全 文 ：天然产物研究与开发 NatProdResDev2008, 20:1000-1004
文章编号:1001-6880(2008)06-1000-05
ReceivedAugust3, 2007;AcceptedOctober29, 2007
FoundationItem:ThisprojectwassupportedbytheNationalScience
FoundationofChina(NSFC, 20602037).
＊CorrespondingauthorTel:86-871-5215967;E-mail:liuxikui@mail.
kib.ac.cn
望谟崖摩和曲枝崖摩的化学成分研究
杨淑敏 1, 2 ,刘锡葵 1＊ ,吴大刚 1 ,朱大元 2
1中国科学院昆明植物研究所 植物化学与西部植物资源持续利用国家重点实验室 ,昆明 650204;
2中国科学院上海生命科学院药物研究所 新药研究国家重点实验室 , 上海 201203
摘 要:为了寻找生物活性成分 , 采用色谱分离法对望谟崖摩和曲枝崖摩进行了化学成分研究。根据波谱学分
析鉴定了化合物结构。从两种植物中分离得到了 15个化合物 , 分别为 8(17), 13(E)-半日花-二烯-15, 19-二酸
(1), 8(17), 13(E)-半日花-二烯-19-酸甲酯-15-醛(2), 15-O-乙酰基-8(17), 13(E)-半日花-二烯-19-酸(3), 15-羟
基-8(17), 13(E)-半日花-二烯-19-酸(4), 15, 19-二羟基-8(17), 13(E)-半日花-二烯(5), 19-羟基-8(17), 13(E)-
半日花-二烯 -15-醛(6), 19-羟基-8(17), 13(Z)-半日花-二烯-15-醛(7), 8(17), 13(E)-半日花-二烯-19-酸-15-醛
(8), 8(17), 13(Z)-半日花-二烯-19-酸-15-醛(9), (+)-儿茶素(10), β-香树素(11), 豆甾-5-烯-3β, 7α-二醇
(12),东莨菪内酯(13), β-谷甾醇(14), 胡萝卜苷(15)。上述化合物均为首次从崖摩属植物中分离得到的半日
花烷型二萜。
关键词:望谟崖摩;曲枝崖摩;半日花烷二萜
中图分类号:Q946.91;R284.2 文献标识码:A
ChemicalConstituentsfromAmooraouangtliensisandA.stelato-squamosa
YANGShu-min1, 2 , LIUXi-kui1＊ , WUDa-gang1 , ZHUDa-yuan2
1StateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina, KunmingInstitute
ofBotany, theChineseAcademyofSciences, Kunming650204 , China;
2StateKeyLaboratoryofDrugResearch, ShanghaiInstituteofMateriaMedica, ShanghaiInstitutes
forBiologicalSciences, theChineseAcademyofSciences, Shanghai201203 , China
Abstract:ThephytochemicalinvestigationsonAmooraouangtliensisandA.stelato-squamosawereconductedinorderto
lookforbioactivecompounds.Ninediterpenoidswereobtainedbythemethodofcolumnchromatography, andontheba-
sisofspectralanalysistheywereidentifiedas8(17), 13(E)-labdadien-15, 19-dioicacid(1), methyl8(17), 13(E)-
labdadien-19-oicacid-15-oate(2), 15-acetoxy-8(17), 13(E)-labdadi-en-19-oicacid(3), 15-hydroxy-8(17), 13(E)-
labdadien-19-oicacid(4), 8(17), 13(E)-labdadien-15, 19-diol(5), 19-hydroxy-8(17), 13(E)-labdadien-15-al(6),
19-hydroxy-8(17), 13(Z)-labdadien-15-al(7), 8(17), 13(E)-labdadien-19-oicacid-15-al(8), 8(17), 13(Z)-labda-
dien-19-oicacid-15-al(9), andsixothercompounds, (+)-catechin(10), β-amyrin(11), stigmast-5-en-3β, 7α-diol
(12), scopoletin(13), β-sitosterol(14), daucosterol(15).Thisisthefirstreportoflabdane-typediterpenefromthege-
nusAmoora.
