全 文 ： Chemical constituents from the stems of Homalium ceylanicum
Yuan Cao1a, Lei Liu2a, Zhiqin Guo1, Qiang Guo1, Yong Jiang2, Xingyun Chai1*, Pengfei Tu1,2*
1. Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029, China
2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China 
Abstract: By means of solvent extraction and repeated chromatography on silica gel, Sephadex LH-20, HPLC, and preparative
TLC, the ethanol extract of the stems of Homalium ceylanicum (Flacourtiaceae/Salicaceae sensu lato) was chemically investigated,
which led to the isolation of 13 constituents, including five lignans (1–5) and three isocoumarins (6–8). Based on the spectroscopic
analysis and comparison of its 1H NMR and 13C NMR data with those in literatures, their structures were identified as (–)-5-
methoxyisolariciresinol 3α-O-β-D-glucopyranoside (1), (+)-lyoniresinol 3α-O-β-D-glucopyranoside (2), (+)-isolarisiresinol 3α-O-β-D-
glucopyranoside (3), (–)-isolarisiresinol 3α-O-β-D-glucopyranoside (4), icariside E5 (5), 3-phenylisocoumarin (6), homalicine (7),
(–)-dihydrohomalicine (8), friedelin (9), 4-hydroxybenzoic acid (10), catechol (11), methyl-α-arabinofuranoside (12), and
uridine (13). All isolates except compounds 6–8 were described from this genus for the first time. Compound 6 was isolated
from this species for the first time.
Keywords: Homalium ceylanicum; Flacourtiaceae; Salicaceae sensu lato; Homalium; Chemical constituent
CLC number: R932 Document code: A Article ID: 1003–1057(2014)3–165–05
Received: 2013-12-02; Revised: 2013-12-23; Accepted: 2013-12-30.
Foundation item: Program for Changjiang Scholar and Innovative
Team in University (Grant No. 985-2-063-112).
aThese authors contribute to the paper equally.
*Corresponding author. Tel.: 86-10-82802859; 86-10-64286350;
E-mail: pengfeitu@vip.163.com; xingyunchai@yeah.net 
http://dx.doi.org/10.5246/jcps.2014.03.021
1. Introduction
The genus Homalium consists of about 180 to 200 species
all over the world and 12 species and 3 variants are found
in China, mainly distributed in southwestern China and
the Taiwan district. H. ceylanicum is a macrophanerophyte,
6–20 (up to 40) meters high, mainly distributed in Sri Lanka,
India, Laos, Thailand, and in Vietnam there is also
distribution. In China, mainly in Yunnan and Tibet as
an excellent kind of afforestation tree, it grows in valley
woodland and forest margins at an altitude of 630–1200 meters.
Its bark rough, branch lets cylindric, color densely brown,
with white protrusions elliptic lenticels; its wood tough,
fine-grained, origins as a good source of commercial use
for building and furniture and so on[1].
As part of systematic research on the constituents with
biological activity and/or structural novelty from the
Flacouritaceous plants, the stems of H. ceylanicum were
chemically investigated, which led to a series of phenolic
glycosides, especially glycosides of 2,5-dihydroxy benzyl
alcohol which are generally accepted as the chemical character
of Salicaceae[2]. In this paper, we describe 13 other compounds
from this species, including five lignan glycosides: (–)-5-
methoxyisolariciresinol 3α-O-β-D-glucopyranoside (1),








(+)-lyoniresinol 3α-O-β-D-glucopyranoside (2), (+)-
isolarisiresinol 3α-O-β-D-glucopyranoside (3), (–)-
isolarisiresinol 3α-O-β-D-glucopyranoside (4), icariside
E5 (5), three isocoumarins: 3-phenylisocoumarin (6),
homalicine (7), (–)-dihydrohomalicine (8), and five types
of compounds: friedelin (9), 4-hydroxybenzoic acid (10),
catechol (11), methyl-α-arabinofuranoside (12), and
uridine (13) (Fig. 1). All compounds except 6–8 were
described from this genus for the first time. Compound 6
was isolated from this species for the first time[3].
