Triterpenoid saponins from the rhizome of Polygonatum sibiricum

Article abstract of DOI:10.1080/10286020.2010.505562

Three new triterpenoid saponins, polygonoides C (1), D (2), and E (3), were obtained from the ethanolic extract of the rhizome of Polygonatum sibiricum Redoute. On the basis of NMR and ESI-MS spectra, and chemical evidence, the structures of the three new

Full text of DOI:10.1080/10286020.2010.505562

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Triterpenoid saponins from the rhizome
of Polygonatum sibiricum
Chang-Ying Hu a , De-Ping Xu b , Yu-Mei Wu c & Shi-Yi Ou a
a Department of Food Science and Engineering , Jinan University ,
Guangzhou, 510632, China
b School of Food Science and Technology, Jiangnan University ,
Wuxi, 214122, China
c Packaging Engineering Institute, Jinan University , Zhuhai,
519070, China
Published online: 13 Sep 2010.
To cite this article: Chang-Ying Hu , De-Ping Xu , Yu-Mei Wu & Shi-Yi Ou (2010) Triterpenoid saponins
from the rhizome of Polygonatum sibiricum , Journal of Asian Natural Products Research, 12:9,
801-808, DOI: 10.1080/10286020.2010.505562
To link to this article: http://dx.doi.org/10.1080/10286020.2010.505562
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Journal of Asian Natural Products Research
Vol. 12, No. 9, September 2010, 801–808
ORIGINAL ARTICLE
Triterpenoid saponins from the rhizome of Polygonatum sibiricum
Chang-Ying Hua*, De-Ping Xub, Yu-Mei Wuc and Shi-Yi Oua
aDepartment of Food Science and Engineering, Jinan University, Guangzhou 510632, China;
c
bSchool of Food Science and Technology, Jiangnan University, Wuxi 214122, China; Packaging
Engineering Institute, Jinan University, Zhuhai 519070, China
(Received 8 March 2010; final version received 28 June 2010)
Three new triterpenoid saponins, polygonoides C (1), D (2), and E (3), were obtained
from the ethanolic extract of the rhizome of Polygonatum sibiricum Redoute. On the
basis of NMR and ESI-MS spectra, and chemical evidence, the structures of the three
new compounds were elucidated as 3-O-a-L-rhamnopyranosyl-(1 ! 2)-b-D-glucopyr-
anosyl-(1 ! 4)-b-D-glucopyranosyl-3b,7b,22b-trihydroxy-oleanolic acid (1), 3-O-
a-L-rhamnopyranosyl-(1 ! 2)-b-D-glucopyranosyl-(1 ! 4)-b-D-glucopyranosyl-
3b,7b,22b-trihydroxy-oleanolic acid methyl ester (2), and 3-O-b-D-glucopyranosyl-
(1 ! 3)-b-D-glucopyranosyl-(1 ! 4)-[a-L-rhamno-pyranosyl-(1 ! 2)]-b-D-gluco-
pyranosyl-3b,21b-dihydroxy-oleanolic acid 28-O-b-D-glucopyranosyl-(1 ! 3)-b-D-
glucopyranosyl-(1 ! 3)-b-D-glucopyranoside (3).
Keywords: Polygonatum sibiricum; triterpenoid saponins; polygonoide C; poly-
gonoide D; polygonoide E
1. Introduction
matory [6], antibacterial [7], antifungal [8],
anti-angiogenic [9], and antiproliferative
activities [10], attempts have been made to
isolate them from a variety of herbal plants
[7–10]. In order to preserve the natural
resource, other groups have even tried to
synthesize them [11,12]. However, until
now reports on terpenoid saponins isolated
from P. sibiricum are still limited [5,13]. It
was believed that there are a relatively large
amount of ursane-type and oleanane-type
terpenoid saponins in P. sibiricum. Aiming
to seek for potentially bioactive and novel
compounds, we isolated three new olea-
nane-type terpenoid saponins from the
rhizome of P. sibiricum. Their structures
were elucidated on the basis of NMR and
ESI-MS spectra and chemical evidence.
Polygonatum sibiricum, widely distributed
in China, is a perennial herbaceous plant
belonging to the family of Liliaceae. P.
sibiricum, especially its root or stem, has
been used as a medicine for more than
2000 years and as foodstuff as well. It is
capable of lowering blood glucose and
lipid levels, regulating and enhancing the
immune system, and preventing aging [1].
In addition, P. sibiricum has been explored
as health care cosmetics of pure Chinese
medicine such as masks, cleansing milk,
conditioner, and toothpaste.
In recent years, many compounds such
as alkaloids [2], polysaccharides [3],
steroidals, and triterpenoid saponins [4,5]
have been isolated from P. sibiricum. Since
triterpenoid saponins possess anti-inflam-
*Corresponding author. Email: hucy0000@sina.com
ISSN 1028-6020 print/ISSN 1477-2213 online
q 2010 Taylor & Francis
DOI: 10.1080/10286020.2010.505562
http://www.informaworld.com