Keywords:Amooraouangtliensis;A.stellato-squamosa;labdane-typediterpene
Introduction
ThegenusAmoora(Meliaceae), mainlydistributedin
IndiaandMalaysia, comprisesca.25-30 species, of
whichsixhavebeenfoundinYunnanProvince, Chi-
na[ 1] .Previously, wereportedneoclerodane, triterpenes
fromthisgenus[ 2-5] .Inthispaper, wecontinuedtode-
scribetheisolationandidentificationofninelabdane-
typediterpenesfromAmooraouangtliensisandA.stel-
lato-squamosa, onthebasisofspectralevidences, they
wereidentifiedas8(17), 13(E)-labdadien-15, 19-di-
oicacid(1), methyl8(17), 13(E)-labdadien-19-oic
acid-15-oate(2), 15-acetoxy-8(17), 13(E)-labdadi-
en-19-oicacid(3), 15-hydroxy-8(17), 13(E)-labda-
dien-19-oicacid(4), 8(17), 13(E)-labdadien-15, 19-
diol(5), 19-hydroxy-8(17), 13(E)-labdadien-15-al
(6), 19-hydroxy-8(17), 13(Z)-labdadien-15-al(7),
8(17), 13(E)-labdadien-19-oicacid-15-al(8)and8
(17), 13(Z)-labdadien-19-oicacid-15-al(9).Thisis
thefirstreportoflabdane-typediterpenefromthegenus
Amoora.Besides, sixothercompounds, (+)-catechin
(10), β-amyrin(11), stigmast-5-en-3β, 7α-diol(12),
scopoletin(13), β-sitosterol(14), daucosterol(15),
wereobtainedfromthesamesource.
Experimental
Apparatusandmaterials
MSspectrawereobtainedwithaVGAutoSpec-3000
spectrometer, at70eVforEI.NMRSpectrawererecor-
dedonaBrukerDRX-500 spectrometerswithTMSas
internalstandard, δinppm, JinHz.Silicagel(200-
300mesh)forCCandGF254 foranalyticalTLCwere
fromtheQingdaoMarineChemicalFactory, P.R.Chi-
na.
ThebarksofA.ouengliensisandthetwigsofA.stelato-
squamosawerecolectedinXishuangbannaofYunnan
Province, P.R.China, inJanuary2002.Theplantwas
identifiedbyProf.Jing-YunCui, XishuangbannaTropi-
calBotanicalGarden, AcademiaSinic, China.
Extractionandisolation
Theair-driedtwigsofA.stelato-squamosa(9.0 kg)
wereextractedwithEtOH/H2O9∶1 atroomtempera-
turefor3 times.Afterevaporation, theresiduewassus-
pendedinH2OandextractedwithEtOAc.TheEtOAc
extract(110 g)wassubjectedtoCC(SiO2;petroleume-
ther/AcOEt1∶0 to8∶2)toafordninefractions(Fr.1-
9), asjudgedbyTLC.Fr.2(50 g)andFr.3(27 g)
wererepeatedlychromatographedonSiO2(petroleume-
ther/AcOEt49∶1 to1∶1, 10∶1 to1∶1, respectively),
afording2(8mg), 14(590mg)fromFr.2;3(7mg), 4
(11mg), 13(410mg)fromFr.3.Fr.4(10g)andFr.5
(9g)wererepeatedlychromatographed(1.SiO2 , petro-
leumether/AcOEt9∶1 to1∶1;2.RP-18 gel, MeOH/
H2O1∶1 to1∶0 respectively), afording5(114 mg),