165 Journal of Chinese Pharmaceutical Sciences http://www.jcps.ac.cn
OH
HO
MeO
OH
OMeR
Oglc
OH
HO
MeO
OMe
OMeR2
R1
2 R1 = R2 = OMe
3 R1 = R2 = H
Oglc
OH
OMe
glc-O
HO
MeO OH
5
O
O
6
O
O
Oglc
O
9
N
NH
O
O
O
OH OH
HO
1 R = OMe
4 R = H
13
3 1
4
6
7
1
3
5
1
7 8 1
2
7
9
5
1
1
3
3
3
5
2
4
6
14
9
15
17
20
13
3
4
1
7
18
57
8
9
7 8
9
4
9
Figure 1. Structures of compounds 1–9 and 13.
7 (∆); 8
166 Cao, Y. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 165–169
2. Experimental
2.1. General procedures
Melt point was determined on X-4 digital display
microscopic apparatus, and temperature is not correct. UV
was measured on Cary-300 ultraviolet spectrophotometer.
IR was measured on a Nexus-470 infrared spectrometer.
NMR spectra were recorded on a Varian Unity-500
spectrometer. ESI-MS was performed on a QSTAR
mass instrument. Optical rotation was determined on
a Perkin-Elmer 243B polarimeter. HPLC was achieved on
a Dionex Summit HPLC system (P680 HPLC, UVD 170U
Four-channel UV-Vis detector) and a Waters 600 pump
and Waters 2487 detector. It is equipped with Inertsil
chromatographic column (250 mm×10 mm, 5 μm), Alltech
ODS C18 chromatographic column (250 mm×10 mm,
5 μm). Column chromatography (CC) was performed
with silica gel (200–300 mesh, Qingdao Haiyang Chem.
Inc., China), ODS (50 μm, Merck, Germany), and Sephadex
LH-20 (Pharmacia).
2.2. Materials
The stems of H. ceylanicum were collected in Yunnan
Province and identified by Mr. Jingyun Cui (Xishuangbanna
Tropical Botanical Garden, Chinese Academy of Sciences).
A voucher specimen is deposited in the Herbarium of the
Peking University Modern Research Center for Traditional
Chinese Medicine, Beijing, China (No. HC200505).
2.3. Extraction and isolation
The dried stems (12.5 kg) of H. ceylanicum were
extracted with 80% EtOH (3 times, 2 h each time). After
removal of the solvent by evaporation in reduced vacuum,
the residue was partitioned in H2O and extracted with
petroleum ether (PE), chloroform (CHCl3), ethyl acetate
(EtOAc), and n-butanol successively, to provide the
corresponding extract fractions.
The EtOAc-soluble fraction (about 70 g) was subjected to
CC over silica gel, eluting with a gradient of CHCl3–MeOH
(10:1→0:1, v/v) to yield 4 fractions and compound 9
(30 mg). Compounds 10 (40 mg) and 11 (8 mg) were
obtained from Fr. 2 and Fr. 3, respectively. Fr. 4 was
subjected to silica gel CC, eluting with CHCl3–MeOH
(10:1, v/v) to obtain compound 6 (300 mg).
