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Chemical constituents from Ainsliaea glabra

光叶兔儿风的化学成分研究



全 文 :广 西 植 物 Guihaia May2014,34(3):402-407           http://journal.gxzw.gxib.cn 
DOI:10.3969/j.issn.1000G3142.2014.03.022
陈亚萍,王书林,沈云亨,等.光叶兔儿风的化学成分研究[J].广西植物,2014,34(3):402-407
ChenYP,WangSL,ShenYH,etal.ChemicalconstituentsfromAinsliaeaglabra[J].Guihaia,2014,34(3):402-407
光叶兔儿风的化学成分研究
陈亚萍1,2,王书林1,沈云亨2,吴志军3∗
(1.成都中医药大学,成都611137;2.第二军医大学药学院天然药化教研室,
上海200003;3.第二军医大学附属长征医院药学部,上海200433)
摘 要:利用正反相硅胶、凝胶(SephadexLHG20)等多种柱色谱法,对光叶兔儿风化学成分进行分离纯化,并
根据理化性质和波谱数据进行结构鉴定.结果表明:已分离得到17个化合物,分别鉴定为蒲公英甾醇乙酸酯
(1),三十二碳烯(2),βG谷甾醇(3),大黄酚(4),扇醇棕榈酸酯(5),亚麻酸甲酯(6),亚油酸(7),植物醇(8),
[24S]G豆甾G4烯G3G酮(9),植物烯醛(10),白桦脂酸(11),13G羰基G十八碳二烯酸(12),EG7,9G11G羰基G棕榈酸
(13),蒲公英酸(14),3βG羟基G胆甾G5G烯(15),环氧树脂烯(16),28GOG月桂酸酯白桦醇(17).化合物1~17均
为首次从该植物中分离得到.
关键词:光叶兔儿风;化学成分;结构鉴定
中图分类号:Q946.91  文献标识码:A  文章编号:1000G3142(2014)03G0402G06
ChemicalconstituentsfromAinsliaeaglabra
CHENYaGPing1,2,WANGShuGLin1,SHENYunGHeng2,WUZhiGJun3∗
(1.ChengduUniversityofTraditionalChineseMedicine,Chengdu611137,China;2.DepartmentofPhytochemistry,
SchoolofPharmacy,SecondMilitaryMedicalUniversity,Shanghai200433,China;3.Departmentof
Pharmacology,ChangzhengHospital,SecondMilitaryMedicalUniversity,Shanghai200003,China)
Abstract:ToinvestigatethechemicalconstituentsofAinsliaeaglabra,severalchromatographiesincludingSilicagel
columnchromatographyandSephadexLHG20gelcolumnchromatographywereappliedtotheisolationandpurificaG
tionofchemicalconstituents.Thestructureswereidentifiedonthebasisofchemicalevidenceandspectraldata.The
resultsshowedthatseventeencompoundswereisolatedfromA.glabraandtheywereidentifiedastaraxasterylaceG
tate(1),dotriacontG1Gene(2),βGsitosterol(3),chrysophanol(4),lupenylpalmitate(5),methyllinolenate(6),linoleic
acid(7),phytol(8),stigmastG4GenG3Gone(9),phytenal(10),betulinicacid(11),(9Z,11E)G13GoxoG9,11GocatadecadienoG
icacid(12),EG7,9GdieneG11Gmethenylpalmiticacid(13),taraxinicacid(14),3βGhydroxyGcholestaG5Gene(15),epoxylyG
copaene(16),28GOGlaurylbetulin(17).Compounds1-17wereobtainedfromthisherbforthefirsttime.
Keywords:Ainsliaeaglabra;chemicalconstituent;structureidentification
  光叶兔儿风(Ainsliaeaglabra)为菊科兔儿风
属植物,中国特有.分布在中国大陆的四川、云南等
地,生长于海拔800~1200m的地区,多生长于林
缘和林下荫湿草丛中,目前尚未由人工引种栽培(中
国科学院中国植物志编辑委员会,2004).在«峨嵋
药植»中,光叶兔儿风是兔儿风药材的基原植物,全
草入药,主要用于治跌打损伤.四川民间也经常作
养阴清肺药,用来治肺痨咳嗽吐血.目前对光叶兔
儿风的研究较少,文献只报道该植物含有木樨草素
和4,5G二羟基桉烷酸甲酯两个化合物 (蒋宁,
收稿日期:2013G11G01  修回日期:2013G12G21
基金项目:国家重大科技专项项目(2009ZX09502G013)
作者简介:陈亚萍(1989G),女,浙江兰溪人,硕士在读,主要从事天然产物研究,(EGmail)zlchenyaping@126.com.
