全 文 ： 药学学报 Acta Pharmaceutica Sinica 2010, 45 (12): 1527−1532 · 1527 ·



Two new phenolic glycosides from the stems of Clematis parviloba
YAN Li-hua1, XU Li-zhen2*, WANG Zhi-min1, ZHANG Qi-wei1, YANG Shi-lin3*
(1. Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China; 2. Institute of
Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100094, China;
3. National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Nanchang 330006, China)
Abstract: To study the chemical constituents of the stems of Clematis parviloba, six compounds were
isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including
column chromatography over silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Two new phenolic
glycosides, 2-((E)-3-carboxybut-2-en-yl)-4-hydroxy-3-methyl-phenyl-O-β-D-glucopyranoside (1) and 4-hydroxy-
phenol-β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-benzoate)] glucopyranoside (2) were isolated, together with a
known phenolic glycoside, 4-hydroxy-3-methoxy-phenol-β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-benzoate)]
glucopyranoside (3) as well as three known megastigmane glycosides, linarionoside A (4), linarionoside C (5),
and staphylionoside K (6). Their structures were determined on the basis of spectroscopic analysis and chemical
evidence. Among them, compounds 1 and 2 were named as clemaparvilosides A (1) and B (2), respectively, and
compounds 3 − 6 were obtained from Clematis genus for the first time.
Key words: Clematis parviloba; phenolic glycoside; megastigmane glycoside
CLC number: R284.1 Document code: A Article ID: 0513-4870 (2010) 12-1527-06
裂叶铁线莲茎中两个新的酚苷类化合物
闫利华 1, 徐丽珍 2*, 王智民 1, 张启伟 1, 杨世林 3*
(1. 中国中医科学院中药研究所, 北京 100700; 2. 中国医学科学院、北京协和医学院药用植物研究所, 北京 100094;
3. 中药固体制剂制造技术国家工程研究中心, 江西 南昌 330006)

摘要: 为了研究裂叶铁线莲茎的化学成分, 采用硅胶、ODS、Sephadex LH-20 柱色谱及半制备高压液相色谱
等技术, 从其 95%乙醇提取物中分离得到 6个化合物。根据理化性质和波谱数据鉴定化合物结构分别为: 2-((E)-3-
carboxybut-2-en-yl)-4-hydroxy-3-methyl-phenyl-O-β-D-glucopyranoside (1)、4-hydroxy-phenol-β-D-[6-O-(4-hydroxy-
3, 5-dimethoxy-benzoate)]glucopyranoside (2)、4-hydroxy-3-methoxy-phenol-β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-
benzoate)] glucopyranoside (3)、linarionoside A (4)、linarionoside C (5) 和 staphylionoside K (6)。其中, 化合物 1～
3为酚苷类化合物, 化合物 4～6为大柱烷苷类化合物; 化合物 1和 2为新化合物, 分别命名为 clemaparvilosides A
(1) 和 B (2); 化合物 3～6 均为首次从该属植物中分离得到。
关键词: 裂叶铁线莲; 酚苷类化合物; 大柱烷苷类化合物

Clematis parviloba Gardn et. Champ (Ranuncu-
laceae) distributes in southwest China. Stems of this
plant have been used in folk medicine for the treatment

Received 2010-08-05.
*Corresponding author Tel: 86-10-62899705, Fax: 86-10-84014128,
E-mail: xulizhen2002@hotmail.com or
yangshilin9705@hotmail.com
of rheumatism, arthralgia, hydropsy, and used as
diuretic, galactopoietic and emmenagogue agents[1].
During our systematic research on the bioactive chemical
constituents of C. parviloba, we have previously isolated
triterpenoid saponins, lignans and coumarins from this
plant[2−4]. Our continuing chemical studies on the
same plant have now resulted in the isolation of two
DOI:10.16438/j.0513-4870.2010.12.003
· 1528 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (12): 1527−1532

new phenolic glycosides, 2-((E)-3-carboxybut-2-en-yl)-
4-hydroxy-3-methyl-phenyl-O-β-D-glucopyranoside
(1) and 4-hydroxy-phenol-β-D-[6-O-(4-hydroxy-3,
5-dimethoxy-benzoate)]glucopyranoside (2), named
as clemaparvilosides A (1) and B (2) respectively,
along with a known phenolic glycoside, 4-hydroxy-3-
methoxy-phenol-β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-
benzoate)] glucopyranoside (3) as well as three known
megastigmane glycosides, linarionoside A (4),
linarionoside C (5) and staphylionoside K (6) (Figure 1).
In this paper, the isolation and structural elucidation of
these compounds are described.


