全 文 ：
111 Journal of Chinese Pharmaceutical Sciences http://www.jcps.ac.cn
Chemical constituents from Paliurus ramosissimus
Chen Chen1,2, Guandi Luo3, Rong Hu*, Hongzheng Fu2*
1. School of Medical Academy, Yangzhou University, Yangzhou 225001, China
2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China
3. Guangdong Sencee Pharmaceutical Co., Ltd., Jieyang 515500, China
Abstract: In the present research, in order to study the chemical constituents of Paliurus ramosissimus (Lour.) Poir., the isolation
of its ingredients was performed by repeated chromatography on silica gel, Sephadex LH-20, ODS and preparative HPLC. Their
structures were elucidated on the basis of combination of mass spectrometry and 1D, 2D NMR spectroscopy. A total of 8
compounds were obtained, and their structures were identified as 3β-hydroxy-27-(3,4-dihydroxybenzoyl)oxylup-20(29)-en-
28-oic acid (1), betulinic acid (2), lupeol (3), 27-O-trans-caffeoylcylicodiscic acid (4), ceanothic acid (5), 24-hydroxyceanothic
acid (6), dihydrokaempferol (7), eriodictyol (8). Among them, compound 1 was a new compound. Compounds 3–4, 7–8 were
isolated from Paliurus ramosissimus (Lour.) Poir. for the first time.
Keywords: Paliurus ramosissimus; Chemical constituents; Structural identification
CLC number: R284 Document code: A Article ID: 1003–1057(2016)2–111–05
Received: 2015-10-22; Revised: 2015-12-05; Accepted: 2015-12-15;
Foundation item: National Natural Science Foundation of China
(Grant No. 81172943).
*Corresponding author. Tel./Fax: 86-10-82805212,
E-mail: drhzfu@sina.com
http://dx.doi.org/10.5246/jcps.2016.02.011
1. Introduction
As a well-known perennial woody plant in southwest,
mid-south region of China, Paliurus ramosissimus (Lour.)
Poir. has been used in the treatment of toothache and
abdomen ache for many years[1]. Active components
such as glycosides, triterpenoids and coumarins have
been investigated for anti-helicobacter pylori activities,
antipyretic activities and antitussive activities[2,3].
Phytochemical studies showed that thirteen triterpe-
noids, thirteen cyclopeptide alkaloids and nine coumarins
were obtained from the roots and fruits of this plant[1,2,4-7].
Given its unique clinical effects, high medicinal
value and broad application prospects, we subjected
a systematic research on the chemical constituents of the
overground parts of Paliurus ramosissimus (Lour.) Poir.
In this paper, we reported the isolation and structural
elucidation of 8 compounds isolated from Paliurus
ramosissimus. Among them, compound 1 was a new
triterpene. Compounds 3–4, 7–8 were isolated from this
plant for the first time (Fig. 1).

























2. Experimental
2.1. General experimental procedures
The HRESI-MS spectra were obtained on Bruker
APEX IV. The 1D and 2D NMR spectra were recorded
Figure 1. Chemical structures of compounds 1–8.
HO
R2
R1
R1 = H2C O
O
OH
OH
R2 = COOH (1)
R1 = CH3 R2 = COOH (2)
R1 = CH3 R2 = CH3 (3)
R1 = H2C O
O OH
OH
R2 = COOH (4)
R
COOH
R = CH3 (5)
R = CH2OH (6)
HO
HOOC OHO
OH O
R1 = H R2 = OH (7)
R1 = OH R2 = H (8)
R2
OH
R1

112 Chen, C. et al. / J. Chin. Pharm. Sci. 2016, 25 (2), 111–115
on a Bruker AV-400 instrument (Bruker BioSpin,
Switzerland) at room temperature. Silica gel (200–300 mesh,
Qingdao Marine Chemical Factory), ODS silica gel
(50 μm, DAISO Co., Ltd, Japan) and Sephadex LH-20
(18–111 μm, Pharmacia) were applied to column
chromatography. HPLC separation was performed on
a YMC C18 semi-preparative column (YMC-pack ODS-A,
300 mm×10 mm, 5 μm, YMC Co., Ltd.).
