Flavonoids of Artemisia argyi
FLAVONOIDS OF Artemisia argyi
UDC 547.972
I. I. Chemesova and E. V. Boiko
We have investigated the flavonoid composition of Artemisia argyi Level. et Vaniot
(family Asteraceae).
The epigeal part of this wormwood collected in the late building phase
in the environs of the village of Kuguki, Ussuri region, (Maritime Territory) in August 1983,
was extracted with 70% aqueous ethanol. The extract, concentrated to a syrupy residue, was
treated with hot distilled water, and the aqueous extract was treated successively with chloroform and ethyl acetate. The chloroform extract proved to be the richest in flavonoids, and
this was chromatographed on a column of silica gel (L 40/100). Elution was performed with
chloroform and with mixtures of chloroform and ethanol. Flavonoids (I-IV) were isolated.
Compound (I) ' ClsHl607, mp 237°C (chloroform--ethanol) " UV spectrum: 1max
EtOH 279,344 nm.
The appearance of a characteristic bathochromic shift (& 26 nm) of the absorption maximum on
the addition of AICI 3 + HCI showed the presence of a free hydroxyl at C-6 [i, 2]. The use
of other complex-forming reagents showed an OH group only at C-5. PMR spectrum (DMSO, 6,
ppm):
7.52 (dd, Jl = 9 Hz, J2 = 2.5 Hz, H-6'); 7.41 (d, J = 2.5 Hz, H-2'); 6.98 (d, J = 9 Hz;
H-5'); 6.75 (s, H-8); 6.52 (s, H-3); 3.80 and 3.78 (3H, s, each 2 × OCH 3 at C-3' and C-4');
3.70 (s, 3H, OCH 3 at C-7). Compound (I) formed a diacetate with the composition C2~H2009, mp
155°C. PMR spectrum (CDCI 3, 6, ppm): 7.50 (dd, Jl = 9 Hz, J2 = 2 Hz, H-6'); 7.25 (d, J =2 Hz,
H-2'); 6.95 (d, J = 9 Hz, H-5'); 6.65 (s, H-8); 6.55 (s, H-3); 3.98 (s, 6H, OCH 3 at C-3' and
C-4'); 3.85 (s, 3H, OCH 3 at C-7); 2.52 and 2.40 (3H, s, each 2 × COOCH 3 at C-5 and C-6).
By an analysis of spectral characteristics and physical constants, the structure of (I)
was determined as 5,6-dihydroxy-3',4',7-trimethoxyflavone.
Japanese scientists have synthesized 5,6-dihydroxy-3',4',7-trimethoxyflavones [3], and this had a melting point close to
that of flavonoid (I) (mp 232°C). Compounds (II), C18H1607, mp 200°C (diacetate with mp
180°C); (III), mp C18H1607, mp 204°C; and (IV), CIvH1407, mp 228°C, were identified on the
basis of their UV, IR, and PMR spectra and a comparison of them with of authentic samples as
eupatorin, cirsilineol, and jaceoside, respectively.
From the same species, Japanese workers have isolated eupatilin and 5-hydroxy-3',4',6,7tetramethoxyflavone [4]. This is the first time that the compound that we have isolated has
been detected in A. ar~yi.
LITERATURE CITED
i.
2.
M. Miski, A. Ulubelen, and T. J. Mabry, Phytochemistry, 22, No. 9, 2093 (1983).
F.A.T.
Barberan, L. Hernandes, F. Ferreres, and F. Tomas, Planta Medica, No. 5, 452
3.
K. Fukui, M. Nakayama, T. Matsui, M. Masumura, and F. Horie, Nippon Kagaku Zasshi, 9,
No. 12, 1270 (1961).
Chongming Wu and Youyou To, Zhongyao Tongbao, iO, No. i, 31 (1985).
(1985).
4.
V. L. Komarov Botanical Institute, Academy of Sciences of the USSR, Leningrad. Pacific
Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR,
Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, p. 832-833, NovemberDecember, 1990. Original article submitted March i, 1990.
0009-3130/90/2606-0713512.50 ©1991 Plenum Publishing Corporation
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