Figure 1 Structures of compounds 1−6

Results and discussion
Compound 1 was isolated as white crystals. Its
molecular formula was established to be C18H24O9
with seven degrees of unsaturation based on a quasi-
molecular ion peak at m/z 407.128 9 ([M+Na]+, calcd.
407.131 8) in the HR-ESI-MS spectrum. The UV
spectrum exhibited absorption maxima at 218 and
287 nm. The IR spectrum indicated the presence of
hydroxyl (3 373 cm−1), α, β-unsaturated carboxyl (1 693
cm−1) and phenyl (1 651, 1 479 cm−1) groups.
The 1H NMR spectrum of 1 (Table 1) showed a
pair of AB-type aromatic protons at δH 6.62 (1H, d, J =
8.4 Hz, H-5) and 6.90 (1H, d, J = 8.4 Hz, H-6), an
olefinic proton at δH 6.68 (1H, br t, J = 7.2 Hz, H-8),
two methyl groups at δH 2.10 (3H, s, CH3-12) and 1.97
(3H, s, CH3-11), a methylene group at δH 3.58 and 3.75
(each 1H, dd, J = 15.0, 7.2 Hz, CH2-7) as well as a set
of signals assignable to one hexose group: an anomeric
proton signal at δH 4.74 (1H, d, J = 7.2 Hz, H-1) and
other six proton signals at δH 3.86−3.32. Consistent
with the 1H NMR spectral analysis, the 13C NMR
spectrum of 1 (Table 1) also revealed the presence of
an aromatic ring (δC 150.4, 130.5, 125.2, 152.0, 114.2,
115.8), two olefinic carbons (δC 143.0, 128.0), two
methyls (δC 12.2, 12.8), a methylene (δC 27.6), and one
hexose including an anomeric carbon at δC 104.5 (C-1)
and other five carbons at δC 78.3−62.6. The remaining
carbon signal was assigned to an α, β-unsaturated
carboxyl group (δC 171.9).
Acid hydrolysis of 1 gave D-glucose, which was
determined to have a β-configuration on the basis of the
large coupling constants of the anomeric proton [δH
4.74 (d, J = 7.2 Hz)]. The proton and carbon signals
of the D-glucose moiety were unambiguously assigned
on the basis of the 1H-1H COSY and HSQC spectral
analysis.
The connections of the functional groups were
determined mainly by the HMBC spectrum. In the
HMBC spectrum (Figure 2), correlations between H-8/
C-10, C-11; H3-11/C-8, C-10; H2-7/C-9 were observed,
indicating the presence of a 3-carboxybut-2-en-yl group[5].
This group was located at C-2 as deduced from the
cross peaks between the methylene protons H2-7 (δH 3.58,
3.75) and C-1 (δC 150.4), C-3 (δC 125.2), separately.
The glucose moiety located at C-1 was evidenced by
correlations between the proton signal at δH 4.74 (H-1)
and the carbon signal at δC 150.4 (C-1). The proton
signal at δH 2.10 (H3-12) correlated with the carbon
signal at δC 130.5 (C-2) and δC 152.0 (C-4), indicating
that methyl group was located at C-3. In addition, the
carbon signal of C-4 (δC 152.0) was obviously shielded
indicating that C-4 was substituted by an oxygenous
group, which could be inferred to be a hydroxyl group
from the molecular formula C18H24O9. The E con-
figuration of the C-8/C-9 double bond was confirmed
from the cross-peaks between the methylene protons
H2-7 (δH 3.58, 3.75) and the methyl protons H3-11
(δH 1.97) in the NOESY spectrum (Figure 3). Conse-
quently, the structure of 1 was determined as 2-((E)-3-
carboxybut-2-en-yl)-4-hydroxy-3-methyl-phenyl-O-β-
D-glucopyranoside, and it was named as clemaparvi-
loside A.
YAN Li-hua, et al: Two new phenolic glycosides from the stems of Clematis parviloba · 1529 ·

