全 文 ：云南崖摩的化学成分研究
罗晓东　吴少华　马云保　吴大刚＊
(中国科学院昆明植物研究所植物化学开放实验室 , 昆明 650204)
摘要:　从云南崖摩(Amoora yunnanensis(H.L.Li)C.Y.Wu.)树皮的乙醇提取物中分离得到8 个化合物 , 通过波
谱方法鉴定它们分别是:3β , 7α, 16β_trihydroxy_stigmast_5 , 22_diene(1)、3β , 7α, 16β_trihydroxy_stigmast_5_ene(2)、ergosta_5 ,
24(28)_dien_3β , 7α_diol(3)、ergosta_5 , 24(28)_dien_3β , 7β , 16β_triol(4)、β_amyrone (5)、β_amyrin (6)、11α, 12α_epoxy_14_
taraxeren_3_one(7)和 6_guaiene_4α, 10α_diol(8)。其中 1 和 2为新化合物。
关键词:　云南崖摩;楝科;3β , 7α, 16β_trihydroxy_stigmast_5 , 22_diene;3β , 7α, 16β_trihydroxy_stigmast_5_ene
中图分类号:R914　　　文献标识码:A　　　文章编号:0577-7496(2001)04-0426-05
The Chemical Constituents of Amoora yunnanensis
LUO Xiao_Dong , WU Shao_Hua , MA Yun_Bao , WU Da_Gang＊
(Laboratory of Phytochemistry , Kunming Institute of Botany , The Chinese Academy of Sciences , Kunming 650204, China)
Abstract:　Two new sterols , 3β , 7α, 16β_trihydroxy_stigmast_5 , 22_diene (1), 3β , 7α, 16β_trihydroxy_stig-
mast_5_ene(2), were isolated together with six known compounds , ergosta_5 ,24(28)_dien_3β , 7α_diol(3),
ergosta_5 ,24(28)_dien_3β ,7β ,16β_triol(4), β_amyrone (5), β_amyrin(6), 11α,12α_epoxy_14_taraxeren_3_
one (7), and 6_guaiene_4α, 10α_diol(8)from the EtOH extract of the bark of Amoora yunnanensis (H.L.
Li)C.Y.Wu.Their structures were deduced on the basis of spectral data.
Key words:　Amoora yunnanensis;Meliaceae;3β ,7α, 16β_trihydroxy_stigmast_5 , 22_diene;3α, 7α, 16β_tri-
hydroxy_stigmast_5_ene
　　The genus Amoora comprising about 25-30 species
is distributed in India and the Malay Peninsula.Six
species are found in Yunnan Province.Amoora yunna-
nensis(H.L.Li)C.Y.Wu., is mainly distributed in
the South of Yunnan[ 1] .According to Pennington and
Styles[ 2] , Amoora cannot be considered as a valid genus.
Up to now , chemical constituents for this genus have not
been reported yet.In our chemical study on Amoora yun-
nanensis , tetranortriterpenoids or protolimonoids that were
considered as chemotaxonomic markers of the family Meli-
aceae , were not isolated.However , two new sterols , 3β ,
7α,16β_trihydroxy_stigmast_5 ,22_diene (1), 3β ,7α,16β_
trihydroxy_stigmast_5_ene (2), along with six know com-
pounds ergosta_5 ,24(28)_dien_3β ,7α_diol(3)[ 3] , ergos-
ta_5 , 24(28)_dien_3β , 7β , 16β_triol (4)[ 4] , β_amyrone
(5)[ 5] , β_amyrin(6)[ 6] , 11α,12α_epoxy_14_taraxeren_3_
one(7)[ 7] , and 6_guaiene_4α,10α_diol (8)[ 8] were ob-
tained from the EtOH extract of the bark of A.yunnanen-
sis (H.L.Li)C.Y.Wu.
1　Results and Discussion
Compound 1 , showed in its EI_MS spectrum a
molecular ion peak at m/ z 444 in accordance with the for-
mula C29H48O3 and the presence of 29 carbons was con-
firmed by its 13C-NMR spectrum and negative_ion
HRFABMS.Its IR spectrum revealed absorption bands for
_OH at 3 405 cm-1 and C C at 1 665 cm-1.The 1H
and 13C_NMR spectra of 1 exhibited the presence of six
methyls (two of them were tertiary methyls), seven
methylenes , ten methines (three of them were oxygenat-
ed), two characteristic quaternary carbons at δC 42.0
and 37.1 , and four olefinic carbons with corresponding
proton signals atδH 5.58(d , J =3.9 Hz), 5.38(dd ,
J =15.4 , 9.0 Hz), 5.29 (dd , J =15.4 , 8.6 Hz).
