全 文 ：270 Chin J Nat Med July 2010 Vol. 8 No. 4 2010 年 7 月 第 8 卷 第 4 期








Chemical Constituents from the Roots of Dysoxylum
densiflorum

LI Chang-Song1, 2, YU Hong-Wei1, LI Guo-You1, ZHANG Guo-Lin1*
1Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 640041;
2Graduate School of Chinese Academy of Sciences, Beijing 100039, China
[ABSTRACT] AIM: To investigate the chemical constituents in the roots of Dysoxylum densiflorum (Blume) Miq..
METHODS: Chromatographic methods were used for separation, and spectroscopic techniques for the identification of
isolated compounds. RESULTS: Thirteen compounds were isolated and identified as β-amyrenone (1), richenone (2),
β-sitosterol (3), cabraleadiol (4), β-amyrin (5), hydroxydammarenone-Ⅱ (6), cabraleadiol monoacetate (7), ocotillone
(8), 3β-hydroxy-5-pregnen-20-one (9), 3β-hydroxy-5α-pregnan-20-one (10), cabraleahydroxylactone (11), toosendan-
sterol B (12) and (-)-epicatechin (13). CONCLUSION: Steroids, triterpenoids and flavonoids are the major constituents
of the roots in Dysoxylum densiflorum. Compounds 1-13 were reported from this plant for the first time, and toosendan-
sterol B (12) from the genus of Dysoxylum for the first time.
[KEY WORDS] Dysoxylum densiflorum; Triterpene; Steroid
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2010)04-0270-04
doi: 10.3724/SP. J. 1009.2010.00270
1 Introduction
The genus Dysoxylum (Meliaceae), mainly distributed
in India and Southeast Asia, is comprised of about 200 spe-
cies, among which 14 are native to China. Many chemical
studies on the plants of this genus resulted in the isolation
of various types of compounds such as limonoids [1-4], di-
terpenoids [5] and alkaloids [6].
D. densiflorum (Blume) Miq. is high value leafy tim-
ber tree, endemic to Xishuangbanna. Degraded limonoids,
sesquiterpenoids, triterpenoids, ligans and steroids were
isolated from the twigs and leaves of D. densiflorum [7], but
no chemical studies on its roots have been reported. In this
paper, thirteen compounds were isolated from the ethanol
extract from the roots of D. densiflorum and identified as
β-amyrenone (1), richenone (2), β-sitosterol (3), cabra-
leadiol (4), β-amyrin (5), hydroxydammarenone-Ⅱ (6),
cabraleadiol monoacetate (7), ocotillone (8), 3β-hydroxy-5-
pregnen-20-one (9), 3β-hydroxy-5α-pregnan-20-one (10),
cabraleahydroxylactone (11), toosendansterol B (12) and
(-)-epicatechin (13).
2 Apparatus and Reagents
Melting point data: X-6 precise melting point appara-
tus (Beijing Fukai Science and Technology Development
Co., Ltd.); Optical rotations: Perkin-Elmer 341 polarimeter;

[Received on] 19-Mar-2010
[*Corresponding author] ZHANG Guo-Lin: Prof., Tel:
86-28-85225401, E-mail: zhanggl@cib.ac.cn
FT-IR spectra: Perkin-Elmer spectrum one FT-IR spec-
trometer; NMR spectra: Bruker Advance 600 spectrometer
(1H: 600 MHz; 13C: 150 MHz), with TMS internal standard;
ESI-MS spectra: Finnigan LCQDECA ion trap mass spec-
trometer; HR-ESI-MS spectra Bruker BioTOF-Q mass
spectrometer (Bruker Daltonics, Billerica, MA, USA). Sil-
ica gel (200-300 μm, Qingdao Marine Chemical Co., Ltd.),
Rp-C18 (40-63 μm, Merck KGaA, Darmstadt, Germany),
MCI gel (CHP 20P, 75–150 μm; Mitsubishi Chemical In-
dustries, Tokyo, Japan)
3 Plant Material
The roots of D. densiflorum (Blume) Miq. were col-
lected in Jinghong County of Yunnan Province, China, in
July 2008. A voucher specimen (08-43) was authenticated
by Prof. CUI Jing-Yun at Xishuangbanna Tropical Botani-
cal Garden, Chinese Academy of Sciences (CAS), and de-
posited in the Herbarium of the Chengdu Institute of Biol-
ogy, Chinese Academy of Sciences, CAS.
