全 文 ：· 742 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (6): 742−746




Chemical constituents of Saxifraga stolonifera (L.) Meeb.
FENG Wei-sheng*, LI Zhen, ZHENG Xiao-ke, LI Yuan-jing, SU Fang-yi, ZHANG Yan-li
(Henan University of Traditional Chinese Medicine, Zhengzhou 450008, China)
Abstract: To study the chemical constituents of Saxifraga stolonifera (L.) Meeb., chromatographic techniques
were applied to separate and purify the compounds, and their structures were confirmed on the basis of physico-
chemical properties and spectral data. Ten compounds were isolated and identified as 5-O-methylnorbergenin
(1), 3, 4-dihydroxyallylbenzene-4-O-β-D-glucopyranoside (2), (7R, 8S)-4, 9, 9′-trihydroxyl-3-methoxyl-7, 8-
dihydrobenzofuran-1′-propylneolignan-3′-O-β-D-glucopyranoside (3), quercetin-3-O-β-D-xylopyranosyl-(1→2)-
β-D-galactopyranoside (4), kaempferol-3-O-α-L-rhamnopyranoside (5), (3S, 5R, 6R, 7E, 9R)-3, 5, 6, 9-tetrahydroxy-
7-megastigmane (6), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (7), p-hydroxyacetophenone
(8), pyrogallic acid (9) and p-hydroxyphenol (10). Compound 1 is a new compound. Compounds 2 − 10 were
isolated from this plant for the first time.
Key words: Saxifraga stolonifera (L.) Meeb.; chemical constituent; 5-O-methylnorbergenin
CLC number: R284.1 Document code: A Article ID: 0513-4870 (2010) 06-0742-05
虎耳草的化学成分研究
冯卫生∗, 李 振, 郑晓珂, 李原京, 苏芳谊, 张艳丽
(河南中医学院, 河南 郑州 450008)

摘要: 为研究虎耳草 [Saxifraga stolonifera (L.) Meeb.] 的化学成分, 用柱色谱方法进行分离, 根据其理化性
质和波谱数据鉴定化合物的结构。分离得到了 10 个化合物, 分别鉴定为 5-甲氧基异虎耳草素 (1)、3, 4-二羟基
烯丙基苯-4-O-β-D-葡糖苷 (2)、(7R, 8S)-4, 9, 9′-三羟基-3-甲氧基-7, 8-二氢苯骈呋喃-1′-丙基新木脂素-3′-O-β-D-
葡糖苷 (3)、槲皮素-3-O-β-D-木糖-(1→2)-β-D-半乳糖苷 (4)、山柰酚-3-O-α-L-鼠李糖苷 (5)、(3S, 5R, 6R, 7E, 9R)-
3, 5, 6, 9-四羟基-7-megastigmane (6)、苄基-O-α-L-鼠李糖-(1→6)-β-D-葡糖苷 (7)、对羟基苯乙酮 (8)、连苯三酚 (9)
和对羟基苯酚 (10)。其中化合物 1 为新化合物, 化合物 2～10 为首次从该植物中分离得到。
关键词: 虎耳草; 化学成分; 5-甲氧基异虎耳草素

Saxifraga stolonifera (L.) Meeb. (Family Saxifra-
gaceae), a Chinese medicinal herb, is widely distributed
in most parts of China. It is used to treat rubella,
eczema, otitis media, erysipelas, hemoptysis, pulmonary
abscess, uterine bleeding, and so on[1]. Recent studies
have shown that it has many pharmacologic effects,
such as anti-cancer[2], anti-oxidant and anti-aging[3].

Received 2009-12-21.
Project supported by the Key Project of Chinese Ministry of Education
(2003078).
*Corresponding author Tel / Fax: 86-371-65680011,
E-mail: fwsh@hactcm.edu.cn
Previous phytochemical investigations showed the
presence of flavonoids, phenolic acids and aliphatics in
this plant[2, 4]. In this paper, the isolation and structure
elucidation of a new compound and nine known
compounds were presented.