These data proposed that 1 possessed a stigmast skeleton
having two double bonds and three hydroxyls substitution.
Two double bonds were assigned to be located at C_5 and
C_6 , as well as C_22 and C_23 , respectively , by compar-
ison of chemical shifts and coupling constants of three
olefinic proton signals with those of relative com-
pounds[ 3 , 9] .The assignment was further confirmed by an
HMBC experiment , in which two olefinic protons (δH
5.39(H_22), 5.29(H_23))showing cross peaks to δC
51.1(d , C_24)and 35.3 (d , C_20), respectively ,
Received:2000-05-09　Accepted:2000-12-18
Supported by the Natural Science Foundation of Yunnan Province(2000C0021Q)and Yunnan Commit tee of Science and Technology(2000YP23).
＊Author for correspondence.
植　物　学　报　2001 , 43(4):426-430 　 　 　 　 　 　 　
Acta Botanica Sinica
unambiguously indicated an olefinic linkage between C_22
and C_23.Long range coupling for the olefinic proton δH
5.58(H_6)to δC 42.0(t , C_4), H_6 to 37.1(s , C_
10), and H_6 to 65.2(d , C_7)in the HMBC spectrum ,
not only confirmed the position of another olefinic linkage
between C_5 and C_6 but also indicated a hydroxyl substi-
tution at C_7.Small coupling constant(J =4.0 Hz)for
H_7 attributed to ea coupling between H_7 and H_8 sug-
gested that the 7_OH occupied anα_configuration[ 9] .The
inference was further supported by NOESY spectrum , in
which aNOE correlation between H_7 andH_8(β_H)was
observed.The other two hydroxyls were placed at C_3 and
C_16 positions , respectively , based on the cross peaks
betweenδH 2.32(2H , m , H_4)to δC 71.4(d , C_3),
andδH4.27 (H_16)to δC 42.0 (C_13)in the HMBC
spectrum of 1.The correlation betweenδH 4.27(H_16)
and 1.14(H_17)in the 1H_1H COSY spectrum also sup-
ported the assignment.The stereochemistry at C_16 was
determined from the NOESY spectrum of 1 , with a NOE
interaction between H_16 andH_17(α_H).Thus , 16_OH
was determined to be a β-configuration.In 13C-NMR
spectrum , the signals for C_26 , C_27 and C_29 were not
in pairs , indicating only one C_24 epimer (24S or 24R)
rather than a mixture
[ 10]
for compound 1.The chemical
shift difference between the epimers published in previous
literatures
[ 9-11]
is too small to identify the configuration at
C_24 in compound 1.Compound 1was deduced to be 3β ,
7α,16β_trihydroxy_stigmast_5 ,22_diene.
The negative_ion HRFABMS spectrum of compound
2 , exhibited the molecular formula as C29H50O3 , which
was supported by
13
C and DEPT spectral data.The IR
spectrum also showed the presence of hydroxyl (3 420
cm-1)and olefinic(1 668 cm-1)absorption bands.The
1H and 13C-NMR spectrum of 2 exhibited signals due to
six methyls (two of which were tertiary methyls), nine
methylenes , ten methines(three of which were oxygenat-
ed), and two olefinic carbons (corresponding carbon δC
123.9(d), 146.4 (s), and proton δH 5.59 (d , J =
5.0 Hz)).These data were similar to those of 1 , sug-
gesting that 2 belonged to a stigmast with one double bond
and three hydroxyls substitutes.The molecular formula
(C29H50O3)was consistent with signals for only one dou-
ble bond in the 13C_NMR spectrum of 2.Comparing the
13C_NMR spectra of the two compounds revealed that two
more methylene groups(δC 34.0 and 26.5)were present
in the 13C_NMR spectrum of 2 , instead ofδC 139.0(d ,
C_22)and 131.1(d , C_23)in the 13C-NMR spectrum of
1.The above data assumed that 2 was 22 , 23_dihydro_
derivative of 1.In an HMBC experiment , the observation
of cross signals betweenδH 1.00(d , J =6.8Hz , H_21)
toδC 34.0(C_22), δH 1.10(m , H_17)and 30.3(d ,
C_20), and H_17 to C_22 confirmed the assumption.The
stereochemistry at the other chiral centers in 2 were
identical to those of 1 , as supported by its 1H , 1H_1H
COSY , andNOESY NMR spectra.Compound 2 also pos-
sessed one C_24 epimer(24S or 24R), the configuration
at C_24 was also not determined.So compound 2was elu-
cidated as 3β ,7α,16β_trihydroxy_stigmast_5_ene.
