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Chemical Constituents from Twigs of Aglaia testicularis C. Y. Wu

马肾果枝条的化学成分研究



全 文 :The genus Aglaia Lour. (Meliaceae) consists
of about 130 species, which are distributed mainly
in the Indo-Malayan region, southern mainland
China, and the Pacific Islands[1]. The cyclopenta[b]
benzofurans and two structurally related groups, the
cyclopenta[bc]benzopyrans and benzo[b]oxepines,
are considered characteristic secondary metabolites
of the genus Aglaia, because they have been isolated
only from this taxon[2]. Many rocaglamide derivatives
exhibit significant insecticidal and antiproliferative
activities[3–4]. Our previous papers reported the phyto-
chemical investigation on Aglaia perviridis[5–6]. Here
we reported the chemical constituents from the twigs of
Aglaia testicularis C. Y. Wu, which is regarded as an
endemic species of the limestone area of southeastern
Yunnan Province, China[7]. Eleven compounds including
an abietane diterpene phlogacantholides B (1), its
glucoside phlogacanthoside A (2), and nine other
马肾果枝条的化学成分研究
夏颖, 贾继荣, 王喆, 杨淑敏*
(首都医科大学化学生物学与药学院, 北京 100069)
摘要: 采用多种色谱方法从马肾果(Aglaia testicularis C. Y. Wu)枝条中分离鉴定了 11 个化合物,分别是火焰花内酯 B (1)、火焰
花内酯苷A (2)、(E)-aglawone (3)、eichlerianic acid (4)、shoreic acid (5)、3β-羟基-5α,8α-表-二氧麦角-6,22-二烯 (6)、豆甾-5-烯-3β,7α-
二醇 (7)、β-谷甾醇 (8)、胡萝卜苷 (9)、东莨菪内酯 (10)、碳二十六酸 (11)。化合物 1 ~ 3, 8 ~ 11 均为首次从该植物中分离得到,
而松香烷二萜内酯类衍生物 1 和 2 则是首次从米仔兰属植物中得到。化合物 1 对人肺癌细胞株 AGZY 83-a 表现出弱的抑制
作用,IC50 值为 20.5 μg mL
-1。这为国产米仔兰属植物的开发应用提供了理论依据。
关键词: 马肾果; 火焰花内酯 B; 火焰花内酯苷 A; 细胞毒活性;化学成分
doi: 10.3969/j.issn.1005–3395.2013.01.007
Chemical Constituents from Twigs of Aglaia testicularis C. Y. Wu
XIA Ying, JIA Ji-rong, WANG Zhe, YANG Shu-min*
(School of Chemical Biology and Pharmaceutical Sciences, Capital Medical University, Beijing 100069, China)
Abstract: Eleven compounds were isolated from the twigs of Aglaia testicularis C. Y. Wu (Meliaceae) by means
of chromatographic technology. On the basis of spectral data, their structures were identified as phlogacantholide
B (1), phlogacanthoside A (2), (E)-aglawone (3), eichlerianic acid (4), shoreic acid (5), 3β-hydroxy-5α,8α-
epidioxyergosta-6,22-diene (6), stigmast-5-en-3β,7α-diol (7), β-sitosterol (8), daucosterol (9), scopoletin (10),
and hexacosanoic acid (11). Compounds 1 – 3 and 8 – 11 were isolated from the plant for the first time, and
the abietane diterpene derivatives, compounds 1 and 2, were not reported previously from the genus Aglaia.
Compound 1 showed weak activity against AGZY 83-a (human lung cancer) cell with the IC50 value of 20.5 μg mL
-1.
The study establishes a theoretical basis for the application of the genus Aglaia distributed in China.