10(17 mg)fromFr.4, 1(9mg)fromFr.5.Fr.9(21 g)
wasrepeatedlysubjectedtoCCoverSiO2 (CHCl3 /
MeOH9∶1 to7∶3)togive15(40 mg).Theair-dried
barksofA.ouengliensis(7.0 kg)wereextractedwith
EtOH/H2O9∶1 atrefluxedtemperaturefor3 times(4
hforeachtime).Afterevaporation, theresiduewas
suspendedinH2O andextractedwithCHCl3.The
CHCl3 extract(110g)wassubjectedtoCC(SiO2;petro-
leumether/AcOEt1∶0to8∶2)toafordeightfractions
(Fr.1-8), asjudgedbyTLC.Fr.3(9g)wasrepeatedly
chromatographedon(1.SiO2 , petroleumether/Me2CO
8∶2 to1∶1;2.RP-18 gel, MeOH/H2O1∶1to1∶0 , suc-
cessively), afording6 and7(93 mg), 8 and9(61
mg), 12(32 mg).Fr.4(20 g)andFr.5(9.5 g)were
repeatedlychromatographed on(1.SiO2 , CHCl3 /
Me2CO9∶1;2.RP-18gel, MeOH/H2O1∶1 to1∶0suc-
cessively), yielding9(9 mg)fromFr.4 and11(29
mg).Fr.6(5.5 g)andFr.7(12 g)wererepeatedly
subjectedtoCCoverSiO2 (CHCl3 /Me2CO, 4∶1 and
3∶1 respectively), producing11(110 mg)fromFr.6;
12(57 mg)fromFr.7.Fr.8(27 g)wasrepeatedlysub-
jectedtoCCoverSiO2(CHCl3 /MeOH9∶1)togive15
(230 mg).
Identification
8(17), 13(E)-Labdadien-15, 19-dioicacid(1)
Whitecrystal;1H NMR(CDCl3 , 400 MHz)δ:5.73
(1H, brs, H-14), 2.20(3H, d, J=1.0 Hz, Me-16),
0.63(3H, s, Me-20);13CNMR(CDCl3 , 100 MHz)δ:
39.9(t, C-1), 20.8(t, C-2), 39.5(t, C-3), 44.6(s,
C-4), 56.8(d, C-5), 27.1(t, C-6), 39.0(t, C-7),
149.0(s, C-8), 56.3(d, C-9), 41.1(s, C-10), 22.5
(t, C-11), 40.4(t, C-12), 161.1(s, C-13), 116.2(d,
C-14), 176.7(s, C-15), 18.7(q, C-16), 106.7(t, C-
17), 29.3(q, C-18), 176.8(s, C-19), 13.3(q, C-
20).Thedatawereinaccordancewiththoserepor-
ted[ 6] .
Methyl8(17), 13(E)-labdadien-19-oicacid-15-
oate(2) Whitecrystal;EI-MSm/z:348 [ M] +(3),
333(7), 302(8), 274(13), 235(15), 189(26), 121
(60), 114(44), 95(50), 82(100), 69(34), 55
(60).1HNMR(CDCl3 , 400 MHz)δ:5.62(1H, s, H-
14), 4.85(1H, s, H-17a), 4.48(1H, s, H-17b), 3.66
(3H, s, OCH3), 2.13(3H, s, Me-16), 1.22(3H, s,
Me-18), 0.58(3H, s, Me-20);13 CNMR(CDCl3 , 100
MHz)δ:39.0(t, C-1), 19.8(t, C-2), 37.9(t, C-3),
44.4(s, C-4), 56.2(d, C-5), 26.0(t, C-6), 38.6(t,
C-7), 147.6(s, C-8), 55.3(d, C-9), 40.4(s, C-10),
1001Vol.20 YANGShu-min, etal:ChemicalConstituentsfromAmooraouangtliensisandA.stelato-squamosa
21.6(t, C-11), 39.7(t, C-12), 161.0(s, C-13),
115.0(d, C-14), 167.3(s, C-15), 18.9(q, C-16),
106.6(t, C-17), 29.0(q, C-18), 183.4(s, C-19),
12.8(q, C-20), 50.8(q, 15-OCH3).Thedatawerei-
denticaltothoseofliterature[ 6] .
