全 文 ：206 Chin J Nat Med May 2009 Vol. 7 No. 3 2009 年 5 月 第 7 卷 第 3 期








Triterpene Saponins from the Leaves of Ilex pernyi

XIE Guang-Bo1,2, JIANG Yong1, LEI Lian-Di1, TU Peng-Fei1*
1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Cen-
ter, Beijing 100083;
2School of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu 610054, China
【ABSTRACT】 AIM: To study the chemical constituents from the leaves of Ilex pernyi. METHODS: The
chemical constituents were isolated by various column chromatographic methods and their structures were identified by
spectral data together with physicochemical analysis. RESULTS: Nine known compounds were isolated and identified
as 2α, 3β, 23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1), hederagenin 3-O-β-D-glucopyranosyl-
(1→2)-O-α-L-arabinopyranoside (2), hederagenin 3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranoside (3), heder-
agenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (4), 3-O-β-D-glucopyranosyl-23-hydroxyursolic acid
(5), chikusetsusaponin Ⅳa (6), 3β-23-dihydroxy-urs-12-en-28-oic acid 3-O-β-D-glucuronopyranoside 6′-O-methyl ester
(7), ilexoside XXXVII (8), 3-O-β-D-glucuronopyranosyl-2α, 3β, 23-trihydroxyurs-12-en-28-oic acid β-D-glucopy-
ranosyl ester (9). CONCLUSION: The nine compounds were isolated from this plant for the first time.
【KEY WORDS】 Ilex pernyi; Aquifoliaceae; Triterpene saponin
【CLC Number】 R284.1 【Document code】 A 【Article ID】1672-3651(2009)03-0206-00
doi: 10.3724/SP. J. 1009.2009.00206
The plants of the genus Ilex are well-known to be
important medicinal plants. More than 10 species from this
genus are used as folk medicines to treat tussis, febris and
angiocardiopathy in China, such as I. chinensis, I. pubes-
cens and I. cornuta[1]. As a part of the systematic chemical
investigation on this genus [2-4], we recently carried out the
research on I. pernyi.
I. pernyi Franch. (Aquifoliaceae), an evergreen shrub,
is distributed mainly in the Yangtze River valley and south
region of Qinling Mountains in the P. R. China. Its leaves
are used as folk medicine to treat tussis and febris in China
[1]. Based on the former research [5,6], we investigated the
saponin constituents of I. pernyi. This paper describes that
nine known triterpene saponins were isolated and identified
from the leaves of I. pernyi.
1 Apparatus and Reagents
NMR spectra were recorded on Varian Unity-500 and

【Received on】 2008-11-09
【Foundation Item】 This project was supported by grants from
National Natural Science Foundation of China (No. 30672608) and
Program for Changjiang Scholars and Innovative Team in Univer-
sity (No. 985-2-063-112)
【*Corresponding author】TU Peng-Fei: Prof., Tel / Fax: +86-10-
82802750, E-mail: pengfeitu@vip.163.com
Varian Inova-500 spectrometers with TMS as an internal
standard. ESI-MS spectra were carried out on a QSTAR
(ABI, USA) mass spectrometer. Semi-preparative HPLC:
Water 600 pump with 600 controller, Waters C18 Nova-Pak
column (300 mm × 7.8 mm, I.D. 5 μm), with ELSD detec-
tor (Alltech); flow rate, 2.5 ml·min−1. Column chromatog-
raphy was carried out on silica gel H-60 (200-300 mesh,
Qingdao Marine Chemical Industry, Qingdao, China),
Sephadex LH-20 (Pharmacia Biotech AB, Uppsala, Swe-
den), D101 porous polymer resin (Tianjin Chemical Indus-
try, Tianjing, China), and ODS gel (25-40 μm, Merck,
USA)
2 Plant Material
The leaves of I. pernyi were collected by Dr. ZHOU
Si-Xiang in April 2005 at the Nature Protection Area of
Shennongjia, Hubei Province, China. It was identified by
Prof. TU Peng-Fei of the College of Pharmacy, Peking
University, Beijing, China. A voucher specimen (MEC 0504)
was deposited at the Herbarium of Peking University Mod-
ern Research Center for Traditional Chinese Medicine.
