Chinese Journal of Natural Medicines 2012, 10(4): 02790283

Chinese
Journal of
Natural
Medicines






Chemical constituents from the stems of Celastrus
orbiculatus
LI Jian-Juan
1
, YANG Jie
1
, L Fang
1
, QI Yin-Tao
1
, LIU Yan-Qing
2
, SUN Yun
2
, WANG Qiang
1*

1
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China;
2
College of Medicine, Yangzhou University, Yangzhou 225001, China
Available online 20 July 2012
[ABSTRACT] AIM: To investigate the chemical constituents from the stems of Celastrus orbiculatus Thunb.. METHODS: The
chemical constituents were isolated and purified by silica gel, Sephadex LH-20 and ODS column chromatography. Their structures
were elucidated on the basis of physical characteristics and spectral data. RESULTS: Eleven compounds were obtained and their
structures were identified as 3-hydroxy-2-oxoolean-12-ene-22, 29-lactone (1), 2, 6-dimethoxybenzoquinone (2), 3-oxoolean-12-en-
28-oic acid (3), 3-oxo-24-norolean-12-en-28-oic acid (4), 23-hydroxybetulonic acid (5), vanillic acid (6), 23-hydroxy-3-oxoolean-12-en-
28-oic acid (7), syringic acid (8), oleanolic acid (9), -sitosterol (10), -daucosterol (11). CONCLUSION: Compound 1 is a new triter-
pene; compounds 25 and 7 were isolated from this genus for the first time and compounds 8 and 9 were firstly isolated from this plant.
[KEY WORDS] Celastrus orbiculatus Thunb.; Triterpenes; Chemical constituents
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)04-0279-05

1 Introduction

Celastrus orbiculatus Thunb.(Celastraceae), widely dis-
tributed in China, has been used as folk remedy for rheuma-
toid arthritis, low back pain, muscles pain, toothache, ame-
norrhea, dysentery, bruises, snake bites, sores and carbuncle
furuncle
[1]
. In the past years, a lot of sesquiterpenes, flavon-
oids, triterpenes and alkaloids have been isolated from the
seeds, fruit and roots of C. orbiculatus
[2]
. However, the
chemical constituents of the stems of C. orbiculatus have
rarely been studied. It was reported recently that ethanol ex-
tract of the stems of C. orbiculatus had significant anti-tumor
activities in vivo and in vitro
[3]
. And the total terpenes in C.
orbiculatus could improve lipoprotein level and morphologi-
cal structure of liver steatosis
[4]
. The pharmacological impor-
tance of C. orbiculatus prompted us to investigate its chemi-
cal constituents. As a result, eleven compounds were isolated,

[Received on]

20-July-2011
[Research funding] This project was supported by the Social De-
velopment Project of Jiangsu Province (No. BE2011738) and the
Priority Academic Program Development of Jiangsu Higher Educa-
tion Institutions.
[-Corresponding author] WANG Qiang: Prof., Tel: 86-25-83271390,
E-mail: qwang49@sohu.com
These authors have no any conflict of interest to declare.
Copyright 2012, China Pharmaceutical University.
Published by Elsevier B.V. All rights reserved
including six triterpenes (1, 3, 4, 5, 7 and 9), two phenolics (6
and 8), two steroids (10 and 11) and a benzoquinone (2). The
structures of these compounds were identified as 3-hydroxy
-2-oxoolean-12-ene-22, 29-lactone (1), 2, 6-dimethoxyben-
zoquinone (2), 3-oxoolean-12-en-28-oic acid (3), 3-oxo-24-
norolean-12-en-28-oic acid (4), 23-hydroxybetulonic acid (5),
vanillic acid (6), 23-hydroxy-3-oxoolean-12-en-28-acid (7),
syringic acid (8), oleanolic acid (9), -sitosterol (10),
-daucosterol (11). Compound 1 is a new triterpene, com-
pounds 2-5 and 7 were isolated from this genus for the first
time and compounds 8 and 9 were firstly isolated from this
plant.
2 Result and Discussion
Compound 1 + 93.8 (c 0.123, CHCl
3
), was
obtained as white powder, and was positive for the Lieber-
mann-Burehard reaction. The molecular formula was deter-
mined as C
30
H
44
O
4
by HRESI-MS m/z : 491.313 1 [M + Na]
+
(Calcd. 491.313 7). The IR spectrum showed absorption
bands at 3 475, 1 766 and 1 707 cm
1
, suggesting the pres-
ence of a hydroxy group and two carbonyl groups.
1
H NMR
spectrum of compound 1 showed the presence of seven terti-
ary methyl groups [
H
0.71, 0.87, 0.91, 0.93, 1.12, 1.20, 1.21
(each 3H, s)], two methine protons [
H
3.90 (1H, s), 4.15 (1H,
d, J = 5.5 Hz)] attached to oxygen functionalities and one
olefinic proton [
H
5.31(1H, t, J = 3.5 Hz)]. Its
13
C NMR
spectrum revealed that its C-skeleton contains 30 carbons,
including two carbonyl carbons (
C
211.1, 182.5), two car-
LI Jian-Juan, et al. /Chinese Journal of Natural Medicines 2012, 10(4): 279283