2　Experimental
2.1　General experimental procedures
Melting points were obtained using a Sichuan Mi-
cromelting apparatus and are uncorrected.Optical rota-
tions were taken with a Horiba SEAP_300 spectropo-
larimeter.IR spectra (KBr)were obtained with a Bio_
Rad FTS_135 infrared spectrophotometer.1H , 13C_NMR
4 期 罗晓东等:云南崖摩的化学成分研究(英) 427　
and 2D_NMR spectra were recorded from a Bruker AM_
400 and a DRX_500 NMR spectrometer with TMS as in-
ternal standard.MS data were obtained with a VG Au-
tospec_3000 spectrometer , at 70 eV for EI.Si gel(200-
300 mesh)for column chromatography and GF254 for TLC
were obtained from the Qindao Marine Chemical Factory.
2.2　Plant materials
The bark of Amoora yunnanensis (H.L.Li)C.Y.
Wu.was collected from Xishuangbanna , Yunnan Province ,
China , in December 1996.It was identified by Prof.TAO
G_D , Xishuangbanna Botanical Garden , the Chinese Acade-
my of Sciences.A voucher specimen was deposited in the
herbarium of the Department of Taxonomy , Kunming Insti-
tute of Botany , The Chinese Academy of Sciences.
2.3　Extraction and isolation
The air_dried and powdered bark (4.1 kg)of A.
yunnanensis was extracted with EtOH (95%)for three
times under reflux (each process lasting 3 h).After re-
moval of the solvent by evaporation , the residues were
suspended in H2O and extracted with EtOAc for three
times.The EtOAc fraction was concentrated in vacuo to
give 56 g of the residue.The residue was separated re-
peatedly by chromatography on silica gel column , eluted
with CHCl3_Me2CO(from CHCl3 to CHCl3_Me2CO 2∶1)
to afford 1(8mg), 2(15 mg), 3(14mg), 4(16 mg),
5(2.42 g), 6(2.88 g), 7(14 mg), and 8(10 mg).
2.4　Identification
3β , 7α, 16β_Trihydroxy_stigmast_5 , 22_diene (1)　
C29H48O3 , white powder , mp 132 -134 ℃, [ α] 26D
-35.3°(c 0.15 , CHCl3);IR νKBrmax cm-1:3 405 ,
2 958 , 2 872 , 1 665 , 1 461 , 1 381 , 1 248 , 1 166 ,
1 056 , 1 028 , 956 , 898 , 754;EIMS m/ z 444 [M] +
(15), 426(70), 408(66), 393(21), 383(15), 365
(50), 323(22), 270(40), 246(20), 189(30), 159
(40), 143(81), 121 (56), 109 (70), 95 (77), 81
(75), 69 (82);HRMS:m/ z [ M -H ] - found:
443.357 3 , required:443.352 5;1H and 13 C-NMR
spectral data , see Tables 1 and 2.
3β , 7α, 16β_Trihydroxy_stigmast_5_ene (2)　
C29H50O3 , white powder , mp 151 -153 ℃, [ α] 26D
-60.0°(c 0.20 , CHCl3);IR νKBrmax cm-1:3 420 ,
2 958 , 2 935 , 2 872 , 1 668 , 1 464 , 1 381 , 1 240 ,
1 052 , 1 032 , 955 , 899 , 869;EIMS m/ z 446 [M] +
(40), 428(100), 410(10), 395(8), 269(12), 150
(25), 145(37), 119 (24), 105 (27), 93 (30), 81
(37), 69(49), 57 (56);HRMS:m/ z [M] + found:
446.371 0 , required:446.376 0;1H and 13 C_NMR
spectral data , see Tables 1 and 2.
