全 文 ： 2012 年 3 月 第 10 卷 第 2 期 Chin J Nat Med Mar. 2012 Vol. 10 No. 2 81

Chinese Journal of Natural Medicines 2012, 10(2): 0081−0083
doi: 10.3724/SP.J.1009.2012.00081
Chinese
Journal of
Natural
Medicines






·Original papers·
Two new lupane triterpenoides from Schefflera venulosa
PENG Ling-Fang, XIA Wei-Jun, HE Lei, CUI Tao*
Yunnan Institute of Materia Medica, Kunming 650111, China
Available online 20 Mar. 2012
[ABSTRACT] AIM: To study the chemical constituents of Schefflera venulosa. METHODS: Compounds were isolated by silica gel
and Rp-C8 column chromatography. The structures were elucidated by NMR and HRESI-MS spectrometry. RESULTS: Two new
compounds were isolated from Schefflera venulosa, and their structures were elucidated as 3-O-β-D-glucopyranosyl-(1→2)-β-D-gluco-
pyranosyl-27-oxo-betulinic acid-28-O-β-D-glucopyranoside (1), 3-O-β-D-glucuronopyranosyl-27-oxo-betulinic acid-28-O-β-D-gluco-
pyranoside (2). CONCLUSION: Compounds 1 and 2 are new lupane triterpenoids.
[KEY WORDS] Araliaceae; Schefflera venulosa; Lupane triterpenoid
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)02-0081-03

1 Introduction
Schefflera venulosa is widely distributed in Yunnan,
Guizhou and Hunan provinces of China, and has been used as
Chinese folk medicine for the treatment of rheumatic arthritis and
headache for a long time. In the past few years, a lot of ste-
roids and triterpenoids have been isolated from S. venulosa [1-2].
In order to further develop this traditional herb, we studied
the chemical constituents of S. venulosa systematically. After
three phenylpropanolds and three new triterpenoids were
isolated [3-4], two new triterpenoids were isolated by chroma-
tographic methods. And the extensively spectroscopic analy-
sis is employed for structural elucidation.
2 Results and Discussion
Compound 1 was obtained as white powder, which was
considered to be a triterpenoid glycoside due to the positive
results for the Liebermann-Burchard reaction and Molish
reagent. Its IR spectrum revealed absorption bands at 3 423
(OH), 2 944 (CH), 1 740 (COOR), 1 710 (CHO), 1 642 (C =
C) cm-1. Its molecular formula was determined as C48H76O19
according to the HRESI-MS from the [M − H]− signal at m/z
955.488 9 (Calcd. for 955.490 1).

[Received on] 05-May-2011
[Research funding] This project was supported by Customized
Research for Scientific Research Institutes of Yunnan Province (Im-
portant project) (No. 2006KFZX-01).
[*Corresponding author] CUI Tao: Prof., Tel: 86-871-6226009-
8301, E-mail: ctao-10@163.com
These authors have no any conflict of interest to declare.
The 13C and DEPT 13C NMR spectra showed 48 signals,
of which 18 were assigned to the saccharide portion and 30 to
the triterpene moiety, including a set of double bonds at δC
151.3, 110.8 and one carbony at δC 175.7. Careful analysis of
1H and 13C NMR spectral data indicated that 1 was a lupane
triterpene glycoside similar to betulinic acid [5]. The differ-
ence between the two compounds was at C-14 and sugar
moieties. NMR spectra showed the signals at δH 10.2 and δC
212.4, which proved that 1 has aldehyde group. In addition,
The upfield shift of C-14 by 16 and the HMBC correlations
clearly revealed that the H-27 (δH 10.2) was long-range cou-
ple to the C-14 (δC 58.7) and C-13 (δC 38.5), which suggested
that 14-CH3 was replaced by 14-CHO.
The FAB--MS and NMR spectral data proved that 1 has
three glucopyranose units. Acidic hydrolysis of 1 gave
D-glucose, which was confirmed by TLC comparison with
authentic samples. Compared with those of betulinic acid, the
upfield shift of C-3 by 10 and the upfield shift of C-28 by 4,
compound 1 was 3, 28-bisdesmoside. Analysis HMBC, H-1’
(δH 4.43) of the glucose 1 moiety was long-range couple to
the c-3 (δC 90.8). In addition, the H-H COSY exhibited cross
peaks between H-1’ (δH 4.43) and H-2’ (δH 3.54) of the glu-
cose 1. Furthermore, in the HSQC experiment, in which a
correlation between H-2’ (δH 3.54) and C-2’ (δC 81.1) of the
glucose 1 was apparent, the glycosidation shifts on C-2 (+7)
of the glucopyranosyl unit indicated the presence of a glu-
copyranosyl residue glycosylated at C-2. Therefore, com-
pound 1 was estabilished as 3-O-β-D-glucopyranosyl-(1→
2)-β-D-glucopyranosyl-27-oxo-betulinic acid-28-O-β-D-glu-
copyranoside. 13C NMR data of 1 see Table 1.
Compound 2 was obtained as white powder, which was
PENG Ling-Fang, et al. /Chinese Journal of Natural Medicines 2012, 10(2): 81−83
82 Chin J Nat Med Mar. 2012 Vol. 10 No. 2 2012 年 3 月 第 10 卷 第 2 期

