Full text of DOI:10.1016/0031-9422(71)85049-5

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SHORT COMMUNICATION
MYRICETIN-7-GLUCOSIDE F ROM THE ANDRAECIUM OF
THE F LOWERS OF
INOPHYLLUM
S. SAN K AR A S U B R AM AN I AN and A. G. R.
Department of Chemistry, Jawaharlal Institute of Postgraduate Medical Education
Pondicherry-6, India
Research,
(Received 18 September 1970)
Abstract-The andraecium of the flowers of Calophyllum inophyllum has been found to contain
glucoside, recorded for the first time, along with small quantities of free myricetin and quercetin.
INTRODUCTION
inophyllum
(Guttiferae) is a moderately sized medicinal tree, found on
coastal regions of South India and grown for ornamental purposes. In a preliminary
the isolation of a new glycoside of myricetin from the andraecium of its
flowers was reported, and the characterization of the glycoside as myricetin-7-glucoside is
now given.
RESULTS AND DISCUSSION
The major flavonoid pigment, m.p.
glucose in equimolar ratio. The colour reactions* of the glucoside were similar to those of
myricetin and different from those of indicating the presence of a
yielded, on acid hydrolysis, myricetin and
pyrogallol structure in the molecule. The deep yellow colour in the H&hammer-Hansel
test indicated a free C-3 hydroxyl, and the positive Wilson boric acid test and the absence of
intense UV fluorescence a free
The m.p. and
of the pigment (Table
were
different from all the previously known glycosides of
TABLE 1. R, AND
(n m ) OF
satd.
Pigment
69% phenol BAW Forestal
30%
0.28
390,262
glucoside
379
443
426
0.41
0.61
0.45
0.42
*
No. 1, ascending, temperature 28 2”.
‘
-
AN
O
N, W e a l t h
R a w
M a t e r i a l s , Vol. II, p. 18, C.S.I.R., New Delhi (1950
39 (1965).
Curr. Sci. 33,431 (1964).
S. S.
A. G. R.
B.
and A. G. R.
Bull. Nat. Inst. Sci. India No.
S.
and S. S.
Comparative Biochemistry of Flavonoids, Academic Press, London (1967).
1679

1680
S. S ANKARA
and A. G. R.
The UV and IR
of the glucoside were almost the same as for myricetin (cf.
the spectra of myricetin-7-methyl ether and myricetin as well as quercetin-7-glucoside and
quercetin). The spectral shifts with
agreement with glycosylation at
NaOAc,
and
were all in
Further chemical evidence for the structure of the compound was obtained by complete
methylation and hydrolysis. The partial methyl ether (monohydroxypentamethoxyflavone)
was different from
melted at 250-251” (no
flavone’ (m.p. 228-229”) and
(m.p. 144”;
green). On alkali fission, it yielded
lished the constitution of the partial methyl ether as
acid. This estab-
flavone which showed UV shift (40 nm) with NaOAc, confirming the presence of a free
Thus, the original glucoside was identified, for the first time, as
glucoside.
EXPERIMENTAL*
The fresh andraecium separated from the petals was extracted with hot
and the combined
extracts concentrated
with petrol
with addition of some water towards the end. The aq. concentrate was shaken
and peroxide free ether. The aq. layer kept in an ice-chest for three days deposited a
yellow solid which on recrystallization
sintering at
came out as yellow needles, m.p.
(earlier
379, 260 nm. The ether layer contained free myricetin and
quercetin, identified by direct comparison with authentic samples.
The glycoside yielded a
190-192” + anhyd.
acetate, m.p. 240-241”
+ NaOAc) and methyl ether, m.p.
it yielded myricetin
in acetone, 40 hr). On acid hydrolysis (7
and glucose in equimolar ratio, identified by direct comparison with authentic samples. The methyl ether of
the glucoside under the same conditions of hydrolysis-gave
m.p.
acid
nm. Alkaline fission of the methyl ether gave trimethoxybenzoic
and mixed m.p. 166-168”).
Acknowledgements-We thank Professor T. R. Govindachari, Director, CIBA Research
Goregaon,
Bombay, and Prof. S. Neelakantan, Madurai University, for spectral data, and the Principal, J.I.P.M.E.R.,
for kind encouragement.
* The compounds recorded above analysed satisfactorily for elements and methoxyl.
T. J. MABRY, in Perspectives in
(edited by J. B. HARBORNE and T. SWAIN), Academic Press,
London (1969).
L.
J
LJ RD
,
in Chemistry of
Compounds (edited by T. A. E IS S MAN), p. 115, Academic Press, New
G
York (1962).
G. HARRIS, Dictionary of Organic Compounds (4th edition), p. 2362, Eyre
S. F. M. DEAN and L. E. HOUGHTON, J. Chem. 125 (1966).
Spottiswoode, London (1965).