The n-butanol–soluble fraction (140 g) was subjected
to CC over silica gel (1.0 kg), eluting with a gradient of
CHCl3–MeOH (10:1→1:1, v/v) to yield 65 fractions, of
which Frs. 1–9 were monitored by TLC. Fr. 2 was applied
to HPLC (Alltech ODS C18 250 mm×10 mm, 5 μm,
70% MeOH, 2.5 mL/min, 254 nm and 280 nm) to yield
compounds 7 (20 mg) and 8 (30 mg). Fr. 5 was separated
with Sephadex LH-20 (MeOH) CC to give Frs. 5.1 and
5.2. Fr. 5.1 was further separated with Sephadex LH-20
repeatedly to yield compound 2 (about 3 g), Fr. 5.2 was
further separated with silica gel CC (EtOAc–MeOH–H2O,
20:1:0.1, v/v/v) and then was subjected to an opening
ODS CC, eluting with a gradient of MeOH–H2O (20:80–
55:45, v/v) to yield two main portions Frs. 5.2.1 and
5.2.2. Fr. 5.2.1 was purified with HPLC (Alltech ODS
C18 250 mm×10 mm, 5 μm; 5% MeOH, 2.5 mL/min,
254 nm and 280 nm) to yield compound 13 (20 mg). Fr. 6
was separated with Sephadex LH-20 (MeOH) CC to give
Fr. 6.1 and Fr. 6.2. Fr. 6.1 was further separated with gel
silica CC (EtOAc–MeOH–H2O, 10:1:0.1, v/v/v) to yield
three main portions Frs. 6.1.1–6.1.3. Fr. 6.1.2 was applied
to HPLC (Alltech ODS C18 250 mm×10 mm, 37% MeOH,
2.5 mL/min, 254 nm and 280 nm) to yield compounds 3
(16 mg), 4 (8 mg) and 5 (6 mg). Fr. 6.1.3 was applied
to HPLC (Inertsill ODS C18 250 mm×10 mm, 5 μm,
33% MeOH, 2.5 mL/min, 254 nm and 280 nm) to yield
compound 1 (7 mg). Fr. 8 was separated with Sephadex
LH-20 (MeOH) CC and accompanied with silica gel CC
(EtOAc–MeOH–H2O, 20:1:0.1, v/v/v) to yield compound
12 (10 mg).
3. Identification
3.1. (–)-5-Methoxyisolariciresinol 3α-O-β-D-glucopy-
ranoside (1)
White solid; –4° (c 0.16, MeOH); ESI-MS (isobutane)
m/z 552 (M+, 5); 1H NMR (CD3OD, 500 MHz) δ: 6.60
(1H, s, H-2), 6.15 (1H, s, H-5), 2.84 (1H, dd, J1 8.5 Hz,
J2 16.5 Hz, H-7a), 2.69 (1H, dd, J1 4.0 Hz, J2 16.5 Hz,
H-7b), 1.93 (2H, m, H-8,8), 6.39 (2H, s, H-2,6), 3.75
(3H, s, 3-OCH3), 3.74 (6H, s, 3,5-OCH3), 4.00 (1H, d,
J 8.0 Hz, H-1), 3.78–3.58 (m), 3.23–3.20 (m), 3.10 (1H,
m), 2.99 (1H, m); 13C NMR (CD3OD, 125 MHz) data see
Table 1. These data are in good agreement with those of
(–)-5-methoxyisolariciresinol 3α-O-β-D-glucopyranoside[4].
3.2. (+)-Lyoniresinol 3α-O-β-D-glucopyranoside (2)
White solid; +26.0° (c 0.5, MeOH); ESI-MS m/z
(rel. int.) 605.1 ([M+Na]+, 86.73%), 581.2 ([M–H]+, 13.65%);
1H NMR (CD3OD, 500 MHz) δ: 6.55 (1H, s, H-2), 6.46
(2H, s, H-2,6), 4.64 (1H, d, J 4.0 Hz, H-7), 3.71 (6H,
s, 3,5-OCH3), 4.32 (1H, d, J 7.5 Hz, H-1), 3.81 (3H,
s, -OCH3), 3.73 (3H, s, -OCH3), 4.36–4.24 (m), 3.91–3.20
(m), 2.72–2.61 (m), 2.09–2.03 (m), 1.70–1.65 (m); 13C NMR
(CD3OD, 125 MHz) data see Table 1. These data are in
good agreement with those of (+)-lyoniresinol 3α-O-β-D-
glucopyranoside[4].
25
D[α]
25
D[α]
167 Cao, Y. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 165–169












3.3. (+)-Isolarisiresinol 3α-O-β-D-glucopyranoside (3)
White solid; +45.4° (MeOH, c 0.84), 1H NMR
(CD3OD, 500 MHz) δ: 6.59 (1H, s, H-2), 6.12 (1H, s,
H-5), 2.81–2.72 (2H, m, H-7), 2.06–2.01 (1H, m, H-8),
3.79–3.57 (m, H-9, H-1), 6.73 (1H, d, J 2.0 Hz, H-2),
6.58 (1H, dd, J1 8.0 Hz, J2 2.0 Hz, H-5), 6.68 (1H, d,
J 8.0 Hz, H-6), 4.06 (1H, d, J 8.0 Hz, H-7), 1.80 (1H,
tt, J1 3.0 Hz, J2 10.5 Hz, H-8), 4.03–3.99 (2H, m, H-9),
3.74 (3H, s, -OCH3), 3.74 (3H, s, -OCH3), 3.27–3.12 (m);
13C NMR (CD3OD, 125 MHz) data see Table 1. These data
are in good agreement with those of (+)-isolarisiresinol
3α-O-β-D-glucopyranoside[5].
