全 文 ： 273 Journal of Chinese Pharmaceutical Sciences http://www.jcps.ac.cn
Triterpenoids from the stems of Casearia velutina Bl.
Fei-Fei Li1, Zhi-Qin Guo2, Xing-Yun Chai2, Peng-Fei Tu1,2*
1. State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China
2. Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029, China
Received date: 2012-01-09.
Foundation item: Changjiang Scholar and Innovative Team in
University (Grant No. 985-2-063-112).
*Corresponding author. Tel.: 86-10-82802750;
E-mail: pengfeitu@vip.163.com
doi:10.5246/jcps.2012.03.036
1. Introduction
Casearia velutina Bl., mainly distributed in the
Yunnan and Hainan provinces in China[1], are shrubs
or small arbors belonging to Flacourtiaceae family.
It is used in folk medicines for the treatment of pro-
fluvium, gastrelcosis and inflammatory infections[2].
Up to now, no phytochemical investigation was
performed except previous one by our group[3,4].
As a part of our systematic investigation on bioactive
constituents from Flacourtiaceae plants found in
China, and to obtain valuable markers for taxonomical
study of this family[5–13], the stems of Casearia
velutina Bl. were systematically investigated. Herein,
we report the isolation and structure elucidation of
11 triterpenoids and its glycosides from this species
(Fig. 1). By the spectroscopic analysis and comparison
of their NMR data with those reported, these com-
pounds were identified as friedelin-2,3-lactone (1),
friedelane (2), epifriedelanol (3), friedelin (4), 2α,3α,19α-
trihydroxy-urs-12-en-28-oic acid (5), 2α,3β,19α-
trihydroxy-urs-12-en-28-oic acid (6), 2α,3α,23-
































Abstract: To investigate the chemical components from the stems of Casearia velutina Bl., the constituents were isolated by
repeated chromatography with silica gel, Sephadex LH-20, and ODS columns. The structures were elucidated by spectroscopic
analysis. Eleven triterpenoids and its glycosides were isolated from the crude extract of C. velutina, and their structures were
identified as friedelin-2,3-lactone (1), friedelane (2), epifriedelanol (3), friedelin (4), 2α,3α,19α-trihydroxy-urs-12-en-28-oic
acid (5), 2α,3β,19α-trihydroxy-urs-12-en-28-oic acid (6), 2α,3α,23-trihydroxy-urs-12-en-28-oic acid (7), 2α,3α,23-trihydroxy-
olean-12-en-28-oic acid (8), 2α,3α,19α,23-tetrahydroxy-urs-12-en-28-oic acid (9), 2α,3α,19α,23-tetrahydroxy-urs-12-en-28-
oic acid-28-O-β-D-glucopyranosyl ester (10), and 3β,19α-dihydroxy-urs-12-en-28-oic acid 3-O-α-L-arabinopyranoside (11).
All the compounds described above were isolated from this species for the first time. Compound 1 is a rarely occurred seco-
friedelolactone in Flacourtiaceae.
Keywords: Casearia velutina Bl.; Flacourtiaceae; Triterpenoid; Chemical constituents
CLC number: R284.1 Document code: A Article ID: 1003–1057(2012)3–273–05
Figure 1. Structures of compounds 1–11.