802
C.-Y. Hu et al.
74.3 indicated the possible substitution by
2. Results and discussion
the hydroxyl groups. For the E ring, the
chemical shift of C-21 (d 41.2) moved
towards downfield, indicating that C-22
might be substituted by the hydroxyl
group. In the HMBC spectrum, there
were correlations between H-21 (d 2.14)
and C-22 (d 74.3), which confirmed that
C-22 bore a hydroxyl group. Proton
signals at 3.72 (dd, J ¼ 11.8, 4.2 Hz)
[16–18] provided the evidence for the
b-configuration of the hydroxyl group at
C-22. For the B ring, there were no
methylene signals for C-6 (d 18) and C-7
(d 33) commonly observed for oleanolic
acid, while there was only one methylene
signal at d 25.5, indicating the substitution
by the hydroxyl group at C-7 which caused
the downfield shift of C-6. In the HMBC
spectrum, the correlations between H-6
(d 2.26) and C-7 (d 68.0) proved that a
hydroxyl group was attached to C-7. The
orientation of the hydroxyl group at C-7
was determined to be b-configuration by
The EtOH extract of the fresh rhizome of
P. sibiricum was concentrated and parti-
tioned further into petroleum ether and
H2O soluble fractions. The H2O phase was
successively separated on the macroporous
adsorption resin AB-8, reversed-phase
silica gel ODS and MCI, and furnished
three oleanane-type triterpenoid saponins
(1–3).
Compound 1 was obtained as a white
amorphous powder and reacted positively
with the Ehrlich reagent. Its molecular
formula was determined as C48H78O19 by
HR-ESI-MS at m/z 957.5051 [M 2 H]2.
1
In the H NMR spectrum (shown in
Table 1), there were seven methyl singlets
at d 0.74, 0.80, 0.84, 0.88, 0.92, 1.03, and
1.13, respectively, one methyl doublet at d
1.11 (d, J ¼ 8.0 Hz), one olefinic proton at
d 5.16 (br s), and three anomeric protons
of sugar at d 5.61 (d, J ¼ 5.1 Hz), 4.84 (d,
J ¼ 7.9 Hz), and 4.78 (d, J ¼ 7.9 Hz),
respectively. The 13C NMR (shown in
Table 2) and 135DEPT spectra revealed 48
carbon signals, of which 18 were assigned
to the sugar moieties and 30 to the aglycone
moiety. The positive results of the Ehrlich
reagent and the fact that the aglycone
moiety contained 30 carbons indicated that
compound 1 was a triterpenoid saponin.
Because of the carbon signals at d 172.9 for
the carbonyl group, d 121.6 and d 144.1 for
the double bond, this compound was
identified as an oleanane type [14,15].
3
the JH7.H6 value (8.9 Hz).
For the study of the sugar moiety, 1
was hydrolyzed to obtain sapogenin and
sugar. After the acetylation of the sugar,
the products were determined to be
glucose and rhamnose with the content
ratio of 2:1 using gas chromatography
coupled with mass spectrometry (GC–
MS). It was inferred that the sugar moiety
of 1 was composed of two glucose and one
rhamnose residue. From the 1H NMR
spectrum, three anomeric protons of sugars
could be seen, which further proved the
existence of three sugars. Since the value
of J1,2 was 7.9 Hz, the configurations of
both glucoses were b while the configur-
ation was a for rhamnose (J ¼ 5.1 Hz).
The bonding position of the sugar moiety
was confirmed by the HMBC experiment
(Figure 1). Strong HMBC correlations
were observed between Glc-1-H-1 at d
4.78 and C-3 of sapogenin at d 91.3, Glc-2-
H-1 at d 4.84, and C-4 of Glc-1 at d 76.9,
which indicated that glucose 1 was
connected to C-3 of sapogenin while
Different from the oleanolic acid,
compound 1 had only eight methylene
signals at d 23.3, 25.5, 25.5, 26.9, 28.0,
38.2, 41.2, and 47.1, respectively. How-
ever, oleanane-type saponin contains 10
methylene carbon signals, which indicates
the existence of two oxygen-containing
substituent groups. Considering three
carbon signals at d 68.0, 74.3, and 91.3,
there should be three oxygen-bearing
carbons, among which C-3 (d 91.3) was
the oxygen-bearing carbon connected to
the sugar. The carbon signals at d 68.0 and