bons (
C
140.7, 124.1) attached to a double bond, two me-
thine carbons (
C
83.1, 83.2) attached to oxygen functional-
ities and seven methyl carbons (
C
16.7, 16.8, 16.9, 21.2, 24.3,
25.2, 29.6). From the carbon number (C30) and the presence
of seven tertiary methyl groups and one double bone com-
pound 1 was deduced to be an oleanane-type triterpene.



The structure of compound 1 was determined by a detailed
analysis of the HSQC, HMBC and ROESY spectral data as
well as the
1
H and
13
C NMR spectral data.
13
C NMR spectral
data of compound 1 were similar to those of wilforlide A
[5]
and
wilforlide B
[6]
, except for ring A. These data suggested that the
B-E ring systems of compound 1 were the same as in wil-
forlides A and B. In the HMBC spectrum of 1, the methine
proton signal at
H
3.90 was correlated with the carbon signals
at
C
45.9 (C-4), 29.6 (C-23) and 16.8 (C-24), suggesting that
the hydroxy group was located at C-3. The proton signal at
H
2.48 (H

-1) was correlated with the carbon signals at

C
83.1
(C-3), 43.8 (C-10), 54.8 (C-5) and the ketone carbon signal at

C
211.1, and the proton signal at
H
3.90 (H-3) was correlated
with the ketone carbon signal at
C
211.1. Thus, the ketone
group was located at C-2. Furthermore, the -configuration of
the hydroxy group was confirmed from the ROESY spectrum,
which showed significant through-space correlation between
H-23 (
H
1.20 ) and H-5 (
H
1.46, H), H-23 (
H
1.20 ) and H-3
(
H
3.90). Based upon the above information, the structure of
compound 1 was unambiguously established as 3-hydroxy-
2-oxoolean-12 -ene-22, 29-lactone. The full assignments of the
1
H and
13
C NMR data of 1 (Table 1) were achieved in combi-
nation with HMBC, HSQC and ROESY experiments (the
structure of compound 1 and some key HMBC and ROESY
correlations are shown in Figs. 1 and 2, respectively).


Table 1
1
H and
13
C NMR spectral data for compound 1 in
CDCl
3
(500 MHz for H, 125 MHz for C)
a