3 Extraction and Isolation
The air-dried and powdered leaves (15 kg) of I. pernyi
were extracted with 70% EtOH (3 × 80 L) at 60oC for 2 h.
Xie Guang-Bo, et al. /Chinese Journal of Natural Medicines 2009, 7(3): 206−209
2009 年 5 月 第 7 卷 第 3 期 Chin J Nat Med May 2009 Vol. 7 No. 3 207

After removal of the solvent under vacuum, the residue was
suspended in H2O (12 L) and extracted with petroleum
ether, EtOAc, and n-BuOH (15 L × 3), successively. The
EtOAc extract (230 g) was subjected to column chroma-
tography over silica gel H-60 eluted with CHCl3-MeOH
(80 : 1–1 : 1) to afford ten fractions (Fr.1-10). Fr.8 was
subjected to column chromatography over Sephadex LH-20
eluted with CHCl3-MeOH (2 : 1), silica gel H-60 eluted
with CHCl3-MeOH (6 : 1) to give Fr. 8-1 and Fr. 8-2. Each
fraction was recrystallized with MeOH to afford com-
pounds 1 (20 mg) and 2 (13 mg). Fr.9 was subjected to
column chromatography over silica gel H-60 eluted with
CHCl3-MeOH (4 : 1) to give Fr 9-1 and Fr. 9-2. Each frac-
tion was purified by column chromatography over silica gel
H-60 and Sephadex LH-20 to afford compounds 3 (10 mg)
and 4 (30 mg). The n-BuOH extract (400 g) was subjected
to column chromatography over D101 porous polymer resin
and eluted with H2O and 10, 30, 50, 70, 95% aq. EtOH,
respectively. The fractions eluted with 50% and 70% aq.
EtOH (97 g) were subjected to column chromatography
over silica gel H-60 eluted with CHCl3-MeOH-H2O (10 : 1 :
0–1 : 1 : 0.1) to afford twelve fractions (Fr. 1-12). Fr. 3 was
subjected to column chromatography over Sephadex LH-20
(MeOH) and ODS gel eluted with MeOH-H2O (7 : 3) to
afford compound 5 (10 mg). Fr.6 was subjected to column
chromatography over silica gel H-60 eluted with
EtOAc-MeOH-H2O (60 : 1 : 0.4–40 : 1 : 0.4) to afford
Fr.6-1 and Fr.6-2. Fr.6-1 was purified by semi-preparative
HPLC [MeOH-H2O (0.5 ‰ TFA) 7 : 3] to afford compound
6 (30 mg). Fr.6-2 was subjected to column chromatography
over ODS gel eluted with MeOH-H2O (3 : 1) to afford
compound 7 (5 mg). Fr.8 was subjected to column chroma-
tography over silica gel H-60 eluted with
CHCl3-MeOH-H2O (4 : 1 : 0.1), ODS gel eluted with
MeOH-H2O (3 : 2 –7 : 3) to afford compound 8 (60 mg). Fr.
9 was subjected to column chromatography over silica gel
H-60 eluted with CHCl3-MeOH-H2O (2 : 1 : 0.1) and ODS
gel eluted with MeOH-H2O (1 : 1 –13 : 7) to afford Fr.9-1.
Fr. 9-1 was further purified by semi-preparative HPLC
[MeOH-H2O (0.5 ‰ TFA) 13 : 7] to afford compound 9 (18
mg).
4 Identification
Compound 1 White amorphous powder; ESI-MS
m/z 673 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
6.24 (1H, d, J = 8.5 Hz, Glc-H-1), 5.41 (1H, t, J = 4.0 Hz,
H-12), 2.48 (1H, d, J = 11.5 Hz, H-18), 1.16, 1.08, 1.07,
1.03 (each 3H, s, 4 × Me), 0.89 (3H, d, J = 6.5 Hz, Me),
0.85 (3H, br s, Me). 13C NMR (125 MHz, pyridine-d5) see
Table 1, 2. Compound 1 was identified as 2α, 3β, 23-trihy-
droxyurs-12-en-28-oic acid β-D-glucopyranosyl ester by
comparison of the spectral data with the literature [7].