Journal of Asian Natural Products Research
803

804
C.-Y. Hu et al.
Table 2. 13C NMR (125 MHz) spectroscopic data of compounds 1–3 (in pyridine-d5).
Aglycone
1
2
3
Sugar
1
2
3
Sugar
3
1
2
3
4
5
6
7
8
38.2
25.5
91.3
38.9
56.3
25.5
68.0
42.6
48.0
36.6
23.3
121.6
144.1
41.6
28.0
26.9
44.0
45.6
47.1
31.0
41.2
74.3
28.3
17.2
16.0
21.3
25.9
172.9
32.7
22.4
–
38.2
25.5
91.2
38.9
56.2
25.5
68.0
42.6
48.0
36.7
23.3
121.6
144.2
41.7
28.0
26.9
44.0
45.5
47.0
31.1
41.2
74.2
28.4
17.2
16.0
21.3
25.9
173.3
32.7
22.4
51.5
38.9
27.1
91.0
39.6
56.5
19.0
33.2
40.5
48.0
37.1
24.5
123.0
144.6
42.2
28.1
26.7
44.1
44.7
47.6
36.7
73.2
38.8
27.2
16.0
16.1
21.6
23.4
177.2
31.8
23.3
–
Glc-1
1
2
3
4
–
101.9
74.0
75.2
76.9
74.6
61.9
–
105.2
79.5
76.3
70.5
75.7
63.8
–
102.3
70.5
72.3
74.2
69.2
19.1
–
–
101.9
74.0
75.2
76.8
74.6
61.8
–
105.2
79.5
76.4
70.5
75.6
63.8
–
102.3
70.5
72.4
74.3
69.2
19.0
–
–
Glc-10
1
2
3
–
93.2
76.9
84.4
71.8
78.7
64.0
–
107.0
76.8
85.0
71.6
78.4
67.7
–
108.7
76.1
78.8
71.3
78.8
67.6
–
103.3
79.2
76.1
81.2
77.9
62.7
–
106.2
75.6
85.3
69.7
78.3
62.7
–
104.5
71.0
72.5
73.3
70.1
19.2
–
106.8
74.8
78.2
70.7
78.1
63.0
–
4
5
6
5
6
Glc-2
1
2
3
4
5
6
Rha
1
Glc-20
9
1
2
3
4
5
6
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
OCH3
Glc-30
1
2
3
4
5
6
–
–
–
–
–
–
–
–
–
–
2
3
4
5
6
Glc-3
1
2
3
4
5
6
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
glucose 2 was connected to C-4 of glucose
1. At the same time, the HMBC spectrum
showed that there was a correlation peak
between Rha-H-1 of rhamnose at d 5.61
and C-2 of glucose 2 at d 79.5. Thus, it
could be concluded that rhamnose was
connected to C-2 of glucose 2.
peak at m/z 971.5222, corresponding to the
molecular formula C49H80O19.
1
The H NMR and 13C NMR spectra
of compound 2 were similar to those of
compound 1, except for the presence of the
methoxyl group at dH 3.70 and dC 51.5 in 2.
The HMBC correlation between the proton
at dH 3.70 and the carbonyl carbon at dC
173.3 (C-28) indicated that the methoxyl
group was connected to the carbonyl carbon
[14] (Figure 1). Thus, compound 2 could be
determined as the methyl ester of 1, i.e. 3-
O-a-L-rhamnopyranosyl-(1 ! 2)-b-D-glu-
copyranosyl-(1 ! 4)-b-D-glucopyranosyl-
Accordingly, the structure of com-
pound 1 was elucidated as 3-O-a-L-
rhamnopyranosyl-(1 ! 2)-b-D-glucopyra-
nosyl-(1 ! 4)-b-D-glucopyranosyl-3b,7b,
22b-trihydroxy-oleanolic acid, named
polygonoide C.
Compound 2 was obtained as a white
amorphous powder, giving a positive
coloration with the Ehrlich reagent. The
HR-ESI-MS showed an [M 2 H]2 ion
3b,7b,22b-trihydroxy-oleanolic
acid
methyl ester, named polygonoide D.
Compound 3 was obtained as a white
amorphous powder and turned gel-like