R1 R2 R3 R4 R5
5 α-OH α-OH CH3 α-OH H
6 α-OH β-OH CH3 α-OH H
7 α-OH α-OH CH2OH H H
9 α-OH α-OH CH2OH α-OH H
10 α-OH α-OH CH2OH α-OH β-D-glc
11 H O-α-L-ara CH3 α-OH H
R3
COOR5R1
R2
R4
HOH2C
COOHHO
HO
O
O
H H H
1 2 R = H
3 R = α-OH
R
4 8
O
1
53 4
10
11
12
9
7
15
20
18
17
2625
24
23
22
3029
28
27
1
53
12 18
2625
2423
21
30
29
28
27
274 F. F. Li et al. / Journal of Chinese Pharmaceutical Sciences 21 (2012) 273–277
trihydroxy-urs-12-en-28-oic acid (7), 2α,3α,23-
trihydroxy-olean-12-en-28-oic acid (8), 2α,3α,19α,23-
tetrahydroxy-urs-12-en-28-oic acid (9), 2α,3α,19α,23-
tetrahydroxy-urs-12-en-28-oic acid-28-O-β-D-glucopy-
ranosyl ester (10), and 3β,19α-dihydroxy-urs-12-en-
28-oic acid 3-O-α-L-arabinopyranoside (11). Among
them, 1 is a rarely occurred seco-friedelane triterpe-
noid in Flacourtiaceae. All compounds were isolated
from this plant for the first time.
2. Experimental
2.1. General
Optical rotations were recorded on a Perkin-Elmer
243B digital polarimeter. NMR spectra were recorded
using Inova 500 MHz NMR spectrometer. ESI-MS
spectra were measured on QSTAR mass spectrometer
and EI-MS spectra were recorded on a TRACE-MS
2000 in m/z. IR spectra were recorded on a NEXUS-
470 FTIR spectrometer. Silica gel (200–300 mesh,
Qindao Haiyang Chemical Co. Ltd.) was used for
column chromatography. Solvents of analytical grade
were purchased from Beijing Chemical Factory.
2.2. Plant material
The stems of C. velutina were collected in Menglun
country, Yunnan province of China in June 2005.
The plant materials were identified by engineer
Jing-Yun Cui (Xishuangbanna Botanical Garden).
A voucher specimen (CV20050605) is deposited
in the herbarium of Peking University Modern
Research Center for Traditional Chinese Medicine.
2.3. Extraction and isolation
The dried stems (7.0 kg) of C. velutina were
extracted three times with 80% EtOH (3×42 L).
After evaporation of the solvent, the soluble fraction
was suspended in H2O and extracted successively
with petroleum ether (PE), EtOAc and n-BuOH. The
PE extract (29 g) was subjected to silica gel chromato-
graph column (CC) and eluted with a gradient of
PE–acetone (6:1–2:3, v/v) to get Frs. A–C. Fr. A was
separated by a silica gel column with PE–acetone
(15:1, v/v) and PE–EtOAc (12:1, v/v) to get
compounds 1 (8 mg), 2 (10 mg) and 3 (8 mg). The
EtOAc extract (56 g) was subjected to silica gel CC
eluted with a gradient of CHCl3–MeOH (40:1–20:1–
10:1–5:1, v/v) to get Frs. 1–8. Compound 4 (60 mg)
was obtained as needle crystals from Fr. 3. Fr. 1 (3 g)
was applied to silica gel CC eluted with PE–EtOAc–
MeOH (15:8:0.5, v/v/v) to yield 5 (40 mg). Fr. 2
was repeatedly subjected to silica gel CC and eluted
with CHCl3–EtOAc (1:5, v/v) and CHCl3–MeOH
(10:1, v/v) to provide 7 (13 mg), 8 (15 mg) and 11
(41 mg). Fr. 7 was subjected to silica gel CC and
eluted with PE–EtOAc (4:3, v/v) to get three
fractions (Frs. 7a–7c). A repeated chromatography of
silica gel with elution by PE–acetone (5:2, v/v) and
CHCl3–MeOH (25:1, v/v), followed by the semi-
preparative HPLC (MeOH–H2O, 56:44, v/v) yielded
compounds 6 (2.5 mg) and 9 (4.5 mg). The n-BuOH
extract (120 g) was subjected to silica gel CC and
eluted with a gradient of CHCl3–MeOH (10:1–2:1,
v/v) to get Frs. I–IX. Fr. IV (25 g) was subjected to
silica gel CC and eluted with PE–acetone (1:2, v/v;
4.5 L) to get eight portions (Frs. IV1–IV8), among
which Fr. IV7 (3.0 g) was applied to silica gel CC,
and eluted with EtOAc–MeOH–H2O (20:1:0.02,
v/v/v) to obtain 10 (10 mg).