Key words: Aglaia testicularis; Phlogacantholide B; Phlogacanthoside A; Cytotoxicity; Chemical constituents
Received: 2012–05–10    Accepted: 2012–07–10
Supported by a foundation from Talent Training Projects of Beijing (2010D005018000008)
XIA Ying. E-mail: 475966501@qq.com
* Corresponding author. E-mail: xiaoyang618@yahoo.com.cn
热带亚热带植物学报 2013, 21(1): 52~56
Journal of Tropical and Subtropical Botany
第1期 53
compounds, (E)-aglawone (3), eichlerianic acid (4),
shoreic acid (5), 3β-hydroxy-5α,8α-epidioxyergosta-
6,22-diene (6), stigmast-5-en-3β,7α-diol (7), β-sitosterol
(8), daucosterol (9), scopoletin (10), and hexacosanoic
acid (11), were also isolated and identified (Fig. 1).
Among them, compounds 1 – 3 and 8 – 11 were
obtained from this plant for the first time, and
abietane-type diterpene lactone (compounds 1 and 2)
were firstly obtained from the genus Aglaia.
Compounds 1 and 2 were also screened for
anticancer activity against AGZY 83-a (human lung
cancer cells) and SMMC-7721 (human liver cancer
cells).
1 Experimental method
1.1 Plant material
The twigs of Aglaia testicularis were collected
in Malipo County of Yunnan Province, China, in
September 2003, and identified by Professor De-ding
TAO, Kunming Institute of Botany, Chinese Academy
of Sciences, China.
1.2 Instrument
Melting points were measured on an XRC-1
apparatus and uncorrected. Optical rotations were
measured with a JASCO DIP-370 polarimeter. IR
spectra were obtained on a Bio-Rad FTS-135 infrared
spectrophotometer with KBr pellets. 1H NMR spectra
were recorded on Bruker AM-400 and DRX-500
spectrometer with TMS as internal standard, δ in ppm,
J in Hz, 13C NMR spectra were recorded on Bruker
AM-400 spectrometer. MS data recorded on an API
Qstar Pulsar Ⅰ spectrometer. The silica gel for TLC
(GF254) and column chromatography (CC, 200 – 300
mesh) were obtained from Qingdao Meijing Chemical
Inc., China. RP-C18 silica gel (40 – 75 μm, Fuji
silysia Chemical Ltd, Aichi, Japan) and Sephadex LH-
Fig. 1 Structures of compounds 1 – 11
夏颖等:马肾果枝条的化学成分研究
54 第21卷热带亚热带植物学报
20 (Amersham Biosciences, Uppsala, Sweden) were
used for column chromatography.
1.3 Extraction and Isolation
Air-dried and crashed twigs of A. testicularis
(11.5 kg) were extracted three times with methanol
at room temperature. The solvent was evaporated in
vacuo to give a crude extract, which was suspended
in water and extracted four times with ethyl acetate.
After the evaporation of ethyl acetate in vacuo,
extracts (123.4 g) were obtained. 109.6 g of them
were subjected to silica gel column chromatography
(CC, 200 – 300 mesh) using petroleum ether-
ethyl acetate (100:0 – 30:70, V/V) as eluent. By
combining the fractions with TLC (GF254) monitoring,
7 fractions (A – G) were obtained. Fraction B was
repeatedly chromatographed over silica gel eluted
with petroleum ether-acetone (100:0 – 85:15) to
produce 11 (457 mg, yield 0.0040%); fraction C
was repeatedly chromatographed over CC silica gel
eluted with petroleum ether-ethyl acetate (95:5 –
85:15) to give 8 (2.0 g, yield 0.017%); fraction C
was subject to repeated on CC silica gel eluted with
chloroform-acetone (97:3 – 85:15) to obtain 3 (9 mg,
yield 0.000078%), 6 (17 mg, yield 0.00015%), and 7
(24 mg, yield 0.00021%); fraction E was submitted to
repeated on CC silica gel eluted with chloroform-ethyl
acetate (95:5 – 3:1), and then purified on a RP-18
and Sephadex LH-20 column eluted with methanol-
water (50:50 – 100:0) to yield 4 (213 mg, yield
0.0019%) and 5 (135 mg, yield 0.0012%); fraction
F (2.5 g) was subjected to CC silica gel eluted with
chloroform-ethyl acetate (7:3 – 1:1), then purified on
a RP-18 and Sephadex LH-20 column successively
eluted with methanol-water (50:50 – 100:0) to give 1
(210 mg, yield 0.0018%) and 10 (28 mg, yield
0.00024%); fraction G was repeatedly chromatographed
over CC silica gel eluted with chloroform-acetone
(70:30 – 50:50) to afford 9 (2.7 g, yield 0.023%).