2.2. Plant materials
The roots, stems and leaves of Paliurus ramosissimus
were purchased from Jieyang City of Guangdong Province,
China, in March 2013, and they were identified by
Prof. Hongzheng Fu. A voucher specimen was deposited
at the State Key Laboratory of Natural and Biomimetic
Drugs, Peking University Health Science Center.
2.3. Extraction and isolation
The air-dried and powdered roots, stems and leaves
(45 kg) of Paliurus ramosissimus were extracted with
95% EtOH for 3 times. The crude extract was concen-
trated under vacuum (10 kg) and the residue was
suspended in methanol, then extracted with petroleum
ether (PE) for 4 times. The remaining methanol layer
was dispersed by H2O and then partitioned with EtOAc
for 4 times. The EtOAc-soluable part (1.5 kg) was
subjected to silica gel column chromatography and
successively eluted with CHCl3–CH3OH system and
then MeOH to yield fractions A–G. Fraction A (164 g)
was eluted by PE–EtOAc (20:1, v/v) on silica gel to
afford ten sections. The seventh section was repeatedly
washed with methanol to give compound 3 (167 mg).
Fraction C (25 g) was eluted by PE–EtOAc and CHCl3–
CH3OH on silica gel to yield six sections. The section 1
was subjected to silica gel eluted with PE–EtOAc (2:1,
v/v) and further purified by Sephadex LH-20 (CH3OH–
CHCl3, 50%) and semi-preparative HPLC to yield
compound 1 (32 mg) and compound 4 (94 mg). The
sections 2 and 3 were successively subjected to silica gel
eluted with PE–EtOAc (3:1, v/v) and further purified
by Sephadex LH-20 (CH3OH–CHCl3, 50%), and then
successively to afford compound 2 (68 mg) and
compound 5 (56 mg). The section 4 was subjected to
silica gel eluted with PE–EtOAc (2:1, v/v) and further
purified by Sephadex LH-20 (CH3OH–CHCl3, 50%),
then was eluted by 71% CH3OH, 80% CH3OH and
90% CH3OH on ODS column to yield compound 6
(18 mg). The sections 5 and 6 were successively subjected
to silica gel eluted with PE–EtOAc (2:1, v/v) and further
purified by Sephadex LH-20 (CH3OH–CHCl3, 50%),
and then successively to afford compound 7 (24 mg)
and compound 8 (13 mg).
3. Structural identification
3.1. 3β-Hydroxy-27-(3,4-dihydroxybenzoyl)oxylup-
20(29)-en-28-oic acid (1)
Compound 1 was a yellow solid with the specific
rotation of –2.1 (c 0.1, MeOH). The HR-ESI-MS
spectra of 1 gave a molecular ion peak at m/z 607.3635
[M-H]–, compatible with the molecular formula C37H52O7.
The IR spectrum showed the presence of hydroxy
(3435 cm–1), carboxylic acid (O-H stretching, 3300–
2500 cm–1), carbonyl (1697 cm–1) and olefin (1641 cm–1)
groups. The 1H and 13C NMR spectra (along with DEPT
and HSQC) (Table 1) showed five methyls and one
terminal methylene, one oxygenated methine, one
oxygenated methylene, one carboxyl carbon, and
one ester group. The structure was established on
the basis of HMBC and 1H-1H COSY correlations
(Fig. 2). In the HMBC spectrum, there were correla-
tions from δH 0.84 (3H, s, H-25) to δC 39.1, 55.8, 52.3,
37.6 (C-1, 5, 9, 10), δH 0.96 (3H, s, H-24) to δC 77.5,
39.2, 55.8, 28.2 (C-3, 4, 5, 23), δH 1.13 (3H, s, H-26)
to δC 35.7, 41.7, 52.3, 46.1 (C-7, 8, 9, 14), δH 1.76 (3H,
s, H-30) to δC 47.4, 150.8, 109.8 (C-19, 20, 29), δH
4.95, 5.07 (each 1H, d, J 11.0 Hz, H-27a, 27b) to δC
41.7, 39.3, 46.1, 24.8, 166.8 (C-8, 13, 14, 15, 7′),
δH 2.01 (1H, m, H-18) to δC 39.3, 56.2, 47.4, 178.7
(C-13, 17, 19, 28). In the 1H-1H COSY spectrum,
there were correlations between H-1/H-2/H-3, H-5/
H-6/H-7, H-9/H-11/H-12/H-13, H-15/H-16, H-19/
H-21/H-22. These NMR data were typical of a 3β-lupane
triterpene[8,9].