4 Extraction and Isolation
The air-dried roots of Dysoxylum densiflorum (10 kg)
were powdered and soaked with 95% ethanol. The extracts
(900 g) were suspended in water and partitioned with pe-
troleum ether, ethyl acetate and n-butanol, successively. The
EtOAc extracts (100 g) were separated over silica gel col-
umn with a CHCl3-MeOH gradient elution to yield Frs.1-4
based on TLC analysis. Frs. 2-4 were separated by repeated
column chromatography over normal and reverse silica gel,
LI Chang-Song, et al. /Chinese Journal of Natural Medicines 2010, 8(4): 270−273
2010 年 7 月 第 8 卷 第 4 期 Chin J Nat Med July 2010 Vol. 8 No. 4 271

and MCI to afford compounds 1 (300 mg), 2 (30 mg), 3
(700 mg), 4 (500 mg), 5 (500 mg), 6 (150 mg), 7 (10 mg), 8
(260 mg), 9 (8 mg), 10 (17mg), 11 (100 mg), 12 (300 mg)
and 13 (2 g), respectively.
5 Identification
β-Amyrenone (1) colorless needles (EtOAc), mp:
166-167 °C. C30H48O, ESI-MS m/z 447 [M + Na] +. 1H
NMR (600 MHz, CDCl3) δ: 1.09 (3H, s, H-23), 1.05 (3H, s,
H-24), 1.07 (3H, s, H-25), 1.02 (3H, s, H-26), 1.14 (3H, s,
H-27), 0.87 (6H, s, H-29 and H-30), 0.84 (3H, s, H-28),
5.21 (1H, dd, J = 3.7, 3.4 Hz, H-12). 13C NMR (150 MHz,
CDCl3) δ: 39.3 (C-1), 34.2 (C-2), 217.7 (C-3), 47.9 (C-4),
55.3 (C-5), 19.7 (C-6), 32.2 (C-7), 39.8 (C-8), 46.9 (C-9),
36.7 (C-10), 23.6 (C-11), 121.5 (C-12), 145.3 (C-13), 41.9
(C-14), 26.1 (C-15), 26.9 (C-16), 32.5 (C-17), 47.3 (C-18),
46.8 (C-19), 31.1 (C-20), 34.7 (C-21), 37.1 (C-22), 26.5
(C-23), 21.5 (C-24), 15.2 (C-25), 16.7 (C-26), 25.9 (C-27),
28.4 (C-28), 33.3 (C-29), 23.7 (C-30). This compound was
identified by comparison of the physical and spectral data
with those reported [8].
(20S, 24S)-Epoxy-25(26)-en-dammaran-3-one (ri-
chenone, 2) colorless needles (EtOAc), mp: 140-141 °C.
20[ ]Da =+53° (c 0.16, CHCl3), C30H48O2, ESI-MS m/z 463 [M
+ Na] +. 1H NMR (600 MHz, CDCl3) δ: 0.89, 0.95, 1.02,
1.04, 1.09, 1.18, 1.71 (3H, each, 7 × CH3), 2.46 (2H, m,
H-2), 4.24 (1H, dd, J = 8.9, 3.3 Hz, H-24), 4.78 (1H, s,
H-26), 5.00 (1H, s, H-26). 13C NMR (150 MHz, CDCl3) δ:
39.9 (C-1), 34.1 (C-2), 218.1 (C-3), 47.4 (C-4), 55.3 (C-5),
19.7 (C-6), 34.6 (C-7), 40.3 (C-8), 49.8 (C-9), 36.8 (C-10),
22.3 (C-11), 25.8 (C-12), 43.1 (C-13), 49.9 (C-14), 31.4
(C-15), 26.9 (C-16), 50.1 (C-17), 15.2 (C-18), 16.1 (C-19),
86.6 (C-20), 26.5 (C-21), 35.2 (C-22), 26.9 (C-23), 82.8
(C-24), 146.2 (C-25), 110.3 (C-26), 17.8 (C-27), 26.8
(C-28), 20.9 (C-29), 16.2 (C-30). The physical and spectral
data are in accordance with those reported [9].