Results and discussion
50% aqueous acetone extract of the whole plants
of Saxifraga stolonifera (L.) Meeb. was subjected to
a series of chromatographic procedures, including
Diaion HP-20, Toyopearl HW-40C and Silica gel
FENG Wei-sheng, et al: Chemical constituents of Saxifraga stolonifera (L.) Meeb. · 743 ·

column chromatography, affording 10 compounds. Their
structures were identified on the basis of spectroscopic
analysis, including a new compound 5-O-methylnor-
bergenin (1) (Figure 1), and nine known compounds, 3,
4-dihydroxyallylbenzene-4-O-β-D-glucopyranoside (2),
(7R, 8S)-4, 9, 9′-trihydroxyl-3-methoxyl-7, 8-dihydro-
benzofuran-1′-propylneolignan-3′-O-β-D-glucopyranoside
(3), quercetin-3-O-β-D-xylopyranosyl-(1→2)-β-D-gala-
ctopyranoside (4), kaempferol-3-O-α-L-rhamnopyrano-
side (5), (3S, 5R, 6R, 7E, 9R)-3, 5, 6, 9-tetrahydroxy-7-
megastigmane (6), benzyl-O-α-L-rhamnopyranosyl(1→
6)-β-D-glucopyranoside (7), p-hydroxyacetophenone
(8), pyrogallic acid (9) and p-hydroxyphenol (10).
1H and 13C NMR data for 1 were complete assigned by
1D and 2D NMR, including NOESY, HSQC and
HMBC. Compounds 2 − 10 were isolated from this
plant for the first time.
Compound 1 was obtained as light brown
amorphous powder (CH3OH), mp 178 − 181 ℃, [α] 20D
+13.3 (c 0.14, CH3OH). It gave a positive result for the
ferric chloride reaction, revealing its phenolic nature.
Its UV spectrum showed absorption at 223 nm and 291
nm. Its HR-ESI-MS showed [M+Na]+ at m/z 351.069 3
(calcd. for C14H16O9Na 351.069 2). Meanwhile, the
IR spectrum showed the presence of hydroxyl (3 393
cm−1), aromatic ring (1 582 cm−1 and 1 475 cm−1) and
ester carbonyl (1 698 cm−1). The 1H NMR spectrum
(Table 1) of 1 exhibited one aromatic proton at δ 7.13
(1H, s), a C-glycosyl moiety at δ 3.44−4.86 and one
methoxyl signal at 3.81 (3H, s). The 13C NMR spectrum
(Table 1) of 1 exhibited 14 carbon signals, including a
C-glycosyl moiety at δ 82.8 (C-5′), 71.8 (C-4′), 81.4
(C-3′), 75.8 (C-2′), 74.6 (C-1′), 62.7 (C-6′), which was
characteristic of bergenin and norbergenin[5, 6]; one
substituted benzene moiety at δ 118.6 (C-1), 107.5 (C-6),
150.8 (C-5), 151.4 (C-4), 144.9 (C-3), 107.6 (C-2); one
ester carbonyl carbon at δ 167.8 (C-7) and one methoxyl
signal at δ 56.3. The above information suggested
that the basic structure of compound 1 is C-glucoside
of gallic acid. The 1H NMR and 13C NMR spectrum
characters were very similar to those of norbergenin[6]
(Figure 1), except for a different substitution at C-5.
In fact, the only difference between them consists in the
hydroxyl at C-5 in norbergenin being replaced by a
methoxyl group in compound 1, which was supported
by the HMBC spectra. In the HMBC spectrum, the
protons of methoxyl group (δ 3.81) correlated with the
carbon signal at δ 150.8 (C-5). This was further
confirmed by NOE correlation between the methoxyl
group and H-6. Thus, the methoxyl group was located
at C-5 in compound 1. The relative stereochemistry of
compound 1 was determined by comparison of the
1H and 13C NMR spectral data with those of bergenin
and related compounds[5−7], the coupling constant
observed in the 1H NMR spectrum, and the NOESY
experiment. In the 1H NMR spectrum, the larger
coupling constant (J = 10.3 Hz) between vicinal proton
suggested their trans diaxial orientations. Additionally,
in the NOESY spectrum there were no NOE correlations
among H-1′, H-2′, H-3′, H-4′, and H-5′, which indicated
that they were in trans-configuration. Based on the
above evidence and according to the literature[6], the
structure of 1 is determined to be 5-O-methylnor-
bergenin (Figure 1).


Figure 1 Key HMBC and NOE correlations of compound 1 and
structure of norbergenin

Table 1 1H NMR and 13C NMR spectral data of compound 1
(CD3OD)
Position 1H NMR (400 MHz) 13C NMR (100 MHz)
1 118.6
2 107.6
3 144.9
4 151.4
5 150.8
6 7.13 (1H, s) 107.5
7 167.8
1′ 4.86 (1H, d, J = 10.3 Hz) 74.6
2′ 3.78 (1H, m) 75.8
3′ 3.95 (1H, m) 81.4
4′ 3.44 (1H, m) 71.8
5′ 3.62 (1H, m) 82.8
6′ 3.68 (1H, m) 62.7
4.00 (1H, m)
OCH3 3.81 (3H, s) 56.3