3. Results and discussion
Compound 1 was obtained as white amorphous
powder. Analysis of its ESI-MS m/z 443 [M+H]+
and NMR data deduced its molecular formula as
C30H50O2. The IR (KBr) νmax (cm–1) absorption at
1736 suggested the presence of the carbonyl group.
Besides, its 1H NMR (500 MHz, CDCl3) data δ:
0.83 (3H, s, Me-25), 0.89 (3H, s, Me-24), 0.95 (3H,
s, Me-26), 0.99 (3H, s, Me-27), 1.00 (3H, s, Me-30),
1.01 (3H, s, Me-29), 1.17 (3H, s, Me-28), 1.20 (3H,
d, J 6.5 Hz, Me-23), 1.93 (1H, m, H-1ax), 2.52 (1H,
td, J1 1.5 Hz, J2 12.5 Hz, J3 13.0 Hz, H-2ax), 2.63 (1H,
ddd, J1 1.5 Hz, J2 7.0 Hz, J3 13.0 Hz, H-2eq), 4.22 (1H,
q, J 6.5 Hz, H-4), and its 13C-NMR data (Table 1)
were in agreement with those in the literature, Thus,
1 was identified as friedelin-2, 3-lactone[14].
Compound 2 was obtained as white needle crystals
(PE–acetone). EI-MS m/z 55 (66), 69 (100), 95 (78),
275 F. F. Li et al. / Journal of Chinese Pharmaceutical Sciences 21 (2012) 273–277
No. 1a 2 a 3 a 4 a 5 b 6 b 7 c 8 c 9 b 10 b 11 c
1 18.0 22.3 16.4 22.3 42.9 48.7 42.7 42.7 42.7 42.2 37.2
2 34.4 41.5 35.2 41.5 66.1 68.6 66.3 66.3 66.3 66.3 25.9
3 175.5 30.6 72.7 213.1 79.4 83.9 78.2 78.2 78.9 79.0 87.7
4 84.9 58.2 49.2 58.2 38.8 40.5 40.4 40.6 41.9 42.1 38.7
5 40.8 42.1 37.8 42.1 48.8 56.0 43.4 43.3 43.6 43.5 55.0
6 38.5 41.3 41.7 41.3 18.6 18.8 17.9 19.1 18.5 18.5 17.9
7 18.0 18.2 17.6 18.2 33.6 33.6 33.4 33.5 32.4 33.1 32.6
8 52.7 53.1 53.2 53.1 40.6 39.9 40.8 40.6 40.5 40.7 39.3
9 38.2 37.4 37.0 37.4 47.7 48.7 47.9 47.6 47.8 47.8 46.6
10 64.0 59.5 61.3 59.5 38.7 38.5 38.1 38.1 38.4 38.4 36.3
11 35.3 35.6 35.6 35.6 24.1 24.7 24.0 24.1 24.7 24.2 23.1
12 30.6 30.5 30.6 30.5 128.0 127.9 126.6 123.4 127.9 128.3 126.7
13 39.3 39.7 38.4 39.7 140.0 140.0 139.8 145.4 140.0 139.3 138.5
14 38.4 38.3 39.7 38.3 42.2 42.2 42.7 42.7 42.2 41.9 41.0
15 32.4 32.4 32.6 32.4 29.5 29.3 28.8 29.2 29.3 29.1 28.1
16 35.4 36.0 36.1 36.0 26.4 26.0 24.6 24.5 25.8 26.1 25.2
17 30.0 30.0 29.7 30.0 48.3 47.9 48.0 47.6 48.3 48.6 46.9
18 42.7 42.8 42.8 42.8 54.6 54.6 54.3 41.3 54.6 54.4 53.1
19 36.0 35.3 35.3 35.3 72.7 72.7 39.0 45.0 72.7 72.6 72.6
20 28.2 28.2 28.2 28.2 42.4 42.4 39.0 30.0 42.4 42.6 41.4
21 32.8 32.8 32.8 32.8 27.0 26.8 31.6 31.8 26.4 26.7 26.4
22 39.2 39.2 39.3 39.2 38.5 38.4 38.1 32.1 38.4 38.4 38.1