Ergosta_5 , 24(28)_dien_3β , 7α_diol (3)　Crys-
talline solids (Me2CO);mp 142 -144 ℃;IR νKBrmax
cm-1:3 359 , 2 961 , 2 935 , 2 869 , 1 665 , 1 642 ,
1 464 , 1 378 , 1 113 , 1 057 , 952 , 888 , 842;1H_NMR
(CDCl3 , 400 MHz):δ5.58 (1H , d , J =5.2 Hz , H_
6), 4.69(1H , s , H_28), 3.83(1H , brs , H_7), 3.56
(1H , m , H_3), 1.02(6H , d , J =6.0 Hz , H_26 , H_
27), 0.99(3H , s , H_19), 0.93(3H , d , J =6.2Hz ,
H_21), 0.67 (3H , s , H_18);13C_NMR(CDCl3 , 100
MHz)spectral data , see Table 6;EIMS m/ z 414 [M] +
(35), 396(95), 381(15), 312(35), 269(25), 175
(22), 159(26), 145(42), 121(42), 107(52), 95
(62), 81(67), 69(85), 55(100).
Ergosta_5 , 24(28)_dien_3β , 7β , 16β_triol (4)　
Colorless needles(Me2CO);mp 176-178 ℃;IRνKBrmax
cm-1:3 371 , 2 965 , 2 935 , 2 857 , 1 642 , 1 464 ,
1 446 , 1 378 , 1 342 , 1 324 , 1 287 , 1 249 , 1 048 ,
1 026 , 863;1H-NMR(CDCl3+CD3OD , 400 MHz):δ
5.19(1H , s , H_6), 4.66 , 4.62(each 1H , s , H_28),
4.27(1H , m , H_16), 3.68(1H , brd , J =8.0 Hz ,
H_7), 3.41 (1H , m , H_3), 0.96 (3H , s , H_19),
0.92(3H , d , J =6.8 Hz , H_26), 0.89(3H , d , J =
6.8 Hz , H_27), 0.88 (3H , d , J =7.2 Hz , H_27),
0.81(3H , s , H_18);13C-NMR(CDCl3+CD3OD , 100
MHz)spectral data , see Table 2;EIMS m/ z 430 [M] +
(30), 412(75), 394(77), 381(20), 328(7), 298
(10), 287(20), 271(15), 251(15), 229(10), 211
(29), 197(17), 159(31), 145(45), 119(48), 105
(57), 95(55), 83(65), 69(82), 55(100).
β_Amyrone(5)　Colorless needles(Me2CO);mp
158-160 ℃;IRνKBrmax cm-1:3 394 , 2 946 , 1 707 ,
1 456 , 1 383 , 1 362 , 1 243 , 1 199 , 1 167 , 1 138 ,
1 074 , 1 025 , 1 001 , 968;1H-NMR (CDCl3 , 400
MHz):δ5.21 (1H , t , J =3.4 Hz , H_12), 1.14 ,
1.10 , 1.07 , 1.06 , 1.02 , 1.01 , 0.97 , 0.92 (each
3H , s , Me×8);13C-NMR(CDCl3 , 100 MHz)spectral
data, see Table 2;EIMS m/z 424 [ M] +(55), 409
(20), 257(5), 231(5), 218(100), 203 (60), 189
(20), 177(8), 161(12), 149(15), 135 (25), 119
(27), 109 (32), 95 (40), 81 (36), 69 (46), 55
(53).
