Steroidal saponins from Anemarrhena asphodeloides

Article abstract of DOI:10.1080/10286020.2013.802689

Two new steroidal saponins, named anemarnoside A (1) and anemarnoside B (2), along with three known compounds, timosaponin J (3), timosaponin B II (4), and timosaponin B (5), have been isolated from Anemarrhena asphodeloides. Their structures were established by spectroscopic techniques (IR, MS, 1D NMR, and 2D NMR) and by comparison with published data.

Full text of DOI:10.1080/10286020.2013.802689

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Steroidal saponins from Anemarrhena
asphodeloides
a
a
b
a
c
Qing-Bo Liu , Ying Peng , Ling-Zhi Li , Pin-Yi Gao , Yu Sun
,
a
a d
Li-Hong Yu & Shao-Jiang Song
a
School of Traditional Chinese Materia Medica, Shenyang
Pharmaceutical University , Shenyang , 110016 , China
b
School of Pharmacy, Shenyang Pharmaceutical University ,
Shenyang , 110016 , China
c
College of Chemical Engineering, Shenyang University of
Chemical Technology , Shenyang , 110142 , China
d
Active Constituents Research Department, Shenyang
Pharmaceutical University (Benxi) Medical Technology Co., Ltd ,
Benxi , 117004 , China
Published online: 25 Jun 2013.
To cite this article: Qing-Bo Liu , Ying Peng , Ling-Zhi Li , Pin-Yi Gao , Yu Sun , Li-Hong Yu & Shao-
Jiang Song (2013) Steroidal saponins from Anemarrhena asphodeloides , Journal of Asian Natural
Products Research, 15:8, 891-898, DOI: 10.1080/10286020.2013.802689
To link to this article: http://dx.doi.org/10.1080/10286020.2013.802689
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Journal of Asian Natural Products Research, 2013
Vol. 15, No. 8, 891–898, http://dx.doi.org/10.1080/10286020.2013.802689
Steroidal saponins from Anemarrhena asphodeloides
a
Qing-Bo Liu , Ying Peng , Ling-Zhi Li , Pin-Yi Gao , Yu Sun , Li-Hong Yu
b
a
c
a
a
ad
and Shao-Jiang Song *
a
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang
b
10016, China; School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016,
1
China; College of Chemical Engineering, Shenyang University of Chemical Technology, Shenyang
1
c
d
10142, China; Active Constituents Research Department, Shenyang Pharmaceutical University
(
Benxi) Medical Technology Co., Ltd, Benxi 117004, China
(
Received 26 February 2013; final version received 1 May 2013)
Two new steroidal saponins, named anemarnoside A (1) and anemarnoside B (2), along
with three known compounds, timosaponin J (3), timosaponin B II (4), and timosaponin
B (5), have been isolated from Anemarrhena asphodeloides. Their structures were
established by spectroscopic techniques (IR, MS, 1D NMR, and 2D NMR) and by
comparison with published data.
Keywords: Anemarrhena asphodeloides; steroidal saponins; NMR
1
.
Introduction
2. Results and discussion
Anemarrhena asphodeloides Bunge
belongs to the family Liliaceae widely
distributed in China. It has been reported
that steroidal saponins were the main
components of Rhizoma anemarrhenae
Compound 1 was isolated as a white
amorphous solid and showed a positive
reaction in Lieberman–Burchard and Ehr-
lich reagent tests. The IR spectrum showed
21
absorption bands for hydroxyl (3386 cm ),
2
carbonyl of ester (1727 cm ), and a
1
[1]. Studies showed that they had a broad
21
glycosidic linkage (1000–1100cm ). Its
spectral features and physicochemical prop-
erties suggested 1 to be a furostanol saponin.
Its molecular formula C H O was
range of pharmacological effects such as
improving senile dementia [2,3], prevent-
ing cerebral ischemia [4], anti-coagulated
blood [5], anti-oxidant [6,7], anti-tumor
4
5 76 19
deduced from the HR-ESI-TOF-MS at m/z
þ
[8,9], anti-osteoporosis [10], anti-inflam-
1
9
43.4873 [M þ Na] . The H NMR spec-
mation [11], lowering blood pressure [12],
and lowering blood sugar [13]. Therefore, a
phytochemical investigation on the saponin
constituents of A. asphodeloides was
carried out. Two new steroidal saponins,
anemarnoside A (1) and anemarnoside B
trumof1showedtwoangularmethylsignals
at d 0.98 and 0.74 (each 3H, s); one
secondary methyl signal at d 0.97 (3H, d,
J ¼ 6.6 Hz); one terminal methyl group of
an alkane at d 0.90 (3H, t, J ¼ 7.2 Hz); three
anomeric signals appearing at d 5.28 (1H, d,
J ¼ 7.2 Hz), 4.91 (1H, d, J ¼ 7.2 Hz), and
(
2), along with three known compounds,
1
3
timosaponin J (3), timosaponin B II (4), and
timosaponin B (5) (Figure 1), were
obtained. In this paper, we report the
isolation and structural elucidation of
these compounds.
4
.81 (1H, d, J ¼ 7.8 Hz). The C NMR
spectrum of 1 revealed characteristic signals
for four methyl groups at d 24.1, 17.1, 13.7,
and 13.4; one ester carbonylatd 173.4;three
anomeric carbons of sugars at d 106.2,
*Corresponding author. Email: songsj99@163.com
q 2013 Taylor & Francis