23 13.5 6.8 11.4 6.8 29.3 29.3 69.7 69.7 71.2 71.2 27.6
24 16.2 14.7 14.7 14.6 22.3 16.9 13.9 17.9 17.0 16.7 16.3
25 17.9 17.9 18.2 17.9 16.8 17.3 17.7 17.5 17.3 17.7 16.6
26 18.6 22.3 18.7 20.2 17.3 17.7 17.8 17.7 17.8 17.1 16.4
27 20.2 18.7 20.1 18.6 24.7 24.7 24.0 24.1 24.7 24.6 23.9
28 32.1 32.1 32.1 32.0 180.6 180.6 181.8 181.6 180.7 177.0 178.8
29 31.8 31.8 35.0 35.1 27.0 26.8 17.9 33.9 27.1 26.7 26.4
30 35.0 35.0 31.8 31.8 16.7 16.8 21.6 21.6 16.8 16.7 15.1
109 (67), 123 (59), 149 (16), 205 (21), 257 (8),
341 (4), 412 [M]+ (5). 1H NMR (500 MHz, CDCl3)
δ: 0.73 (3H, s, H-24), 0.87 (3H, s, H-25), 0.88 (3H,
d, J 7.0 Hz, H-23), 0.95 (3H, H-30), 1.00 (3H, s,
H-26), 1.01 (3H, s, H-29), 1.05 (3H, s, H-27), 1.18
(3H, s, H-28); 13C NMR data were listed in Table 1.
All the data above were in agreement with those
reported for friedelane[15].
Compound 3 was isolated as white solids. EI-MS
m/z 55 (65), 69 (100), 95 (95), 109 (76), 123 (62),
165 (47), 205 (26), 275 (14), 341 (2), 428 [M]+ (3).
1H NMR (500 MHz, CDCl3) δ: 0.85 (3H, s, H-24),
0.94 (3H, s, H-25), 0.94 (3H, d, J 7.5 Hz, H-23),
0.96 (3H, s, H-30), 0.99 (3H, s, H-26), 0.99 (3H, s,
H-29), 1.00 (3H, s, H-27), 1.17 (3H, s, H-28), 3.73
(1H, m, H-3); 13C NMR data were listed in Table 1.
All the above data were in agreement with those of
epifriedelanol in literature[16], and thus, compound 3
was identified.
Compound 4 was isolated as white solids. EI-MS
m/z 55 (59), 69 (98), 95 (100), 109 (77), 123 (79),
163 (34), 205 (36), 218 (24), 273 (25), 302 (12), 341
(5), 426 [M]+ (9). 1H NMR (500 MHz, CDCl3) δ:
0.73 (3H, s, H-24), 0.88 (3H, s, H-25), 0.89 (3H, d,
J 7.0 Hz, H-23), 0.95 (3H, s, H-30), 1.01 (3H, s,
H-26), 1.02 (3H, s, H-29), 1.06 (3H, s, H-27), 1.19
(3H, s, H-28); 13C NMR data were showned in
Table 1. All the data above were in agreement with
those of friedelin[17].
Compound 5 was obtained as white solids. 1H NMR
(500 MHz, C5D5N) δ: 5.57 (1H, brt, J 3.5 Hz, H-12),
4.29 (1H, td, J1 4.0 Hz, J2 11.0 Hz, H-2), 3.74 (1H,
d, J 11.0 Hz, H-3), 1.63 (3H, s), 1.40 (3H, s), 1.25
(3H, s), 1.10 (3H, d, J 6.5 Hz), 1.10 (3H, s), 0.97
(3H, s), 0.89 (3H, s); 13C NMR data were presented
in Table 1. All the data above were in consistent
with those of 2α,3α,19α-trihydroxy-urs-12-en-28-oic
acid[18].