β-Sitosterol (3) white powder. It was characterized by
comparing it with authentic sample on TLC.
(20S, 24S)-Epoxydammarane-3α, 25-diol
(cabraleadiol, 4) colorless needles (EtOAc), mp: 170-172
°C. 20[ ]Da =+15° (c 0.10, CHCl3), C30H52O3, ESI-MS m/z:
483 [M + Na] +. 1H NMR (600 MHz, CDCl3) δ: 3.64 (1H, m,
H-24 ), 3.39 (1H, s, H-3), 0.84 (3H, s, H-29), 0.86 (3H, s,
H-19), 0.89 (3H, s, H-30), 0.94 (3H, s, H-28), 0.97 (3H, s,
H-18), 1.11 (3H, s, H-27), 1.15 (3H, s, H-21), 1.19 (3H, s,
H-26). 13C NMR (150 MHz, CDCl3) δ: 33.7 (C-1), 25.4
(C-2), 76.3 (C-3), 37.6 (C-4), 49.6 (C-5), 18.3 (C-6), 35.2
(C-7), 40.6 (C-8), 50.6 (C-9), 37.3 (C-10), 21.6 (C-11), 27.0
(C-12), 42.8 (C-13), 50.2 (C-14), 31.4 (C-15), 25.8 (C-16),
49.8 (C-17), 15.5 (C-18), 16.1 (C-19), 86.5 (C-20), 27.1
(C-21), 34.9 (C-22), 26.4 (C-23), 86.3 (C-24), 70.3 (C-25),
27.8 (C-26), 24.1 (C-27), 28.3 (C-28), 22.1 (C-29), 16.5
(C-30). The physical and spectral data resemble those re-
ported [10].
β-Amyrin (5) colorless needles (EtOAc), mp:
196-199 °C. C30H50O, ESI-MS m/z 449 [M + Na] +. 1H
NMR (600 MHz, CDCl3) δ: 0.79, 0.83, 0.87, 0.87, 0.94,
0.97, 0.99, 1.13 (3H, each, 8 × CH3), 5.18 (1H, dd, J = 3.7,
3.4 Hz, H-12). 13C NMR (150 MHz, CDCl3) δ: 38.6 (C-1),
26.2 (C-2), 79.0 (C-3), 38.8 (C-4), 55.2 (C-5), 18.4 (C-6),
32.7 (C-7), 39.8 (C-8), 47.7 (C-9), 37.2 (C-10), 26.9 (C-11),
121.7 (C-12), 145.2 (C-13), 41.7 (C-14), 28.1 (C-15), 25.9
(C-16), 32.5 (C-17), 47.3 (C-18), 46.8 (C-19), 31.1 (C-20),
34.7 (C-21), 36.9 (C-22), 27.3 (C-23), 15.5 (C-24), 15.6
(C-25), 16.8 (C-26), 23.7 (C-27), 28.4 (C-28), 33.3 (C-29),
23.5 (C-30). The physical and spectral data are in agree-
ment with those of β-amyrin [11].
Hydroxydammarenone-Ⅱ (6) white powder, mp:
127-130 °C. 20[ ]Da =+62° (c 0.16, CHCl3), C30H50O2,
ESI-MS m/z 465 [M + Na] +. 1H NMR (600 MHz, CDCl3) δ:
5.11 (1H, m, H-24), 2.50 (1H, m, H-2), 2.43 (1H, m, H-2),
0.89, 0.94, 1.00, 1.03, 1.08, 1.15, 1.62, 1.68 (3H, each, 8 ×
CH3). 13C NMR (150 MHz, CDCl3) δ: 39.8 (C-1), 34.0
(C-2), 218.0 (C-3), 47.4 (C-4), 55.3 (C-5), 19.6 (C-6), 34.5
(C-7), 40.2 (C-8), 49.9 (C-9), 36.8 (C-10), 22.0 (C-11), 27.5
(C-12), 42.4 (C-13), 50.2 (C-14), 31.1 (C-15), 24.7 (C-16),
49.7 (C-17), 15.9 (C-18), 15.2 (C-19), 75.3 (C-20), 25.4
(C-21), 40.5 (C-22), 22.5 (C-23), 124.7 (C-24), 131.4
(C-25), 25.7 (C-26), 17.6 (C-27), 26.7 (C-28), 20.9 (C-29),
16.3 (C-30). The physical and spectral data are in consistent
with those reported [12].