8
92
Q.-B. Liu et al.
OR2
26
2
7
2
1
OR2
26
2
3
2
1
OH
1
8 20
25
1
2
17
23
25
2
0
2
2
18
O
24
1
1
1
2
22
17
1
5
9
O
1
4
1
3
H
16
15
24
11
9
9
27
19
O
13
16
2
1
4
1
4
H
1
0
8
H
H
2
14 15
1
0
8
R O
3
7
H
1
5
H
6
7
H
R1O 3
6
H
1
R =S , R =S
1 1 2
2
2 R =S , R =S
1
1
2
2
OR2
OR2
O
HO
O
H
O
O
H
H
H
R O
1
H
H
H
R O
1
H
3
R =S , R =S
4 R =S , R =S
1 1 2 2
1
1
2
2
OR2
OH
Gal
OH
O
S1=
HO
OH
1
'
O
O
HO
HO
H
O
1
''
H
OH
Glc
H
H
H
R O
OH
O
1
S2=
HO
HO
5
R =S , R =S
2
1'''
1
1
2
OH
Glc
H
Figure 1. The structures of compounds 1–5.
05.2, and 102.6. The above evidences
indicated that 1 was a furostanol saponin
1
signal H-21 (d 0.90) and the carbon signals
C-20 (d 17.3), C-17 (d 57.5). The 25R
configuration of 1 was deduced on the basis
of differences in chemical shifts for the
with three sugar units. The NMR data of
(Table 1) were very similar to those of
1
timosaponin J [14], indicating the same
partial structure with rings A, B, C, and D. A
feature differing from that of timosaponin J
wasthesubstitutionofthecarbonylgroupC-
geminal protons of H -26 appearing at d
2
3.97 (H -26) and 3.49 (H -26)
b
a
(eab ¼ 0.48), since the difference is
usually $0.57 for 25S compounds and
#0.48 for 25R compounds [15,16]. The
nuclear overhauser effect spectroscopy
(NOESY) spectrum of 1 showed nuclear
overhauser effect (NOE) correlations
2
0 in timosaponin J by a new methylene
carbon signal C-20 (d 17.3) in 1. That was
confirmed by HMBC spectrum which
showed the correlations between the methyl