The water layer after extracted with ethyl acetate
was subjected to D101 eluted with water and then
with methanol. After the evaporation of methanol in
vacuo, the residues (93.5 g) were chromatographed
over CC silica gel eluted with chloroform-methanol
(95:5 – 6:4) to give 6 fractions (H – M). Fraction
G (18.9 g) was submitted to CC silica gel eluted
with chloroform-methanol (95:5 – 60:40) and then
purified on a RP-18 and Sephadex LH-20 column
successively eluted with methanol-water (from 50:50 –
100:0) to yield 2 (46 mg, yield 0.0004%).
1.4 Bioassays
The anticancer active evaluation of compounds 1
and 2 towards AGZY 83-a (human lung cancer cells)
and SMMC-7721 (human liver cancer cells) by MTT
method was examined, the experimental detail was
just as what had been reported previously[11].
2 Structural identification
Phlogacantholide B (1)[8]  C20H28O4; Colorless
needles (acetone); mp 196℃ – 197℃, [α]D
26.3 –204.9˚
(c 1.02, MeOH); IR (KBr) v: 3421, 2963, 2927, 2854,
1736, 1680, 1635, 1458, 1381, 1153, 1127, 1057,
1015, 990 cm-1; EI-MS m/z (%): 332 [M]+ (2), 314
(11), 301 (38), 283 (26), 271 (100), 241 (7), 231 (26),
219 (35), 201 (21), 192 (27), 180 (84), 162 (53), 154
(45), 145 (23), 135 (28), 123 (100), 109 (40), 105
(46), 91 (54), 79 (36), 67 (32), 55 (37); HR-ESIMS
m/z: 355.1896 (calcd. for C20H28O4Na 355.1885);
1H
NMR (C5D5N, 500 MHz): δ 5.17 (1H, s, H-14), 4.88
(1H, t, J = 8.1 Hz, H-12), 3.98, 3.68 (1H each, both d,
J = 10.8 Hz, H2-19), 2.34 (3H, s, Me-17), 1.16 (3H,
s, Me-18), 1.13 (1H, d, J = 12.6 Hz, H-5), 1.00 (3H,
s, Me-20); 13C NMR (C5D5N, 100 MHz): δ 36.0 (t,
C-1), 19.1 (t, C-2), 36.1 (t, C-3), 39.1 (s, C-4), 52.5 (d,
C-5), 18.8 (t, C-6), 29.6 (t, C-7), 130.7 (s, C-8), 137.2
(s, C-9), 38.4 (s, C-10), 33.3 (t, C-11), 78.2 (d, C-12),
162.8 (s, C-13), 70.0 (d, C-14), 120.8 (s, C-15), 175.2
(s, C-16), 9.5 (q, C-17), 27.9 (q, C-18), 64.3 (t, C-19),
19.5 (q, C-20).
