全 文 ： 2010 年 1 月 第 8 卷 第 1 期 Chin J Nat Med Jan. 2010 Vol. 8 No. 1 21








Chemical Constituents from the Stems and Leaves of
Elaeocarpus glabripetalus

ZHANG Sheng1, TAO Zheng-Ming2, ZHANG Yi3, SHEN Zheng-Wu1*, QIN Guo-Wei3*
1School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203;
2Zhejiang Institute of Subtropical Crops, Wenzhou 325005;
3Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
[ABSTRACT] AIM: To investigate the chemical constituents of Elaeocarpus glabripetalus Merr.. METHODS: The
compounds were isolated and purified by repeated column chromatography and their structures were identified by phys-
icochemical and spectral methods, respectively. RESULTS: Eleven compounds were isolated from the stems and leaves
of this plant, and identified as kaempferol (1), β-sitosterol (2), cucurbitacin D (3), methyl gallate (4), ethyl gallate (5),
quercetin (6), 3,4-dihydroxybenzoic acid (7), mogroside I E1 (8), 5R, 6R-epoxymogroside I E1 (9), kaempferol
-7-O-α-L-arabinopyranoside (10) and rutin (11). CONCLUSION: Compounds 2 and 3 were isolated from this plant for
the first time and the other nine compounds were isolated from the genus of Elaeocarpus for the first time. Structure of
compound 8 was firstly confirmed by X-ray analysis. Compound 9 can modestly increase adiponectin production (1.32
fold at 25μg·mL-1) in adipocytes.
[KEY WORDS] Elaeocarpus glabripetalus; Elaeocarpus; Cucurbitacins
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2010)01-0021-04
doi: 10.3724/SP. J. 1009.2010.00021
1 Introduction
There are about 200 species in the genus of Elaeo-
carpus (Elaeocarpaceae), among which 38 species grow in
China. Most Elaeocarpus plants are evergreen trees, dis-
tributed in tropical and subtropical regions. They grow rap-
idly with thick tree-crown, being used for building materi-
als and ornamental purposes. Up to now, phytochemical
studies on Elaeocarpus plants have resulted in the isolation
of alkaloids, triterpenoids, gallogens, cucurbitacins, and
flavonoids, which possess various bioactivities such as
anti-malarial, anti-tumor and anti-depression[1-6]. However,
the plant Elaeocarpus glabripetalus has not been studied
before. In an effort to search for bioactive principles, to-
tally eleven compounds were isolated from EtOAc fraction
of its ethanol extracts. By the determination of physico-
chemical and spectral data compared with literature, the
compounds were identified as kaempferol (1), β-sitosterol
(2), cucurbitacin D (3), methyl gallate (4), ethyl gallate (5),
quercetin (6), 3,4-dihydroxybenzoic acid (7), mogroside I
E1 (8), 5R, 6R-epoxymogroside I E1 (9), kaempferol-

[Received on] 15-June-2009
[Research Funding] This project is supported by Science and
Technology Commission of Shanghai Municipality (No.
06DZ22028)
[*Corresponding author] QIN Guo-Wei: Prof., E-mail:
gwqin@mail.shcnc.ac.cn; SHEN Zheng-Wu: Prof., E-mail:
jeff_shen_1999 @yahoo.com
7-O-α-L-arabinopyranoside (10) and rutin (11), respectively.
Among them, compounds 2 and 3 were firstly obtained
from the plant and the other nine compounds were firstly
isolated from Elaeocarpus plants. Besides, crystal structure
of 8 has been determined by X-ray diffraction analysis for
the first time (Fig. 1).
Natural cucurbitacins constitute a group of diverse
triterpenoids with well-known bitterness and toxicity.
Structurally, they are characterized by the tetracyclic skele-
ton, namely, 19-(10→9b)-abeo-10a-lanost-5-ene with a
variety of oxygenation functionalities at different positions.