3.4. (–)-Isolarisiresinol 3α-O-β-D-glucopyranoside (4)
White solid; –32° (c 0.11, MeOH); ESI-MS (isobutane)
m/z 523 ([M+1]+, 2), 522 (M+, 1); 1H NMR (CD3OD,
500 MHz) δ: 6.59 (1H, s, H-2), 2.83 (1H, dd, J1 10.0 Hz,
J2 16.5 Hz, H-7a), 2.68 (1H, dd, J1 3.0 Hz, J2 16.5 Hz,
H-7b), 1.91 (2H, m, H-8, 8), 6.12 (1H, s, H-7), 6.63 (1H,
d, J 2.0 Hz, H-2), 6.59 (1H, dd, J1 8.5 Hz, J2 1.5 Hz,
H-5), 6.68 (1H, d, J 8.0 Hz, H-6), 3.98 (1H, d, J 8.0 Hz,
H-1), 3.75 (3H, s, -OCH3), 3.72 (3H, s, -OCH3), 3.77–3.58
(m), 3.24–3.20 (m), 3.10 (1H, m), 2.99 (1H, m); 13C NMR
(CD3OD, 125 MHz) data see Table 1. These data are in
good agreement with those of (–)-isolarisiresinol 3α-O-β-
D-glucopyranoside[4].
3.5. Icariside E5 (5)
White solid; ESI-MS (+ve ion), m/z 545 [M+Na]+,
m/z 383 [(M+Na)–162]+; 1H NMR (CD3OD, 500 MHz)
δ: 2.91 (1H, dd, J1 5.5 Hz, J2 13.5 Hz, H-7a), 2.67 (1H,
dd, J1 9.0 Hz, J2 13.5 Hz, H-7b), 3.91 (1H, m, H-8),
6.87 (1H, d, J 2.0 Hz, H-2), 6.86 (1H, d, J 2.0 Hz, H-6),
6.53–6.49 (3H, m, H-5,7,2), 6.42 (1H, dd, J1 2.0 Hz,
J2 8.0 Hz, H-8), 6.25 (1H, dt, J1 5.5 Hz, J2 16.5 Hz, H-8),
4.16 (2H, dd, J1 1.5 Hz, J2 5.5 Hz, H-9), 4.62 (1H, d,
J 7.0 Hz, H-1), 3.63 (3H, s, 3-OCH3), 3.77 (3H, s, 3-OCH3),
3.78–3.30 (m), 3.08–3.05 (1H, m); 13C NMR (CD3OD,
125 MHz) data see Table 1. These data are in good
agreement with those of icariside E5[6].
3.6. 3-Phenylisocoumarin (6)
Faint yellow solid; ESI-MS m/z 223 [M+H]+; 1H NMR
(CDCl3, 500 MHz) δ: 6.96 (1H, s, H-4), 7.72 (1H, dt,
J1 1.0 Hz, J2 7.5 Hz, H-7), 8.31 (1H, d, J 7.5 Hz, H-9),
7.89 (2H, dd, J1 1.5 Hz, J2 8.0 Hz, H-2,6), 7.52–7.41
(5H, m); 13C NMR (CDCl3, 125 MHz) δ: 162.3 (C-1),
153.6 (C-3), 101.8 (C-4), 120.6 (C-6), 125.9 (C-7),
134.8 (C-8), 128.1 (C-9), 129.7 (C-10), 132.0 (C-1),
129.9 (C-4), 125.2 (C-5), 128.8 (C-6). These data are in
good agreement with those of 3-phenylisocoumarin[7,8].