β_Amyrin (6)　Colorless needles (Me2CO);mp
172-174 ℃;IRνKBrmax cm-1:3 295 , 2 947 , 2 925 ,
2 854 , 1 736 , 1 464 , 1 384 , 1 361 , 1 307 , 1 097 ,
1 034 , 996 , 952 , 815 , 659;1H-NMR (CDCl3 , 400
MHz):δ5.19 (1H , t , J =3.6 Hz , H_12), 3.22
(1H , dd , J =10.8 , 4.8 Hz , H_3), 1.04 , 1.02 ,
0.96 , 0.87 , 0.84 , 0.82 , 0.79(each 3H , s , Me×
8);13C-NMR (CDCl3 , 100 MHz)spectral data , see
Table 2;EIMS m/ z 426 [M] + (10), 365 (8), 123
428　 植　物　学　报　　Acta Botanica Sinica 43 卷
Table 1　1H_NMR spectral data of compounds 1 and 2 (CDCl3 , 400MHz)＊
H 1 2 H 1 2
1 1.56 , 1.85 m 1.55, 1.85 m 19 0.98 s 0.99 s
2 1.68 , 1.86 m 1.70, 1.86 m 20 2.30 m 1.27 m
3 3.55 m 3.56 m 21 1.06 d(6.8) 1.00 d(6.8)
4 2.32 m 2.28, 2.36 m 22 5.39 dd(15.4 , 9.0) 1.32 m
6 5.58 d(3.9) 5.59 d(5.0) 23 5.29 dd(15.4 , 8.6) 1.23 m
7 3.85 t(4.0) 3.83 t(4.0) 24 1.62 m 0.97 m
8 1.55 m 1.55 m 25 1.68 m 1.70 m
9 1.22 m 1.22 m 26 0.82 d(6.4) 0.81 d(7.0)
11 1.52 , 1.80 m 1.52, 1.78 m 27 0.78 d(6.4) 0.79 d(7.0)
12 1.98 m 2.0 m 28 1.22 m 1.18 m
14 1.30 m 1.32 m 29 0.82 t(7.2) 0.83 t(7.6)
15 2.32 , 1.20 m 2.37, 1.22 m 27 0.78 d(6.4) 0.79 d(7.0)
16 4.27 m 4.39 m 28 1.22 m 1.18 m
17 1.14 m 1.10 m 29 0.82 t(7.2) 0.83 t(7.6)
18 0.89 s 0.87 s
＊ All values are in ppm , coupling constants in Hz , with TMS as internal standard.
Table 2　13C_NMR spectral data of compounds 1-7(CDCl3 , 100 MHz)
1 2 3 4 5 6 7
C_1 37.0 t 37.0 t 37.1 t 36.8 t 39.4 t 38.9 t 38.6 t
C_2 31.4 t 31.4 t 31.9 t 31.1 t 34.2 t 27.0 t 33.9 t
C_3 71.4 d 71.4 d 73.4 d 72.7 d 217.4 s 79.1 d 216.2 s
C_4 42.0 t 42.0 t 41.8 t 41.4 t 47.4 s 38.8 s 47.4 s
C_5 146.3 s 146.4 s 146.3 s 143.4 s 55.4 d 55.3 d 54.8 d
C_6 123.8 d 123.9 d 123.9 d 125.5 d 19.7 t 18.9 t 20.1 t
C_7 65.2 d 65.3 d 71.5 d 71.0 d 32.6 t 32.7 t 33.2 t
C_8 37.5 d 37.5 d 42.1 d 41.4 d 39.9 s 39.9 s 38.9 s
C_9 42.4 d 42.4 d 49.5 d 48.3 d 47.0 d 47.7 d 51.7 d
C_10 37.1 s 37.2 s 37.4 s 36.8 s 37.2 s 37.0 s 37.6 s
C_11 20.4 t 20.4 t 21.9 t 20.7 t 23.7 t 23.6 t 52.9 d
C_12 39.5 t 39.3 t 39.6 t 39.6 t 121.6 d 121.8 d 58.2 d
C_13 42.0 s 42.0 s 43.0 s 42.6 s 145.3 s 145.2 s 36.4 s
C_14 46.9 d 47.5 d 55.8 d 53.7 d 42.0 s 41.8 s 156.8 s
C_15 34.9 t 36.5 t 26.4 t 38.4 t 28.4 t 28.4 t 119.2 d
C_16 72.9 d 72.7 d 28.3 t 72.3 d 26.2 t 26.2 t 35.3 t
C_17 61.0 d 61.0 d 56.0 d 60.5 d 32.6 s 32.5 s 35.4 s
C_18 13.0 q 12.8 q 11.8 q 12.7 q 47.4 d 47.3 d 48.3 d
C_19 18.2 q 18.3 q 19.2 q 18.9 q 46.9 t 46.9 t 39.8 t
C_20 35.3 d 30.3 d 35.7 d 36.3 d 31.1 s 31.1 s 28.7 s
C_21 21.0 q 18.3 q 18.8 q 18.9 q 34.8 t 34.8 t 36.6 t
C_22 139.0 d 34.0 t 30.9 t 31.1 t 37.2 t 37.2 t 38.2 t
C_23 131.1 d 26.5 t 34.8 t 33.9 t 28.4 q 28.1 q 26.3 q
C_24 51.1 d 46.0 d 156.9 s 157.1 s 21.5 q 15.6 q 21.5 q
C_25 31.7 d 29.2 d 33.8 d 33.9 d 15.2 q 15.5 q 16.2 q
C_26 21.6 q 19.8 q 21.9 q 21.7 q 16.8 q 16.9 q 26.7 q
C_27 18.7 q 19.0 q 22.0 q 21.8 q 26.2 q 26.0 q 30.3 q
C_28 25.1 t 23.2 t 106.0 t 105.9 t 27.0 q 27.3 q 29.9 q
C_29 12.2 q 12.0 q 32.3 q 33.3 q 33.7 q
C_30 23.7 q 23.7 q 19.6 q
(5), 109(10), 93(11), 69(18), 55(21).