∗通讯作者:吴志军,博士,副教授,主要从事中药活性成分及资源评价研究工作,(EGmail)wuzhijun999@sina.com.
2007),分别为黄酮类和倍半萜内酯,与兔儿风属植
物的化学成分类型一致.为进一步开发和利用这一
民间中草药,作者对光叶兔儿风的化学成分进行了
较为系统的研究.本文报道通过硅胶柱色谱、凝胶
色谱等多种分离手段,从石油醚部位分离得到17个
化合物,利用理化性质和波谱学分析方法并参阅相
关文献数据,鉴定其结构为蒲公英甾醇乙酸酯(1),
三十二碳烯(2),βG谷甾醇(3),大黄酚(4),扇醇棕榈
酸酯(5),亚麻酸甲酯(6),亚油酸(7),植物醇(8),
[24S]G豆甾G4烯G3G酮(9),植物烯醛(10),白桦脂酸
(11),13G羰基G十八碳二烯酸 (12),EG7,9G11G羰基G
棕榈酸(13),蒲公英酸(14),3βG羟基G胆甾G5G烯
(15),环氧树脂烯(16),28GOG月桂酸酯白桦醇(17).
这些化合物均为首次从该植物中分离得到.
1 仪器与材料
1.1仪器
NMR测定用BrukerspeckospinACG600P核磁
共振仪;ESIGMS测定用安捷伦6410LCGMSGMS质
谱仪.柱层析用硅胶 H(200~300目)和薄层层析
用硅胶GF254均为青岛海洋化工厂生产;SephadeG
xLHG20为Pharmacia公司产品;ODSC18反相硅胶
填料为 Merk公司出品;试剂均为分析纯.
1.2材料
光叶兔儿风药材2012年5月采自四川省峨眉
山海拔800~1200m处,由四川省成都中医药大学
峨眉学院闵伯清老师鉴定为光叶兔儿风(Ainsliaea
glabra).
2 方法与结果
2.1提取和分离
干燥光叶兔儿风药材10kg,先把药材粉碎成
粗粉,再用80%的乙醇加热回流提取3次,每次提
取1h,合并3次提取液,提取液减压浓缩回收溶剂
至无醇味,约20L.浓缩液分别用石油醚、乙酸乙
酯、正丁醇进行萃取,得到3个萃取部位,分别为
159、89、292g.石油醚部位(159g)正相硅胶柱色
谱,石油醚G丙酮系统梯度洗脱,TLC检识并合并相
同流分.分为1~4段.
第4段上凝胶后再经正相硅胶色谱柱用500∶
1石油醚G丙酮系统逐渐加大极性纯化得到化合物
1、2、4.第3段上硅胶柱,用100∶1石油醚G丙酮作
为流动性开始洗脱,再经反复硅胶柱色谱、Sephadex
LHG20凝胶柱色谱以及C18反相硅胶柱色谱,分离
得到化合物5~8.第2段有27g,经过正相硅胶柱
后的化合物3,再经SephadexLHG20凝胶柱色谱得
到化合物9、10,其余部分经反相硅胶柱用甲醇∶水
9∶1系统得到化合物13,甲醇∶水7∶3系统分离
得到化合物11、12,经SephadexLHG20凝胶柱色谱
二氯甲烷∶甲醇1∶1系统分离得到15~17,第1
段正相硅胶经50∶1石油醚G丙酮,再经过Sephadex
LHG20凝胶柱色谱二氯甲烷∶甲醇1∶1纯化得到
化合物14.
所得化合物纯化后称量得:化合物1(16mg),
化合物2(5mg),化合物3(106mg),化合物4(8
mg),化合物5(26mg),化合物6(20mg),化合物7
(19mg),化合物8(5mg),化合物9(9mg),化合物
10(14mg),化合物11(16mg),化合物12(10mg),
化合物13(16mg),化合物14(140mg),化合物15
(6mg),化合物16(35mg),化合物17(13mg).
2.2结构鉴定
化合物 1  无色针晶 (CHCl3),分子式为
C32H52O2,ESIGMS:m/z468[M]+.1HGNMR(600
MHz,CDCl3)δH:0.73(2H,s,HG5),0.84(3H,s,HG
25),0.85(3H,s,HG24),0.85(3H,s,HG23),0.87
(3H,s,HG28),0.92(3H,s,HG27),1.02(3H,s,HG
26),1.02(3H,d,J=6.7Hz,HG29),2.04(3H,s,
GAc),4.48(1H,dd,J=5.5,10.9Hz,HG3),4.60,
4.61(2H,s,HG30);13CGNMR(150MHz,CDCl3)
δC:14.8(CG27),16.0(CG25),16.5(CG26),16.6(CG
24),18.3(CG6),19.6(CG29),21.5(CG2′)21.6(CG11),
23.8(CG2),25.6(CG28),25.7(CG12),25.7(CG21),
26.8(CG15),28.0(CG23),34.1(CG7),34.6(CG17),
37.2(CG10),37.9(CG4),38.4(CG1),38.4(CG22),39.0
(CG16),39.3(CG13),39.5(CG19),42.2(CG8),42.2
(CG14),48.7(CG18),50.5(CG9),55.6(CG5),81.1(CG
3),107.3(CG30),154.8(CG20),171.2(CG1′).上述
数据与文献报道的蒲公英甾醇乙酸酯一致(KhaG
lilovetal.,2003),故鉴定化合物1为蒲公英甾醇乙
酸酯.