3.7. Homalicine (7)
White solid; ESI-MS m/z 423 [M+Na]+; 1H NMR
(DMSO-d6, 500 MHz) δ: 7.16 (1H, dd, J1 2.0 Hz, J2 8.0 Hz,
H-4), 7.69 (1H, d, J 7.0 Hz, H-6), 7.86 (1H, t, J 7.5 Hz,
H-7), 7.45 (1H, t, J 8.0 Hz, H-8), 8.16 (1H, d, J 8.0 Hz,
H-9), 4.94 (1H, d, J 7.0 Hz, H-1), 3.74 (1H, dd, J1 5.0 Hz,
J2 10.0 Hz, C-5), 5.40 (1H, d, J 4.0 Hz, -OH), 5.19
(1H, br s, -OH), 5.11 (1H, d, J 4.5 Hz, -OH), 4.71 (1H,
t, J 5.5 Hz, -OH), 3.50–3.16 (m), 7.61–7.52 (4H, m);
13C NMR (DMSO-d6, 125 MHz) δ: 160.7 (C-1), 151.5
(C-3), 101.9 (C-4), 136.7 (C-5), 126.1 (C-6), 134.8 (C-7),
128.3 (C-8), 129.6 (C-9), 117.9 (C-10),132.4 (C-1), 112.5
(C-2), 157.4 (C-3), 117.4 (C-4), 128.1 (C-5), 119.4
(C-6), 100.2 (C-1), 72.8 (C-2), 76.1 (C-3), 69.3 (C-4),
76.7 (C-5), 60.2 (C-6). These data are in good agree-
ment with those of homalicine[9,10].
3.8. (–)-Dihydrohomalicine (8)
White solid; ESI-MS m/z 425 [M+Na]+; 1H NMR
(DMSO-d6, 500 MHz) δ: 5.66 (1H, dd, J1 3.0 Hz, J2 11.5 Hz,
No. 1b 2a 3b 4b 5b
1 129.2 129.7 129.2 129.2 133.2
2 112.3 107.1 112.5 112.4 115.7
3 147.3 146.9 147.1 147.2 148.4
4 145.3 138.4 145.9 146.0 145.4
5 117.3 147.6 117.4 117.4 113.8
6 133.5 126.3 134.4 133.7 122.6
7 33.6 33.8 33.9 33.6 39.2
8 41.4 40.4 39.6 41.2 42.8
9 65.5 65.7 65.3 65.5 66.8
1 137.9 138.9 138.6 138.7 135.4
2 107.9 107.0 114.4 114.0 109.1
3 149.2 148.2 148.9 149.0 153.4
4 135.1 134.7 145.2 145.3 145.0
5 149.2 148.2 116.1 116.0 138.9
6 107.9 107.0 123.2 123.5 119.1
7 49.5 42.6 48.0 48.6 131.5
8 45.2 46.3 46.0 45.4 129.7
9 70.8 70.7 69.6 70.8 63.7
1 103.9 104.5 105.2 103.8 105.4
2 75.0 74.8 75.2 75.0 76.0
3 77.9 77.4 78.2 77.9 77.9
4 71.4 71.6 71.7 71.4 71.3
5 78.2 78.0 77.9 78.2 78.1
6 62.5 62.9 62.8 62.5 62.5
3-OMe 56.4 56.3 56.5 56.4 –
4-OMe – – – – 56.4
5-OMe – 59.4 – – –
3-OMe 56.9 56.7 56.5 56.5 56.3
5-OMe 56.9 56.7 – – –
7-OMe – – – – –
Table 1. 13C NMR data of compounds 1–5 (at 125 MHz)
a Measured in CD3COCD3; b in CD3OD.