Journal of Asian Natural Products Research
893
1 13
Table 1. H NMR (600 MHz) and C NMR (125 MHz) spectral data of the aglycone moieties of
compounds 1 and 2 in pyridine-d .
5
1
2
No.
d
C
d
H
d
C
d
H
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
31.0
27.1
75.4
31.0
37.2
26.9
26.7
35.5
40.8
35.4
21.0
38.6
42.6
54.1
35.5
74.7
57.5
13.7
24.1
17.3
13.4
173.4
32.6
29.4
33.8
74.9
17.1
1.85 O, 1.48 m
1.86 m, 1.23 m
4.28 m
1.85 O
2.16 m
1.98 m, 1.49 m
1.23 m, 0.97 O
1.36 m
31.0
27.1
75.4
31.1
37.1
26.9
26.7
35.0
40.2
35.3
20.8
39.9
40.9
57.0
35.0
84.5
68.2
13.9
24.2
76.9
22.0
163.9
91.4
29.8
35.3
75.7
17.6
1.85 O, 1.46 m
1.84 m, 1.20 m
4.32 br s
1.85 O
2.15 m
1.97 m, 1.48 m
1.19 m, 0.91 m
1.43 m
1.29 m
1.21 m
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
1.29 m, 1.18 m
1.66 m, 0.93 m
1.23 m, 1.20 m
1.89 m, 1.18 m
0.78 m
0.92 m
2.10 m, 1.43 m
5.27 m
2.26 d (5.4)
0.87 s
0.97 s
2.31 m, 1.35 m
5.42 m
1.26 m
0.74 s
0.98 s
1.50 m, 1.33 m
0.90 t (7.2)
1.72 s
2.48 m, 2.41 m
2.01 m, 1.64 m
1.92 m
3.97 O, 3.49 t (7.8)
0.97 d (6.6)
4.55 O
2.51 m, 2.15 m
1.89 O
4.13 O, 3.53 dd (9.6, 7.2)
1.07 d (6.0)
Note: Overlapped signals are indicated by ‘O.’
(
Figure 3) between a-oriented proton H-14
d 0.78), H-16 (d 5.42), and H-17 (d 1.26),
were ascertained by HMBC correlations
(Figure 2) between the anomeric proton
(
0
which indicated the a-configurations of H-
6 and H-17. Thus, the aglycone of 1 was
identified as (25R)-20,22-seco-5b-furost-
2-one-3b,26-diol. Acid hydrolysis of 1
signal H-1 (d 4.91) and the carbon signal C-
00 0
1
3 (d 75.4), between H-1 (d 5.28) and C-2 (d
0
00
81.9), and between H-1 (d 4.81) and C-26
(d 74.9). On the basis of the foregoing
evidence, the structure of 1 was determined
as (25R)-26-O-b-D-glucopyranosyl-20,22-
seco-5b-furost-22-one-3b,26-diol-3-O-b-
D-galactopyranosyl-(1 ! 2)-O-b-D-glu-
copyranoside, named anemarnoside A.
Compound 2 was isolated as a white
amorphous solid and showed a positive
reaction in Lieberman–Burchard and
Ehrlich reagent tests. The IR spectrum
showed absorption bands for hydroxyl
2
afforded D-glucose and D-galactose in a
ratio of 2:1 by thin layer chromatography
(
analyses. The b-anomeric configurations
TLC) and gas chromatography (GC)
for the two glucoses were determined from
3
their large J coupling constants (J ¼ 7.8,
1
,2
7.2 Hz), meanwhile the b-anomeric con-
figuration for the galactose was determined
3
from their large J1,2 coupling constant
(
J ¼ 7.2 Hz) [17]. The sugar sequences and
2
1
its linkage to C-3 and C-26 of the aglycone
(3392 cm ) and a glycosidic linkage

8
94
Q.-B. Liu et al.
OH
O
HO
HO
O
OH
H
O
H
O
OH
OH
O
H
HO
OH
O
O
H
HO
HO
O
H
OH
1
H
OH
O
HO
HO
O
OH
H
H
OH
O
OH
OH
O
H
HO
OH
O
H
O
O
HO
HO
H
OH
H
2
Figure 2. Key HMBC correlations of compounds 1 and 2.
2
1
(
1000–1100 cm ). Its spectral features
and physicochemical properties suggested
to be a furostanol saponin. Its molecular
formula C H O was deduced from the
d 106.3, 105.3, and 102.7. The above
evidences indicated that 2 was a furostanol
saponin with three sugar units. Comparison
of the NMR spectral data of 2(Table1) with
that of timosaponin B II [18] revealed that
they have the same partial structure with
rings A, B, C, and D. However, significant
differences were recognized in the signals
from the ring E part and the side chain
moiety, where a tertiary oxygenated carbon
(d 76.9) and an oxygen-bearing trisubsti-
tuted olefinic groups (d 163.9 and 91.4)
were supposed to be located. These were
confirmed by the HMBC spectrum which
showed the correlations between the
methyl proton H-21 (d 1.72) and the carbon
signal C-20 (d 76.9), and between the
olefinic proton H-23(d 4.55) and the carbon
2
4
5 74 19
HR-ESI-TOF-MS at m/z 941.4717
þ
1
[
M þ Na] . The H NMR spectrum of 2
showed three angular methyl signals at
d 1.72, 0.97, and 0.87 (each 3H, s); one
secondary methyl signal at d 1.07 (3H, d,
J ¼ 6.0 Hz); one olefinic proton at d 4.55
(
1H, O); three anomeric signals appearing
at d 5.27 (1H, d, J ¼ 7.2 Hz), 4.90 (1H, d,
J ¼ 7.2 Hz), and 4.82 (1H, d, J ¼ 7.2 Hz).
1
3
The C NMR spectrum of 2 revealed the
characteristic signals for four methyl
groups at d 24.2, 22.0, 17.6, and 13.9;
one pair of olefinic carbons at d 163.9 and
9
1.4; three anomeric carbons of sugars at