Compounds 3, 8 and 9 are cucurbitacins, firstly isolated
from E. glabripetalus. Previous studies showed that 3 had
significant cytotoxicity against a variety of human cancer
cell lines including lung cancer, colon cancer, oral epider-
moid carcinoma, hormone-dependent prostate cancer, and
human umbilical vein endothelial cells; and 8 and 9 pos-
sessed potent inhibitory effects on Epstein-Barr virus early
antigen induction. Our results will benefit further studies on
the plant for lead discovery. Adiponectin is a major insu-
lin-sensitizing adipokine predominantly secreted from adi-
posytes. Its deficiency is causally associated with a cluster
of obesity-related metabolic and cardiovascular complica-
tion. Thus, promotion of adiponectin production will have
beneficial effects on these diseases. In our study three cu-
curbitacins 3, 8 and 9 were sent for in vitro tests, only 9
modestly increased adiponectin production (1.32 fold at 25
μg·mL-1) in adipocytes.
ZHANG Sheng, et al. /Chinese Journal of Natural Medicines 2010, 8(1): 21−24
22 Chin J Nat Med Jan. 2010 Vol. 8 No. 1 2010 年 1 月 第 8 卷 第 1 期



Fig. 1 ORTEP drawing of the X-ray crystallographic
structure of 8

2 Apparatus and Material
2.1 Apparatus and reagents
Perkin-Elmer 577 IR Spectrometer (KBr); Bruker
AM-400 NMR Spectrometer (TMS); Finnigan LCQ-DECA
and MAT-95 Mass Spectrometers; TLC GF254 plates from
Jiang-You Co. Ltd., Yantai, Silica get for columns from
Qingtao Marine Chemical Co.; Sephadex LH-20 from
Pharmacia; ODS C18 from Merck; H2SO4 (T20090209),
HCL (T20070702), n-butanol (T20050526) are in analytical
grade. 95% ethanol (KJ20060817), petroleum ether
(F20090421), ethyl acetate (T20070720), CHCl3
(T20090728), MeOH (T20090312) are in chemical grade
(Shanghai Chemical Company, Ltd.).
2.2 Plant materials
The plant stems and leaves were collected from Zhejiang
Province in June, 2007. The specimen was identified by
Prof. Tao Zheng-Ming as Elaeocarpus glabripetalus Merr.
and deposited in herbarium of Zhejiang Institute of Sub-
tropical Crops.
3 Extraction and Isolation
Air-dried stems and leaves of E. glabripetalus (5.7 kg)
were powdered and extracted with 95% ethanol. The etha-
nol extracts were suspended in water and extracted by pe-
troleum ether, ethyl acetate and n-butanol, successively.
The EtOAc extracts (85 g) were subjected to column chro-
matography over silica gel, eluted with a gradient
CHCl3-MeOH solvent system to afford 9 fractions. Each
fractions were separated by repeated column chromatogra-
phy over normal and reverse silica gel, and Sephadex
LH-20 to afford compounds 1 (74 mg), 2 (26 mg), 3 (422
mg), 4 (5 mg), 5 (40 mg), 6 (34 mg), 7 (13 mg), 8 (39 mg),
9 (54 mg), 10 (21 mg) and 11 (158 mg), respectively.
4 Structural identification
Kaempferol (1) C15H10O6, yellow powders, posi-
tive to HCl-Mg reaction and negative to α-naphthol testing,
indicating a flavone; ESI-MS m/z 287 [M + H]+, (-) ESI-MS
m / z 2 8 5 [ M－H ] - , I R ( K B r ) : 3 3 4 2 , 1 6 5 8 ,
1 618, 1 508, 1 383, 1 303, 1 174, 818 cm−1. 1H NMR
(CD3COCD3, 400 MHz ) δ: 6.16 (1H, d, J=1.6 Hz, H-6),
6.37 (1H, d, J=1.6 Hz, H-8), 6.89 (2H, d, J=8.8 Hz, H-3, 5),
8.07 (2H, d, J=8.8 Hz, H-2, 6). The above data were iden-
tical to those in literature of kaempferol (3, 4’, 5, 7
-tetrahydroxyflavone)[7].
β-Sitosterol (2) C29H50O, colorless crystals,
EI-MS m/z 414 [M] +. co-TLC showed the same Rf and spot
color with standard sample after spraying 10%
H2SO4-EtOH solution and heating. The mixed melting point
did not decrease.