化合物2 无色油状物,分子式为C32H64,EIG
MS:m/z448[M]+.1HGNMR(600MHz,CDCl3)
δH:0.88(3H,t,J=7.2Hz,HG32),1.26(48H,br.s,
HG5G28),2.05(2H,m,HG3),4.93(1H,d,J=12.4
3043期            陈亚萍等:光叶兔儿风的化学成分研究
图1 化合物1~17的化学结构
Fig.1 Thestructuresofcompounds1-17
Hz,HG1),4.99(1H,d,J=17.2Hz,HG1),5.81(1H,
m,HG2);13CGNMR(150 MHz,CDCl3)δ:29.1(CG
4),29.3(CG5),29.5(CG29),29.8(CG7G28),29.9(CG
6),32.1(CG30),33.8(CG3),114.2(CG1),139.4(CG
2).上述数据与文献报道的三十二碳烯一致(Chen
etal.,2010),故鉴定化合物2为三十二碳烯.
化合物3 白色针状结晶(CHCl3),分子式为
C29H50O,EIGMS:m/z414[M]+.与对照品βG谷甾
醇点于同一薄层板,以三个不同展开系统(石油醚∶
丙酮=10∶1,石油醚∶乙酸乙酯=5∶1,二氯甲烷
∶甲醇=50∶1)展开,Rf值均一致(米君令等,
2013),故鉴定化合物3为βG谷甾醇.
化合物 4  黄色晶体 (CHCl3),分子式为
C15H10O4,EIGMS:m/z254 [M]+.1HGNMR(600
404 广 西 植 物                  34卷
MHz,CDCl3)δ:2.46(3H,s,HG15),7.08(1H,brs,
HG2),7.28(1H,dd,J=1.5,8.4Hz,HG7),7.67(1H,
dd,J=7.8,8.1Hz,HG6),7.81(1H,dd,J=1.2,7.8
Hz,HG5);13CGNMR(150MHz,CDCl3)δ:22.4(CG
15),113.9(CG13),116.0(CG12),120.0(CG7),121.5
(CG4),124.5(CG5),124.7(CG2),133.4(CG14),133.8
(CG11),137.1(CG6),149.5(CG3),162.5(CG8),162.9
(CG1),182.1(CG10),192.7(CG9).上述数据与文献
报道的大黄酚一致(Luetal.,2003),故鉴定化合物
4为大黄酚.
化合物 5  浅黄色无定形粉末,分子式为
C48H84O2,EIGMS:m/z496[M]+.薄层喷硫酸乙
醇溶液加热显红色.LiebermannGBurchard反应呈
阳性,提示为三萜类化合物.1HGNMR(600MHz,
CDCl3)δ:0.78(3H,t,J=8.0Hz,HG18′),0.83(3H,
s,HG28),0.84(3H,s,HG24),0.85(3H,s,HG23),
0.87(3H,s,HG25),0.92(3H,s,HG27),1.04(3H,s,
HG26),1.25G1.32(14CH2,br.s,HG4′G17′),1.39
(2H,m,HG3′),1.66(3H,s,30GCH3),2.28(2H,t,J
=6.2Hz,HG2′),2.37(1H,m,HG19),4.47(1H,dd,
J=5.2,6.8Hz,HG3),4.56,4.68(2H,br.s,HG29);
13CGNMR(150MHz,CDCl3)δ:14.3(CG18′),14.6
(CG27),16.1(CG26),16.3(CG25),16.7(CG24),18.1
(CG28),18.3(CG6),19.4(CG30),21.1(CG11),22.8
(CG17′),23.9(CG2),25.2(CG12),25.3(CG3′),27.6
(CG15),28.1(CG23),29.3G29.9(CG4′G15′),30.0(CG
21),32.1(CG16′),34.4(CG7),35.0(CG2′),35.7(CG
16),37.2(CG10),38.0(CG4),38.2(CG13),38.5(CG
1),40.1(CG22),41.0(CG8),43.0(CG14),43.1(CG
17),48.4(CG18),50.5(CG9),50.5(CG19),55.5(CG
5),0.7(CG3),109.5(CG29),151.0(CG20),173.8(CG
1′).上述数据与文献报道的羽扇醇棕榈酸酯一致
(张云峰等,2006;Hideyukietal.,2001),故鉴定化
合物5为羽扇醇棕榈酸酯.
