The Alkaloids Chemistry and Pharmacology 04

369 Pages·1965·16.99 MB·English

by  R.H.F Manske

THE ALKALOIDS
Chemistry and Physiology
VOLUME IV
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THE ALKALOIDS
Chemistry and Physiology
Edited by
R. H. F. MANSKE H. L. HOLMES
Dominion Rubber Research Laboratory Cambridge, Massachusetts
Guelph, Ontario
VOLUME IV
1954
ACADEMIC PRESS INC., PUBLISHERS
NEW YORK
Copyright, 1954, by
ACADEMIC PRESS INC.
125 EAST2 3 ST~RE~ET
NEWY ORK1 0, N. Y.
All Rights Reserved
NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM, BY PHOTOSTAT, MICROFILM,
OR ANY OTHER MEANS, WITHOUT WRITTEN PERMISSION FROM THE PUBLISHERS.
Library of Congress Catalog Card Number: (50-5522)
Printed in the United States of America
PREFACE
The present volume contains an account of the chemistry and biosyn-
thesis of the various classes of isoquinolines in ten separate chapters; we
hope that it will serve as a textbook in this field of chemistry.
The two additional chapters on two classes of alkaloids whose st,ructures
are as yet unknown are designed to provide an up-to-date critical summary.
This completes the chemistry portion of our series, except for a chapter
on miscellaneous alkaloids which will appear in Volume V along with the
chapters on pharmacology.
Once more we are pleased to thank not only our fellow chemists for
their generous reception of our past volumes but also our very conscientious
and patient contributors. We also thank the many authors who have sent
us reprints of their recent work to aid us in the compilation of a supplement.
R. H. F. M.
H. L. H.
March, 196.4
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CONTENTS
Preface . . . . . . . . . . . . . . . . . . . . . . . v
The Biosynthesis of Isoquinolines . . . . . . . 1
By R . H . F . MANSKED, ominion Rubber Research Laboratory. Guelph. Ontario
Simple Isoquinoline Alkaloids
By L . RETI. Buenos Aires. Argentina
I. Introduction . . . . . . . . . . . . . . . . . . 7
I1 . The Anhalonium Alkaloids . . . . . . . . . . . . . . 8
I11 . Extraction and Separation of the Anhalonium Alkaloids . . . . 9
IV . The Anhalonium Isoquinolines . . . . . . . . . . . . . 1 0
V . Structure and Synthesis of the Anhalonium Alkaloids . . . . . 1 3
VI . Other Natural Simple Isoquinolines . . . . . . . . . . . 1 5
VII . Pharmacology . . . . . . . . . . . . . . . . . . 1 9
VIII . References . . . . . . . . . . . . . . . . . . . 2 0
Cactus Alkaloids
By L . RETI. Buenos Aires. Argentina
I . Introduction . . . . . . . . . . . . . . . . . . 2 3
I1. Constitution and Occurrence . . . . . . . . . . . . . 2 3
111 . Location of the Alkaloids in Tissues of the Cacti . . . . . . . 2 5
IV . Extraction of Cactus Alkaloids . . . . . . . . . . . . 2 5
V . References . . . . . . . . . . . . . . . . . . . 2 6
The Benzylisoquinoline Alkaloids
By ALFREDB URGERU, niversity of Virginia, Charlottesville. Virginia
I . Introduction . . . . . . . . . . . . . . . . . . 2 9
I1 . Papaverine . . . . . . . . . . . . . . . . . . . 3 0
I11 . Laudanosine . . . . . . . . . . . . . . . . . . . 48
IV . Monophenolic Bases of the Laudanosine Type . . . . . . . . 5 7
V . Biogenesis of the Bensylisoquinoline Alkaloids . . . . . . . . 6 9
VI . References . . . . . . . . . . . . . . . . . . . 71
The Protoberberine Alkaloids
By R . H . F . MANSKED, ominion Rubber Research Laboratory, Guelph, Ontario,
and WALTERR . ASHFORDM, erck & Co., Ltd., Montreal, Quebec
I . Introduction . . . . . . . . . . . . . . . . . 7 8
I1 . Occurrence . . . . . . . . . . . . . . . . . . . 7 8
I11 . Berberine . . . . . . . . . . . . . . . . . . 7 8
IV . Canadine . . . . . . . . . . . . . . . . . . . . 91
V . Palmatine . . . . . . . . . . . . . . . . . . . 9 2
VI . Shobakunine . . . . . . . . . . . . . . . . . . 9 3
VII . Tetrahydropalmatine . . . . . . . . . . . . . . . . 9 3
VIII . Jatrorrhisine and Columbamine . . . . . . . . . . . . 9 5
IX. Corypalmine and Isocorypalmine . . . . . . . . . . . . 9 5
vii
...