Journal of Asian Natural Products Research
805
29
30
20
21
22
19
12
26
18
17
OH
13
11
25
O
1
4
C
14 16
28
9
6
2
Glc1
OH
OR
10
8
15
27
O
3
5
7
O
Glc2
OH
OH
O
23
24
O
O
OH
H
HO
HO
H
O
HO
H
Me
HO
OH
OH
Rha
Figure 1. The structures and key HMBC correlations of compounds 1 and 2, respectively. R ¼ H in
1 and CH3 in 2.
when containing a small amount of water.
It also gave positive results for the Ehrlich
reagent. The HR-ESI-MS showed an
[M 2 H]2 ion peak at m/z 1589.7235,
corresponding to the molecular formula
C72H118O38.
this compound was also an oleanane type.
In the 135DEPT spectrum, there were only
nine carbon signals of methylenes for the
aglycone moiety, indicating the existence
of one oxygen-containing substituent
group. The carbon signals of A, B, C,
and D rings in compound 3 were almost
identical to those of oleanolic acid, with
the exception of the E ring. The chemical
shift of C-20 in 3 shifted towards down-
field about 5 ppm, C-22 about 6 ppm, and
C-21 about 40 ppm [14,15], suggesting
the existence of the hydroxyl group at
C-21. Proton signals at 3.84 (dd, J ¼ 12.0,
4.4 Hz) suggested that the configura-
tion of the hydroxyl group should be b
[16,18]. Thus, the sapogenin moiety in
3 should be 3b,21b-dihydroxy-oleanolic
acid.
1
In the H NMR spectrum, there were
seven methyl signals ranging from d 0.81
to 1.23 of sapogenin, while another methyl
signal at d 1.83 was assigned to the
rhamnose. There were eight protons with
chemical shifts at d 4.62, 4.73, 4.86, 4.92,
5.06, 5.41, 5.62, and 5.83 respectively,
among which the proton at d 5.83 was
assigned to H-12 and the other seven
signals to the anomeric protons of sugars.
In the 13C NMR spectrum, there were
72 carbon signals, among which 42 were
assigned to the sugar moieties and 30 to
the aglycone moiety. Based on the positive
result of the Ehrlich reagent and the
fact that the aglycone moiety contained
30 carbons, compound 3 was triterpenoid
saponin as well. Because of the carbon
signals at d 177.2 for the carbonyl group,
d 123.0 and d 144.6 for the double bond,
For the study of the sugar moiety, 3 was
hydrolyzed to obtain the sapogenin and the
sugar. After the acetylation of the sugar, the
products were determined to be glucose and
rhamnose with the content ratio of 6:1 using
GC–MS. It was inferred that the sugar
moiety of 3 was composed of six glucose

806
C.-Y. Hu et al.
H
OH
O
C
O
Glc1
OH
O
O
O
H
Glc2
OH
Glc1'
OH
OH
O
HO
OH
O
H
O
HO
O
OH
H
H
O
O
O
Me
O
OH
OH
H
HO
H
OH
OH
Rha
Glc2'
OH
OH
OH
OH
Glc3
HO
O
O
H
Glc3'
OH
OH
HO
OH
Figure 2. The structure and key HMBC correlations of compound 3.
and one rhamnose residue. In the 1H NMR
spectrum, the J values of anomeric protons
of glucose were 6.8–7.2 Hz indicating the
b configuration, while the configuration
was a for rhamnose (J ¼ 5.1 Hz).
Glc-30-H-1 at d 5.06 to Glc-20-C-3 at d 85.0
indicated that glucose 30 was attached to
the C-3 of glucose 20 (Figure 2).
In the HMBC spectrum, the cross-peak
between Glc-1-H-1 at d 4.73 and the
oxygen-bearing carbon at d 91.0 indicated
that glucose 1 was attached to the C-3 of
the sapogenin. The HMBC correlation
between the Glc-2-H-1 at d 4.86 and the
Glc-1-C-4 at d 81.2 indicated that glucose 2
was attached to the C-4 of glucose 1. At the
same time, the correlation between the
Rha-H-1 at d 5.62 and the Glc-1-C-2 at
d 79.2 indicated that rhamnose was
attached to the C-2 of glucose 1. The
HMBC correlation between the Glc-3-H-1
at d 5.41 and the Glc-2-C-3 at d 85.3
indicated that glucose 3 was attached to the
C-3 of glucose 2. Thus, the structure of 3
was elucidated as 3-O-b-D-glucopyrano-
syl-(1 ! 3)-b-D-glucopyranosyl-(1 ! 4)-
[a-L-rhamnopyranosyl-(1 ! 2)]-b-D-glu-
copyranosyl-3b,21b-dihydroxy-oleanolic
In the 13C NMR spectrum, there were
seven anomeric carbon signals at d 108.7,
107.0, 106.8, 106.2, 104.5, 103.3, and 93.2,
respectively. The connection mode of
sugars can be determined by 2D NMR
spectra.
The anomeric carbon signal at d 93.2
showed the existence of the ester glycosi-
dic bond. In the HMBC spectrum, the
cross-peak between Glc-10-H-1 at d 4.62
and the carbonyl carbon at d 177.2 (C-28)
indicated that glucose 10 was attached to
the C-28 of sapogenin by the ester bond.
The anomeric proton Glc-20-H-1 at d 4.92
showed HMBC correlations with the C-3
at d 84.4 of glucose 10, indicating that
glucose 20 was attached to the C-3 of
glucose 10. The HMBC correlations from