Proton G
H
Carbon G
C

1 2.08 ( d, 12.5 ) 1 53.5
1 2.48 ( d, 12.5 ) 2 211.1
3 3.90 ( s ) 3 83.1
5 1.46 ( m ) 4 45.9
6 1.45 ( m ) 5 54.8
1.68 ( m ) 6 18.8
7 1.48 ( m ) 7 33.0
1.62 ( m ) 8 40.1
9 1.86 ( m ) 9 47.7
11 1.87 ( m ) 10 43.8
1.94 ( m ) 11 23.7
12 5.31 ( t, 3.5 ) 12 124.1
15 1.10 ( m ) 13 140.7
1.74 ( m ) 14 42.9
16 0.89 ( m ) 15 24.5
1.92 ( m ) 16 25.4
18 2.16 ( m ) 17 35.5
19 1.51 ( m ) 18 43.6
1.92 ( m ) 19 40.0
21 1.94 ( m ) 20 39.7
21 2.26 ( d, 11.5 ) 21 34.0
22 4.15 ( d, 5.5 ) 22 83.2
23 1.20 ( s ) 23 29.6
24 0.71 ( s ) 24 16.8
25 0.91 ( s ) 25 16.7
26 0.93 ( s ) 26 16.9
27 1.12 ( s ) 27 24.3
28 0.87 ( s ) 28 25.2
30 1.21 ( s ) 29 182.5
30 21.2
a
Data were recorded on a Bruker AV-500 spectrometer, assignments
were confirmed by HSQC and HMBC.


Fig. 1 Structure of compound 1


Fig. 2 Key HMBC (HC) and ROESY () correlations of
compound 1
LI Jian-Juan, et al. /Chinese Journal of Natural Medicines 2012, 10(4): 279283

Compound 2 Yellow needle crystal (CHCl
3
), C
8
H
8
O
4
,
mp 185187 C, ESI-MS m/z 169 [M + 1]
+
.
1
H NMR (500
MHz, CDCl
3
) : 5.84 (2H, s, H-3, 5), 3.81 (6H, s, 2, 6-
OCH
3
).
13
C NMR (125 MHz, CDCl
3
) : 186.8 (C-4), 176.7
(C-1), 157.3 (C-2, 6), 107.4 (C-3, 5), 56.5 (2, 6-OCH
3
).
Compound 2 was identified as 2, 6-dimethoxybenzoquinone
by comparison of the physical and spectral data with the re-
ported data
[7]
.
Compound 3 White needle crystal (CH
3
OH), C
30
H
46
O
3,
mp 178179 C, ESI-MS m/z 455.4 [M + H]
+
.
1
H NMR(500
MHz, CDCl
3
) : 0.80 (3H, s), 0.90 (3H, s), 0.92 (3H, s), 1.02
(3H, s), 1.04 (3H, s), 1.08 (3H, s), 1.13 (3H, s), 2.3-2.7 (2H, m),
5.30 (1H, t, J = 3.6 Hz, H-12).
13
C NMR (125 MHz, CDCl
3
) :
36.8 (C-1), 32.4 (C-2), 217.7 (C-3), 39.1 (C-4), 55.3 (C-5),
19.5 (C-6), 33.8 (C-7), 39.3 (C-8), 47.4 (C-9), 46.9 (C-10),
23.6 (C-11), 122.4 (C-12), 143.6 (C-13), 41.7 (C-14), 32.2
(C-15), 21.4 (C-16), 46.6 (C-17), 41.0 (C-18), 45.8 (C-19),
30.7 (C-20), 32.4 (C-21), 26.4 (C-22), 27.7 (C-23), 15.0
(C-24), 15.0 (C-25), 17.0 (C-26), 25.8 (C-27), 183.9 (C-28),
33.0 (C-29), 23.5 (C-30). Compound 3 was identified as
3-oxoolean-12-en-28-oic acid by comparison of the physical
and spectral data with the reported data
[8]
.
Compound 4 White powder (CHCl
3
CH
3
OH),
C
29
H
44
O
3
, mp 240242 C, ESI-MS m/z 441.3 [M H]