Cucurbitacin D (3) C30H44O7, white powders, (-)
ESI-MS m/z 561 [M + COOH]-. 1H NMR (CD3COCD3, 400
MHz ) δ: 0.93 (3H, s, H-18), 1.33 (3H, s, H-19), 1.10 (1H,
m, H-1β), 1.26 (3H, s, H-29), 1.28 (3H, s, H-28), 1.31 (3H,
s, H-21), 0.98 (3H, s, H-30), 1.38 (3H, s, H-26), 1.40 (3H, s,
H-27), 1.85 (2H, m, H-15), 1.98 (1H, d, J = 8.0 Hz, H-8),
2.12 (1H, m, H-7β), 2.40 (1H, dd, J = 7.6, 15.6 Hz, H-7α),
2.56 (1H, d, J = 14.0 Hz, H-1α), 2.67 (1H, d, J = 6.8 Hz,
H-12β), 3.05 (1H, d, J = 12.8 Hz, H-17), 3.45 (1H, d, J =
14.4 Hz, H-12α), 3.74 (1H, s, 16-OH), 3.86 (1H, s, 25-OH),
4.10 (1H, s, 20-OH), 4.42 (1H, t, J = 7.6 Hz, H-2), 4.50 (1H,
s, H-6), 4.58 (1H, dd, J = 6.0, 12.8 Hz, H-16), 5.81 (1H, d,
J = 4.8 Hz, 2-OH), 6.84 (1H, d, J=15.6 Hz, H-23), 6.97 (1H,
d, J = 14.8 Hz, H-24). 13C NMR (C5D5N, 100 MHz) δ: 18.8
(C-30), 19.9 (C-18), 20.5(C-19), 21.8 (C-28), 24.1(C-7),
25.5 (C-21), 29.4 (C-26), 29.7 (C-27), 29.9 (C-29),
34.1(C-10), 36.9 (C-1), 42.7 (C-8), 46.3 (C-15), 48.6 (C-14),
48.7 (C-9), 49.2 (C-12), 50.9 (C-4), 57.3 (C-13), 59.2
(C-17), 70.2 (C-16), 70.3 (C-2), 72.4 (C-25), 79.2 (C-20),
120.0 (C-23), 120.7 (C-6), 141.3 (C-5), 155.5 (C-24), 204.2
(C-22), 212.9 (C-3), 213.3 (C-11). The above data were
identical to those in literature of cucurbitacin D[8, 9].
Methyl gallate (4) C8H8O5, pale yellow powders,
positive to FeCl3 testing (shows deep blue), indicating to be
a phenol compound. ESI-MS m/z 369 [2M + H]+, (-)
ESI-MS m/z 183 [M－H]-. 1H NMR (CD3COCD3, 400
MHz) δ: 3.78 (3H, s, OCH3), 7.11 (2H, s, H-2, 6). The
above data were identical to those in literature of methyl
gallate[10].
Ethyl gallate (5) C9H10O5, yellow powders, posi-
tive to FeCl3 testing (shows deep blue), indicating to be a
phenol compound. (－ ) ESI-MS m/z 197 [M－H]-, IR
(KBr) : 3 446, 1 706, 1619, 1 535, 1 385, 1 315, 1 255, 1
199, 763 cm−1. 1H NMR (CD3COCD3, 400 MHz ) δ:
1.31(3H, t, J=7 Hz, CH3), 4.25(2H, q, J = 7 Hz, OCH2),
7.12 (2H, s, H-2, 6). 13C NMR (CD3COCD3, 100 MHz) δ:
14.27 (CH3-), 60.54 (OCH2-), 109.41 (C-2, 6), 121.84(C-1),
138.15 (C-4), 145.60 (C-3, 5), 166.32 (C=O). The above
data were identical to those in literature of ethyl gallate [10].
Quercetin (6) C15H10O7, yellow powders, positive
to HCl-Mg reaction and α-naphthol testing, indicating to be
a flavone glycoside; IR (KBr) : 3 403, 3 318, 1 660, 1 612, 1
ZHANG Sheng, et al. /Chinese Journal of Natural Medicines 2010, 8(1): 21−24
2010 年 1 月 第 8 卷 第 1 期 Chin J Nat Med Jan. 2010 Vol. 8 No. 1 23

560, 1 519, 1 319, 1 168, 825 cm−1. ESI-MS m/z 303 [M +
H]+, (-) ESI-MS m/z 301[M－H]+. 1H NMR (CD3COCD3,
400 MHz) δ: 3.33 (1H, OH), 6.26 (1H, d, J = 1.6 Hz, H-6),
6.50 (1H, d, J = 1.6 Hz, H-8), 6.99 (1H, d, J = 8.4 Hz, H-5),
7.69 (1H, dd, J = 2.0, 8.0 Hz, H-6), 7.82 (1H, d, J = 2.0 Hz,
H-2), 8.70 (1H, OH), 12.17 (1H, OH-5). The above data
were identical to those in literature of quercetin[11].