Journal of Asian Natural Products Research
807
acid 28-O-b-D-glucopyranosyl-(1 ! 3)-b-
D-glucopyranosyl-(1 ! 3)-b-D-glucopyr-
anoside, named polygonoide E.
The concentrated liquid was extracted
using petroleum ether until the phase
of petroleum ether turned colorless.
The residual phase was separated by
macroporous adsorption resin AB-8
(80 mm £ 1500 mm) after concentration,
and eluted by deionized water and ethanol
with different concentrations. Fraction A
eluted by 10% ethanol and fraction B
eluted by 30% ethanol were collected.
After concentration, fraction A was eluted
on a MCI column by deionized water, 10%
ethanol, and 20% ethanol in sequence. The
eluent of 10% ethanol was concentrated
and eluted again on an ODS column by
deionized water and ethanol with different
concentrations. The eluent of 10–15%
ethanol was concentrated, followed by
separation and purification on the ODS
column repeatedly. After characterization
by thin layer chromatograph (TLC),
compound 3 (67 mg) was obtained.
Fraction B was concentrated and
eluted by deionized water and 10–50%
ethanol on the MCI column. The eluent
of 30% ethanol was collected. It was then
concentrated and eluted again on the ODS
column by deionized water and ethanol
with different concentrations. The eluent
of 30–40% ethanol was collected. After
concentration, it was separated and pur-
ified repeatedly on the ODS column. After
characterization by TLC, 103 mg of
compound 1 and 52 mg of 2 were obtained.
3. Experimental
3.1 General experimental procedures
Melting points were determined with an
X4 micro-melting point apparatus and are
uncorrected. The [a ]D values were
obtained in MeOH at 208C on a Perkin-
Elmer 341 digital polarimeter. HR-ESI-
MS were recorded on a Micromass UK Ltd
spectrometer. NMR spectra were recorded
in pyridine-d5 with a Bruker Avance 500
NMR spectrometer, using TMS as the
internal standard.
Macroporous adsorption resin AB-8
(30–40 mm; Chemical Plant of Nankai
University, Tianjin, China), Sephadex LH-
20 (20–80 mm; Pharmacia Fine Chemical
Co. Ltd, Uppsala, Sweden), Cosmosil ODS
(40–80 mm; Nacalai Tosoh Inc., Uetikon,
Switzerland), and MCI gel CHP20P (75–
150 mm; Mitsubishi Kasei Co., Tokyo,
Japan) were used for column chromatog-
raphy. HSGF254 (precoated plate, Qingdao
Haiyang Chemical Co., Qingdao, China)
was used for thin layer chromatography.
3.2 Plant material
The rhizomes of P. sibiricum Redoute were
collected from Xi’an, Shanxi Province of
China in September 2007. The plant
material was identified by Prof. Jingxiang
Yang (Institute of Botany North-West,
Chinese Academy of Science). The voucher
specimen has been deposited in the
herbarium of the Institute of Botany
North-West, Chinese Academy of Science.
3.3.1 Polygonoide C (1)
A white amorphous powder, mp 236–
2388C, [a]2D0 þ 31.0 (MeOH, c ¼ 0.71).
1H NMR and 13C NMR spectral data are
shown in Tables 1 and 2, respectively. HR-
ESI-MS m/z: 957.5051 [M 2 H]2 (calcd
for C48H77O19, 957.5059).
3.3 Extraction and isolation
Fresh rhizoma (25 kg) of P. sibiricum was
extracted three times for 2 h, each time with
20% ethanol (v/v) at 608C. The material to
liquid ratio was 1:5 (kg/l). The ethanol
extracts were evaporated under reduced
pressure to give a residue (15 liters).
3.3.2 Polygonoide D (2)
A white amorphous powder, mp 241–
2438C, [a]2D0 þ 33.0 (MeOH, c ¼ 0.70).
1H NMR and 13C NMR spectral data
are shown in Tables 1 and 2, respectively.