22
D[α]

113 Chen, C. et al. / J. Chin. Pharm. Sci. 2016, 25 (2), 111–115































Furthermore, the 1H NMR spectrum showed signals
of a 1,3,4-trisubstituted benzene ring at δH 8.13 (1H, d,
J 1.8 Hz, H-2′), 7.30 (1H, d, J 8.2 Hz, H-5′), 7.94 (1H,
dd, J1 8.2 Hz, J2 1.8 Hz, H-6′), and the HMBC spectrum
showed that δH 8.13 (H-2′) and 7.94 (H-6′) were corre-
lated with δC 166.8 (C-7′) respectively. On the basis of
these, the structure of group 1 was determinated. The
downfield chemical shifts of an oxygenated methylene
moiety (δH 4.95, 5.07, H-27a, 27b) suggested an ester
(or ether) connection at this position, and the HMBC
correlation between these oxygenated methylene protons
and C-7′ (δC 166.8) indicated that the group 1 was linked
to this methylene moiety. Depended on the above,
compound 1 was elucidated as 3β-hydroxy-27-(3,4-
dihydroxybenzoyl)oxylup-20(29)-en-28-oic acid.
3.2. Betulinic acid (2)
Colorless needles; 1H NMR (400 MHz, DMSO-d6)
δ: 4.69 (1H, s, H-29b), 4.56 (1H, s, H-29a), 4.28 (1H,
d, J 5.1 Hz, 3-OH), 3.30 (1H, m, H-3), 2.97 (1H, m,
H-19), 1.65 (3H, s, H-30), 0.93 (3H, s, H-27), 0.87
(6H, s, H-23, 26), 0.76 (3H, s, H-25), 0.65 (3H, s, H-24).
13C NMR (100 MHz, DMSO-d6) δ: 38.7 (C-1), 27.6
(C-2), 77.2 (C-3), 39.0 (C-4), 55.4 (C-5), 18.4 (C-6),
34.4 (C-7), 40.7 (C-8), 50.4 (C-9), 36.8 (C-10), 20.9
(C-11), 25.5 (C-12), 38.0 (C-13), 42.5 (C-14), 30.6
(C-15), 32.2 (C-16), 55.9 (C-17), 47.1 (C-18), 49.0
(C-19), 150.8 (C-20), 29.7 (C-21), 37.2 (C-22), 28.6
(C-23), 16.4 (C-24), 16.3 (C-25), 16.2 (C-26), 14.8 (C-27),
177.7 (C-28), 110.1 (C-29), 19.4 (C-30). The 1H NMR
and 13C NMR data were in agreement with those in the
literature[10], and the structure of compound 2 was
identified as betulinic acid.