Journal of Asian Natural Products Research
895
OH
O
HO
HO
O
OH
H
H
O
H
O
OH
HO
OH
O
OH
O
H
O
O
H
HO
HO
H
OH
1
H
OH
O
HO
HO
O
OH
H
H
OH
O
OH
HO
OH
O
H
O
OH
H
O
O
HO
HO
H
OH
H
2
Figure 3. Key NOE correlations of compounds 1 and 2.
3
signal C-22 (d 163.9). The 25S configur-
ation of 2 was deduced on the basis of
differences in chemical shifts for the
J1,2 coupling constants (J ¼ 7.2, 7.2 Hz),
meanwhile the b-anomeric configuration
for the galactose was determined from their
3
geminal protons of H -26 appearing at
2
large J coupling constant (J ¼ 7.2 Hz)
1
,2
d
4.13 (H -26) and 3.53 (H -26)
a b
[17]. The sugar sequences and its linkage
to C-3 and C-26 of the aglycone were
ascertained by HMBC correlations
(
[
eab ¼ 0.600 . 0.57 for 25S compound)
14,19]. The orientation of the C-20
hydroxyl group was determined to be a-
configuration by the observed NOE corre-
lation (Figure 3) between b-oriented
methyl proton H-18 (d 0.87) and methyl
proton H-21 (d 1.72). Hence, the aglycone
of 2 was identified as (25S)-5b-furost-
(
Figure 2) between the anomeric proton
0
signal H-1 (d 4.90) and the carbon signal
0
0
C-3 (d 75.4), between H-1 (d 5.27) and C-
0
000
2
(d 82.0), and between H-1 (d 4.82) and
C-26 (d 75.7). On the basis of the foregoing
evidence, the structure of 2 was determined
as (25S)-26-O-b-D-glucopyranosyl-5b-
furost-22(23)-en-3b,20a,26-triol-3-O-b-
D-galactopyranosyl-(1 ! 2)-O-b-D-gluco-
pyranoside, named anemarnoside B.
2
2(23)-en-3b,20a, 26-triol. Acid hydroly-
sis of 2 afforded D-glucose and D-galactose
in a ratio of 2:1 by TLC and GC analysis.
The b-anomeric configurations for the two
glucoses were determined from their large