Compound 2 White amorphous powder; ESI-MS
m/z 789 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
5.44 (1H, br s, H-12), 5.16 (1H, d, J = 7.5 Hz, Glc-H-1),
5.15 (1H, d, J = 7.0 Hz, Ara-H-1), 3.26 (1H, dd, J = 14.0,
4.0 Hz, H-18), 1.19, 0.99, 0.99, 0.97, 0.90, 0.90 (each 3H, s,
6 × Me). 13C NMR (125 MHz, pyridine-d5) see Table 1, 2.
Compound 2 was characterized as hederagenin 3-O-β-D-
glucopyranosyl-(1→2)-O-α-L-arabinopyranoside by com-
parison of the spectral data with the literature[8].
Compound 3 White amorphous powder; ESI-MS
m/z 819 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
5.45 (1H, br s, H-12), 5.39 (1H, d, J = 8.0 Hz, Glc′-H-1),
5.08 (1H, d, J = 7.0 Hz, Glc-H-1), 3.26 (1H, dd, J = 13.0,
3.5 Hz, H-18), 1.21, 1.08, 0.99, 0.97, 0.90, 0.87 (each 3H, s,
6 × Me). 13C NMR (125 MHz, pyridine-d5) see Table 1, 2.
Compound 3 was identified as hederagenin 3-O-β-D-glu-
copyranosyl-(1→2)-O-β-D-glucopyranoside by comparison
of the spectral data with the literature[9].
Compound 4 White amorphous powder; ESI-MS
m/z 803 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
6.53 (1H, br s, Rha-H-1), 5.43 (1H, br s, H-12), 5.14 (1H, d,
J = 8.0 Hz, Glc-H-1), 1.68 (1H, d, J = 6.0 Hz, Rha-H-6),
1.20, 1.11, 0.98, 0.96, 0.89, 0.89 (each 3H, s, 6 × Me). 13C
NMR (125 MHz, pyridine-d5) see Table 1, 2. Compound 4
was characterized as hederagenin 3-O-α-L-rhamnopy-
ranosyl-(1→2)-O-β-D-glucopyranoside by comparison of
the spectral data with the literature[10].
Compound 5 White amorphous powder; ESI-MS
m/z 657 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
5.53 (1H, br s, H-12), 5.18 (1H, d, J = 7.5 Hz, Glc-H-1),
2.67 (1H, d, J = 11.5 Hz, H-18), 1.17, 1.05, 0.96, 0.98 (each
3H, s, 4 × Me), 0.89 (3H, d, J = 6.5 Hz, Me), 0.91 (3H, d, J
= 6.5 Hz, Me). 13C NMR (125 MHz, pyridine-d5) see Table
1, 2. Compound 5 was identified as 3-O-β-D-glucopy-
ranosyl-23-hydroxyursolic acid by comparison of the spec-
tral data with the literature[11].
Compound 6 White amorphous powder; ESI-MS
m/z 817 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
6.30 (1H, d, J = 8.0 Hz, Glc-H-1), 5.38 (1H, br s, H-12),
5.02 (1H, d, J = 8.0 Hz, GlcA-H-1), 3.35 (1H, dd, J = 11.5,
4.0 Hz, H-3), 3.16 (1H, dd, J = 13.5, 4.0 Hz, H-18), 1.28,
1.25, 1.06, 0.96, 0.88, 0.86, 0.80 (each 3H, s, 7 × Me). 13C
NMR (125 MHz, pyridine-d5) see Table 1, 2. Compound 6
was characterized as chikusetsusaponin Ⅳa by comparison
of the spectral data with the literature[12].