15-Acetoxy-8(17), 13(E)-labdadien-19-oicacid
(3) Colorlessoilysolid;1HNMR(CDCl3 , 400MHz)
δ:5.39(1H, d, J=7.0 Hz, H-14), 4.88(1H, s, H-
17a), 4.63(1H, s, H-17b), 4.75(2H, d, J=7.0 Hz,
H-15), 1.71(3H, s, Me-16), 1.29(3H, s, Me-18),
2.01(3H, s, CH3CO);13CNMR(CDCl3 , 100 MHz)δ:
39.0(t, C-1), 19.8(t, C-2), 37.9(t, C-3), 44.1(s,
C-4), 55.3(d, C-5), 26.0(t, C-6), 38.3(t, C-7),
147.9(s, C-8), 56.3(d, C-9), 40.3(s, C-10), 21.7
(t, C-11), 38.6(t, C-12), 142.7(s, C-13), 118.0(d,
C-14), 61.3(t, C-15), 16.4(q, C-16), 106.3(t, C-
17), 28.9(q, C-18), 183.5(s, C-19), 12.7(q, C-
20), 20.9(q, 15-CH3CO), 171.1(s, 15-COCH3).
Thesedatawereconsistentwiththosereported[ 7] .
15-Hydroxy-8(17), 13(E)-labdadien-19-oicacid
(4) Colorlessoilysolid;EI-MSm/z:320[ M] +(3),
305(24), 302(25), 287(28), 274(20), 259(24),
241(24), 235(19), 189(70), 161(29), 147(40),
133(52), 121(100), 107(49), 93(42), 81(47), 67
(18), 55(12).1HNMR(CDCl3 , 400 MHz)δ:5.35
(1H, d, J=6.7 Hz, H-14), 4.83(1H, s, H-17a),
4.50(1H, s, H-17b), 4.13(2H, d, J=6.7 Hz, H-
15), 1.64(3H, s, Me-16), 1.20(3H, s, Me-18), 0.57
(3H, s, Me-20);13CNMR(CDCl3 , 100 MHz)δ:39.1
(t, C-1), 19.9(t, C-2), 37.9(t, C-3), 44.2(s, C-4),
56.3(d, C-5), 26.0(t, C-6), 38.7(t, C-7), 147.9(s,
C-8), 55.5(d, C-9), 40.4(s, C-10), 21.9(t, C-11),
38.4(t, C-12), 140.5(s, C-13), 122.9(d, C-14),
59.4(t, C-15), 16.3(q, C-16), 106.5(t, C-17), 29.0
(q, C-18), 183.7(s, C-19), 12.8(q, C-20).Thedata
wereidenticaltothosereported[ 8] .
8(17), 13(E)-Labdadien-15, 19-diol(5) EI-MS
m/z:306[ M] +(4), 291(12), 275(45), 257(73),
189(45), 161(64), 153(90), 135(82), 109(82),
107(100), 95(85), 81(74), 79(48), 67(38).1H
NMR(CDCl3 , 400 MHz)δ:5.36(1H, t, J=6.9 Hz, H-
14), 4.80(1H, s, H-17a), 4.49(1H, s, 17b), 4.13
(2H, d, J=6.9 Hz), 3.73 , 3.36(each1H, d, J=
11.0 Hz, H-19), 1.65(3H, s, Me-16), 0.95(3H, s,
Me-18), 0.63(3H, s, Me-20);13CNMR(CDCl3 , 100
MHz)δ:38.3(t, C-1), 19.0(t, C-2), 35.4(t, C-3),
39.5(s, C-4), 56.2(d, C-5), 24.4(t, C-6), 38.6(t,
C-7), 148.0(s, C-8), 56.3(d, C-9), 38.8(s, C-10),
22.2(t, C-11), 39.0(t, C-12), 140.5(s, C-13),
123.0(d, C-14), 59.4(t, C-15), 16.3(q, C-16),
106.6(t, C-17), 27.0(q, C-18), 65.0(t, C-19), 15.3
(q, C-20).Thedatawereequaltothoseoflitera-
ture[ 6] .
