. . . .. . . .. . . . . . .. . . .. . 227
IV. Genes Encoding Enzymes Involved in Terpenoid Indole Alkaloid
V. BMieotsaybnothliecs Eisn. g. .i .n .e .e . .ri. n. .g . .. .. .. .. .... .. .. .. .... . . .. .. .. . . . . .. .. ... . .. .. .... .. .. .. .. .. .. .. .. .. .. .. . ... .. .. .. . . .. .. . . . . .. . .. . . . . . . . . 227604
VI. Regulation of Alkaloid Biosynthesis .. . . . . .. . . .. . . . .. . . . .. . . . .. . . .. . . . . . . . . .. . , 271
VII. Conclusions . . . .. . . . .. . . . .. . . . .. . . .. . . . .. . . . . . .. . .. .. . . . .. . . .. . . . .. . . .. . . . . . . . . . .. 287
References . .. . . . .. . . . .. . . .. . . . . . . . . . .. . .. . . . . .. . . . . . . . . . . .. . . . .. . . , . . . . . .. . . .. , .. 288
V
vi CONTENTS
Macrocyclic Peptide Alkaloids from Plants
HIDEJIIT OKAWAK,O ICHTI AKEYYAU, KIOH ITOTSUYANAANGDI H, IROSHMIO RITA
I. Introduction... ................................................................... 301
11. Peptide Alkaloids from Higher Plants.. ........................................ 303
111. Cyclic Oligopeptides from Higher Plants ...................................... 324
References ....................................................................... 378
CUMULATIIVNDEE XO F TITLES........ ................................................. 389
INDEX .................................................................................. 399
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors’ contributions begin.
YUKIOH ITOTSUYAN(A30G1I) , Department of Pharmacognosy, Tokyo Uni-
versity of Pharmacy and Life Science, Hachioji, Tokyo 192-03, Japan
HIDEJIIT OKAW(3A0 1), Department of Pharmacognosy, Tokyo University
of Pharmacy and Life Science, Hachioji, Tokyo 192-03, Japan
PAULOR . H. MOREN(O2 21), Division of Pharmacognosy, LeidedArnster-
dam Center for Drug Research, University of Leiden, 2300RA Leiden,
The Netherlands
HIROSHMI ORITA(3 01), Department of Pharmacognosy, Tokyo University
of Pharmacy and Life Science, Hachioji, Tokyo 192-03, Japan
TURAONZ TUR(K7 9), Chemical Laboratory, University of Kent at Canter-
bury, Canterbury, Kent Cn 7NH, England
SHIN-ICHISRAOK A(Il ), Faculty of Pharmaceutical Sciences, Chiba Univer-
sity, Inage-ku, Chiba, Japan
HIROMITSTUA KAYA(Ml)A, Faculty of Pharmaceutical Sciences, Chiba Uni-
versity, Inage-ku, Chiba, Japan
KOICHTI AKEY(3A0 1), Department of Pharmacognosy, Tokyo University
of Pharmacy and Life Science, Hachioji, Tokyo 192-03, Japan
ROBERVTA N DER HEIJDEN(2 21), Division of Pharmacognosy, Leiden/Am-
sterdam Center for Drug Research, University of Leiden, 2300RA Leiden,
The Netherlands
ROBERTV ERPOORT(2E2 1), Division of Pharmacognosy, Leiden/Amster-
dam Center for Drug Research, University of Leiden, 2300RA Leiden,
The Netherlands
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PREFACE
It is only nine years since the last review of the Gelsemium alkaloids
appeared in this series. However, two areas that have received substantial
attention in the intervening period warrant this timely review by Takayama
and Sakai: the isolation of new alkaloids, including several with new skeleta,
and the very substantial, and highly successful, efforts at synthesis of the
principal alkaloids through both biomimetic and total synthesis.
One class of alkaloids, those containing quinolinequinone or quinoli-
nequinoneimine moieties, is unusual because representative members of
the series have been isolated from plant, fungal, and marine sources based
on their potent biological activities. Ozturk reviews, for the first time in
this series, the excitipg growth in the number of structures deduced in the
past few years and the intense efforts to synthesize the biologically active
members of this series. In addition, advances in the understanding of the
biogenesis of these metabolites are discussed.
Chapter 3, by Verpoorte, van der Heijden, and Moreno, summarizes the
tremendous progress achieved in the past twenty years in the use of cell
culture systems to delineate and express the pathway of monterpene indole
alkaloid biosynthesis in Catharanthus roseus. The authors review the forma-
tion of the precursor units and then examine the enzymatic aspects of
secondary metabolism. They conclude with an overview of the influence
of exogenous materials on the regulation of alkaloid biosynthesis.
The final chapter, by Itokawa, Takeya, Hitotsuyanagi, and Morita, re-
views the various macrocyclic peptide alkaloids isolated from plants. In
addition to a general overview of the many new peptide and amide alkaloids
that have been isolated recently from a diverse range of plant families, this
review places particular emphasis on the structure-activity relationships,
the conformational analysis, and the antitumor activity of the RA series
of cyclic oligopeptides from Rubia spp.
Geoffrey A. Cordell
University of Illinois at Chicago
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