.
1
H
NMR (500 MHz, CDCl
3
) : 0.85 (3H, s), 0.90 (3H, s), 0.93
(3H, s), 0.99 (3H, d, J = 6.5 Hz), 1.12 (3H, s), 1.13 (3H, s),
2.30-2.33 (1H, m), 2.43- 2.45 (1H, m), 2.84 (1H, dd, J = 13.8,
4.0 Hz, H-18), 5.30 (1H, t, J = 3.5, H-12).
13
C NMR (125
MHz, CDCl
3
) : 40.1 (C-1), 37.4 (C-2), 213.6 (C-3), 44.8
(C-4), 53.6 (C-5), 23.9 (C-6), 31.6 (C-7), 39.1 (C-8), 45.3
(C-9), 36.7 (C-10), 22.0 (C-11), 122.5 (C-12), 143.8 (C-13),
41.8 (C-14), 27.6 (C-15), 23.0 (C-16), 46.5 (C-17), 41.3 (C-
18), 45.8 (C-19), 30.7 (C-20), 33.8 (C-21), 32.4 (C-22), 11.6
(C-23), 13.1 (C-25), 17.0 (C-26), 25.8 (C-27), 180.4 (C-28),
33.0 (C-29), 23.5 (C-30). Compound 4 was identified as
3-oxo-24-norolean-12-en-28-oic acid by comparison of the
physical and spectral data with the reported data
[9]
.
Compound 5 White powder (petroleum etherCHCl
3
),
C
30
H
46
O
4
, mp 214217 C.
1
H NMR (500 MHz, CDCl
3
) :
0.98 (3H, s), 0.99 (3H, s), 1.00 (3H, s), 1.04 (3H, s), 1.69 (3H,
s), 2.27 (1H, m), 2.62 (1H, m), 3.41 (1H, d, J = 11.5 Hz),
3.63 (1H, d, J = 11.5 Hz), 4.61 (1H, d, J = 1.5 Hz), 4.74 (1H,
d, J = 11.5 Hz).
13
C NMR (125 MHz, C
5
D
5
N) : 38.4 (C-1),
36.2 (C-2), 217.2 (C-3), 47.0 (C-4), 49.6 (C-5), 19.9 (C-6),
33.5 (C-7), 40.8 (C-8), 52.4 (C-9), 36.6 (C-10), 21.7 (C-11),
26.0 (C-12), 38.6 (C-13), 42.7 (C-14), 31.1 (C-15), 32.6
(C-16), 56.4 (C-17), 47.5 (C-18), 49.6 (C-19), 151.1 (C-20),
30.0 (C-21), 37.3 (C-22), 68.0 (C-23), 17.2 (C-24), 16.0
(C-25), 15.9 (C-26), 14.6 (C-27), 178.6 (C-28), 109.6 (C-29),
19.3 (C-30). Compound 5 was identified as 23-hydroxybe-
tulonic acid by comparison of the physical and spectral data
with the reported data
[10-11]
.
Compound 6 White powder (EtOAc), C
8
H
8
O
4
, mp
250252 C, ESI-MS m/z 167 [M H]

.
1
H NMR (500 MHz,
DMSO) : 3.80 (3H, s, -OCH
3
), 6.83 (1H, dd, J = 3.0, 8.0
Hz), 7.43 (1H, d, J = 2.0 Hz), 7.44 (1H, dd, J = 2.0, 7.6 Hz),
9.82 (1H, br s), 12.47 (1H, br s). Compound 6 was identified
as vanillic acid by comparison of the physical and spectral
data with the reported data
[12]
.
Compound 7 White powder (CHCl
3
CH
3
OH), C
30
H
45
O
4
, mp 224226 C, ESI-MS m/z 469.3 [M H]

.
1
H NMR
(500 MHz, CDCl
3
) : 0.84 (3H, s), 0.90 (3H, s), 0.93 (3H, s),
1.00 (3H, s), 1.14 (3H, s), 1.15 (3H, s), 2.29 (1H, m ), 2.59 (1H,
m), 2.86 (1H, dd, J = 13.5, 4.0 Hz, H-18), 3.42 (1H, d, J =
11.0 Hz), 3.64 (1H, d, J = 11.0 Hz), 5.30 (1H, t, J = 3.5 Hz,
H-12).
13
C NMR (125 MHz, CDCl
3
) : 15.2, 16.9, 17.2, 19.2,
23.0, 23.56, 23.60, 25.9, 27.7, 30.7, 32.1, 32.4, 33.1, 33.9,
35.2, 36.7, 38.8, 39.4, 41.2, 41.9, 45.9, 46.6, 46.9, 49.3, 52.4,
67.0, 122.3, 143.8, 182.1, 219.0. Compound 7 was identified
as 23-hydroxy-3-oxoolean-12-en-28-oic acid by comparison
of the physical and spectral data with the reported data
[13]
.
Compound 8 White amorphous powder (CHCl
3