19-Hydroxy-8(17), 13(E)-labdadien-15-al(6)
Colorlesscrystal;1HNMR(CDCl3 , 400 MHz)δ:9.93
(1H, d, J=8.1 Hz, H-15), 5.82(1H, d, J=7.8 Hz,
H-14), 4.80(1H, s, H-17a), 4.44(1H, s, H-17b),
3.70, 3.34(1H, d, J=10.9 Hz, H-19), 2.11(3H, s,
Me-16), 0.93(3H, s, Me-18), 0.62(3H, s, Me-20);
13CNMR(CDCl3 , 100MHz)δ:38.4(t, C-1), 18.9(t,
C-2), 35.2(t, C-3), 39.4(s, C-4), 56.2(d, C-5),
24.4(t, C-6), 38.4(t, C-7), 147.5(s, C-8), 56.2(d,
C-9), 38.8(s, C-10), 22.3(t, C-11), 39.0(t, C-12),
164.9(s, C-13), 127.1(d, C-14), 191.4(d, C-15),
17.6(q, C-16), 106.6(t, C-17), 27.0(q, C-18),
64.8(t, C-19), 15.2(q, C-20).Thedatawereidenti-
caltothoseofliterature[ 9] .
19-Hydroxy-8(17), 13(Z)-labdadien-15-al(7)
Colorlesscrystal;1HNMR(CDCl3 , 400 MHz)δ:9.78
(1H, d, J=8.1 Hz, H-15), 5.84(1H, d, J=7.8 Hz,
H-14), 4.84(1H, s, H-17a), 4.50(1H, s, H-17b),
3.70, 3.34(1H, d, J=10.9 Hz, H-19), 1.93(3H, s,
Me-16), 0.93(3H, s, Me-18), 0.62(3H, s, Me-20);
13CNMR(CDCl3 , 100MHz)δ:38.4(t, C-1), 18.9(t,
C-2), 35.2(t, C-3), 39.4(s, C-4), 56.2(d, C-5),
24.4(t, C-6), 38.4(t, C-7), 147.5(s, C-8), 56.2(d,
C-9), 38.8(s, C-10), 21.3(t, C-11), 31.0(t, C-12),
164.8(s, C-13), 129.0(d, C-14), 191.1(d, C-15),
24.5(q, C-16), 106.8(t, C-17), 27.0(q, C-18),
64.8t, C-19), 15.2(q, C-20).Thedatawereinac-
cordancewiththosereported[ 9] .
8(17), 13(E)-Labdadien-19-oicacid-15-al(8)
Colorlessoilysolid;1HNMR(CDCl3 , 400 MHz)δ:
9.98(1H, d, J=8 Hz, H-15), 5.86(1H, d, J=8 Hz,
H-14), 4.86, 4.47(each1H, s, H-17), 2.14(3H, s,
Me-16), 1.22(3H, s, Me-18), 0.58(3H, s, Me-20);
1002 NatProdResDev Vol.20
13CNMR(CDCl3 , 100 MHz)δ:39.1(t, C-1), 19.9(t,
C-2), 37.9(t, C-3), 44.1(s, C-4), 56.1(d, C-5),
26.0(t, C-6), 38.6(t, C-7), 147.5(s, C-8), 56.4(d,
C-9), 40.5(s, C-10), 21.4(t, C-11), 39.5(t, C-12),
164.8(s, C-13), 127.2(d, C-14), 191.4(d, C-15),
17.7(q, C-16), 106.6(t, C-17), 28.9(q, C-18),
182.8(s, C-19), 12.8(q, C-20).Thesedatawerecon-
sistentwiththosereported[ 7] .
8(17), 13(Z)-Labdadien-19-oicacid-15-al(9)
Colorlessoilysolid;1H NMR(CDCl3 , 400 MHz)δ:
9.82(1H, d, J=8.1 Hz, H-15), 5.89(1H, d, J=8.0
Hz, H-14), 4.92, 4.56(1H, s, H-17), 1.97(3H, s,
Me-16), 1.24(3H, s, Me-18), 0.61(3H, s, Me-20);
13CNMR(CDCl3 , 100 MHz)δ:39.1(t, C-1), 19.8(t,
C-2), 37.8(t, C-3), 44.2(s, C-4), 55.4(d, C-5),
26.0(t, C-6), 38.6(t, C-7), 147.5(s, C-8), 56.2(d,
C-9), 40.5(s, C-10), 21.4(t, C-11), 39.5(t, C-12),
164.8(s, C-13), 127.2(d, C-14), 191.4(d, C-15),
24.3(q, C-16), 106.6(t, C-17), 29.0(q, C-18),
183.7(s, C-19), 12.8(q, C-20).Thedatawereinac-
cordancewiththosereported[ 7] .