Table 1 1H (600 MHz) and 13C NMR (150 MHz) spectral data
of 1 in CD3OD (J in Hz)
No. δC δH (J Hz)
1 150.4
2 130.5
3 125.2
4 152.0
5 114.2 6.62 (d, 8.4)
6 115.8 6.90 (d, 8.4)
7 27.6 3.58 (dd, 15.0, 7.2)
3.75 (dd, 15.0, 7.2)
8 143.0 6.68 (br t, 7.2)
9 128.0
10 171.9
11 12.8 1.97 (s)
12 12.2 2.10 (s)
1 104.5 4.74 (d, 7.2)
2 75.1 3.45 (m)
3 78.3 3.42 (m)
4 71.5 3.37 (m)
5 78.1 3.32 (m)
6 62.6 3.68 (dd, 12.0, 5.4)
3.86 (dd, 12.0, 2.4)


Figure 2 Key HMBC (H→C) correlations of compound 1


Figure 3 Key NOESY (H→H) correlations of compound 1

Compound 2 was obtained as white crystals. Its
molecular formula was established as C21H24O11 with
ten degrees of unsaturation based on a quasi-molecular
ion peak [M+Na]+ at m/z 475.121 7 (calcd. 475.121 6) in
the HR-ESI-MS spectrum. The UV spectrum exhibited
absorption maxima at 219 and 279 nm. The IR
spectrum showed the presence of hydroxyl (3 197 cm−1),
aromatic ester carbonyl (1 690 cm−1) and phenyl (1 587,
1507 cm−1) groups.
The 1H and 13C NMR spectra of 2 (Table 2)
showed proton signals at δH 7.34 (2H, s, H-2, 6) and
3.85 (6H, s, 3, 5-OCH3), together with carbon signals
at δC 120.9 (C-1), 108.5 (C-2, 6), 149.1 (C-3, 5),
142.9 (C-4), 167.9 (C-7), and 56.9 (3, 5-OCH3)
suggesting the existence of a symmetrical 1, 3, 4, 5-
tetrasubstituted phenyl group. The group was deduced
to be a 4-hydroxy-3, 5-dimethoxy-benzoate moiety[6].
This was confirmed by the HMBC correlations (Figure
4) between H-2, H-6/C-7; H-2, H-6/C-4; CH3O-
3, 5/C-3, 5. In addition, one 1, 4-bissubstituted
phenyl group was observed in the 1H and 13C NMR
spectra [A2B2 system at δH 6.90 (2H, d, J = 9.0 Hz,
H-2, 6) and 6.53 (2H, d, J = 9.0 Hz, H-3, 5); δC 152.3
(C-1), 119.5 (C-2, 6), 116.6 (C-3, 5), 153.9 (C-4)]
and confirmed by the HMBC correlations between
H-2, H-6/C-4; H-3, H-5/C-1. The 1H and 13C NMR
spectra of 2 also revealed the presence of a sugar
moiety [an anomeric proton at δH 4.73 (1H, d, J = 7.2
Hz, H-1) and other protons at δH 4.71−3.42; carbon
signals at δC 103.7, 75.0, 77.9, 72.1, 75.6, 65.3].
Acid hydrolysis of 2 afforded D-glucose, and the
large coupling constant of 7.2 Hz for the anomeric
proton H-1 (δH 4.73) indicated β-configuration for the
D-glucose moiety. The proton and carbon signals of the
D-glucose moiety were unambiguously assigned on the
basis of the 1H-1H COSY and HSQC spectral analysis.
The connections between the glucose moiety and
aromatic units were established mainly based on the
HMBC spectrum. In the HMBC spectrum (Figure 4),
the anomeric proton signal at δH 4.73 (H-1) correlated
with the carbon signal at δC 152.3 (C-1), and the proton
signals at δH 4.38 and 4.71 (H2-6) correlated with the
carbonyl signal at δC 167.9 (C-7), indicating that the
β-D-glucose moiety was attached to C-1 and C-7.
Thus, all the proton and carbon signals of 2 were
fully assigned as shown in Table 2. Consequently,
the structure of 2 was determined as 4-hydroxy-
phenol-β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-benzoate)]
glucopyranoside, and it was named as clemaparviloside B.
Four known compounds were identified by
comparison of their physical and spectral data with
the literature values as 4-hydroxy-3-methoxy-phenol-
β-D-[6-O-(4-hydroxy-3, 5-dimethoxy-benzoate)] glu-
copyranoside (3)[7], linarionoside A (4)[8], linarionoside
C (5)[8] and staphylionoside K (6)[9], separately. To
the best of our knowledge, this is the first report of
megastigmane glycoside constituents in the genus
Clematis and family Ranunculaceae.
· 1530 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (12): 1527−1532