11α, 12α_Epoxy_14_taraxeren_3_one (7)　Color-
less needles(MeOH);mp 248-250 ℃;IRνKBrmax cm-1:
3 396 , 3 044 , 2 958 , 2 922 , 2 865 , 1 706 , 1 638 ,
1 449 , 1 384 , 1 367 , 1 272 , 1 172 , 1 155 , 1 113 ,
1 055 , 998 , 919;1H-NMR(CDCl3 , 400MHz):δ5.55
(1H , dd , J =8.2 , 3.4Hz , H_15), 3.15(1H , t , J =
4.9 Hz , H_11), 2.81 (1H , d , J =4.9 Hz , H_12),
4 期 罗晓东等:云南崖摩的化学成分研究(英) 429　
1.21 , 1.10 , 1.07 , 1.06 , 0.98 , 0.96 , 0.95 , 0.85 ,
0.80 (each 3H , s , Me ×8);13C-NMR (CDCl3 , 100
MHz)spectral data , see Table 2;EIMS m/ z 438 [ M] +
(40), 423(8), 405 (10), 335 (3), 314 (8), 299
(10), 259(10), 217 (5), 204 (10), 191 (5), 173
(6), 159(8), 149(13), 135 (36), 108(100), 95
(23), 81(27), 69(42).
6_Guaiene_4α,10α_diol (8)　White powder;mp
90-92 ℃;IRνKBrmax cm-1:3 333 , 2 963 , 2 932 , 2 870 ,
1 666 , 1 462 , 1 374 , 1 301 , 1 274 , 1 214 , 1 193 ,
1 132 , 1 106 , 1 088 , 979 , 958 , 933 , 907 , 858;1H-
NMR(CDCl3 , 500 MHz):δ5.50 (1H , d , J =2.4
Hz , H_6), 2.25(1H , m , H_11), 2.20(2H , m , H_
8), 2.18(1H , m , H_5), 1.27(3H , s , H_14), 1.21
(3H , s , H_15), 0.98 (3H , d , J =5.6 Hz , H_12),
0.97(3H , d , J =5.5 Hz , H_13);13C-NMR(CDCl3 ,
125 MHz):δ149.6(s , C_7), 121.4(d , C_6), 80.2
(s , C_4), 75.3(s , C_10), 50.7(d , C_5), 50.3(d ,
C_1), 42.6 (t , C_9), 40.5 (t , C_3), 37.3(d , C_
11), 25.1(t , C_2), 22.6(q , C_13), 21.5(t , C_8),
21.4(q , C_14), 21.2 (q , C_15), 20.4(q , C_11);
EIMS m/ z 238 [M] +(1), 220 (42), 205 (20), 187
(13), 177 (21), 162 (100), 147 (40), 134 (35),
123(12), 119(55), 107(45), 98(17), 93(51), 83
(35), 79(45), 69(38), 55(68).
Acknowledgements:　The authors are grateful to the
members of analytical group in the Laboratory of Phyto-
chemistry , Kunming Institute of Botany , The Chinese
Academy of Sciences , for the spectral measurements.
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430　 植　物　学　报　　Acta Botanica Sinica 43 卷