CH
3
OH), C
9
H
10
O
5
, mp 205206 C, ESI-MS m/z 197 [ M
H]

.
1
H NMR (500 MHz, CD
3
OD) : 3.88 (6H, s, 3, 5-OCH
3
),
7.33 (2H, s, H-2, 6).
13
C NMR (125 MHz, CD
3
OD) : 170.3
(COOH), 122.5 (C-1), 108.9 (C-2, 6), 149.4 (C-4), 142.1
(C-3, 5), 57.2 (3, 5-OCH
3
). Compound 8 was identified as
syringic acid by comparison of the physical and spectral data
with reported data
[14]
.
Compound 9 White powder (CHCl
3
CH
3
OH), C
30
H
46
O
3
, mp 306308 C, ESI-MS m/z 455 [M H]

,
1
H NMR
(500 MHz, CDCl
3
) : 0.75 (3H, s), 0.77 (3H, s), 0.90 (3H, s),
0.91 (3H, s), 0.93 (3H, s), 0.99 (3H, s), 1.13 (3H, s), 2.81 (1H,
dd, J = 13.3, 4.7 Hz, H-18), 3.22 (1H, dd, J = 4.5, 11.5 Hz),
5.28 (1H, t, J = 3.5, H-12).
13
C NMR (125 MHz, CDCl
3
) :
38.4 (C-1), 27.2 (C-2), 79.0 (C-3), 38.8 (C-4), 55.3 (C-5),
18.3 (C-6), 32.7 (C-7), 39.3 (C-8), 47.7 (C-9), 37.1 (C-10),
23.4 (C-11), 122.7 (C-12), 143.6 (C-13), 43.6 (C-14), 27.7
(C-15), 23.6 (C-16), 46.5 (C-17), 41.1 (C-18), 45.9 (C-19),
30.7 (C-20), 33.8 (C-21), 32.4 (C-22), 28.1 (C-23), 15.5
(C-24), 15.3 (C-25), 17.1 (C-26), 25.9 (C-27), 182.4 (C-28),
33.0 (C-29), 23.0 (C-30). Compound 9 was identified as
oleanolic acid by comparison of the physical and spectral
data with reported data
[15]
.
Compound 10 Colorless needle crystal (petroleum
etherEtOAc), C
29
H
50
O, mp 136139 C.
1
H NMR (500
MHz, CDCl
3
) : 0.68 (3H, s), 0.80 (3H, s), 0.82 (3H, d, J =
4.0 Hz), 0.84 (3H, d, J = 1.5 Hz), 0.92 (3H, d, J = 6.5 Hz),
1.01 (3H, s), 3.53 (1H, m), 5.35 (1H, d, J = 5.2 Hz).
13
C
NMR (125 MHz, CDCl
3
) : 32.2 (C-1), 31.7 (C-2), 71.8(C-3),
42.3 (C-4), 140.8 (C-5), 121.7 (C-6), 31.9 (C-7), 31.9 (C-8),
50.1 (C-9), 36.5 (C-l0), 21.1 (C-11), 28.2 (C-12), 45.8 (C-13),
56.8 (C-14), 24.3 (C-15), 39.9 (C-16), 56.4 (C-17), 11.9
(C-18), 19.0 (C-19), 36.1 (C-20), 18.8 (C-21), 26.1 (C-22),
34.0 (C-23), 42.3 (C-24), 23.1 (C-25), 12.0 (C-26), 29.2
(C-27), 19.8 (C-28), 19.4 (C-29). Compound 10 was identi-
fied as -sitosterol by comparison of the physical and spectral
data with reported data
[16]
.
LI Jian-Juan, et al. /Chinese Journal of Natural Medicines 2012, 10(4): 279283