3,4-Dihydroxybenzoic acid (7) C7H6O4, white
powders, EI-MS m/z 154 [M]+. 1H NMR (CD3COCD3, 400
MHz ) δ: 6.90 (1H, d, J = 8.0 Hz, H-6), 7.47 (1H, d, J = 8.4
Hz, H-5), 7.53 (1H, s, H-2). The above data were identical
to those in literature of 3, 4-dihydroxybenzoic acid[10].
Mogroside I E1 (8) C36H62O9, white powders,
ESI-MS m/z 661 [M + Na]+, (－ ) ESI-MS m/z 683
[M+COOH]-. 1H NMR (400 MHz, CD3OD) δ: 0.87 (3H, s,
H-28), 0.92 (3H, s, H-18), 0.96 (3H, d, J = 6.0 Hz, H-21),
1.06 (3H, s, H-19), 1.11 (3H, s, H-26), 1.12 (3H, s, H-30),
1.15 (3H, s, H-29), 1.19 (3H, s, H-27), 3.42 (1H, s, H-3),
3.65 (1H, dd, J = 5.2, 12.0 Hz, H-24), 3.81 (1H, d, J = 10.0
Hz, H-11), 5.48 (1H, d, J = 5.2 Hz, H-6). 13C NMR
(100MHz, DMSO-d6) δ: 17.2 (C-18), 19.2 (C-21), 19.4
(C-30), 24.5 (C-7), 25.3 (C-26), 26.3 (2 C, C-19, C-29),
27.0 (C-1), 27.9 (C-27), 28.0 (C-28), 28.2 (C-16), 28.9 (2 C,
C-2, C-23), 33.7 (C-22), 34.5 (C-15), 35.9 (C-10), 36.2
(C-20), 40.6 (C-9), 40.8 (C-12), 42.1 (C-4), 43.3 (C-8), 47.2
(C-13), 49.6 (C-14), 50.8 (C-17), 61.8 (C-G6), 70.8 (C-G4),
72.4 (C-25), 74.5 (C-G2), 77.2 (C-11), 77.3 (C-G5), 77.9
(C-G3), 78.1 (C-24), 87.2 (C-3), 106.1 (C-G1), 117.9 (C-6),
144.3 (C-5). The above data were identical to those in lit-
erature of mogroside I E1[12].
X-Ray Crystal Data of 8 C36H64O9; crystal size
(mm) 0.311 × 0.083 × 0.080; orthorhombic crystal, space
group P2(1)2(1)2(1); unit cell dimensions a = 6.742 6 (8) Å,
b = 20.772 (3) Å, c = 24.273 (3) Å; volume 3 399.6 (7) Å3;
Z = 4; formula weight 640.87; density (calcd.) 1.252
Mg·m-3; absorption coefficient 0.088 mm−1; F (000) = 1 408.
The reflection data were collected on a Bruker Smart Apex
CCD diffractometer, using graphite-monochromated radia-
tion Mo Kα λ = 0.710 73 Å. A total of 18009 reflections
was collected, of which 3602 unique reflections with I > 2σ
(I) utilized for the analysis, and were used for refinement.
The final R and Rw were 0.093 7 and 0.136 9 respectively,
with goodness-of-fit of 1.107.