· 744 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (6): 742−746

Experimental
General experimental procedures
Melting points were determined on a Kofler micro-
melting point apparatus and uncorrected. Optical
rotations were obtained using a Perkin-Elmer 341
polarimeter. UV spectra were measured with a
Shimadzu UV-VIS 2201 spectrophotometer. IR spectra
were measured with a Shimadzu FTIR-8201 PC
spectrometer. The 1H and 13C NMR spectra were
obtained on a Bruker DPX-400 spectrometer (400 MHz
for 1H NMR and 100 MHz for 13C NMR) with TMS
as internal reference. HR-TOF-MS were recorded on
an APEX II spectrometer. Column chromatography
was performed on Diaion HP-20 (Mitsubishi Chemical
Corp., Japan), silica gel (160–200 mesh, Qingdao
Haiyang Chemical Co., Ltd., China), Toyopearl
HW-40C (TOSOH Corp., Japan). Sephadex LH-20
(Pharmacia, Sweden). TLC was conducted on self-made
silica gel G (Qingdao Haiyang Chemical Co., Ltd.,
China) plates. The chemical reagents were purchased
from Beijing Chemical Plant and Tianjin No. 3 Reagent
Plant.
Plant materials
Dried Saxifraga stolonifera (L.) Meeb. were
collected in Xixia county, Henan Province in China,
and identified by Prof. Dong Cheng-ming of Henan
University of Traditional Chinese Medicine.
Extraction and isolation
Air-dried whole plants of S. stolonifera (3.5 kg)
were extracted two times with 50% aqueous acetone at
room temperature and filtered. The combined extract
was evaporated in vacuo to yield gross extract (256 g),
which was dissolved in suitable amount of water, and
then was subjected to Diaion HP-20 porous polymer
resin and eluted with H2O and 10%, 20%, 30% CH3OH
successively. The fraction eluted with H2O was subjected
to Toyopearl HW-40C column chromatography and
eluted with H2O and 10%, 20%, 30%, 40%, 50% CH3OH
successively to afford 150 fractions. Then fractions
45-99 were rechromatographed on Toyopearl HW-40C,
Sephadex LH-20 and silica gel to yield compound 7
(87 mg), 8 (11 mg), 9 (12 mg) and 10 (25 mg). The
fraction eluted with 10% CH3OH was subjected to
Toyopearl HW-40C column chromatography and eluted
with H2O and 10%, 20%, 30%, 40%, 50% CH3OH
successively to afford 280 fractions. Then fractions
25-40 and 86-110 were rechromatographed on Toyopearl
HW-40C, Sephadex LH-20 and silica gel to yield
compound 1 (13 mg) and 6 (12 mg) separately. The
fraction eluted with 20% CH3OH was subjected to
Toyopearl HW-40C column chromatography and eluted
with H2O and 10%, 20%, 30%, 40%, 50% CH3OH
successively to afford 200 fractions. Then fractions
31-60 were rechromatographed on Toyopearl HW-40C,
Sephadex LH-20 and silica gel to yield compound 2
(18 mg), 3 (16 mg) and 4 (17 mg). The fraction
eluted with 30% CH3OH was subjected to Toyopearl
HW-40C column chromatography and eluted with H2O
and 10%, 20%, 30%, 40%, 50% CH3OH successively
to afford 158 fractions. Then fractions 71-120 were
rechromatographed on Toyopearl HW-40C and Sephadex
LH-20 gel to yield compound 5 (12 mg).
Identification
Compound 1 Light brown amorphous powder,
mp 178−181 ℃, [α] 20D +13.3 (c 0.14, CH3OH). UV
(CH3OH) λmax: 223, 291 nm. IR (KBr): υmax cm−1: 3 393,
2 926, 1 697, 1 582, 1 475, 1 334, 868, 766. HR-ESI-
MS m/z: 351.069 3 (calcd. for C14H16O9Na 351.069 2).
The 1H NMR (400 MHz, CD3OD) and 13C NMR (100
MHz, CD3OD) spectral data see Table 1.
Compound 2 Colorless oil, 1H NMR (400 MHz,
CD3OD) δ: 7.02 (1H, d, J = 1.6 Hz, H-2), 6.74 (1H, d,
J = 8.1 Hz, H-5), 6.71 (1H, dd, J = 1.5, 8.1 Hz, H-6),
5.91 (1H, m, H-8), 5.01 (2H, m, H-9), 4.72 (1H, d, J =
7.3 Hz, H-1′), 3.25 (2H, d, J = 6.8 Hz, H-7). 13C NMR
(100 MHz, CD3OD) δ: 133.1 (C-1), 119.2 (C-2), 146.6
(C-3), 146.6 (C-4), 116.9 (C-5), 124.7 (C-6), 40.5 (C-7),
139.2 (C-8), 115.6 (C-9), 104.5 (C-1′), 74.9 (C-2′), 77.6
(C-3′), 71.3 (C-4′), 78.3 (C-5′), 62.4 (C-6′). Combining
literature[8] identified that the compound 2 was 3, 4-
dihydroxyallylbenzene-4-O-β-D-glucopyranoside.
Compound 3 Colorless oil, 1H NMR (400 MHz,
CD3OD) δ: 6.96 (1H, d, J = 1.7 Hz, H-2), 6.91(1H, br s,
H-2′), 6.84 (1H, dd, J = 8.2, 1.7 Hz, H-2), 6.80 (1H, d,
J = 8.2 Hz, H-5), 6.76 (1H, br s, H-6′), 5.50 (1H, d, J =
6.4 Hz, H-7), 4.97 (1H, d, J = 6.8 Hz, H-1′′), 3.80 (3H,
s, -OCH3), 3.76 (2H, m), 3.52 (2H, t, J = 6.8 Hz, H-9′),
3.41 (1H, dd, J = 12.1, 6.3 Hz, H-8), 2.61 (2H, t, J = 8.0
Hz, H-7′), 1.80 (2H, m, H-8′). 13C NMR (100 MHz,
CD3OD) δ: 134.3 (C-1), 110.7 (C-2), 149.1 (C-3), 147.7
(C-4), 116.2 (C-5), 119.9 (C-6), 89.4 (C-7), 55.2 (C-8),
64.8 (C-9), 137.1 (C-1′), 118.1 (C-2′), 142.5 (C-3′),
FENG Wei-sheng, et al: Chemical constituents of Saxifraga stolonifera (L.) Meeb. · 745 ·