Cabraleadiol monoacetate (7) white powder, mp:
148-151 °C. 20[ ]Da =0° (c 0.14, CHCl3), C32H54O4, ESI-MS
m/z 525 [M + Na] +, 541 [M + K] +. 1H NMR (600 MHz,
CDCl3) δ: 0.84 (3H, s, H-29), 0.87 (3H, s, H-19), 0.89 (3H,
s, H-29), 0.92 (3H, s, H-30), 0.98 (3H, s, H-18), 1.11 (3H, s,
H-21), 1.15 (3H, s, H-2), 1.19 (3H, s, H-26), 3.64 (1H, m,
H-24 ), 4.63 (1H, m, H-3), 2.08 (3H, s, -COCH3 ). 13C
NMR (150 MHz, CDCl3) δ: 34.3 (C-1), 22.9 (C-2), 78.4
(C-3), 36.7 (C-4), 50.7 (C-5), 18.1 (C-6), 35.1 (C-7), 40.6
(C-8), 50.6 (C-9), 37.2 (C-10), 21.6 (C-11), 26.9 (C-12),
42.8 (C-13), 50.1 (C-14), 31.4 (C-15), 25.8 (C-16), 49.8
(C-17), 15.5 (C-18), 16.0 (C-19), 86.5 (C-20), 27.1 (C-21),
34.8 (C-22), 26.4 (C-23), 86.3 (C-24), 70.2 (C-25), 27.7
(C-26), 24.1 (C-27), 27.8 (C-28), 21.7 (C-29), 16.6 (C-30),
21.3 (CH3CO), 170.7 (C = O). The physical and spectral
data are in agreement with those reported [10].
Ocotillone (8) white powder, mp: 160-162 °C.
20[ ]Da = +52° (c 0.13, CHCl3), C30H50O3, ESI-MS m/z 481[M
+ Na] +. 1H NMR (600 MHz, CDCl3) δ: 3.64 (1H, m, H-24 ),
2.45 (2H, m, H-2), 0.88 (3H, s, H-18), 0.94 (3H, s, H-28),
1.01 (3H, s, H-30), 1.04 (3H, s, H-29), 1.08 (3H, s, H-19),
1.11 (3H, s, H-21), 1.15 (3H, s, H-26), 1.19 (3H, s, H-27).
13C NMR (150 MHz, CDCl3) δ: 39.9 (C-1), 34.1 (C-2),
218.1 (C-3), 47.4 (C-4), 55.4 (C-5), 19.7 (C-6), 34.6 (C-7),
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272 Chin J Nat Med July 2010 Vol. 8 No. 4 2010 年 7 月 第 8 卷 第 4 期

40.3 (C-8), 50.2 (C-9), 36.8 (C-10), 22.3 (C-11), 27.0
(C-12), 43.0 (C-13), 50.0 (C-14), 31.4 (C-15), 26.4 (C-16),
49.8 (C-17), 16.0 (C-18), 15.2 (C-19), 86.5 (C-20), 24.1
(C-21), 34.8 (C-22), 25.8 (C-23), 86.4 (C-24), 70.3 (C-25),
27.1 (C-26), 26.7 (C-27), 27.8 (C-28), 20.9 (C-29), 16.3
(C-30). The physical and spectral data are in consistent with
those of ocotillone [13].
3β-Hydroxy-5-pregnen-20-one (9) white powder, mp:
190-193°C. 20[ ]Da =+25° (c 0.22, CHCl3), C21H32O2, ESI-MS
m/z 339 [M + Na] +, 355[M + K] +. 1H NMR (600 MHz,
CDCl3) δ: 0.62 (3H, s, H-19), 1.08 (3H, s, H-18), 2.11 (3H,
s, H-21), 3.51 (1H, m, H-3), 5.34 (1H, t, J = 2.3 Hz, H-6),
2.52 (1H, m, H-17). 13C NMR (150 MHz, CDCl3) δ: 37.3
(C-1), 31.5 (C-2), 71.7 (C-3), 42.3 (C-4), 140.8 (C-5), 121.4
(C-6), 31.6 (C-7), 31.8 (C-8), 50.0 (C-9), 36.5 (C-10), 21.1
(C-11), 38.8 (C-12), 43.9 (C-13), 56.9 (C-14), 24.4 (C-15),
22.8 (C-16), 63.7 (C-17), 13.2 (C-18), 19.4 (C-19), 209.4
(C-20), 31.9 (C-21). This compound was identified by
comparison of its physical and spectral data with those re-
ported [14].