(+)-Catechin(10) Paleyelowcrystal;EI-MSm/
z:290 [ M] +(52), 279(2), 256(3), 152(43), 139
(100), 123(34), 110(4), 94(7), 55(10).1HNMR
(CDCl3 , 400 MHz)δ:7.04(1H, d, J=1.9 Hz, H-2′),
6.83(1H, dd, J=8.1, 1.9 Hz, H-6′), 6.77(1H, d, J
=8.1 Hz, H-5′), 6.01(1H, d, H-6), 5.91(1H, d, J
=2.2 Hz, H-8), 4.87(1H, brs, H-2), 4.20(1H, m,
H-6), 2.85(1H, dd, J=16.6, 4.4 Hz, H-4b), 2.73
(1H, dd, J=16.6, 3.3 Hz, H-4a);13CNMR(CDCl3 ,
100MHz)δ:79.3(d, C-2), 66.9(d, C-3), 28.9(t, C-
4), 157.5(s, C-5), 96.1(d, C-6), 157.5(s, C-7),
95.5(d, C-8), 157.1(s, C-9), 99.7(s, C-10), 132.2
(s, C-1′), 115.4(d, C-2′), 145.3(s, C-3′), 145.2
(s, C-4′), 115.2(d, C-5′), 119.3(d, C-6′).These
datawereconsistentwiththosereported[ 10] .
β-Amyrin(11) Colorlessneedles.EI-MSm/z:426
[ M] +(49), 411(15), 257(12), 247(11), 229(11),
218(100), 203(68), 189(51), 176(29), 161(28),
147(32), 135(57), 121(49), 109(58), 95(68), 81
(57), 69(64), 55(50).1HNMR(CDCl3 , 400 MHz)
δ:5.19(1H, t, J=3.6 Hz, H-12), 1.04, 1.02, 0.96,
0.87, 0.84, 0.82 , 0.79(each3H, s, Me×8);13 C
NMR(CDCl3 , 100 MHz)δ:38.7(t, C-1), 27.0(t, C-
2), 79.1(d, C-3), 33.8(s, C-4), 55.3(d, C-5), 18.9
(t, C-6), 32.7(t, C-7), 39.9(s, C-8), 47.7(d, C-9),
37.0(s, C-10), 23.6(t, C-11), 121.8(d, C-12),
145.2(s, C-13), 41.8(s, C-14), 28.4(t, C-15), 26.2
(t, C-16), 32.5(s, C-17), 47.3(d, C-18), 49.6(t, C-
19), 31.1(s, C-20), 34.8(t, C-21), 37.2(t, C-22),
28.1(q, C-23), 15.6(q, C-24), 15.5(q, C-25), 16.9
(q, C-26), 20.6(q, C-27), 27.3(q, C-28), 33.3(q,
C-29), 23.7(q, C-30).Thedatawereidenticalto
thoseofreported[ 11] .
Stigmast-5-en-3β , 7α-diol(12) Whiteneedles.EI-
MSm/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).1HNMR(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), 0.90(3H, d, J
=6.4 Hz, Me), 0.82(3H, t, J=7.8 Hz, Me), 0.78
(3H, d, J=4.4 Hz, Me), 0.77(3H, d, J=6.7 Hz,
Me), 0.66(3H, s, Me);13CNMR(CDCl3 , 100 MHz)
δ:37.1(t, C-1), 31.4(t, C-2), 71.4(d, C-3), 42.1
(t, C-4), 46.3(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).Thedatawere
equaltothoseofliterature[ 12] .
Scopoletin(13), β-sitosterol(14)anddaucosterol(15)
wererespectivelyidentifiedbyTLCwithauthenticsam-
ples.
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