Institute of Modern Traditional Chinese Medicine, Zhejiang University, Hangzhou, 310058, People’s Republic of
China, e-mail: tjk@zju.edu.cn. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 108-110, March-April, 2007. Original
article submitted December 27, 2006.
0009-3130/07/4302-0128
©
2007 Springer Science+Business Media, Inc.
128
O
HO
H
O
CH
3
OH
O
OH
HO
HO
H
O
OH
OH
OH O
O
COCH
2
O
HO
HO
1''
1'''
6'''
1'''
1
Chemistry of Natural Compounds, Vol. 43, No. 2, 2007
CHEMICAL CONSTITUENTS FROM
Clematis terniflora
Lin Zhang, Xiaoling Luo, and Jingkui Tian*
UDC 547.972
One new flavonol glycoside named terniflonoside A (
1
) and four known flavonol glycosides were isolated from
the whole plants of Clematis terniflora. The structure was determined by 1D and 2D NMR, ESI-MS
techniques, and chemical methods.
Key words
: Clematis terniflora, terniflonoside A.
Clematis terniflora Tamura is a folk medicinal plant that grows in southeastern China. The whole plant is used for
treating rheumatoid arthritis [1]. In the course of our ongoing search for anti-inflammatory compounds, we have isolated some
compounds from Ranunculus ternatus [2, 3]; here we report the isolation and structural elucidation of five flavonol glycosides,
kaempferol-7-O-(6-caffenic-)-glucosyl-(1→3)-rhamnoside (
1
), kaempferol-3-O-glucoside (
2
), kaempferol-3-O-rutinoside (
3
),
kaempferol-3,7-O-dirhamnoside (
4
), and rutin (
5
) from Clematis terniflora. Compound
1
was a new compound, named
terniflonoside A.
Compound
1
, a yellow amorphous solid, showed molecular formula C
36
H
36
O
18
as determined from its HR-ESIMS (m/z
757.1969 [M+H]
+
, calcd. 757.1974). In the positive and negative ESIMS, it showed signals of quasi-molecular ion peaks at m/z
757 [M+H]
+
and 755 [M-H]
–
respectively, The fragment ion peaks at m/z 595 [M–162(caffeoyl)+H]
+
, 433 [595–162
(glucosyl)]
+
and 287 [433–146 (rhamnosyl)]
+
indicated the presence of a rhamnosyl inner unit. D-Glucose and L-rhamnose were
detected by GC analysis after acid hydrolysis and preparation of their thiazolidine derivatives. The UV spectrum of
1
showed
two absorption maxima at 335 and 265 nm, indicating the presence of substituted aromatic rings and
α
,
β
-unsaturated ketones
in the molecule. The
1
H NMR spectrum of compound 1 (Table 1) showed the typical pattern of a flavonol with a kaempferol
aglycon together with signals ascribable to sugar moieties and acyl residue. The two anomeric protons arising from the sugar
moieties appeared at δ 5.48 (1H, d, J = 2.5 Hz) and 4.52 (1H, d, J = 7.8 Hz), which correlated respectively with signals at 98.5
and 105.2 ppm in the HMQC spectrum. The
1
H NMR spectrum showed also the presence of a caffeoyl residue (Table 1). All
the
1
H and
13
C NMR signals of 1 were assigned using
1
H–
1
H COSY, HMQC, HMBC, and NOESY experiments.
Fig. 1. Structure and key HMBC correlations of compound 1.