3β-Hydroxy-5α-pregnan-20-one (10) white powder,
mp: 226-228°C. 20[ ]Da =+88° (c 0.17, CHCl3). C21H34O2,
ESI-MS m/z 341 [M + Na] +, 357 [M + K] +. 1H NMR (600
MHz, CDCl3) δ: 0.60 (3H, s, H-18), 0.81 (3H, s, H-19),
2.11 (3H, s, H-21), 3.59 (1H, m, H-3), 2.51 (1H, m, H-17).
13C NMR (150 MHz, CDCl3) δ: 37.0 (C-1), 32.0 (C-2), 71.3
(C-3), 38.2 (C-4), 44.8 (C-5), 28.6 (C-6), 31.5 (C-7), 35.5
(C-8), 54.3 (C-9), 35.5 (C-10), 21.3 (C-11), 39.1 (C-12),
44.2 (C-13), 56.7 (C-14), 24.4 (C-15), 22.8 (C-16), 63.8
(C-17), 13.4 (C-18), 12.3 (C-19), 209.6 (C-20), 31.5 (C-21).
The physical and spectral data are in accordance with those
reported [15].
Cabraleahydroxylactone (11) white powder, mp:
240-243°C. 20[ ]Da =+11° (c 0.09, CHCl3), C27H44O3, ESI-MS
m/z 439 [M + Na] +. 1H NMR (600 MHz, CDCl3) δ: 0.84
(3H, s, H-25), 0.86 (3H, s, H-19), 0.90 (3H, s, H-27), 0.94
(3H, s, H-26), 0.96 (3H, s, H-18), 1.36 (3H, s, H-21), 3.39
(1H, brs, H-3), 2.64 (1H, m, H-23β), 2.54 (1H, m, H-23α),
2.11 (1H, m, H-22β), 1.92 (1H, m, H-22α), 1.98 (1H, m,
H-17), 1.82 (1H, m, H-16), 1.75 (1H, m, H-12β). 13C NMR
(150 MHz, CDCl3) δ: 33.6 (C-1), 25.4 (C-2), 76.2 (C-3),
37.6 (C-4), 49.5 (C-5), 18.2 (C-6), 35.1 (C-7), 50.3 (C-8),
50.4 (C-9), 37.3 (C-10), 26.8 (C-11), 21.3 (C-12), 43.2
(C-13), 40.6 (C-14), 31.2 (C-15), 25.0 (C-16), 49.4 (C-17),
15.5 (C-18), 16.0 (C-19), 90.1 (C-20), 25.4 (C-21), 31.2
(C-22), 29.2 (C-23), 176.7 (C-24), 22.1 (C-25), 28.3 (C-26),
16.3 (C-27). This compound was identified by comparison
of the physical and spectral data with those reported [16].
(3α, 20S)-Dihydroxy-5α-pregnan-16-one (toosen-
dansterol B, 12) white powder, mp: 174-176 °C. 20[ ]Da =−72°
(c 0.12, CHCl3), C21H34O3, ESI-MS m/z 357 [M + Na] +. 1H
NMR (600 MHz, CDCl3) δ: 0.79 (3H, s, H-18), 0.81 (3H, s,
H-19), 1.21 (3H, d, J = 6.3 Hz, H-21), 1.83 (1H, d, J = 9.0
Hz, H-17α), 3.98 (1H, m, H-20), 4.06 (1H, br s, H-3β), 4.44
(1H, br s, 20-OH). 13C NMR (150 MHz, CDCl3) δ：31.9
(C-1), 28.9 (C-2), 66.4 (C-3), 35.8 (C-4), 39.0 (C-5), 28.2
(C-6), 32.0 (C-7), 34.1 (C-8), 54.1 (C-9), 36.2 (C-10), 20.1
(C-11), 38.8 (C-12), 41.9 (C-13), 50.8 (C-14), 38.9 (C-15),
223.0 (C-16), 66.0 (C-17), 13.5 (C-18), 11.2 (C-19), 69.3
(C-20), 21.6 (C-21). This compound was identified by
comparison of the physical and spectral data with those
reported [17].