5R, 6R-Epoxymogroside I E1 (9) C36H62O10,
white powders, ESI-MS m/z 677[M + Na]+. 1H NMR
(CD3OD, 400 MHz ) δ: 0.86 (3H, s, H-18), 0.89 (3H, s,
H-30), 0.92 (3H, s, H-29), 0.96 (3H, d, J = 5.6 Hz, H-21),
1.13 (3H, s, H-28), 1.16 (3H, s, H-19), 1.18 (3H, s, H-27),
1.20 (3H, s, H-26), 1.26 (2H, m, H-15), 1.35 (2H, m, H-16),
1.49 (1H, m, H-1a), 1.50 (2H, m, H-2),1.60 (1H, d, J = 8.0
Hz, H-8), 1.82 (2H, m, H-22), 1.86 (2H, m, H-23), 1.92 (1H,
m, H-1b), 2.05 (2H, m, H-7), 2.16 (1H, dd, J = 8.4, 16.0 Hz,
H-10), 2.37 (1H, dd, J = 11.6, 17.6 Hz, H-17), 3.21 (2H, d,
J = 10.4 Hz, H-12), 3.28 (1H, d, J = 10.4 Hz, H-24), 3.33
(1H, m, H-6), 3.44 (1H, s, H-3), 3.65 (1H, dd, J = 7.2, 12.0
Hz, Glu-H-6a), 3.72 (1H, dd, J=5.2, 12.0 Hz, Glu-H-6b),
3.82 (1H, d, J = 10.8 Hz, H-11), 4.22 (1H, d, J = 7.2 Hz,
Glu-H-1). 13C NMR (CD3OD, 100 MHz) δ: 17.6 (C-18),
19.6 (C-21), 21.6 (C-1), 21.7 (C-30), 24.3 (C-28), 25.3
(C-7), 25.5 (C-19), 26.1 (C-29), 26.3 (C-26), 26.5 (C-27),
29.2 (C-23), 31.5 (C-16), 34.9 (C-2), 35.7 (C-22), 37.5
(C-15), 41.1 (C-10), 41.3 (C-20), 42.4 (C-9), 43.9 (C-12),
47.7 (C-4), 48.9 (C-8), 50.1 (C-13), 51.1 (C-14), 52.5
(C-17), 56.1 (C-6), 63.3 (C-6), 70.1 (C-5), 72.2 (C-4), 74.4
(C-25), 75.9 (C-2), 78.0 (C-3), 78.2 (C-5), 80.2 (C-11),
80.7 (C-24), 88.6 (C-3), 107.5 (C-1). The above data were
identical to those in literature of 5R, 6R-epoxymogroside I
E1 [12].
Kaempferol-7-O-α-L-arabinopyranoside (10)
C20H18O10, yellow powders, positive to HCl-Mg reaction
and α-naphthol testing, indicating to be a flavone glycoside;
ESI-MS m/z 419 [M + H]+, (-) ESI-MS m/z 417 [M－H]-.
1H NMR (CD3OD, 400 MHz) δ: 3.0~4.0(8H, m, Ara-OH 和
-OH), 5.14 (1H, d, J = 6.0Hz), 6.19 (1H, d, J = 1.6Hz, H-6),
6.38 (1H, d, J = 1.6Hz, H-8), 6.88 (2H, d, J = 8.8Hz, H-3,
5), 8.05 (2H, d, J = 8.8Hz, H-2, 6). 13C NMR (CD3OD,
100MHz) δ: 65.58 (C-5), 67.78 (C-3), 71.58 (C-2), 72.82
(C-4), 93.55 (C-8), 98.67 (C-6), 103.17 (C-10), 114.94
(C-3), 115.05 (C-5), 121.40 (C-1), 130.99 (C-2), 131.10
(C-6), 134.37 (C-3), 157.25 (C-2), 157.64 (C-5), 160.46
(C-4), 161.89 (C-9), 164.80 (C-7), 178.38 (C-4). The above
data were identical to those in literature of kaempferol-7-
O-α-L-arabinopyranoside[13].
