Institute of Modern Traditional Chinese Medicine, Zhejiang University, Hangzhou, 310058, People’s Republic of
China, e-mail: firstname.lastname@example.org. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 108-110, March-April, 2007. Original
article submitted December 27, 2006.
2007 Springer Science+Business Media, Inc.
Chemistry of Natural Compounds, Vol. 43, No. 2, 2007
CHEMICAL CONSTITUENTS FROM
Lin Zhang, Xiaoling Luo, and Jingkui Tian*
One new flavonol glycoside named terniflonoside A (
) 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.
: 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 . 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-3-O-glucoside (
), kaempferol-3-O-rutinoside (
), and rutin (
) from Clematis terniflora. Compound
was a new compound, named
, a yellow amorphous solid, showed molecular formula C
as determined from its HR-ESIMS (m/z
, calcd. 757.1974). In the positive and negative ESIMS, it showed signals of quasi-molecular ion peaks at m/z
and 755 [M-H]
respectively, The fragment ion peaks at m/z 595 [M–162(caffeoyl)+H]
, 433 [595–162
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
two absorption maxima at 335 and 265 nm, indicating the presence of substituted aromatic rings and
in the molecule. The
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
H NMR spectrum showed also the presence of a caffeoyl residue (Table 1). All
C NMR signals of 1 were assigned using
H COSY, HMQC, HMBC, and NOESY experiments.
Fig. 1. Structure and key HMBC correlations of compound 1.