Vlll CONTENTS
X . Scoulerine . . . . . . . . . . . . . . . . . . . 9 7
XI . Sinactine . . . . . . . . . . . . . . . . . . . . . 98
XI1 . Cheilanthifoline. . . . . . . . . . . . . . . . . . 9 8
XI11 . Ophiocarpine . . . . . . . . . . . . . . . . . . 99
XIV . Capaurine and Capauridine . . . . . . . . . . . . . . 10 0
XV . Capaurimine . . . . . . . . . . . . . . . . . . 10 2
XVI . Stylopine and Coptisine . . . . . . . . . . . . . . . 10 2
XVII . Corydaline . . . . . . . . . . . . . . . . . . . 10 3
XVIII . Corybulbine . . . . . . . . . . . . . . . . . . .10 7
XIX . Isocorybulbine . . . . . . . . . . . . . . . . . . 10 8
XX . Thalictrifoline . . . . . . . . . . . . . . . . . . 10 8
XXI . Thalictricavine . . . . . . . . . . . . . . . . . . 10 8
XXII . Nandinine . . . . . . . . . . . . . . . . . . . 10 9
XXIII . Worenine . . . . . . . . . . . . . . . . . . . . 110
XXIV . Umbellatine . . . . . . . . . . . . . . . . . . . 11 1
XXV . Neprotine . . . . . . . . . . . . . . . . . . . 11 1
XXVI . Thalictrine . . . . . . . . . . . . . . . . . . . 11 2
XXVII . Coreximine . . . . . . . . . . . . . . . 1 . . . 11 2
XXVIII . References . . . . . . . . . . . . . . . . . . . 11 3
The Aporphine .Alkaloids
By R . H . F . MANSKET, he Donzin.ion Rubber Research Laboratory, Guelph, Ontario
I . Introduction . . . . . . . . . . . . . . . . . .11 9
I1 . Glaucine . . . . . . . . . . . . . . . . . . . . 120
I11 . Glaucentrine . . . . . . . . . . . . . . . . . . 12 2
IV . Boldine . . . . . . . . . . . . . . . . . . . . 123
V. Laurotetanine . . . . . . . . . . . . . . . . . .12 5
VI . N-Methyllaurotetanine . . . . . . . . . . . . . . . 12 6
VII . Dicentrine . . . . . . . . . . . . . . . . . . .12 6
VIII . Actinodaphnine . . . . . . . . . . . . . . . . . .12 7
IX . Domesticine . . . . . . . . . . . . . . . . . . .12 8
X . Nantenine . . . . . . . . . . . . . . . . . . .12 8
XI . Phanostenine . . . . . . . . . . . . . . . . . .12 9
XI1. Crebanine . . . . . . . . . . . . . . . . . . . 12 9
XI11 . Corydine . . . . . . . . . . . . . . . . . . . . 129
XIV . Isocorydine . . . . . . . . . . . . . . . . . . . 13 0
XV . Corytuberine . . . . . . . . . . . . . . . . . .13 0
XVI . Suaveoline . . . . . . . . . . . . . . . . . . 13 2
XVII . Bulbocapnine . . . . . . . . . . . . . . . . . .132
XVIII . Laurepukine . . . . . . . . . . . . . . . . . . .134
XIX . Isothebaine . . . . . . . . . . . . . . . . . . .13 5
XX. Tuduranine . . . . . . . . . . . . . . . . . .136
XXI . Laureline . . . . . . . . . . . . . . . . . . . .13 7
XXII . Pukateine . . . . . . . . . . . . . . . . . . .138
XXIII . Anolobine . . . . . . . . . . . . . . . . . . .13 9
XXIV . Stephanine . . . . . . . . . . . . . . . . . . .14 1
XXV . Roemerine . . . . . . . . . . . . . . . . . . . 14 1
XXVI . Anonaine . . . . . . . . . . . . . . . . . . . . 142
XXVII . Other Aporphines . . . . . . . . . . . . . . . . . 14 2
XXVIII . References . . . . . . . . . . . . . . . . . . . 14 3
CONTENTS ix
The Protopine Alkaloids
By R . H . F . MANSKED. ominion Rubber Research Laboratory. Guelph. Ontario
I . Introduction . . . . . . . . . . . . . . . . . . 14 7.