(-)-Epicatechin (13) light yellow powder, mp:
242-243 °C. 20[ ]Da =−61° (c 0.40, MeOH), C15H14O6,
ESI-MS m/z 313 [M + Na] +. 1H NMR (600 MHz, CD3OD)
δ: 6.98 (1H, d, J = 1.8 Hz, H-2′), 6.75 (1H, d, J = 7.8 Hz,
H-5′), 6.79 (1H, dd, J = 7.8, 1.8 Hz, H-6′), 5.94 (1H, d, J =
2.5 Hz, H-8), 5.92 (1H, d, J = 2.5 Hz, H-6), 4.56 (1H, s,
H-2β), 4.17 (1H, m, H-3β), 2.86 (1H, dd, J = 16.5, 4.5 Hz,
H-4α), 2.72 (1H, dd, J = 16.5, 2.6 Hz, H-4β). 13C NMR
(150 MHz, CD3OD) δ: 79.7 (C-2), 67.7 (C-3), 29.1 (C-4),
157.8 (C-5), 95.7 (C-6), 157.4 (C-7), 96.2 (C-8), 157.2
(C-9), 99.9 (C-10), 132.1 (C-1′), 115.2 (C-2′), 145.6 (C-3′),
145.8 (C-4′), 115.7 (C-5′), 119.1 (C-6′). The physical and
spectral data resemble those reported [18].
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密花樫木根的化学成分
李昌松 1, 2, 余红伟 1, 李国友 1, 张国林 1*
1 中国科学院成都生物所, 成都 640041
2 中国科学院研究生院, 北京 100039
【摘 要】 目的：阐阐阐阐阐阐(Dysoxylum densiflorum (Blume) Miq.)根的化学成分进行研究。方法：运用多种层析
手段进行分离纯化, 通过波谱数据和理化性质进行化合物的鉴定。结果：分离鉴定了 13 个化合物, 分别为 β-白檀酮
(β-amyrenone, 1)、richenone (2)、β-谷甾醇 (β-sitosterol, 3)、cabraleadiol (4)、β-香树脂醇 (β-amyrin, 5)、龙脑香醇酮 (hy-
droxydammarenone- , Ⅱ 6) 、 cabraleadiol monoacetate (7) 、 ocotillone (8) 、 3β-hydroxy-5-pregnen-20-one (9) 、
3β-hydroxy-5α-pregnan-20-one (10)、cabraleahydroxylactone (11)、川楝子甾醇 B [(3α, 20S)-dihydroxy-5α-pregnan-16-one, 12]、
表儿茶素 [(-)-epicatechin, 13]。结论：甾甾、甾甾和甾酮甾化合物甾阐阐阐阐根的甾甾成分。化合物 1-13 为首次从阐阐阐
阐中分得, 化合物 12 为首次从该属中得到。
【关键词】 阐阐阐阐; 甾甾; 甾甾

·会 讯·
NCRI 肿瘤学术会议
NCRI Cancer Conference
Subject category: Biology Chemistry Pharmacology
Start Date: 2010-11-7
End Date: 2010-11-10
Country: United Kingdom
Venue name: BT Convention Centre
Organized by: NCRI Conference Secretariat
Supported by: NCRI
Contact person: Sharon Vanloo
Tel: +44 20 7061 8134
Fax: +44 20 7061 8461
Email: sharon.vanloo@ncri.org.uk
Address: PO Box 49709, 61 Lincolns Inn Fields, London WC2A 3WZ
Useful Link: (Please enter http://) http://www.ncri.org.uk/ncriconference
General Information:
The NCRI Cancer Conference is the major forum in the UK for showcasing the
best British and international cancer research. The 2010 Conference will take place
at the BT Convention Centre in Liverpool, further enhancing opportunities for
networking and sharing knowledge while continuing to bring together leading ex-
perts across all disciplines.