147.5 (C-4′), 130.6 (C-5′), 119.6 (C-6′), 32.7 (C-7′),
35.6 (C-8′), 62.5 (C-9′), 102.9 (C-1′′), 74.9 (C-2′′), 77.7
(C-3′′), 71.4 (C-4′′), 78.2 (C-5′′), 62.2 (C-6′′), 56.4
(-OCH3). Its 1H NMR and 13C NMR data were in
good agreement with those of literature[9] and identified
the compound 3 to be (7R, 8S)-4, 9, 9′-trihydroxyl-3-
methoxyl-7, 8-dihydrobenzofuran-1′-propylneolignan-3′-
O-β-D-glucopyranoside.
Compound 4 Yellow amorphous powder, 1H NMR
(400 MHz, CD3OD) δ: 7.71 (1H, d, J = 1.6 Hz, H-2′),
7.62 (1H, dd, J = 8.0, 1.6 Hz, H-6′), 6.85 (1H, d, J = 8.0
Hz, H-5′), 6.36 (1H, br s, H-8), 6.17 (1H, br s, H-6),
5.40 (1H, d, J = 7.2 Hz, H-1′′), 4.77 (1H, d, J = 6.4 Hz,
H-1′′′). 13C NMR (100 MHz, CD3OD) δ: 158.3 (C-2),
135.2 (C-3), 179.6 (C-4), 163.2 (C-5), 99.8 (C-6), 165.9
(C-7), 94.6 (C-8), 158.2 (C-9), 105.7 (C-10), 123.1
(C-1′), 116.2 (C-2′), 145.9 (C-3′), 149.8 (C-4′), 117.4
(C-5′), 123.4 (C-6′), 101.4 (C-1′′), 80.0 (C-2′′), 74.7
(C-3′′), 70.3 (C-4′′), 75.1 (C-5′′), 61.9 (C-6′′), 105.3
(C-1′′′), 76.9 (C-2′′′), 77.0 (C-3′′′), 71.0 (C-4′′′), 66.5
(C-5′′′). Combining literature[10] identified that the
compound 4 was quercetin-3-O-β-D-xylopyranosyl-
(1→2)-β-D-galactopyranoside.
Compound 5 Yellow amorphous powder, 1H NMR
(400 MHz, acetone-d6) δ: 7.86 (2H, d, J = 8.5 Hz, H-2′,
6′), 7.03 (2H, d, J = 8.6 Hz, H-3′, 5′), 6.48 (1H, d, J =
1.8 Hz, H-8), 6.28 (1H, d, J = 1.8 Hz, H-6), 5.55 (1H,
d, J = 1.2 Hz, H-1′′), 0.92 (3H, d, J = 5.7 Hz, H-6′′).
13C NMR (100 MHz, acetone-d6) δ: 159.6 (C-2), 135.8
(C-3), 179.6 (C-4), 163.2 (C-5), 99.8 (C-6), 165.9 (C-7),
94.7 (C-8), 158.5 (C-9), 105.7 (C-10), 122.8 (C-1′),
132.4 (C-2′, 6′), 116.2 (C-3′, 5′), 161.8 (C-4′), 102.5
(C-1′′), 72.5 (C-2′′), 72.1 (C-3′′), 73.3 (C-4′′), 71.6
(C-5′′), 17.9 (C-6′′). Combining literature[11] identified
that the compound 5 was kaempferol-3-O-α-L-rham-
nopyranoside.
Compound 6 Colorless oil, 1H NMR (400 MHz,
CD3OD) δ: 6.07 (1H, dd, J = 16.1, 1.2 Hz, H-7), 5.79
(1H, dd, J = 15.8, 6.1 Hz, H-8), 4.33 (1H, m, H-9), 4.03
(1H, m, H-3), 1.76 (2H, m, H-4), 1.66 (1H, t, H-2), 1.44