I1. Occurrence . . . . . . . . . . . . . . . . . . .148
I11 . Cryptopine . . . . . . . . . . . . . . . . . . .14 9
IV . Cryptocavine . . . . . . . . . . . . . . . . . .155
V . Protopine . . . . . . . . . . . . . . . . . . .15 7
VI. Allocryptopine . . . . . . . . . . . . . . . . . .15 9
VII . Hunnemanine . . . . . . . . . . . . . . . . . .16 0
VIII . Cryptopalmatine . . . . . . . . . . . . . . . . . 1 61
IX. Corycavine . . . . . . . . . . . . . . . . . . .16 2
X . Corycavamine . . . . . . . . . . . . . . . . . .16 3
.
XI Corycavidine . . . . . . . . . . . . . . . . . .16 3
XI1. References . . . . . . . . . . . . . . . . . . .164
Phthalideisoquinoline Alkaloids
By JAROSLASVT ANEKC,h arles Universitp. Praha, Czechoslovakia,
and R . H . F . MANSKED, ominion Rubber Research Laboratonj, Guelph, Ontario
I . Introduction . . . . . . . . . . . . . . . . . . 1 68
I1 . Constitution . . . . . . . . . . . . . . . . . . 1 69
I11 . Syntheses . . . . . . . . . . . . . . . . . . . . 180
IV . Discovery, Isolation, and Properties . . . . . . . . . . . 18 3
V . Physiology and Pharmacology . . . . . . . . . . . . .18 9
VI . References . . . . . . . . . . . . . . . . . . .19 0
Bisbenzylisoquinoline Alkaloids
By MARSHALL KULKAD, ominion Rubber Research Laboratory, Guelph, Ontario
I . Introduction . . . . . . . . . . . . . . . . . .19 9
I1 . Alkaloids Containing One Diphenyl Ether Linkage . . . . . . 20 3
I11 . Alkaloids Containing Two Diphenyl Ether Linkages . . . . . .21 1
.
IV Alkaloids Containing Three Diphenyl Ether Linkages . . . . .23 7
V . References . . . . . . . . . . . . . . . . . . . 24 3
The Cularine Alkaloids
By R . H . F . MANSKED, ominion Rubber Research Laboratorg, Guelph, Ontario
I . Introduction . . . . . . . . . . . . . . . . . .219
I1. Cularine . . . . . . . . . . . . . . . . . . . . 249
I11 . Cularimine . . . . . . . . . . . . . . . . . . .25 1
IV . Cularidine . . . . . . . . . . . . . . . . . . .252
V . References . . . . . . . . . . . . . . . . . . .25 2
a-Naphthaphenanthridine Alkaloids
By R . H . F . MANSKED, ominion Rubber Research Laboratory, Guelph. Ontario
I . Introduction . . . . . . . . . . . . . . . . . . 25 3
I1 . Occurrence . . . . . . . . . . . . . . . . . . .25 3
I11 . Structure . . . . . . . . . . . . . . . . . . . . 256
IV . Pharmacology . . . . . . . . . . . . . . . . . . 26 1
.
V References . . . . . . . . . . . . . . . . . . .26 2