25
D[α]
25
D[α]
168 Cao, Y. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 165–169
H-3), 7.43 (1H, d, J 7.5 Hz, H-6), 7.65 (1H, t, J 7.5 Hz, H-7),
7.34 (1H, t, J 8.0 Hz, H-8), 7.96 (1H, d, J 8.0 Hz, H-9),
7.14 (1H, d, J 8.0 Hz, H-4), 7.46 (1H, t, J 7.5 Hz, H-5),
7.03 (1H, dd, J1 2.0 Hz, J2 8.0 Hz, H-6), 4.88 (1H, d, J 7.0 Hz,
H-1), 3.68 (1H, ddd, J1 2.0 Hz, J2 5.5 Hz, J3 12.5 Hz,
H-5), 5.33 (1H, d, J 5.0 Hz, -OH), 5.11 (1H, d, J 4.5 Hz,
-OH), 5.03 (1H, d, J 5.0 Hz, -OH), 4.57 (1H, t, J 5.5 Hz, -OH),
3.47–3.15 (m); 13C NMR (DMSO-d6, 125 MHz) δ: 164.0
(C-1), 78.5 (C-3), 38.4 (C-4), 139.0 (C-5), 127.3 (C-6), 133.4
(C-7), 124.2 (C-8), 129.0 (C-9), 128.8 (C-10), 139.8 (C-1),
115.5 (C-2), 156.9 (C-3), 113.9 (C-4), 127.1 (C-5), 119.3
(C-6), 99.7 (C-1), 72.7 (C-2), 76.2 (C-3), 69.2 (C-4), 76.5
(C-5), 60.1 (C-6). These data are in good agreement
with those of (–)-dihydrohomalicine[9,10].
3.9. Friedelin (9)
White crystal (in petroleum ether), mp. 261–263 ºC;
ESI-MS m/z 427 [M+H]+, 444 [M+NH4]+; 1H NMR
(CDCl3, 500 MHz) δ: 0.88 (3H, d, J 6.5 Hz, H-3), 0.73
(3H, s, H-24), 0.88 (3H, s, H-25), 1.01 (3H, s, H-26), 1.06
(3H, s, H-27), 1.19 (3H, s, H-28), 1.01 (3H, s, H-29), 0.96
(3H, s, H-30); 13C NMR (CDCl3, 125 MHz) δ: 22.3 (C-1),
41.5 (C-2), 213.3 (C-3), 58.2 (C-4), 42.1 (C-5), 41.3 (C-6),
18.2 (C-7), 53.1 (C-8), 37.4 (C-9), 59.5 (C-10), 35.6 (C-11),
30.5 (C-12), 39.7 (C-13), 38.3 (C-14), 32.8 (C-15), 36.0
(C-16), 30.0 (C-17), 42.8 (C-18), 35.3 (C-19), 28.2 (C-20),
32.4 (C-21), 39.2 (C-22), 6.8 (C-23), 14.6 (C-24), 17.9
(C-25), 20.2 (C-26), 18.7 (C-27), 32.1 (C-28), 31.8 (C-29),
35.0 (C-30). These data are in good agreement with those
of friedelin[11].
3.10. 4-Hydroxybenzoic acid (10)
White crystal (in MeOH), mp. 213–214 ºC; ESI-MS
m/z 244 [M+NH4]+; 1H NMR (CD3OD, 500 MHz) δ: 7.82
(2H, d, J 9.0 Hz, H-2,6), 6.76 (2H, d, J 9.0 Hz, H-3,5);
13C NMR (CD3OD, 125 MHz) δ: 122.6 (C-1), 133.0
(C-2,6), 116.0 (C-3,5), 163.2 (C-4), 170.1 (C-7). These
data are in good agreement with those of 4-hydroxy-
benzoic acid[12].
3.11. Catechol (11)
White crystal (in MeOH), mp. 105 ºC; 1H NMR
(CD3COCD3, 500 MHz) δ: 6.66 (2H, dd, J1 3.5 Hz, J2 6.0
Hz, H-3,6), 6.80 (2H, dd, J1 3.5 Hz, J2 6.0 Hz, H-4,5); 13C
NMR (CD3COCD3-d6, 125 MHz) δ: 146.0 (C-1,2), 116.2
(C-3,6), 120.8 (C-4,5). These data are in good agreement
with those of catechol[13].
3.12. Methyl-α-arabinofuranoside (12)
Colorless power; 1H NMR (CD3OD, 500 MHz) δ: 3.92
(1H, d, J 4.5 Hz, H-1), 3.79–3.51 (m); 13C NMR (CD3OD,
125 MHz) δ: 109.2 (C-1), 82.5 (C-2), 78.9 (C-3), 84.6
(C-4), 62.8 (C-5), 60.5 (-OCH3). These data are in good
agreement with those of methyl-α-arabinofuranoside[14].