808
C.-Y. Hu et al.
HR-ESI-MS m/z: 971.5222 [M 2 H]2
(calcd for C49H79O19, 971.5216).
[6] S.Y. Kim, K.H. Son, H.W. Chang, S.S.
Kang, and H.P. Kim, Arch. Pharm. Res.
22, 313 (1999).
[7] A.H. Ahmed, Asian J. Chem. 21, 5510
(2009).
3.3.3 Polygonoide E (3)
[8] N.A. Khan and A. Srivastava, Nat. Prod.
Res. 23, 1128 (2009).
A white amorphous powder and turned
gel-like when containing a small amount
of water, mp 257–2598C, [a]2D0 þ 34.0
(MeOH, c ¼ 0.81). 1H NMR and 13C NMR
spectral data are shown in Tables 1 and 2,
respectively. HR-ESI-MS m/z: 1589.7235
[M 2 H]2 (calcd for C72H117O38,
1589.7223).
[9] H. Hua, L. Feng, X.P. Zhang, L.F. Zhang,
and J. Jin, Phytomedicine 16, 703 (2009).
[10] S.G. Cao, P. Brodie, M. Callmander, R.
Randrianaivo, J. Razafitsalama, E. Rako-
tobe, V.E. Rasamison, K. TenDyke, Y.C.
Shen, E.M. Suh, and D.G.I. Kingston,
J. Nat. Prod. 72, 1705 (2009).
[11] C. Gauthier, J. Legault, and A. Pichette,
Mini Rev. Org. Chem. 6, 321 (2009).
[12] Q.C. Liu, P. Wang, L. Zhang, T.T. Guo,
G.K. Lv, and Y.X. Li, Carbohydr. Res.
344, 1276 (2009).
[13] C.X Wang, Isolation and Identification of
Triterpenoid Saponins and Active Poly-
saccharides from Polygonatum Sibiricum
Red [D] (Jiangnan university, Wuxi, 2008).
[14] D.Q. Yu, Handbooks of Analytical Chem-
istry (Chemistry Industrial Press, Beijing,
1989), Vol. 5, p. 714.
Acknowledgements
We appreciate the Science and Technology
Bureau of Zhuhai City (Guangdong Province,
China, PC 20071044) and also the Department
of Education of Guangdong Province
(cgzhzd0709) for supporting this research
project.
References
[1] H.Z. Zheng, Z.H. Dong, and J. She,
Modernization of Traditional Chinese
Medicine and Application (Xueyuan
Press, Beijing, 1998), pp. 4071–4074.
[2] L.R. Sun, X. Li, and S.X. Wang, J. Asian
Nat. Prod. Res. 7, 127 (2005).
[3] L. Liu, Q. Dong, X.T. Dong, J.N. Fang,
and K. Ding, Carbohydr. Polym. 70, 304
(2007).
[4] D.P. Xu, C.Y. Hu, and Y. Zhang, J. Asian
Nat. Prod. Res. 11, 1 (2009).
[5] D.P. Xu, J. Sun, B. Qi, B. Cui, and
Z. Wang, Chin. Tradit. Herb. Drugs 10,
1470 (2006).
[15] S.S. Yu, Chemistry of Triterpenoids
(Chemistry Industrial Press, Beijing,
2008), pp. 121–123.
[16] D. Caceres-Castillo, G.J. Mena-Rejon, R.
Cedillo-Rivera, and L. Quijano, Phyto-
chemistry 4, 1057 (2008).
[17] S. Guo and L. Kenne, Phytochemistry 5,
419 (2000).
[18] G.J. Mena-Rejon, A.R. Perez-Espadas,
R.E. Moo-Puc, R. Cedillo-Rivera,
I.L. Bazzocchi, I.A. Jimenez-Diaz, and
L. Quijano, J. Nat. Prod. 70, 863 (2007).