Table 2 1H and 13C NMR spectral data of compounds 2 and 3a
(J in Hz). aNMR spectra of 2 were recorded on a VARIAN
INOVA 600 spectrometer in MeOD, while, NMR spectra of 3
were recorded on a Bruker AV 500 spectrometer in DMSO-d6
2 3
No.
δC δH δC δH
1 103.7 4.73 (d, 7.2) 101.4 4.75 (d, 7.5)
2 75.0 3.44 (m) 73.4 3.30 (m)
3 77.9 3.45 (m) 76.5 3.30 (m)
4 72.1 3.42 (m) 70.0 3.20 (m)
5 75.6 3.62 (m) 74.1 3.68 (m)
6 65.3 4.38 (dd, 12.0, 7.2) 64.2 4.17 (dd, 11.5, 7.0)
4.71 (dd, 12.0, 1.8) 4.58 (dd, 11.5, 1.5)
1 152.3 150.7
2 119.5 6.90 (d, 9.0) 102.6 6.56 (d, 2.0)
3 116.6 6.53 (d, 9.0) 148.1
4 153.9 144.5
5 116.6 6.53 (d, 9.0) 115.2 6.49 (d, 8.5)
6 119.5 6.90 (d, 9.0) 107.6 6.44 (dd, 8.5, 2.0)
3-OCH3 55.6 3.61 (3H, s)
1 120.9 120.8
2, 6 108.5 7.34 (2H, s) 107.5 7.17 (2H, s)
3, 5 149.1 148.0
4 142.9 141.6
7 167.9 165.8
3, 5-OCH3 56.9 3.85 (6H, s) 56.2 3.75 (6H, s)


Figure 4 Key HMBC (H→C) correlations of compound 2

Experimental
General experimental procedures Melting points
were determined using a Fisher-Johns melting point
apparatus and are uncorrected. Optical rotations were
measured on a JASCO DIP-360 digital polarimeter.
UV spectra were obtained on a Philips PYE Unican
Pu8800 spectrophotometer, and IR spectra on a Nicolet
5700 instrument with Centaurus FT-IR Microscope.
NMR spectra were run on a VARIAN INOVA 600
spectrometer. EI-MS measurements were performed
on a ZabSpec mass spectrometer. ESI-MS data were
recorded on a Q-Trap LC/MS/MS with turbo ion spray
source. HR-ESI-MS data were obtained on an
ACCUTOF CS (GEOL) instrument. Precoated silica
gel GF254 plates (Qingdao Haiyang Chem. Co.) were
employed for TLC. Spots were visualized under UV
light (254 nm) or by spraying with 10% H2SO4 in 95%
EtOH followed by heating. For column chromatography,
silica gel (Qingdao Haiyang Chem. Co.), reversed- phase
C18 silica gel (Merck) and Sephadex LH-20 (Pharmacia)
were used. The MPLC was performed on a system
equipped with a Büchi pump and Büchi columns. The
HPLC was performed on a Waters Delta Prep HPLC
system and Waters Nova-Pak HR C18 (6 μm, 7.8 mm ×
300 mm) semi-preparative column was used.
Plant materials The stems of Clematis parviloba
were collected in Yunnan Province, People’s Republic
of China, in 1997, and authenticated by Prof. Yulin Lin
(Institute of Medicinal Plant Development, Chinese
Academy of Medical Sciences). A voucher specimen
was deposited in the Natural Medicine Research Center
of the Institute of Medicinal Plant Development,
Chinese Academy of Medical Sciences.
Extraction and isolation
The air-dried stems of C. parviloba (9.5 kg) were
ground and extracted three times with 95% EtOH under
reflux. The combined extract was concentrated under
reduced pressure to yield 450 g of residue, which was
suspended in water and extracted successively with
petroleum ether (60−90 ℃), CHCl3, EtOAc, and n-BuOH.
The EtOAc extract (25 g) was chromatographed
over a silica gel column eluting with CHCl3-MeOH
(1∶0−0∶1), and monitored by TLC analysis to yield
twenty combined fractions (Fr. A1−Fr. A20). Fr. A8
(600 mg) was subjected to an ODS column eluting with
MeOH-H2O (4∶6−1∶0) and further purified by semi-
preparative HPLC with 8% MeCN to afford compounds
2 (10 mg) and 3 (10 mg). Fr. A11 was subjected to
HPLC eluting with 27% MeOH to afford compound 4
(20 mg).
The n-BuOH extract (200 g) was subjected to a
macroporous resin (AB-8) column eluting with water,
10%, 30%, 50% and 90% EtOH, separately. The
30% EtOH fraction (20 g) was subjected to Sephadex
LH-20 chromatography eluting with MeOH to yield
five combined fractions (Fr. B1−Fr. B5). Fr. B2 (15 g)
was subjected to MPLC over silica gel eluting with
CHCl3-MeOH-H2O (85∶15∶1.5−0∶1∶0.1) to give
five fractions (Fr. B2-1−Fr. B2-5). Fr. B2-4 was
subjected to HPLC eluting with 23% MeOH to afford
compounds 5 (10 mg) and 6 (10 mg). Fr. B5 (1 g) was
purified repeatedly by Sephadex LH-20 chromatography
eluting with MeOH to afford compound 1 (100 mg).
Acid hydrolysis of 1 and 2
A solution of each compound (1 or 2) (2 mg) in 2
YAN Li-hua, et al: Two new phenolic glycosides from the stems of Clematis parviloba · 1531 ·