Phlogacanthoside A (2)[8]  Whiter powder;
C26H38O9; [α]D
27.6 –182.4˚ (c 1.53, MeOH); IR (KBr)
v: 3440, 2927, 2853, 1740, 1679, 1638, 1381, 1159,
1074, 1036, 1017, 615, 585 cm-1; FAB+-MS m/z (%):
495 [M + 1]+ (65), 479 (100), 407 (16), 315 (28),
第1期 55
203 (20), 145 (65), 85 (92); HR-ESIMS m/z (%):
517.2421 (calcd. for C26H38O9Na 517.2413);
1H NMR
(CD3OD, 500 MHz): δ 4.94 (1H, s, H-14), 4.77 (1H, t,
J = 8.1 Hz, H-12), 4.20 (1H, d, J = 7.8 Hz, H-1′), 4.08,
3.36 (1H each, both d, J = 9.5 Hz, H2-19), 3.87 (1H,
dd, J = 14.8, 2.2 Hz, H-6′a), 3.68 (1H, dd, J = 14.8,
5.4 Hz, H-6′b), 3.36 (1H, m, H-3′), 3.30 (1H, m, H-4′),
3.25 (1H, m, H-5′), 3.18 (1H, brt, J = 8.0 Hz, H-2′),
1.97 (3H, s, Me-17), 1.27 (1H, d, J = 12.6 Hz, H-5),
1.15 (3H, s, Me-18), 1.05 (3H, s, Me-20); 13C NMR
(CD3OD, 100 MHz): δ 37.2 (t, C-1), 19.8 (t, C-2),
37.0 (t, C-3), 38.9 (s, C-4), 53.8 (d, C-5), 19.5 (t, C-6),
30.1 (t, C-7), 130.9 (s, C-8), 138.7 (s, C-9), 39.4 (s,
C-10), 33.4 (t, C-11), 79.8 (d, C-12), 163.8 (s, C-13),
70.8 (d, C-14), 121.7 (s, C-15), 177.3 (s, C-16), 9.1 (q,
C-17), 28.1 (q, C-18), 73.8 (t, C-19), 19.7 (q, C-20),
105.0 (d, C-1′), 75.2 (d, C-2′), 78.3 (d, C-3′), 71.7 (d,
C-4′), 77.8 (d, C-5′), 62.8 (t, C-6′).
(E)-Aglawone (3)[9]  C21H32O2; White needles
(acetone), mp 123℃ – 125℃; 1H NMR (CDCl3,
500 MHz): δ 6.49 (1H, q, J = 7.5 Hz, H-20), 4.06 (1H,
t, J = 2.6 Hz, H-3), 2.20 (1H, dd, J = 17.0, 7.4 Hz,
H-15a), 1.96 (1H, dd, J = 17.0, 14.5 Hz, H-15b), 1.85
(3H, d, J = 7.5 Hz, Me-21), 1.01 (3H, s, Me-18), 0.83
(3H, s, Me-19); 13C NMR (CDCl3, 100 MHz): δ 31.9
(t, C-1), 28.9 (t, C-2), 66.5 (d, C-3), 36.3 (t, C-4), 39.0
(d, C-5), 28.3 (t, C-6), 31.9 (t, C-7), 34.2 (d, C-8),
54.0 (d, C-9), 36.2 (s, C-10), 20.5 (t, C-11), 35.8 (t,
C-12), 43.4 (s, C-13), 50.1 (d, C-14), 37.9 (t, C-15),
206.8 (s, C-16), 148.0 (s, C-17), 17.8 (q, C-18), 11.2
(q, C-19), 128.8 (d, C-20), 13.2 (q, C-21).