Compound 6 was isolated as white amorphous.
ESI-MS m/z: 511 [M+Na]+. 1H NMR (500 MHz,
Table 1. 13C NMR (125 MHz, in C5D5N) data for 1–9, and the aglycons of 10 and 11, δ in ppm
a Measured in CDCl3, b in C5D5N and c in CD3OD.
276 F. F. Li et al. / Journal of Chinese Pharmaceutical Sciences 21 (2012) 273–277
C5D5N) δ: 5.57 (1H, brt, J 3.5 Hz, H-12), 4.24 (1H,
ddd, J1 3.5 Hz, J2 9.5 Hz, J3 11.0 Hz, H-2), 3.38
(1H, d, J 9.5 Hz, H-3), 1.70 (3H, s), 1.42 (3H, s),
1.25 (3H, s), 1.11 (3H, d, J 9.0 Hz), 1.10 (3H, s),
1.05 (3H, s), 0.99 (3H, s); 13C NMR data were
showed in Table 1. All the data above were in
agreement with those of 2α,3β,19α-trihydroxy-urs-
12-en-28-oic acid[19].
Compound 7 was isolated as white solids. 1H NMR
(500 MHz, CD3OD) δ: 5.18 (1H, t, J 3.5 Hz, H-12),
3.64 (1H, ddd, J1 3.5 Hz, J2 9.5 Hz, J3 11.0 Hz,
H-2), 3.44 (2H, d, J 11.0 Hz, H-3, 23a), 3.21 (1H,
d, J 11.0 Hz, H-23b), 1.12 (3H, s), 0.98 (3H, s), 0.91
(3H, d, J 6.0 Hz), 0.85 (3H, s), 0.84 (3H, d, J 6.0 Hz),
0.79 (3H, s); 13C NMR data were summaried in
Table 1. All the data above were in agreement
with those of 2α,3α,23-trihydroxy-urs-12-en-28-oic
acid[20].
Compound 8 was isolated as white solids. ESI-MS
m/z: 511 [M+Na]+. 1H NMR (500 MHz, CD3OD) δ:
5.19 (1H, t, J 3.5 Hz, H-12) , 3.62 (1H, ddd, J1 3.5 Hz,
J2 10.0 Hz, J3 10.0 Hz, H-2), 3.44 (2H, d, J 11.0 Hz,
H-3, 23a), 3.21 (1H, d, J 11.0 Hz, H-23b), 3.64 (1H,
d, J 2.7 Hz, H-3), 1.08 (3H, s), 0.99 (3H, s), 0.91
(3H, s), 0.89 (3H, s), 0.76 (3H, s), 0.64 (3H, s); 13C
NMR data were showed in Table 1. All NMR data
above were in agreement with those of 2α,3α,23-
trihydroxy-olean-12-en-28-oic acid after a detailed
comparison with those of methyl ester of compound
8 in literature[21]. Thus, with the aid of ESI analysis
compound 8 was identified.
Compound 9 was isolated as white powders.
1H NMR (500 MHz, C5D5N) δ: 5.57 (1H, t, J 3.5 Hz,
H-12), 4.26 (1H, ddd, J1 3.5 Hz, J2 9.5 Hz, J3 11.0 Hz,
H-2), 3.90 (1H, d, J 10.5 Hz, H-23a), 3.73 (1H, d,
J 10.5 Hz, H-23b), 3.44 (2H, d, J 11.0 Hz, H-3),
1.65 (3H, s), 1.40 (3H, s), 1.11 (3H, s), 1.10 (3H, s),
1.01 (3H, s), 0.85 (3H, d, J 6.0 Hz); 13C NMR data
were showed in Table 1. All the data above were in
agreement with those of 2α,3α,19α,23-tetrahydroxy-
urs-12-en-28-oic acid according to the reference[22].
