Chemistry of Natural Compounds, Vol. 44, No. 3, 2008
A TRITERPENE GLYCOSIDE AND FLAVONOIDS
FROM LEAVES OF Akebia quinata
M. G. Sutiashvili, M. D. Alaniya,* A. V. Skhirtladze,
and E. P. Kemertelidze
UDC 547.918.972
Decne. growing in
We previously communicated the isolation from the polar fraction of leaves of
Akebia quinata
Georgia oftwotriterpeneglycosides3- -(α-L-Rha -1,2-L-Ara )-28- -(α-L-Rha -1,4-β-D-Glc -1,6-β-D-Glc )ofoleanolicacid
O
O
p
p
p
p
p
and a second glycoside of hederagenin with the same sugar chain [1] that had the structure of the corresponding
hederacolchisides B and C, which were isolated previously from and [2] and from the pericarp
Hedera helix
H. caucasigena
of
. Both glycosides were found in the leaves of this plant and characterized for the first time.
A. quinata
In continuation of studies of the leaves of
growing in Georgia, we isolated three pure compounds from the
A. quinata
slightly polar ethylacetate fraction by adsorption chromatography over a column of silica gel.
13
Compound 1, C H O . The C NMR spectrum of glycoside 1 exhibited resonances for the aglycon part at 13.1,
41 66 12
15.9, 17.4, 26.1, 33.4, and 23.6 ppm, typical of the six methyls of hederagenin at C-24, C-25, C-26, C-27, C-29, and C-30. The
C-12—C-13 double bond was recorded at δ 123.0 and 144.9 ppm; C-23 with a primary hydroxyl, at δ 64.2 ppm. A resonance
at 81.7 ppm indicated that the C-3 genin hydroxyl was glycosylated; at δ 180.2 ppm, a free carboxyl on C-17.
The PMR spectrum of 1 showed resonances at δ 4.57 and 5.20 ppm that belonged to two anomeric protons of
L-arabinose and L-rhamnose, respectively. The L-rhamnose methyl was recorded at δ 1.26 ppm. Resonances with integrated
intensities corresponding to nine biose protons were found at δ 3-4 ppm. The resonance for C-2′ of L-arabinose was observed
13
in the C NMR spectrum at δ 76.3 ppm and indicated that the rhamnose was bonded to this sugar through the C-2 hydroxyl
[3].
Based on the results and the literature, 1 was characterized as hederagenin-3- -α-L-Rha -(1→2)-α-L-Ara , or
O
p
p
α-hederin, which was isolated previously from
sp. Osbeck [4].
Clematis
Compound 2, C H O , mp 201-204°C and 3, C H O , mp 180-182°C, were hydrolyzed by rhamnodiastase to
27 30 16
27 30 15
13
give rutinose [5, 6]. The aglycon of 2 was kaempferol; of 3, quercetin. The PMR and C NMR spectra and TLC
mobility compared with an authentic sample identified 2 as kaempferol-3- -β-D-rutinoside or nicotiflorin [5]; 3, quercetin-
O
3-β-D-rutinoside, or rutin [6].
REFERENCES
1.
2.
3.
M. Sutiashvili, E. Yarosh, S. Lavua, A. Pishet, and V. Mshvildadze,
, 6, No. 5, 546 (2006).
Khim. Zh. Gruz.
, 20, 708 (1965).
R. Tschesche, W. Smidt, and G. Wulf,
Z. Naturforsch.
R. Zh. Karimov, R. U. Umarova, Z. Saatov, M. G. Levkovich, and N. D. Abdullaev,
, 670
Khim. Prir. Soedin.
(1998).
4.
5.
H. Kizu and T. Tomimori,
, 28C, 3555 (1980).
Chem. Pharm. Bull.
M. Alaniya, E. Kemertelidze, and N. Komissarenko,
Flavonoids from the Genus Astragalus . Flora of Georgia
[in Russian], Metsniereba, Tbilisi (2002).
M. D. Alaniya, N. F. Komissarenko, and E. P. Kemertelidze, , 531 (1971).
Khim. Prir. Soedin.
L
6.
I. G. Kutateladze Institute of Pharmaceutical Chemistry, Georgia, Tbilisi, 0159, ul. P. Saradzhishvili, 36, fax (995)
32 52 00 23, e-mail: merialania@yahoo.com. Translated from Khimiya Prirodnykh Soedinenii, No. 3, p. 321, May-June, 2008.
Original article submitted February 18, 2008.
0009-3130/08/4403-0402 ©2008 Springer Science+Business Media, Inc.
402
Sutiashvili