Eichlerianic acid (4)[10]  C30H50O4; Colorless
crystal (acetone), mp 124℃ – 126℃; FAB–-MS m/z
(%): 473 [M – 1]– (100), 371 (12), 339 (5); 1H NMR
(CDCl3, 500 MHz): δ 4.78, 4.60 (1H each, both s, H2-
28), 3.55 (1H, m, H-24), 1.67 (3H, s, Me-29), 1.23
(3H, s, Me-27), 1.09 (3H, s, Me-26), 1.07 (3H, s, Me-
21), 0.96 (3H, s, Me-30), 0.83 (3H, s, Me-18), 0.79
(3H, s, Me-19); 13C NMR (CDCl3, 100 MHz): δ 24.5
(t, C-1), 34.3 (t, C-2), 177.2 (s, C-3), 147.5 (t, C-4),
41.0 (d, C-5), 31.3 (t, C-6), 33.7 (t, C-7), 39.8 (s, C-8),
49.6 (d, C-9), 38.9 (s, C-10), 22.2 (t, C-11), 25.7 (t,
C-12), 42.8 (d, C-13), 50.3 (s, C-14), 28.1 (t, C-15),
26.7 (t, C-16), 50.5 (d, C-17), 15.2 (q, C-18), 20.1 (q,
C-19), 86.6 (s, C-20), 23.8 (q, C-21), 34.5 (t, C-22),
26.3 (t, C-23), 83.2 (q, C-24), 70.5 (s, C-25), 24.5 (q,
C-26), 27.3 (q, C-27), 113.2 (s, C-28), 23.1 (q, C-29),
16.1 (q, C-30).
Shoreic acid (5)[11]  C30H50O4; Colorless crystal
(acetone), mp 103℃ – 104℃; 1H NMR (CDCl3,
500 MHz): δ4.87, 4.66 (1H each, both brs, H2-28),
3.65 (1H, m, H-24), 1.73 (3H, s, Me-29), 1.19 (3H, s,
Me-27), 1.14 (3H, s, Me-21), 1.11 (3H, s, Me-26), 1.01
(3H, s, Me-18), 0.89 (3H, s, Me-30), 0.85 (3H, s, Me-
19); 13C NMR (CDCl3, 100 MHz): δ 28.2 (t, C-1),
33.9 (t, C-2), 179.2 (s, C-3), 147.5 (t, C-4), 41.2 (d,
C-5), 24.6 (t, C-6), 34.3 (t, C-7), 40.1 (s, C-8), 50.8
(d, C-9), 39.1 (s, C-10), 22.2 (t, C-11), 26.9 (t, C-12),
42.9 (d, C-13), 50.4 (s, C-14), 31.5 (t, C-15), 25.8 (t,
C-16), 49.8 (d, C-17), 15.3 (q, C-18), 20.2 (q, C-19),
86.6 (s, C-20), 27.1 (q, C-21), 34.8 (t, C-22), 26.3 (t,
C-23), 86.3 (q, C-24), 70.4 (s, C-25), 27.8 (q, C-26),
24.0 (q, C-27), 113.4 (s, C-28), 23.2 (q, C-29), 16.3 (q,
C-30).
3β-Hydroxy-5α,8α-epidioxyergosta-6,22-diene
(6)[12]  C28H44O3; Colorless needles (acetone), mp
180℃ – 182℃; EI-MS m/z (%): 428 [M]+(2), 410 (4),
396 (100), 376 (5), 363 (17), 352 (3), 337 (8), 271
(4), 253 (8), 197 (2), 175 (2), 143 (3), 107 (3), 95 (4),
69 (10), 58 (15); 1H NMR (CDCl3, 500 MHz): δ 6.48
(1H, d, J = 8.1 Hz, H-7), 6.22 (1H, d, J = 8.3 Hz, H-6),
5.19 (1H, dd, J = 15.2, 7.6 Hz, H-23), 5.12 (1H, dd,
J = 15.2, 7.6 Hz, H-22), 3.94 (1H, m, H-3), 0.91 (3H,
d, J = 6.4 Hz, Me-28), 0.88 (3H, s, Me-19), 0.84 (3H,
d, J = 6.6 Hz, Me-26), 0.83 (3H, s, Me-18), 0.82 (3H,
d, J = 6.4 Hz, Me-27); 13C NMR (CDCl3, 100 MHz): δ
34.6 (t, C-1), 30.1 (t, C-2), 66.4 (d, C-3), 36.9 (t, C-4),
82.1 (s, C-5), 135.4 (d, C-6), 130.7 (d, C-7), 79.4 (s,
C-8), 51.4 (d, C-9), 37.1 (s, C-10), 23.4 (t, C-11), 39.3
(t, C-12), 44.5 (s, C-13), 51.6 (d, C-14), 20.6 (t, C-15),
28.6 (t, C-16), 56.2 (d, C-17), 12.8 (q, C-18), 18.2 (q,
C-19), 39.7 (d, C-20), 20.9 (q, C-21), 135.1 (d, C-22),
132.4 (d, C-23), 42.7 (d, C-24), 33.0 (d, C-25), 19.9 (q,
C-26), 19.6 (q, C-27), 17.6 (q, C-28).