8
96
Q.-B. Liu et al.
The known compounds were readily
voucher specimen (No. 20100907) has
been deposited in the Herbarium of
Shenyang Pharmaceutical University,
Liaoning, P.R. China.
identified as timosaponin J (3) [14],
timosaponin B II (4) [19], and timosaponin
B (5) [19] by comparing NMR spectral
data with those reported in the literature.
3
.3 Extraction and isolation
3
.
Experimental
The fresh rhizome of A. asphodeloides
3
.1 General experimental procedures
(
6 kg) was extracted three times (3 £ 2 h)
Optical rotations were measured on a
JASCO P-1020 polarimeter (Jasco Co.,
Tokyo, Japan). IR spectra were obtained on
a Shimadzu ftir-8400s spectrophotometer
with 70% EtOH at 808C. The EtOH extract
was evaporated under reduced pressure to
give a residue (387.0 g), which was
suspended in water and then extracted
with petroleum ether, ethyl acetate, and n-
butanol successively. The n-butanolic
fraction (92.8 g) was subjected to macro-
porous adsorption resin D101 CC, and
(Shimadzu Corporation, Kyoto, Japan).
NMR spectra were recorded on Bruker
ARX-300 and ARX-600 instruments (Bru-
ker Co., Billerica, MA, USA). HR-ESI-
TOF-MS experiments were performed on a
MicroTOF spectrometer (Bruker Co.,
Karlsruhe, Germany). High performance
liquid chromatography (HPLC) prep-
aration was performed on a Hitachi
preparative HPLC system (Hitachi Ltd,
Tokyo, Japan) equipped with Refractive
Index Detector (L-2490) and prep-ODS
eluted with gradient system EtOH–H O
2
(30:100 to 90:100) to afford four fractions
(Frs 1–4). Fr. 3 (15.4 g) was subjected to
CC on Sephadex LH-20 eluting with 70%
MeOH, and five fractions (Frs 3-1–5) were
obtained. Fr. 3-2 (1.75 g) was subjected to
CC on reversed-phase ODS, using MeOH–
H O (20:100 to 80:100) as the eluent to
2
(
5 mm £ 10 mm £ 250 mm). GC was done
on an Agilent 7890A Gas Chromatograph
Agilent technologies, Inc., Santa Clara,
CA, USA) equipped with HP-5 capillary
column
afford four fractions (Frs 3-2-1–4). Fr. 3-2-
3 (75 mg) was purified by HPLC (column:
10 mm £ 250 mm; RP-18, 5 mm; flow rate:
(
2.0 ml/min) with MeOH–H O (80:20) as
2
(30 m £ 320 mm £ 0.25 mm).
mobile phase to afford compound 1 (20 mg;
t ¼ 23.7 min). Fr. 3-2-2 (109 mg) was
Sephadex LH-20 (20–100 mm, Pharmacia
Fine Chemical Co. Ltd, NJ, USA), silica
gel (200–300 mesh, Qingdao Marine
Chemistry Ltd, Qingdao, China), and
Cosmosil octadecyl silane (ODS) (40–
R
further purified by HPLC (column:
10 mm £ 250 mm; RP-18, 5 mm; flow
rate: 2.0 ml/min) with MeOH–H O
2
(70:30) as mobile phase to afford com-
pound 2 (20 mg; t ¼ 33.4 min) and com-
8
0 mm, Nacalai Tosoh, Inc., Uetikon,
R
Switzerland) were used for column chro-
matography (CC). TLC was conducted on
silica gel GF254 (Qingdao Marine Chem-
istry Ltd, Qingdao, China).
pound 3 (18 mg; t ¼ 36.7 min). Fr. 3-2-4
R
(213 mg) was further purified using silica
gel CC eluting with a solvent system of
CH Cl –MeOH–H O (8:2:0.25) to yield
2
2
2
compound 4 (40 mg) and compound
5
(37 mg).
3
.2 Plant material
The rhizome of A. asphodeloides was
collected from Liaoning Province of China
in September 2010. The plant material was
identified by Prof. Qishi Sun (Department
of Traditional Chinese Materia Medica,
Shenyang Pharmaceutical University). A
3
.3.1 Anemarnoside A (1)
A white amorphous solid, positive Lieber-
2
5
D
mann–Burchard test; ½aꢀ
246.5
(c ¼ 0.054, MeOH); IR (KBr) v
max
21
(cm ): 3386, 2928, 1727, 1635, 1447,

Journal of Asian Natural Products Research
897
1 13
Table 2. H NMR (300 MHz) and C NMR (125 MHz) spectral data of the sugar moieties of
compounds 1 and 2 in pyridine-d .
5
1
2
No.
d
C
d
H
d
C
d
H
(
(
(
3-O)-b-D-Gal
0
1
0
102.6
81.9
75.3
70.0
76.7
62.3
4.91 d (7.2)
102.7
82.0
75.3
70.0
76.8
62.3
4.90 d (7.2)
4.65 dd (9.0, 7.2)
4.26 brt (9.0)
4.56 O
4.02 O
4.42 O, 4.45 O
2
4.67 dd (9.0, 7.2)
4.29 brt (9.0)
4.57 O
4.03 m
4.44 O, 4.42 O
0
3
0
4
0
5
0
6
2
Gal )-b-D-Glc
0
0
0
0
0
0
0
0
0
0
0
0
1
2
3
4
5
6
106.2
77.0
78.1
71.8
78.6
62.9
5.28 d (7.2)
4.09 brt (7.2)
4.19 O
4.30 O
3.96 m
4.56 d (11.4), 4.50 d (11.4)
106.3
77.0
78.2
71.8
78.6
62.9
5.27 d (7.2)
4.08 brt (7.2)
4.21 O
4.25 O
3.83 m
4.54 m, 4.50 m
26-O)-b-D-Glc
0
0
0
0
0
0
00
00
00
00
00
00
1
2
3
4
5
6
105.2
75.3
78.7
71.8
78.5
63.0
4.81 d (7.8)
4.02 O
4.20 O
4.22 O
3.86 m
4.43 m, 4.38 O
105.3
75.5
78.8
71.9
78.5
63.1
4.82 d (7.2)
4.02 O
4.28 brt (9.0)
4.32 O
3.86 m
4.50 m, 4.45 m
Note: Overlapped signals are indicated by ‘O’.
1 13
381, 1167, 1074, 1045, and636; Hand C
1
NMR spectral data, see Tables 1 and 2; HR-
Then the aqueous layer was concentrated
in vacuo to appropriate volume, and the
solution was examined by TLC (EtOAc–
þ
ESI-TOF-MS: m/z 943.4873 [M þ Na]
(
calcd for C H O Na, 943.4879).
4
BuOH–H O–HOAc, 4:4:1:1) and com-
2
5
76 19
pared with the authentic samples, galactose
and glucose were detected. Each remaining
aqueous layer was concentrated to dryness
to give a residue, which was dissolved in
pyridine (1.0 ml), and then L-cysteine
methyl ester hydrochloride (2.0mg) was
added to the solution. The mixture was
heated at 608C for 2 h, and 0.5 ml TMSI (N-
tremethylsilyimidazole) was added, fol-
lowed by heating at 608C for 2 h. The
reaction product was subjected to GC
analysis on Agilent 7890A (HP-5,
3
.3.2 Anemarnoside B (2)
A white amorphous solid, positive Lie-
bermann–Burchard test; ½aꢀ 275.4
2
D
5
(
c ¼ 0.052, MeOH); IR (KBr) v
max
2
cm ): 3393, 2928, 1649, 1380, 1167,
1
(
1 13
015, 894, and 636; H and C NMR
1
spectral data, see Tables 1 and 2; HR-ESI-
þ
TOF-MS: m/z 941.4717 [M þ Na] (calcd
for C H O Na, 941.4722).
45 74 19
3
0m £ 320 mm, 0.25mm) with flame ion-
3
1
.4 Acid hydrolysis of compounds
and 2
ization detector (FID) detection. Column
temperature: 120–2808C with the rate of
Each compound (3.0mg) was hydrolyzed
with 2M HCl (5.0ml), heated for 4 h at 958C
and extracted with CHCl3 (3 £ 5.0 ml).
88C/min, and the carrier gas was N (1.4ml/
2
min), injection temperature: 2508C; injec-
tion volume: 1 ml. The absolute configur-