(1H, m, H-2), 1.27 (3H, d, J = 6.4 Hz, H-10), 1.19 (3H, s,
H-11), 1.13 (3H, s, H-13), 0.83 (3H, s, H-12). 13C NMR
(100 MHz, CD3OD) δ: 40.7 (C-1), 46.5 (C-2), 65.3
(C-3), 45.7 (C-4), 77.8 (C-5), 78.9 (C-6), 136.1 (C-7),
131.2 (C-8), 69.6 (C-9), 24.2 (C-10), 27.5 (C-11), 26.2
(C-12), 27.1 (C-13). Combining literature[12] identified
that the compound 6 was (3S, 5R, 6R, 7E, 9R)-3, 5, 6,
9-tetrahydroxy-7-megastigmane.
Compound 7 Pale yellow oil, 1H NMR (400
MHz, CD3OD) δ: 7.40 (2H, br d, J = 7.2 Hz, H-2, 6),
7.33 (2H, m, H-3, 5), 7.27 (1H, m, H-4), 4.78 (1H, br s,
H-1′′), 4.33 (1H, d, J = 7.6 Hz, H-1′), 1.27 (3H, d, J =
6.5 Hz, H-6′′). 13C NMR (100 MHz, CD3OD) δ: 138.8
(C-1), 129.3 (C-2, 3, 5, 6), 128.7 (C-4), 71.7 (C-7),
103.1 (C-1′), 75.0 (C-2′), 77.9 (C-3′), 71.6 (C-4′), 76.9
(C-5′), 68.1 (C-6′), 102.2 (C-1′′), 72.1 (C-2′′), 72.2
(C-3′′), 73.9 (C-4′′), 69.8 (C-5′′), 18.0 (C-6′′). These
1H NMR and 13C NMR data were in basic agreement
with those of literature[13, 14] and identified the compound
7 to be benzyl-O-α-L-rhamnopyranosyl (1→6)-β-D-
glucopyranoside.
Compound 8 Colorless needles, 1H NMR (400
MHz, acetone-d6) δ: 7.84 (2H, d, J = 8.8 Hz, H-2, 6),
6.88 (2H, d, J = 8.8 Hz, H-3, 5), 2.46 (3H, s). 13C NMR
(100 MHz, acetone-d6) δ: 196.4 (C=O), 129.1 (C-1),
131.4 (C-2, 6), 116.1 (C-3, 5), 164.2 (C-4), 26.1 (CH3).
Combining literature[15] identified that the compound 8
was p-hydroxyacetophenone.
Compound 9 White needles, 1H NMR (400 MHz,
acetone-d6) δ: 6.50 (1H, t, J = 8.1 Hz, H-5), 6.36 (2H, d,
J = 8.1 Hz, H-4, 6). 13C NMR (100 MHz, acetone-d6)
δ: 146.5 (C-1, 3), 133.5 (C-2), 119.7 (C-5), 107.8 (C-4, 6).
Combining literature[16] identified that the compound 9
was pyrogallic acid.
Compound 10 Colorless needles, 1H NMR (400
MHz, acetone-d6) δ: 6.82 (2H, m, H-2, 6), 6.68 (2H, m,
H-3, 5). 13C NMR (100 MHz, acetone-d6) δ: 145.8
(C-1, 4), 120.6 (C-2, 6), 116.0 (C-3, 5). Combining
literature[17] identified that the compound 10 was p-
hydroxyphenol.
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