Stigmast-5-en-3β,7α-diol (7)[13]  C29H50O2;
White needles (acetone), mp 218℃ – 220℃; EI-MS
夏颖等:马肾果枝条的化学成分研究
56 第21卷热带亚热带植物学报
m/z (%): 430 [M]+ (25), 412 (100), 398 (35), 271 (8),
252 (7), 229 (6), 211 (6), 175 (8), 161 (12), 147 (11),
135 (15), 109 (10), 93 (13), 81 (19), 69 (21), 55 (35);
1H NMR (CDCl3, 400 MHz): δ 5.58 (1H, dd, J = 6.5,
1.8 Hz, H-6), 3.83 (1H, brs, H-7), 3.56 (1H, m, H-3),
1.03 (3H, s, Me-19), 0.90 (3H, d, J = 6.4 Hz, Me-
21), 0.82 (3H, t, J = 7.8 Hz, Me-29), 0.78 (3H, d, J =
4.4 Hz, Me-27), 0.77 (3H, d, J = 6.7 Hz, Me-26), 0.66
(3H, s, Me-18); 13C NMR (CDCl3, 100 MHz): δ 37.1
(t, C-1), 31.4 (t, C-2), 71.4 (d, C-3), 42.1 (t, C-4),
146.3 (s, C-5), 123.9 (d, C-6), 65.4 (d, C-7), 37.6 (d,
C-8), 42.2(d, C-9), 37.3 (s, C-10), 20.8 (t, C-11), 39.2
(t, C-12), 42.3 (s, C-13), 49.5 (d, C-14), 24.3 (t, C-15),
29.3 (t, C-16), 55.8 (d, C-17), 11.7 (q, C-18), 19.1 (q,
C-19), 36.1 (d, C-20), 18.3 (q, C-21), 34.0 (t, C-22),
28.3 (t, C-23), 45.9 (d, C-24), 29.3 (d, C-25), 18.8 (q,
C-26), 19.8 (q, C-27), 23.1 (t, C-28), 12.0 (q, C-29).
β-sitosterol (8), daucosterol (9), and scopoletin
(10) were identified by TLC with standard samples,
respectively.
Hexacosanoic acid (11)[14]  C26H52O2;White
powder, EI-MS m/z (%): 396 [M]+ (6), 382 (20), 368
(75), 354 (73), 340 (64), 325 (23), 311 (30), 297 (34),
283 (31), 269 (35), 255 (33), 241 (44), 227 (35), 213
(29), 199 (32), 185 (83), 171 (49), 157 (21), 143 (23),
129 (100), 111 (36), 97 (43), 85 (22).
3 Result and discussion
Compounds 1 – 3 and 8 – 11 were obtained from
this plant for the first time, and abietane-type diterpene
lactone 1 and 2 were firstly obtained from the genus
Aglaia. Rocaglamides, the characteristic components
of the genus Aglaia, were not isolated in our experiment.
Compounds 1 and 2 were screened for anticancer
activity against AGZY 83-a (human lung cancer
cells) and SMMC-7721 (human liver cancer cells).
Compound 1 exerted weak activity against AGZY
83-a with the IC50 value of 20.5 μg mL
-1, Compound
2 exhibited weaker activities against AGZY 83-a and
SMMC-7721 with IC50 values of 52.6 μg mL
-1 and
49.2 μg mL-1, respectively.
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