mol·L−1 HCl - dioxane (1∶1, 1 mL ) was heated at a
temperature of 95 ℃ for 4 h. The reaction mixture
was evaporated to dryness under N2. Then, the residue
was dissolved in water (10 mL) and extracted with
CHCl3 (2×10 mL). The aqueous layer was repeatedly
evaporated to dryness with H2O until the solvent was
neutral, and then analyzed by HP-TLC over silica gel
(CHCl3-n-BuOH-MeOH-HOAc-H2O, 17∶10∶7∶2∶3).
The presence of D-glucose was established by com-
parison with authentic samples.

Identification
Compound 1: white crystals from MeOH; mp
196−198 ℃; [α] 20D −9.4 (c 0.64, MeOH); positive
ESI-MS m/z: 407 [M+Na]+; positive HR-ESI-MS m/z:
407.128 9 (calcd. for C18H24O9Na, [M+Na]+, 407.131 8);
UV (MeOH) λmax nm (log ε): 218 (4.29), 287 (3.44).
IR (KBr) νmax cm−1: 3 397, 1 693, 1 651, 1 479, 1 375,
1 254, 1 203, 1 080, 1 053, 999, 804, 766, 640. EI-MS
m/z (rel. int.%): 222 (32), 204 (100), 189 (20), 175 (12),
161 (25), 91 (4), 77 (3). 1H and 13C NMR data were
listed in Table 1.
Compound 2: white crystals from MeOH; mp
178−180 ℃; [α] 20D −39.1 (c 0.23, MeOH); negative
ESI-MS m/z: 451[M−H]−, positive HR-ESI-MS m/z:
475.121 7 (calcd. for C21H24O11Na, [M+Na]+, 475.121 6).
UV (MeOH) λmax nm (log ε): 219 (6.22), 279 (5.84).
IR (microscope transmission) νmax cm−1: 3 197, 1 690,
1 587, 1 507, 1 454, 1 337, 1 219, 1 108, 829, 775, 661,
631. 1H and 13C NMR data were listed in Table 2.
Compound 3: white crystals from MeOH; mp
186−188 ℃; [α] 20D −19.4 (c 0.15, MeOH); negative
ESI-MS m/z: 481 [M−H]−, UV (MeOH) λmax nm (log ε):
219 (6.76), 281 (6.45). IR (microscope transmission)
νmax cm−1: 3 376, 3 189, 1 709, 1 616, 1 514, 1 449,
1 337, 1 203, 1 066, 939, 855, 758, 656, 623. 1H and
13C NMR data were listed in Table 2. The structure
was identified as reported as the literature[7].
Compound 4: white amorphous powder, [α] 20D −44.7
(c 0.76, MeOH); ESI-MS m/z: 397 [M+Na]+; 1H and 13C
NMR data were listed in Tables 3 and 4, respectively.
These data were consistent with those of linarionoside
A in the literature[8].
Compound 5: white amorphous powder, [α] 20D −52.2
(c 0.59, MeOH); ESI-MS m/z: 559 [M+Na]+; 1H and
13C NMR data were listed in Tables 3 and 4, respectively.
These data were consistent with those of linarionoside
C in the literature[8].
Compound 6: white amorphous powder, [α] 20D −67.5
(c 0.53, MeOH); ESI-MS m/z: 559 [M+Na]+; 1H and
13C NMR data were listed in Tables 3 and 4, respectively.
These data were consistent with those of staphylionoside
K in the literature[9].