3.3. Lupeol (3)
White powder; 1H NMR (400 MHz, DMSO-d6) δ:
4.68 (1H, br s, H-29b), 4.54 (1H, br s, H-29a), 4.27 (1H,
d, J 5.1 Hz, 3-OH), 3.32 (1H, br s, H-3), 2.97 (1H,
m, H-19), 1.64 (3H, s, H-30), 0.99 (3H, s, H-27),
0.91 (3H, s, H-26), 0.87 (3H, s, H-23), 0.77 (3H, s,
H-28), 0.76 (3H, s, H-25), 0.65 (3H, s, H-24). 13C NMR
(100 MHz, DMSO-d6) δ: 38.7 (C-1), 27.5 (C-2), 77.2
(C-3), 39.0 (C-4), 55.3 (C-5), 18.4 (C-6), 34.3 (C-7),
40.8 (C-8), 50.3 (C-9), 37.1 (C-10), 20.9 (C-11), 25.1
(C-12), 38.0 (C-13), 42.8 (C-14), 27.6 (C-15), 35.5
(C-16), 43.0 (C-17), 48.2 (C-18), 47.7 (C-19), 150.7
(C-20), 29.7 (C-21), 39.4 (C-22), 28.6 (C-23), 16.2
(C-24), 16.4 (C-25), 16.3 (C-26), 14.8 (C-27), 18.2
(C-28), 110.1 (C-29), 19.4 (C-30). The 1H NMR and
13C NMR data were in agreement with those in the
literature[11], and the structure of compound 3 was
identified as lupeol.
Position δH δC δH δC
1 1.66, 0.96 39.1 20 150.8
2 1.82 28.0 21 2.17, 1.46 30.8
3 3.37 77.5 22 2.21, 1.51 37.0
4 39.2 23 1.05 (s) 28.2
5 0.89 55.8 24 0.96 (s) 16.2
6 1.50, 1.35 18.6 25 0.84 (s) 16.6
7 1.66 35.7 26 1.13 (s) 16.7
8 41.7 27 5.07 (d, 11.0)
4.95 (d, 11.0)
63.1
9 1.50 52.3 28 178.7
10 37.6 29 4.94 (brs)
4.74 (brs)
109.8
11 1.44, 1.18 21.2 30 1.76 (s) 19.3
12 1.96, 1.00 25.7 Group 1
13 2.95 39.3 1′ 122.3
14 46.1 2′ 8.13 (d, 1.8) 117.3
15 2.11, 1.75 24.8 3′ 147.0
16 2.61, 1.58 33.1 4′ 152.4
17 56.2 5′ 7.30 (d, 8.2) 116.1
18 2.01 49.9 6′ 7.94 (dd, 8.2, 1.8) 122.7
19 3.53 47.4 7′ 166.8
Table 1. 1H NMR (400 MHz) and 13C NMR (100 MHz) spectral data
of compound 1 in Pyr-d5 (J in Hz)
Figure 2. HMBC and COSY correlations of compound 1.
HO
COOH
O C
O
OH
OH
1
2
3 4 5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25 26
27
28
29
30
1
2 3
4
56
7
H
COSY
HMBC

114 Chen, C. et al. / J. Chin. Pharm. Sci. 2016, 25 (2), 111–115
3.4. 27-O-trans-Caffeoylcylicodiscic acid (4)
Yellow solid; ESI-MS: m/z 633.80 [M-1]–; 1H NMR
(400 MHz, CD3OD) δ: 7.56 (1H, d, J 15.8 Hz, H-7′),
7.06 (1H, d, J 1.5 Hz, H-2′), 6.98 (1H, dd, J1 8.2 Hz,
J2 1.5 Hz, H-6′), 6.80 (1H, d, J 8.2 Hz, H-5′), 6.28
(1H, d, J 15.8 Hz, H-8′), 4.76 (1H, br s, H-29a), 4.70
(1H, d, J 12.9 Hz, H-27a), 4.64 (1H, br s, H-29b), 4.53
(1H, d, J 12.9 Hz, H-27b), 3.16 (1H, dd, J1 11.1 Hz,
J2 4.7 Hz, H-3), 3.08 (1H, m, H-19), 1.74 (3H, s, H-30),
1.05 (3H, s, H-26), 0.95 (3H, s, H-23), 0.92 (3H, s,
H-25), 0.77 (3H, s, H-24). 13C NMR (100 MHz, CD3OD)
δ: 40.1 (C-1), 28.0 (C-2), 79.5 (C-3), 40.0 (C-4), 57.0
(C-5), 19.4 (C-6), 36.7 (C-7), 42.7 (C-8), 53.4 (C-9),
38.6 (C-10), 22.2 (C-11), 26.7 (C-12), 40.4 (C-13),
46.9 (C-14), 25.3 (C-15), 33.8 (C-16), 57.2 (C-17),
50.7 (C-18), 48.4 (C-19), 151.8 (C-20), 31.6 (C-21),
37.9 (C-22), 28.6 (C-23), 16.2 (C-24), 17.1 (C-25),
17.2 (C-26), 64.3 (C-27), 180.0 (C-28), 110.4 (C-29),
19.7 (C-30), 127.6 (C-1′), 115.3 (C-2′), 146.8 (C-3′),
149.7 (C-4′), 116.5 (C-5′), 123.0 (C-6′), 147.0 (C-7′),
115.2 (C-8′), 169.4 (C-9′). The 1H NMR and 13C NMR
data were in agreement with those in the literature[12],
and the structure of compound 4 was identified as
27-O-trans-caffeoylcylicodiscic acid.