Compound 10 was isolated as white solids. ESI-MS
m/z 689 [M+Na]+. 1H NMR (500 MHz, C5D5N) δ: 6.31
(1H, d, J 8.0 Hz, H-1), 5.54 (1H, brt, J 3.5 Hz, H-12),
4.26 (1H, ddd, J1 3.5 Hz, J2 9.5 Hz, J3 11.0 Hz, H-2),
4.06 (1H, d, J 9.5 Hz, H-3), 3.90 (1H, d, J 10.5 Hz,
H-23a), 3.73 (1H, d, J 10.5 Hz, H-23b), 1.63 (3H,
s), 1.36 (3H , s), 1.23 (3H, s), 1.06 (3H, s), 1.05 (3H,
s), 0.86 (3H, d, J 6.0 Hz); 13C NMR (125 MHz,
C5D5N) δ: 95.8 (C-1′), 74.0 (C-2′), 79.3 (C-3′), 71.2
(C-4′), 79.0 (C-5′), 62.3 (C-6′), and the 13C NMR
data for aglycone were showed in Table 1. All the
data above were in agreement with those of reported
2α,3α,19α,23-tetrahydroxy-urs-12-en-28-oic cid-28-
O-β-D-glucopyranosyl ester[18].
Compound 11 was isolated as white solids. 1H NMR
(500 MHz, CD3OD) δ: 5.15 (1H, t, J 3.5 Hz, H-12),
4.12 (1H, d, J 6.5 Hz, H-1), 3.64 (1H, dd, J1 3.0 Hz,
J2 11.0 Hz, H-5a), 3.64 (1H, dd, J1 4.0 Hz, J2 11.0 Hz,
H-5′b), 3.35 (1H, t, J 10.0 Hz, H-3), 1.28 (3H, s),
1.07 (3H, s), 0.96 (3H, s), 0.86 (3H, s), 0.84 (3H, d,
J 6.5 Hz, H-30), 0.75 (3H, s), 0.69 (3H, s); 13C NMR
(125 MHz, CD3OD) δ: 105.8 (C-1′), 71.6 (C-2′), 72.6
(C-3′), 67.6 (C-4′), 65.0 (C-5′), and the 13C NMR
data for aglycone were showed in Table 1. All
the data above were in agreement with those of
3β,19α-dihydroxy-urs-12-en-28-oic acid 3-O-α-L-
arabinopyranoside[23], and the compound was there-
fore determined.
Aacknowledgements
This work was supported by program for Changjiang
Scholar and Innovative Team in University (Grant
No. 985-2-063-112).
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爪哇脚骨脆中三萜类化学成分研究
李飞飞1, 郭志琴2, 柴兴云2, 屠鹏飞1,2*
1. 北京大学医学部 天然药物及仿生药物国家重点实验室, 北京 100191
2. 北京中医药大学 中药现代研究中心, 北京 100029

摘要: 从大风子科植物爪哇脚骨脆的树干中分离得到11个已知三萜类化合物, 经波谱解析及与文献对照方法, 分别鉴
定为木栓酮-2,3-内酯 (1), 木栓烷 (2), 表木栓醇 (3), 木栓酮 (4), 2α,3α,19α-三羟基-乌苏烷-12-烯-28-羧酸 (5), 2α,3β,19α-三
羟基-乌苏烷-12-烯-28-羧酸 (6), 2α,3α,23-三羟基-乌苏烷-12-烯-28-羧酸 (7), 2α,3α,23-三羟基-齐墩果烷-12-烯-28-羧酸 (8),
2α,3α,19α,23-四羟基-乌苏烷-12-烯-28-羧酸 (9), 2α,3α,19α,23-四羟基-乌苏烷-12-烯-28-羧酸-28-O-β-D-葡萄糖酯 (10), 及
3β,19α-双羟基-乌苏烷-12-烯-28-羧酸3-O-α-L-阿拉伯糖苷 (11). 其中化合物1为大风子科植物中稀有的裂环木栓烷三萜,
所有化合物皆为首次从本植物中分离得到。
关键词: 爪哇脚骨脆; 大风子科; 三萜; 化学成分