Full text of DOI:10.1016/0031-9422(71)85053-7

1
971, Vol. 10, 1687. Pergamon Press. Printed in England.
ANGIOSPERMAE
ANACARDLACEAE
LIGNOCERIC ACID AND OTHER COMPOUNDS OF
XORGE A. DOMINGUEZ,
F.
and
B. DE
Departamento de Quimica, Instituto
y de Estudios Superiores de Monterrey, Monterrey, N.L.,
(Received 2 November 1970)
Plant. Schinus
L. ‘pirul’.
Uses. The fruits, gum exudates and the leaves are used with medical purposes.’
4
Previous work. On the essential oil
and tannins and sister
Plant material. Twigs and leaves collected in Monterrey, N.L. were extracted succes-
sively with petrol,
and
chromatographed on silica gel.
m.p. IR, NMR, mixed m.p.
(Found: C, 0, C,
Mol. wt. M+ 426; m.p. IR
Important IR peaks: 3660, 3580 (m), 2900 (s), 2840 (m), 1620 (w), 1450 (m), 1435 (n),
360, 1080, 870 LB color red, green, blue, to black, TNM test positive. UV
12 nm (c-1430). Acetate: m.p. Important IR peaks;
Light
Lignoceric acid,
CO TLC. New compound:
H,
8
1.63; H, 0,
1
2
3420 (m), 2900-2830 (s), 1740 (s), 1620 (w), 1455 (m), 1435 (m), 1370(m), 1360(m), 1225(s),
1
045(m), 880
eluted by
mixed m.p.,
-
38”
and superimposable IR spectra of alcohol and acetate.
(m.p., mixed m.p. IR, UV,
Reactions for alkaloids were
negative.
Acknowledgements-The FORGE for a research grant and to Prof. Dr. P.
mass spectrum.
from SYNTEX for the
*
Part XV in the series “Studies on Mexican Medicinal Plants”.
Medicinales de (4th Edition) p. 261, Editorial Botas, Mexico (1959).
Ann. Chim. Appl.
(1948); C.A. d (1951).
Quim. Farm. 1,133 (1931).
and L. B. Pharm.
M. MARTINEZ
,
A.
G.
M.
Sci.
G
ONZALEZ,
K. K.
(1962).
1971, Vol.
pp. 1687 to 1688. Pergamon Press. Printed in England.
APOCYNACEAE
TRITERPENES FROM MELODZNUS AUSTRALZS
L. A. MITSCHER and E. N.
Division of Natural Products Chemistry, College of Pharmacy, The Ohio State University, Columbus,
Ohio 43210, U.S.A.
(Received 21 July 1970)
A
NUMBER of interesting
alkaloids have been isolated from the root bark of the
Southeast Asian woody shrub, Melodinus Maider and In our hands a
Present address: Faculty of Pharmacy, The American University, Beirut, Lebanon.
H. H. A. LINDE, Helv. (1965).
1
687

1688
specimen of the aerial parts yielded very little alkaloid
g of a crude mixture from
kg). Accordingly, we turned our attention to the more plentiful terpene fraction
2
g,
triterpenes lupeol and
M.
Although a related species,
no studies of a similar type have been carried out on
Accordingly, the ground leaves and stems were extracted with
monogynous, is reported to contain the
by
percolation and the extractives were separated into broad chemical classes in the usual
fashion (Experimental). The terpene-sterol fraction was chromatographed on silicic acid
columns with fractions monitored by TLC and weight. Only two substances of consequence
were present and these were identified as betulin and oleanolic acid after spectroscopic
examination, preparation of suitable derivatives, and comparison with authentic specimens.
Betulin and oleanolic acids are relatively common triterpenes but this is the first report of
their occurrence in
sp. and is presented for its chemotaxonomic
EXPERIMENTAL
The plant parts consisted of the dry, powdered leaves and stems of Melodinus
Maider and
Betche, and were purchased in 1965 from the Meer Corporation, New York, N.Y., as lot number 6-23835.
The ground plant (16.3 kg) was percolated at room temp. with
plant. The solvent was removed under reduced pressure at a temperature not in excess of 40” to give 1.15 kg
of a dark, gummy residue. This residue was partitioned between 2% citric acid and A con-
siderable portion (300 insoluble in either phase. The alkaloids were recovered from the citric acid
etc., to yield g (0.03 of a complex dark mixture.
layer was evaporated and this residue (309 g) was further subfractionated by partition between
containing Evaporation of the layer produced 135 g of
250 1. sufficing to exhaust the
(
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solution by alkalinization and extraction with
The
hexane and
crude teroene-sterols. A portion of this (24
was chromatographed in the usual way over 400 g of
1
00
ml each fraction). These weighed 8.67 and
purity was achieved treating mg of crystals with C and
in as eluant. In this way 305 of pure crystals, m.p.
diacetate, m.p. dibenzoate, m.p.
dihydro derivative m.p.
( p y r i d i n e ) ;
Compound A (subsequently
as betulin) was present in fractions 22-35
from
244-247”. Ultimate
on silica gel G using
8
14”
Further elutioniof nt he original column with 2
(
2.68 g) which crystallized with great difficulty from
of this material was chromatographed over
CHATTERJI, N.
and M. L. DHAR, J. Sci. Znd. Res. India
262 (1959);
Res
Zndia
546 (1954).
R. HEGENAUER, Chemotaxonomie der
Vol. III, 145, Birkhauser Verlag, Base1 (1964).