Encyclopedia of the Alkaloids: Volume 4

397 Pages·1983·6.92 MB·English

by  John S. Glasby (auth.)

ENCYCLOPEDIA OF
THE ALKALOIDS
Volume 4
A Continuation Order Plan is available for this series. A continuation order will
bring delivery of each new volume immediately upon publication. Volumes are
billed only upon actual shipment. For further information please contact the
publisher.
ENCYCLOPEDIA OF
THE ALKALOIDS
Volume 4
John S. Glasby
rer (Organics Division) Ltd.
Manchester, England
PLENUM PRESS • NEW YORK AND LONDON
Library of Congress Cataloging in Publication Data
Glasby, John Stephen.
Encyclopedia of the alkaloids.
Includes bibliographical references and index.
I. Alkaloids - Dictionaries. I. Title.
QD42l.G54 547.7'2'0321 75-17753
@1983 Plenum Press, New York
Softcover reprint of the hardcover 1s t edition 1983
All rights reserved
ISBN-13: 978-1-4615-9324-9 e-ISBN-13: 978-1-4615-9322-5
001: 10.1007/978-1-4615-9322-5
Preface
Volume 4 of the Encyclopedia of the Alkaloids covers the literature to the end of 1981 and
includes those compounds which have been discovered since Volume 3 was published in
1977. There is also a small number of entries giving recently determined structure or addi
tional information regarding alkaloids given in the preceding three volumes.
It is a great pleasure to thank the staff of the John Rylands Science Library of the Univer
sity of Manchester for kindly providing me with access to the literature on this subject.
Woodhouses, JOHN S. GLASBY
Manchester, England
May, 1982
Contents
A ............................... I N ................................ 251
B .............................. 72 0 ................................ 262
C .............................. 79 P ................................ 273
0 ............................. 108 Q. ............................... 299
E ............................. 141 R ................................ 300
F ............................. 152 S ................................ 31O
G ............................. 158 T ................................ 339
H ............................. 167 U ................................ 358
I .............................. 192 V ................................ 361
J ............................. 207 W ............................... 367
K ............................. 210 X ................................ 368
L ............................. 217 Y. ............................... 369
M ............................ 227 Z ................................ 370
Formula Index. . . . . . . . . . . . . . . . . . .. 371
A
ACETYLALLOYOHIMBINE (Alkaloid NRB6)
C23H2SN203
M.p. Indefinite
I
I
OAc
The root bark of Rauwolfia nitida yields this yohimbine-type alkaloid which has been ob
tained as an off-white amorphous powder having no definite melting point. The base is lae
vorotatory with a specific rotation of [aJ52 -89° (c 0.01, CHCI3) and gives an ultraviolet
spectrum in MeOH with absorption maxima at 225,284 and 290 nm. The structure has
been established from chemical and spectroscopic analysis.
M. A. Amer, W. E. Court, Phytochem., 20,2569 (1981)
14-ACETYLBROWNINE ___ :(OMe
M.p. 123-124°C
--J"OAC
This aconitine alkaloid has been isolated from the aerial parts of Delphinium oreophilum by
Russian workers and subsequently from Consolida ambigua (formerly Delphinium ajacis)
by Pelletier and his colleagues. It forms colourless needles when crystallized from EtOH
and has a specific rotation of [alB? +27.8° (c 1.0, CHCI3). The structure has been eluci
dated from spectroscopic evidence.
V. G. Khazlikhim et al., Khim. Prir. Soedin., 869 (1977)
S. W. Pelletier et al., Lloydia, 43, 395 (1980)
(+ )-ACETYLCEPHALOTAXINE
OMe
1
CephalotaxusJortunei yields this minor alkaloid which crystallizes as colourless rods from
EtOH. The above structure has been determined from chemical correlations and the infra
red, NMR and mass spectra.
G.-E. Ma et al., Hua Hsueh Hsueh Pao, 35,201 (1977)
N-ACETYLDELECTINE
___. .-. C
oMe
J~"OH
--
Et
An aconitine alkaloid, N-acetyldelectine occurs in the seeds of Delphinium dictyocarpum. It
yields colourless crystals from C6H6 and has the structure given above based upon spectro
scopic data and chemical hydrolysis.
B. T. Salimov et al., Khim. Prir. Soedin., 128 (1977)
17 -O-ACETYL-19, 20-DIHYDROVOACHALOTINE
Voacanga chalotiana contains this base which forms colourless needles when crystallized
from EtOH. It is laevorotatory with a specific rotation of [0')6° -540 (CHCI3). The ultra
violet spectrum in MeOH has two absorption maxima at 228 and 283 nm. The structure has
been elucidated from chemical analysis and spectroscopic examination.
E. Bombardellietal., Phytochem., 15,2021 (1976)
O-ACETYLGEIBALANSINE
o:n
OMe
OAc
~I ~
~ N~ 0
2
A minor constituent of Geijera blanasae, this base has been assigned the structure given
above on the basis of chemical transformations and the infrared, NMR and mass spectra.
A. Ahond, C. Popuat, J. Pusset, Phytochem., 18, 1415 (1979)
7-ACETYLINTERMEDINE
AC0'ej0;ft:
OH
I
N
A pyrrolizidine alkaloid, this base is a minor constituent of Symphytum uplandicum. The
structure has been established from a study of the hydrolysis products and spectroscopic ex
amination.
c. C. J. Culvenor et al., Austral. l. C hem., 33, 1105 (1980)
ll-ACETYLISOHYPGNA VINE
M.p. 187.5-188SC ~O
o
A napelline-type alkaloid, II-acetylishohypognavine occurs in the basic extract of Aconi
tum japonicum. It forms colourless needles when crystallized from EtOH and is dextrorota
tory with a specific rotation of [a]d9 + 74.1 0 (c 0.8, CHCI3). The structure has been deter
mined from chemical correlations and the infrared, NMR and mass spectra.
S. Sakai et al., l. Pharm. Soc., lapan, 99,647 (1979)
7-ACETYLLYCOPSAMINE
AC0'cd0~OH
OH
I
N
A minor pyrrolizidine alkaloid, this base has been isolated from Symphytum uplandicum. It
has the structure given above based upon chemical analysis, hydrolysis and the infrared,
NMR and mass spectra.
C. C. J. Culvenor et at., Austral. l. Chem., 33, 1105 (1980)
3
I-ACETYL-7-METHOXy-p-CARBOLINE
tJr---0.
M.p. 22~225°C (dec.) M.O~~IN
Ac
A l3-carboline alkaloid, this base occurs in Banisteriopsis caapi. It forms pale yellow nee
dles when crystallized from CHCh and gives an ultraviolet/visible spectrum in CHCl3 with
absorption maxima at 260,289 and 334 nm. The structure has been established from chem
ical correlations and spectroscopic examination.
Y. Hashimoto, K. Kananishi, Phytochem., IS, 1559 (1976).
I-ACETYL-3-METHOXYCARBONYL-p-CARBOLINE
Ac
A constituent of Vestia Iycioides, this base forms pale yellow needles on crystallization
from CHCh-MeOH. It gives an ultraviolet/visible spectrum in EtOH having absorption
maxima at 283 and 374 nm with a shoulder at 270 nm. The structure has been established
from chemical and spectroscopic data.
F. Faini, M. Castillo, R. Torres, Phytochem., 17,338 (1978)
Na-ACETYL-N-METHYLPHLEGMARINE
Cl~3~20
One of the numerous alkaloids isolated from Lycopodium species, this minor base has the
structure given above based upon chemical correlations and the infrared, NMR and mass
spectra.
L. Nyembo et al., Can. J. Chem., 56,851 (1978)
4