considered to be a triterpenoid glycoside due to the positive
results for the Liebermann-Burchard reaction and Molish
reagent. Its IR spectrum revealed absorption bands at 3 427
(OH), 2 945 (CH), 1 741(COOR), 1 709 (CHO), 1 618 (C =
C) cm-1. Its molecular formula was determined as C42H64O15
according to the HRESI-MS from the [M − H] − signal at m/z
807.414 5 (Calcd. for 807.416 6).
Careful analysis of 1H and 13C NMR spectral data indi-
cated that 2 was a lupane triterpene glycoside similar to 1.
The difference of the two compounds was at sugar moieties.
In addition, The FAB--MS and NMR spectral data proved that
2 has one glucopyranose unit and one glucuronopyranose unit.
Acidic hydrolysis of 2 gave D-glucose and D-glucuronic acid,
which was confirmed by TLC comparison with authentic
samples. Compared with those of betulinic acid, the upfield
shift of C-3 by 10 and the upfield shift of C-28 by 4, 2 was a
3, 28-bisdesmoside. The HMBC correlations clearly revealed
that the anomeric proton (H-1″) of the glucose moiety was
long-range couple to the C-28 (δC 175.7). Therefore, com-
pound 2 was estabilished as 3-O-β-D-glucuronopyranosyl-
27-oxo-betulinic acid-28-O-β-D-glucopyranoside. 13C NMR
data of 2 see Table 1.
Table 1 13C NMR data for compounds 1 and 2 ( CD3OD, 100 MHz)
Aglycone 1 2 Sugar 1 2
1 39.9 39.9 3-O-sugar 1’ 104.5 106.7
2 26.8 26.2 Glc/GluA 2’ 81.1 74.1
3 91.2 90.8 (inner) 3’ 77.6 78.4
4 40.4 40.3 4’ 71.3 71.1
5 56.8 56.9 5’ 78.4 78.8
6 19.0 19.2 6’ 62.4 172.4
7 36.3 36.4 Glc 1’’ 105.4
8 43.6 43.6 (termimal) 2’’ 76.3
9 55.1 55.1 3’’ 78.3
10 38.5 38.5 4’’ 71.9
11 22.2 22.7 5’’ 78.5
12 25.1 25.1 6’’ 62.7
13 38.5 39.1 28-O-sugar 1’’’ 95.2 95.3
14 58.7 58.7 Glc 2’’’ 74.1 74.1
15 27.5 27.2 3’’’ 77.7 78.4
16 33.4 33.6 4’’’ 71.6 71.1
17 57.4 57.4 5’’’ 78.8 78.8
18 49.0 49.0 6’’’ 62.6 62.4
19 52.2 52.2
20 151.3 151.3
21 32.1 31.4
22 37.4 37.4
23 28.3 28.4
24 16.7 16.9
25 16.9 17.0
26 17.4 17.4
27 212.4 212.4
28 175.7 175.7
29 110.8 110.9
30 19.3 19.4

3 Experimental
3.1 General
Column chromatography was performed on silica gel
(200-300 mesh; Qingdao Marine Chemical, Inc., China),
Lichroprep Rp-C8 (40−63 µm; Merck). Fractions were moni-
tored by TLC, and spots were visualized by spraying with
10% H2SO4 in EtOH, followed by heating. MS experiments
were performed on VG Auto Spec-3000 spectrometer. NMR
spectra were recorded on a DRX-500 MHz NMR spectrometer.
3.2 Plant material
Schefflera venulosa were collected in September 2007
from Kunming, Yunnan Province, China and indentified by
GAO Li, a senior engineer of Yunnan Institute of Materia
PENG Ling-Fang, et al. /Chinese Journal of Natural Medicines 2012, 10(2): 81−83
2012 年 3 月 第 10 卷 第 2 期 Chin J Nat Med Mar. 2012 Vol. 10 No. 2 83