3.13. Uridine (13)
White solid; 1H NMR (DMSO-d6, 500 MHz) δ: 11.3
(1H, s, H-3), 5.63 (1H, d, J 8.0 Hz, H-5), 7.88 (1H, d,
J 9.5 Hz, H-6), 5.76 (1H, d, J 5.5 Hz, H-1), 5.38–3.51
(7H, m); 13C NMR (DMSO-d6, 125 MHz) δ: 150.2 (C-2),
162.9 (C-4), 101.3 (C-5), 140.2 (C-6), 87.1 (C-1), 73.0
(C-2), 69.4 (C-3), 84.3 (C-4), 60.3 (C-5). These data are
in good agreement with those of uridine[15].
4. Conclusions
A phytochemical investigation on the stems of H.
ceylanicum led to the isolation and structural identification of
13 compounds, including five lignans, three isocoumarins
and seven other compounds. Except compounds 6–8,
all other compounds were isolated from this genus for
the first time, and 6 was isolated from this species for
the first time. These data will be useful for the further
research and development on its medicinal or economic
values, and also be alternative information for the chemo-
taxonomic study on this genus.
It was pointed out that polyphenols, such as the previously
reported phenolic glycosides[2] and lignans 1–5 from this
species, were mainly evolved for helping plants to adapt to
ecological pressure, including filtering ultraviolet (UV)-B
light, defending against microbial or predator attack, trans-
ferring signals, and enhancing the structural rigidity[16,17]. This
evolutionary view is supported by the experimental results,
for instance, a series of crude extract of Homalium species
was reported to exhibit significant antibacterial activities[18],
although evidence is needed to show the relation with
phenols or lignans. Another example comes from Hussain
M.T. et al[10], who synthesized a series of derivatives of
compounds 6–8, and a biological evaluation exhibited
that this type of compounds displayed very pronounced
antibacterial effects against Pseudomonas aeruginosa,
potentially suggesting that the plants produce 6–8 or its
analogues to fight against the invasion of diverse pathogens.
This explanation will provide inspirations, at least in part,
for the drug discovery from natural products, such as 6–8
and their derivatives by which H. ceylanicum produce to
defense against bacterial could be explored as laxatives,
emetics, cardiotonics and muscle relaxants, because of the
similar physiology between humans and other mammals[16].
Acknowledgements
This work was financially supported by Program for
Changjiang Scholar and Innovative Team in University
(Grant No. 985-2-063-112).
169 Cao, Y. et al. / J. Chin. Pharm. Sci. 2014, 23 (3), 165–169
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斯里兰卡天料木茎的化学成分研究
曹愿1a, 刘蕾2a, 郭志琴1, 郭强1, 姜勇2, 柴兴云1*, 屠鹏飞1,2*
1. 北京中医药大学 中药现代研究中心, 北京 100029
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 

摘要: 对斯里兰卡天料木茎的乙醇提取物进行化学成分研究。应用硅胶柱层析, Sephadex LH-20柱色谱, HPLC和制
备薄层等多种色谱方法进行分离和纯化, 从中分离得到了13个化学成分, 包括5个木脂素类(1–5), 3个异香豆素类(6–8)和7个
其他类化合物。经波谱解析并与文献数据相比对, 其结构分别鉴定为: (–)-5-甲氧基异落叶松脂素3α-O-β-D-吡喃葡萄糖苷 (1),
(+)-南烛木树脂酚-3α-O-β-D-葡萄糖苷 (2), (+)-异落叶松脂素3α-O-β-D-吡喃葡萄糖苷 (3), (–)-异落叶松脂素3α-O-β-D-吡喃
葡萄糖苷 (4), icariside E5 (5), 3-苯基异香豆素 (6), homalicine (7), (–)-dihydrohomalicine (8), 木栓酮 (9), 儿茶酚 (10), 对羟基
苯甲酸 (11), 甲基呋喃阿拉伯糖苷 (12), 尿苷 (13)。除了化合物6–8外, 其他化合物均为首次从该属植物中得到, 化合物6为
首次从该种植物中分离得到。
关键词: 斯里兰卡天料木; 大风子科; 广义杨柳科; 天料木属; 化学成分