Rutin (11) C27H30O16, yellow powders, positive to
HCl-Mg reaction and α-naphthol testing, indicating to be a
flavone glycoside; ESI-MS m/z 633[M + Na]+, (－) ESI-MS
m/z 609[M－H]-. 1H NMR (CD3OD, 400 MHz) δ: 1.12 (3H,
d, J = 2.4 Hz, ), 3.25-3.55 (8H, m), 3.63 (1H, dd, J = 1.6,
3.6 Hz, ), 3.80 (1H, d, J = 10.0 Hz, ), 4.51 (1H, d, J = 1.6
Hz, ), 5.10 (1H, d, J = 2.0 Hz, H-1), 6.18 (1H, d, J = 2.0
Hz, H-6), 6.37 (1H, d, J = 2.4 Hz, H-8), 6.86 (1H, d, J = 8.4
Hz, H-5), 7.62 (1H, dd, J = 2.0, 8.4 Hz, H-6), 7.66 (1H, d,
J = 2.0 Hz, H-2). 13C NMR (CD3OD, 100MHz) δ: 18.39
(C-6), 69.03 (C-2), 70.19 (C-6), 71.85 (C-4), 72.57
(C-3), 72.70 (C-5), 74.40 (C-4), 76.21 (C-2), 77.67
(C-5), 78.64 (C-3), 95.35 (C-8), 100.42 (C-6), 102.90
(C-1), 105.23 (C-1), 106.09 (C-10), 116.52 (C-2), 118.18
(C-5), 123.58 (C-1), 124.05 (C-6), 136.12 (C-3), 146.30
(C-3), 150.28 (C-4), 158.96 (C-9), 159.80 (C-2), 163.44
(C-5), 166.48 (C-7), 179.87 (C-4). The above data were
identical to those in literature of rutin[14].
5 Induction of Adiponectin in 3T3-L1 Adipo-
cytes
3T3-L1 cells were maintained in DMEM supplemented
with 10% fetal bovine serum. For differentiation, the cells
were induced by incubation with 0.25 µmol·L-1 dexa-
methasone, 0.5 mmol·L-1 3-isobutyl-methylxanthione, and
ZHANG Sheng, et al. /Chinese Journal of Natural Medicines 2010, 8(1): 21−24
24 Chin J Nat Med Jan. 2010 Vol. 8 No. 1 2010 年 1 月 第 8 卷 第 1 期

10 µg·mL-1 insulin for 2 d. This is followed by incubation
with 10 µg·mL-1 insulin for 2 d. The cells were then main-
tained in DMEM with 10% fetal bovine serum for another 4
d. Fully differentiated mature adipocytes were then treated
with compound 9 in a serum-free conditioned medium con-
taining 0.5% BSA for 72 h. Adiponectin concentrations
released in the conditioned medium were quantified with an
in house immunoassay specific to mouse adiponectin, as
described elsewhere[15].
Acknowledgements
The X-ray crystallographic analysis of compound 8
was determined at Shanghai Institute of Organic Chemistry,
Chinese Academy of Sciences. We greatly appreciate Dr.
XU Ai-min of Faculty of Medicine, the University of Hong
Kong for testing of adiponectin production in adipocytes.
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秃瓣杜英茎叶化学成分
张 盛 1, 陶正明 2, 张 毅 3, 沈征武 1*, 秦国伟 3*
1 上海中医药大学中药学院, 上海 201023; 2 浙江省亚热带作物研究所, 温州 325028;
3 中国科学院上海药物研究所, 上海 201203
【摘 要】 目的：研究秃瓣杜英 Elaeocarpus glabripetalus Merr.茎叶的化学成分。方法：采用硅胶柱色谱、Sephadex
LH-20 柱色谱、ODS 反相柱色谱等方法对秃瓣杜英茎叶 95%乙醇提取物进行分离和纯化, 应用理化性质及波谱方法对实
验得到的单体化合物进行结构鉴定。结果：分离并鉴定 11 个化合物, 分别为：山柰酚(1)、β-谷甾醇(2)、葫芦素 D(3)、没
食子酸甲酯(4)、没食子酸乙酯(5)、槲皮素(6)、3, 4-二羟基苯甲酸(7)、Mogroside I E1(8)、5R, 6R-Epoxymogroside I E1(9)、
山奈酚-7-O-α-L-吡喃阿拉伯糖苷(10)、芦丁(11)。结论：化合物 2 和 3 为首次从该植物中分离得到, 其余 9 个化合物均为
首次从杜英属植物中分得, 对化合物 8 的结构首次进行了 X-衍射分析。化合物 9 在体外实验中能增加脂肪细胞分泌脂联素
的水平(25 μg·mL-1 浓度时增加 1.32 倍)。
【关键词】 秃瓣杜英; 杜英属; 葫芦素

【基金项目】上海市科委资助项目(No.06DZ22028)