Compound 11 White amorphous powder (CD
3
OD),
C
35
H
60
O
6
, mp 298300 C ESI-MS m/z 611.6 [M + Cl]

, It
was identified by comparison with the authentic sample on
TLC, eluting with different developing solvents. It showed
the same color and equal R
f
to the standard of -daucosterol.
So compound 11 was identified as -daucosterol.
Compound 1 is a new compound. The known compounds
211 were determined by comparison of their spectral data and
physical characteristics with those reported. Many triterpenes
were isolated from the EtOAc extract of the stems of C. or-
biculatus and most of them contain a ketonic carbonyl at C-3.
These triterpenes may be related to the pharmacological effects
of the stems of C. orbiculatus. So, the activity of these triter-
penes with a ketonic carbonyl at C-3 can be further studied.
3 Experimental
3.1 Apparatus and reagents
Melting points were determined on an X4 micro melt-
ing-point apparatus (uncorrected). NMR spectra were re-
corded on Bruker AV-500 spectrometer with TMS as the in-
ternal standard. MS spectra were measured on Agilent 1100
series LC/MSD Trap ESI spectrometer. HR-ESI-MS spectra
were measured on Agilent TOF MSD 1946D spectrometer.
IR spectra were carried out on Nicolet Impact-410 spec-
trometer. Optical rotations were measured on Jasco P-1020
polarimeter. Column chromatography was performed on
silica gel (75150 m, 4575 m; Qingdao Marine Chemical
Factory, Qingdao, China.), Sephadex LH-20 (Pharmacia
Factory, Sweden), ODS (50 m, YMC Factory, Kyoto, Japan).
Thin-layer chromatography was performed on silica gel G
(Qingdao Marine Chemical Factory, Qingdao, China.). All
solvents used were of pure analytical grade.
3.2 Plant material
The stems of C. orbiculatus were collected in Hunan
Province, China, and identified by Prof. WANG Qiang. A
voucher specimen has been deposited in the Department of
Chinese Materia Medica Analysis, China Pharmaceutical
University.
3.3 Extraction and isolation
The stems of C. orbiculatus (25 kg) were extracted with
95% EtOH (2 h 3) under reflux. Evaporation of the solvent
under reduced pressure gave the EtOH extract (1 000 g),
which was suspended in H
2
O and partitioned with petroleum
ether, EtOAc and n-BuOH, respectively. The EtOAc extract
(280 g) was subjected to silica gel column (4575 m) and
eluted with CHCl
3
-MeOH (100 : 0 to 1 : 1) to obtain eleven
fractions (Fr. AFr. K). From fractions Fr. B and Fr. E, com-
pounds 10 (39.9 mg) and 11 (226.3 mg) were obtained by
recrystallization, respectively. Fr. C (30 g) was separated over
silica gel column (4575 m) eluted with petroleum eth-
erEtOAc (20 : 1 to 1 : 1) to give eight sub-fractions (Fr.
C
1
Fr. C
8
) on the basis of TLC comparison. Fr. C
1
afforded
compound 2 (7.2 mg) by repeated silica gel column chroma-
tography with petroleum ether-EtOAc solvent system and
recrystallization technique. Fr. C
2
was purified by Sephadex
LH-20 (CHCl
3
-MeOH, 1 : 1) and recrystallization technique
to yield compound 3 (16.9 mg). Fr. C
3
,

Fr. C
7
and Fr. C
8
were
purified by recrystallization technique, respectively to yield
compounds 4 (81.7 mg), 7 (31.9 mg) and 8 (41.3 mg). Fr. C
4

was subjected to ODS column (MeOH-H
2
O, 60% to 90%) to
afford compound 9 (10.1 mg). Fr. C
5
was subjected to ODS
column (MeOH-H
2
O, 50% to 100%) to afford compound 1
(5.6 mg). Fr. C
6
was subjected to ODS column (MeOH-H
2
O,
50% to 80%) and then purified by Sephadex LH-20
(CHCl
3
-MeOH, 1 : 1) to yield compounds 5 (4.9 mg) and 6
(26.7 mg).
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