3.5. Ceanothic acid (5)
Colorless needles; 1H NMR (400 MHz, DMSO-d6)
δ: 12.04 (2H, s, 2×COOH), 4.95 (1H, br s, 3-OH), 4.69
(1H, br s, H-29a), 4.58 (1H, br s, H-29b), 3.92 (1H, s,
H-3), 2.93(1H, m, H-19), 2.51 (1H, s, H-1), 1.65 (3H,
s, H-30), 0.99 (3H, s, H-23), 0.98 (3H, s, H-25), 0.90
(3H, s, H-24), 0.87 (3H, s, H-26), 0.80 (3H, s, H-27).
13C NMR (100 MHz, DMSO-d6) δ: 66.0 (C-1), 176.6
(C-2), 83.7 (C-3), 43.2 (C-4), 56.4 (C-5), 18.6 (C-6),
34.1 (C-7), 43.0 (C-8), 44.3 (C-9), 48.9 (C-10), 23.6
(C-11), 25.6 (C-12), 38.5 (C-13), 41.6 (C-14), 29.9 (C-15),
32.2 (C-16), 55.9 (C-17), 49.0 (C-18), 47.0 (C-19),
150.8 (C-20), 30.6 (C-21), 36.8 (C-22), 31.2 (C-23),
19.5 (C-24), 18.6 (C-25), 16.6 (C-26), 15.0 (C-27),
177.7 (C-28), 110.1 (C-29), 19.9 (C-30). The 1H NMR
and 13C NMR data were in agreement with those in the
literature[13], and the structure of compound 5 was
identified as ceanothic acid.
3.6. 24-Hydroxyceanothic acid (6)
Colourless flakes; ESI-MS: m/z 501.46 [M-1]–; 1H NMR
(400 MHz, Pyr-d5) δ: 4.92 (1H, s, H-3), 4.83 (1H, br s,
H-29a), 4.64 (1H, br s, H-29b), 4.60 (1H, d, J 10.8 Hz,
H-24a), 3.66 (1H, d, J 10.8 Hz, H-24b), 3.47 (1H, m, H
-19), 3.22 (1H, s, H-1), 1.77 (3H, s, H-23), 1.63 (3H, s,
H-30), 1.43 (3H, s, H-25), 1.09 (3H, s, H-26), 1.02 (3H,
s, H-27). 13C NMR (100 MHz, Pyr-d5) δ: 66.1 (C-1),
177.3 (C-2), 85.5 (C-3), 48.2 (C-4), 56.9 (C-5), 18.2
(C-6), 34.9 (C-7), 41.7 (C-8), 45.1 (C-9), 49.7 (C-10),
24.0 (C-11), 26.0 (C-12), 38.8 (C-13), 43.2 (C-14),
30.3 (C-15), 32.7 (C-16), 56.3 (C-17), 49.5 (C-18),
47.4 (C-19), 150.9 (C-20), 31.0 (C-21), 37.3 (C-22),
25.4 (C-23), 66.4 (C-24), 18.7 (C-25), 16.8 (C-26),
14.8 (C-27), 178.6 (C-28), 109.5 (C-29), 19.3 (C-30).