8
98
Q.-B. Liu et al.
ations of the monosaccharides were con-
firmed to be D-galactose and D-glucose by
comparison of the retention times of
[5] J.X. Dong and G.Y. Han, Planta Med. 57,
60 (1991).
[
4
6] J. Zhang, Z. Meng, M.Y. Zhang, D.Z. Ma,
S. Xu, and H. Kodama, Clin. Chim. Acta
2
its Me Si ethers with those of standard
3
89, 79 (1999).
samples [tR (D-glucose) ¼ 19.843min, tR
[7] N. Kaname, J. Zhang, Z. Meng, S. Xu, K.
Sugahara, Y. Doi, and H. Kodama, Clin.
Chim. Acta 295, 129 (2000).
(
D-galactose) ¼ 20.165min)].
[
8] Y. Ni, X.G. Gong, M. Lu, H.M. Chen, and
Y. Wang, Cell Biol. Int. 32, 337 (2008).
9] X.F. Huang, Y.Y. Lin, and L.Y. Kong,
J. Integr. Plant Biol. 50, 717 (2008).
Acknowledgments
[
This work was financially supported by
National Key Technology R&D Program in
the 11th Five Year Plan of China
[
[
[
10] H. Nian, L.P. Qin, W.S. Chen, Q.Y.
Zhang, H.C. Zheng, and Y. Wang, Acta
Pharmacol. Sin. 27, 728 (2006).
11] W.Q. Lu, Y. Qiu, T.J. Li, X.l. Tao, L.N.
Sun, and W.S. Chen, Arch. Pharm. Res.
(
2009ZX09103), ‘Liaoning Bai QianWan
Talents Program’ (2011921044), 2011 Social
Development Project of Liaoning Science and
Technology Committee (2011404012-3),
Liaoning Province Doctoral Scientific Research
Start-up Funds (20111139), and 2012 Project of
Shenyang Science and Technology Bureau
32, 1301 (2009).
12] Z.S. Li, D.L. Li, S. Huang, Y. Ding, B.P.
Ma, and S.Q. Wang, Acta Pharm. Sin. 38,
4
96 (2003).
(
F12-161-9-00).
[
[
13] N. Nakashima, I. Kimura, M. Kimura, and
H. Matsuura, J. Nat. Prod. 56, 345 (1993).
14] L.P. Kang, J. Zhang, Y. Cong, B. Li, C.Q.
Xiong, Y. Zhao, D.W. Tan, H.S. Yu, Z.Y.
Yu, Y.W. Cong, C. Liu, and B.P. Ma,
Planta Med. 78, 611 (2012).
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