Compound 7 White amorphous powder; ESI-MS
m/z 685 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
5.45 (1H, br s, H-12), 5.20 (1H, d, J = 8.0 Hz, GlcA-H-1),
3.69 (3H, s, GlcA-6-OMe), 2.60 (1H, d, J = 11.5 Hz, H-18),
1.17, 1.02, 0.92, 0.88 (each 3H, s, 4 × Me), 0.98 (3H, d, J =
7.0 Hz, Me), 0.97 (3H, d, J = 6.0 Hz, Me). 13C NMR (125
MHz, pyridine-d5) see Table 1, 2. Compound 7 was identi-
fied as 3β-23-dihydroxy-urs-12-en-28-oic acid 3-O-β-
Xie Guang-Bo, et al. /Chinese Journal of Natural Medicines 2009, 7(3): 206−209
208 Chin J Nat Med May 2009 Vol. 7 No. 3 2009 年 5 月 第 7 卷 第 3 期

Table 1 13C NMR data (125 MHz, in pyridine-d5) for aglycon of compounds 1-9
Position 1 2 3 4 5 6 7 8 9
1 48.0 38.7 38.1 39.4 38.7 38.6 39.7 38.8 47.6
2 68.9 25.9 25.6 26.1 28.7 26.6 26.0 25.9 66.9
3 78.2 82.1 82.2 81.1 82.0 89.0 82.1 82.2 87.7
4 43.6 43.5 42.9 43.2 42.5 39.5 43.4 43.4 42.4
5 48.1 47.9 47.5 47.8 48.1 55.7 47.5 47.6 47.1
6 18.5 18.2 17.7 18.2 18.2 18.5 18.1 18.3 18.1
7 33.2 32.8 32.5 32.0 33.0 33.1 33.0 33.3 33.0
8 40.2 39.7 39.2 39.4 39.9 39.9 39.9 40.5 40.1
9 47.9 48.1 47.5 49.4 48.3 48.0 48.0 47.7 48.0
10 38.3 36.9 36.3 36.5 37.0 36.9 36.9 36.9 37.7
11 23.8 23.8 23.0 23.4 23.7 23.7 23.6 24.1 23.7
12 126.0 122.5 122.0 122.3 125.6 122.8 125.6 128.2 126.9
13 138.4 144.8 144.3 144.5 139.2 144.1 139.2 139.2 138.3
14 42.5 42.1 41.6 41.9 43.0 42.1 42.5 42.1 44.7
15 28.6 28.3 27.8 28.0 30.0 28.2 28.9 29.2 28.6
16 24.6 23.7 23.2 23.5 24.9 23.4 24.9 26.1 24.5
17 48.3 46.6 46.1 47.6 47.5 47.0 47.4 48.6 48.3
18 53.3 42.0 41.4 41.7 53.5 41.7 53.5 54.4 53.2
19 39.3 46.4 46.0 46.3 39.4 46.2 39.5 72.6 39.2
20 39.1 30.9 30.4 30.7 39.7 30.7 30.9 42.1 39.0
21 30.8 34.2 33.9 33.0 37.4 34.0 33.2 26.6 30.7
22 36.8 33.2 32.2 32.9 31.0 32.5 33.0 37.7 36.7
23 66.5 64.8 64.6 63.6 64.2 28.2 64.3 64.7 63.5
24 14.4 13.4 13.0 14.0 13.7 16.9 13.6 13.6 14.6
25 17.6 16.0 15.5 15.8 16.1 15.5 16.2 16.2 17.3
26 17.8 17.4 16.9 17.9 17.5 17.4 17.4 17.4 17.5
27 23.8 26.1 25.3 26.0 23.6 26.1 23.9 24.5 23.7
28 176.2 180.1 179.6 179.9 179.6 176.3 179.8 176.9 176.1
29 17.4 33.2 32.7 32.9 17.5 33.1 17.4 26.9 17.6
30 21.2 23.8 23.2 23.5 21.4 23.6 21.8 16.6 21.2

Table 2 13C NMR data (125 MHz, in pyridine-d5) for sugar moieties of compounds 1-9
Position 1 2 3 4 5 6 7 8 9
28-Glc1) 3-Ara1) 3-Glc 3-Glc 3-Glc 3-GlcA1) 3-GlcA 3-Glc 3-GlcA
1 95.7 103.9 103.3 104.3 105.8 107.2 106.4 105.8 105.5
2 74.0 81.3 83.5 79.6 75.8 75.5 75.4 75.8 75.0
3 78.9 73.6 77.5 77.1 78.3 77.9 77.2 78.3 77.9
4 71.2 68.3 70.7 71.7 71.6 73.4 73.1 71.6 73.2
5 79.2 65.0 78.0 77.7 78.6 78.1 77.8 78.6 77.0
6 62.3 62.0 62.4 62.8 172.7 170.7 62.8 172.5
6-OMe 51.9
2′-Glc 2′-Glc 2′-Rha1) 28-Glc 28-Glc 28-Glc
1 105.9 105.4 101.2 95.7 95.7 95.6
2 76.2 76.3 72.1 74.1 74.0 74.0
3 78.2 77.5 72.2 78.9 78.9 78.8
4 71.4 70.7 73.9 71.1 71.2 71.1
5 78.3 77.8 69.2 79.3 79.2 79.1
6 62.5 62.0 18.4 62.2 62.3 62.2
1) Glc = β-D-glucopyranose; Ara = α-L-arabinopyranose; GlcA = β-D-glucuronopyranose; Rha = α-L-rhamnopyranose
Xie Guang-Bo, et al. /Chinese Journal of Natural Medicines 2009, 7(3): 206−209
2009 年 5 月 第 7 卷 第 3 期 Chin J Nat Med May 2009 Vol. 7 No. 3 209

D-glucuronopyranoside 6′-O-methyl ester by comparison of
the spectral data with the literature [13].