The 1H NMR and 13C NMR data were in agreement with
those in the literature[14], and the structure of compound 6
was identified as 24-hydroxyceanothic acid.
3.7. Dihydrokaempferol (7)
Yellow needles; 1H NMR (400 MHz, DMSO-d6) δ:
7.32 (2H, d, J 8.3 Hz, H-2′,6′), 6.79 (2H, d, J 8.3 Hz,
H-3′,5′), 5.93 (1H, d, J 1.6 Hz, H-8), 5.89 (1H, d, J 1.6 Hz,
H-6), 5.06 (1H, d, J 11.0 Hz, H-2), 4.59 (1H, d, J 11.0 Hz,
H-3). 13C NMR (100 MHz, DMSO-d6) δ: 82.9 (C-2), 71.5
(C-3), 197.9 (C-4), 163.3 (C-5), 96.1 (C-6), 166.8 (C-7),
95.0 (C-8), 162.6 (C-9), 100.5 (C-10), 127.6 (C-1′),
129.5 (C-2′), 114.9 (C-3′), 157.8 (C-4′), 114.9 (C-5′), 129.5
(C-6′). The 1H NMR and 13C NMR data were in agreement
with those in the literature[15], and the structure of
compound 7 was identified as dihydrokaempferol.
3.8. Eriodictyol (8)
Colorless needles; 1H NMR (400 MHz, CD3OD) δ:
6.93 (1H, s, H-2′), 6.81 (2H, s, H-5′,6′), 5.91 (1H, d,
J 2.0 Hz, H-6), 5.90 (1H, d, J 2.0 Hz, H-8), 5.30 (1H,
dd, J1 13.0 Hz, J2 3.0 Hz, H-2), 3.09 (1H, dd, J1 17.0 Hz,
J2 13.0 Hz, H-3a), 2.71 (1H, dd, J1 17.0 Hz, J2 3.0 Hz,

115 Chen, C. et al. / J. Chin. Pharm. Sci. 2016, 25 (2), 111–115
H-3b). 13C NMR (100 MHz, CD3OD) δ: 79.1 (C-2),
42.7 (C-3), 196.3 (C-4), 163.4 (C-5), 95.6 (C-6), 167.0
(C-7), 94.8 (C-8), 164.1 (C-9), 102.0 (C-10), 130.4 (C-1′),
113.3 (C-2′), 145.1 (C-3′), 145.5 (C-4′), 114.8 (C-5′),
117.8 (C-6′). The 1H NMR and 13C NMR data were in
agreement with those in the literature[16], and the structure
of compound 8 was identified as eriodictyol.
Acknowledgements
This study was supported by the National Natural
Science Foundation of China (Grant No. 81172943). We
are indebted to Prof. Hongzheng Fu for the technical
support, and Xulin Sun and Weiqing Zhang for the NMR
spectra and MS spectra.
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马甲子的化学成分研究
陈晨1,2, 罗观堤3, 胡荣1*, 付宏征2*
1. 扬州大学 医学院, 江苏 扬州 225001
2. 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
3. 广东世信药业有限公司, 广东 揭阳 515500
摘要: 对马甲子地上部分的化学成分进行研究, 采用反复硅胶、葡聚糖凝胶、ODS以及制备型高效液相色谱技术进
行分离纯化。通过质谱和一维、二维核磁共振波谱方法鉴定其结构。从中共分离并鉴定了8个化合物, 分别为3β-羟基-
27-(3,4-二羟基)羽扇豆-20(29)-烯-28-酸 (1),桦木酸 (2), 羽扇豆醇 (3), 27-O-trans-caffeoylcylicodiscic acid (4), 美洲茶酸 (5),
24-羟基美洲茶酸 (6), 二氢山萘酚 (7), 圣草素 (8)。其中, 化合物1是一个新的化合物, 化合物3–4, 7–8为首次从该种植物中
分离得到。
关键词: 马甲子; 化学成分; 结构鉴定