Table 3 1H NMR spectral data of compounds 4−6 (600 MHz, CD3OD) (J in Hz)
No. 4 5 6
H-2 1.49 (t, 12.0) 1.48 (t, 12.0) 1.48 (t, 12.0)
1.83 (ddd, 2.4, 3.6, 12.0) 1.82 (ddd, 2.4, 3.6, 12.0) 1.82 (ddd, 2.4, 3.6, 12.0)
H-3 4.04 (m) 4.05 (m) 4.03 (m)
H-4 2.01 (dd, 9.6, 16.2) 2.00 (dd, 10.2, 16.8) 2.01 (dd ,10.2, 16.2)
2.33 (dd, 4.8, 16.2) 2.33 (dd, 4.8, 16.8) 2.33 (dd, 4.2, 16.2)
H-7 1.93 (td, 5.4, 12.0) 1.95 (td, 4.8, 12.0) 2.06 (td, 4.8, 13.8)
2.20 (td, 5.4, 12.0) 2.22 (td, 4.8, 12.0) 2.15 (td, 4.8, 13.8)
H-8 1.48 (m) 1.54 (m) 1.52 (m)
H-9 3.69 (t, 6.0) 3.87 (t, 6.6) 3.83 (t, 6.6)
H-10 1.16 (d, 6.0) 1.19 (d, 6.6) 1.25 (d, 6.6)
H-11 1.04 (s) 1.04 (s) 1.04 (s)
H-12 1.05 (s) 1.05 (s) 1.07 (s)
H-13 1.64 (s) 1.64 (s) 1.65 (s)
H-1 / 1 4.41 (d, 7.8) 4.42 (d, 7.8) / 4.34 (d, 7.8) 4.42 (d, 7.8) / 4.34 (d, 7.8)
H-2 / 2 3.15 (t, 7.8) 3.15 (m) / 3.15 (m) 3.15 (m) / 3.15 (m)
H-3 / 3 3.35 (t, 9.0) 3.35 (t, 8.4) / 3.35 (t, 8.4) 3.35 (t, 8.4) / 3.35 (t, 8.4)
H-4 / 4 3.27 (m) 3.26 (m) / 3.26 (m) 3.26 (m) / 3.26 (m)
H-5 / 5 3.27 (m) 3.26 (m) / 3.26 (m) 3.26 (m)/ 3.26 (m)
H-6 / 6 3.67 (dd, 5.4, 12.0) 3.67 (dd, 5.4, 12.0) / 3.67 (dd, 5.4, 12.0) 3.66 (dd, 6.6, 12.0) / 3.66 (dd, 6.6, 12.0)
3.85 (dd, 2.4, 12.0) 3.85 (dd, 1.8, 12.0) / 3.85 (dd, 1.8, 12.0) 3.84 (dd, 1.2, 12.0) / 3.84 (dd, 1.2, 12.0)
· 1532 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (12): 1527−1532

Table 4 13C NMR spectral data of compounds 4−6 (150 MHz,
CD3OD)
No. 4 5 6 No. 4 5 6
1 38.8 38.8 38.8 1 102.3 102.2 102.3
2 47.5 47.5 47.6 2 75.2 75.2 75.2
3 73.3 73.3 73.3 3 78.1 78.1 78.1
4 39.8 39.8 39.8 4 71.7 71.7 71.7
5 125.1 125.0 125.1 5 77.9 77.9 77.9
6 138.5 138.7 138.6 6 62.8 62.8 62.8
7 25.5 25.3 25.0 1 102.3 103.9
8 40.7 38.9 (−1.8) 38.0 (−2.7) 2 75.2 75.3
9 69.2 76.1 (+6.9) 77.9 (+8.7) 3 78.2 78.3
10 23.3 19.7 (−3.6) 21.8 (−1.5) 4 71.8 71.7
11 28.8 28.8 28.8 5 77.9 77.9
12 30.3 30.3 30.3 6 62.9 62.9
13 20.0 20.1 20.1

Acknowledgments: The authors are grateful to Prof. Puzhu
Cong for his valuable advice on MS analysis, as well as to Prof.
Zailin Li and Yulin Lin for collecting and authenticating the plant
material.
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