Compound 8 White amorphous powder; ESI-MS
m/z 835 [M + Na]+. 1H NMR (500 MHz, pyridine-d5) δ:
6.28 (1H, d, J = 8.0 Hz, 28-Glc-H-1), 5.53 (1H, br s, H-12),
5.11 (1H, d, J = 8.0 Hz, 3-Glc-H-1), 2.90 (1H, s, H-18),
1.62, 1.36, 1.19, 0.97, 0.97 (each 3H, s, 5 × Me), 1.04 (3H,
d, J = 6.5 Hz, Me). 13C NMR (125 MHz, pyridine-d5) see
Table 1, 2. Compound 8 was characterized as ilexoside
XXXVII by comparison of the spectral data with the litera-
ture[14].
Compound 9 Colorless gum; ESI-MS m/z 849 [M +
Na]+. 1H NMR (500 MHz, pyridine-d5) δ: 6.22 (1H, d, J =
8.0 Hz, Glc-H-1), 5.37 (1H, br s, H-12), 5.27 (1H, br s,
GlcA-H-1), 2.46 (1H, d, J = 11.5 Hz, H-18), 1.25, 1.08,
1.00, 0.98 (each 3H, s, 4 × Me), 0.87 (3H, d, J = 6.5 Hz,
Me), 0.84 (3H, br s, Me). 13C NMR (125 MHz, pyridine-d5)
see Table 1, 2. Compound 9 was identified as 3-O-β-D-
glucuronopyranosyl-2α, 3β, 23-trihydroxyurs-12-en-28-oic
acid β-D-glucopyranosyl ester by comparison of the spec-
tral data with the literature [15,16].
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猫儿刺叶中的三萜皂苷类成分
谢光波 1,2, 姜 勇 1, 雷连娣 1, 屠鹏飞 1*
1 北京大学药学院天然药物及仿生药物国家重点实验室, 北京 100083;
2 电子科技大学生命科学与技术学院, 成都 610054
【摘 要】 目的：研究猫儿刺(Ilex pernyi Franch)叶中的化学成分。方法：运用多种色谱方法进行分离纯化, 采用波谱解
析并结合理化性质鉴定化合物结构。结果：分离得到 9 个化合物：2α, 23-二羟基-乌索酸-28-O-β-D-吡喃葡萄糖苷 (1), 常
春藤皂苷元-3-O-β-D-吡喃葡萄糖基 (1→2)-α-L-吡喃阿拉伯糖苷 (2), 常春藤皂苷元-3-O-β-D-吡喃葡萄糖基 (1→2)-β-D-
吡喃葡萄糖苷 (3), 常春藤皂苷元-3-O-α-L-吡喃鼠李糖基 (1→2)-β-D-吡喃葡萄糖苷 (4), 23-羟基-乌索酸-3-O-β-D-吡喃葡
萄糖苷 (5), 竹节参苷Ⅳa (6), 23-羟基-乌索酸-3-O-β-D-吡喃葡萄糖醛酸甲酯苷 (7), 铁冬青苷XXXVII (8), 3-O-β-D-吡喃葡
萄糖醛酸基-2α, 23-二羟基-乌索酸-28-O-β-D-吡喃葡萄糖苷 (9)。结论：9 个化合物均为首次从该植物中分离得到。
【关键词】 猫儿刺; 冬青科; 三萜皂苷