Medica.
3.3 Extraction and isolation
The dry S. venulosa (2.0 kg) were extracted under reflux
with 70% EtOH three times (2, 1.5, 1.5 h). The combined
70% EtOH extracts were evaporated to dryness under vac-
uum. The dryness (165 kg) was applied to a silica gel column
chromatography with CHCl3/CH3OH (10 : 0−4 : 6, V/V) gra-
dient to give 6 fractions (A-F). Fraction D was applied to
Lichroprep Rp-C8 column chromatography with CH3OH/H2O
(2 : 8−8 : 2, V/V) gradient to afford compounds 1 (212 mg)
and 2 (164 mg).
3-O-β-D-Glucopyranosyl-(1→2)-β-D-glucopyranosyl-
27-oxo-betulinic acid-28-O-β-D-glucopyranoside (1, Fig. 1),
C48H76O19, white powder, [α]16 D − 21.7° ( c 0.273, MeOH),
UV(MeOH)λmax: 203 nm; IR(KBr)ν: 3 423, 2 944, 1 740, 1
710,1 642 cm−1; FAB- - MS m/z 955 [M − H] − ,793 [M – Glc
– H]− ,631 [M – Glc × 2 – H]− ,469 [M – Glc × 3 – H]−;
HR-ESI-MS m/z 955.488 9 [M – H]−, Calcd. for 955.490 1;
13H NMR (CD3OD, 500 MHz) δ: 1.01 (3H, s, H-23), 0.81
(3H, s, H-24), 1.02 (3H, s, H-25), 0.87 (3H, s, H-26), 10.16

Fig. 1 Selected HMBC correlations of compound 1
(H, s, H-27), 4.71 (1H, br s, H-29b), 4.65 (1H, br s, H-29a),
1.71 (3H, s, H-30), 4.43 (1H, d, J = 7.4o[ Hz, H-1’], 4.66 (1H,
d, J = 7.7 Hz, H-1’’), 5.51 (1H, d, J = 8.3 Hz, H-1’’’); 13C
NMR data see Table 1.
3-O-β-D-Glucuronopyranosyl-27-oxo-betulinic acid-28-
O-β-D-glucopyranoside (2), C42H64O15, white powder, [α]16 D
− 36.4° ( c 0.166, MeOH); UV(MeOH)λ max : 203 nm;
IR(KBr)ν: 3 427, 2 945, 1 741, 1 709, 1 618 cm-1. FAB--MS
m/z 807 [M−H]-, 645 [M−Glc−H]-, 469 [M−Glc−GluA−H]-,
HR-ESI-MS m/z 807.414 5 [M − H]-, Calcd. for 807.416 6;
13H NMR (CD3OD, 500 MHz) δ: 1.01 (3H, s, H-23), 0.81
(3H, s, H-24), 1.01 (3H, s, H-25), 0.87 (3H, s, H-26), 10.16
(1H, s, H-27), 4.76 (1H, br s, H-29b), 4.66 (1H, br s, H-29a),
1.71 (3H, s, H-30), 4.33 (1H, d, J = 7.6 Hz, H-1’), 5.51 (1H,
d, J = 8.2 Hz, H-1’’’),13C NMR data see Table 1.
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密脉鹅掌柴中两个新的羽扇豆烷型三萜
彭玲芳, 夏伟军, 何 雷, 崔 涛*
云南省药物研究所, 昆明 650111
【摘 要】 目的：对密脉鹅掌柴的化学成分进行研究。方法: 采用硅胶柱色谱、Rp-C8 柱色谱等方法分离化学成分, 应用
UV、IR、MS、NMR、2D-NMR 等方法进行结构分析。结果: 从密脉鹅掌柴中分离鉴定了 2 个新的化合物：3-O-β-D-吡喃葡萄
糖醛酸基-14-醛基-白桦脂酸苷-28-O-β-D-吡喃葡萄糖(1), 3-O-β-D-吡喃葡萄糖基(1→2)-β-D-吡喃葡萄糖基-14-醛基-白桦脂酸苷
-28-O-β-D-吡喃葡萄糖(2)。结论: 化合物 1 和 2 为新的羽扇豆烷型三萜。
【关键词】 五加科; 密脉鹅掌柴; 羽扇豆烷型三萜

【基金项目】 云南省科研院所技术开发研究专项(重点项目)(No. 2006KFZX-01)