化合物6 无色油状物,分子式为C19H34O2,
EIGMS:m/z292 [M]+.1 HGNMR(600 MHz,
CDCl3)δ:0.86(3H,t,J=7.5Hz,HG18),1.38-1.30
(8H,m,HG4,5,6,7),1.63G1.59(2H,m,HG3),2.10G
2.03(4H,m,HG8,17),2.30(2H,t,J=7.5Hz,HG
2),2.80G2.75(4H,m,HG11,14),3.66(3H,s,
GOCH3),4.2G5.29(6H,m,HG9,10,12,13,15,
16);13CGNMR(150 MHz,CDCl3)δ:14.2(CG18),
22.7(CG17),25.1(CG3),25.8(CG4),27.3(CG8),29.8G
29.3(3C,CG5,6,7),31.7(CG2),34.2(CG11),51.6
(GOCH3),130.4G128.1(6C,CG9,10,12,13,15,16),
174.4(CG1).上述数据与文献报道的亚麻酸甲酯一
致(Sungranetal.,2010),故鉴定化合物6为亚麻
酸甲酯.
化合物7 淡黄色油状物,分子式为C18H32O2,
EIGMS:m/z280 [M]+.1 HGNMR(600 MHz,
CD3OD)δ:0.90(3H,t,J=6.5Hz,HG18),1.26G1.33
(14H,m,HG4G7,HG15G17),1.64(2H,m,HG3),2.05
(4H,dd,J=7.1,13.6Hz,HG8,14),2.36(2H,t,J=
7.5Hz,HG2),2.77(2H,m,HG11),5.36(4H,m,HG
9,10,12,13);13CGNMR(150MHz,CD3OD)δ:14.1
(CG18),22.6(CG17),24.6(CG3),25.8(CG16)180.5
(CG1),27.1(CG15),29.0(CG4),29.1(CG14),29.2(CG
8),29.5(CG5),29.6(CG6),31.5(CG7),31.9(CG11),
34.1(CG2),128.0(CG10),127.9(CG13),130.0(CG9),
130.2(CG12).上述数据与文献报道的亚油酸一致
(李雪虎等,2010),故鉴定化合物7为亚油酸.
化合物8 无色晶体(CH3OH),分子式为
C20H40O,ESIGMS:m/z296[M]+.1HGNMR(600
MHz,CDCl3)δ:0.86,0.85(各3H,d,J=4.0,HG19),
0.88,0.87(各3H,d,J=0.8,HG16,17),1.66(2H,
m,HG9,20),1.95(2H,t,J=7.2Hz,HG4),4.14
(2H,d,J=6.8Hz,HG2),5.40(1H,t,J=7.0Hz,HG
2);13CGNMR(150MHz,CDCl3)δ:16.2(CG20),19.7
(CG18),19.8(CG19),22.7(CG16),23.3(CG17),24.5
(CG9),25.2(CG5),25.2(CG13),28.6(CG15),32.8(CG
7),37.4(CG8),32.9(CG11),37.4(CG10),37.4(CG
12),37.5(CG6),39.3(CG14),39.9(CG4),59.4(CG1),
123.2(CG2),140.7(CG3).上述数据与文献报道的
植物醇一致(Dirketal.,2004),故鉴定化合物8为
植物醇.
化合物9 淡黄色油状物,分子式为C29H48O,
ESIGMS:m/z412 [M]+.1HGNMR(600 MHz,
CDCl3)δ:0.71(3H,s,HG18),0.83(9H,d,J=
6.8Hz,HG21,26,27),0.91(3H,d,J=5.7Hz,HG
29),1.18(3H,s,HG19),5.72(1H,s,HG4);13CG
NMR(150 MHz,CDCl3)δ:12.1(CG18),17.5(CG
29),18.9(CG21),19.2(CG19),19.9(CG27),21.2(CG
26),23.02(CG11),24.3(CG28),26.3(CG15),28.3(CG
23),29.3(CG25),29.9(CG16),32.2(CG7),33.1(CG
6),34.0(CG2),34.0(CG22),35.8(CG1),35.9(CG8),
36.3(CG20),38.8(CG10),39.8(CG12),42.6(CG13),
5043期            陈亚萍等:光叶兔儿风的化学成分研究
46.0(CG24),54.0(CG9),56.0(CG14),56.3(CG17),
123.9(CG4),171.9(CG5),199.8(CG3).上述数据与
文献报道的[24S]G豆甾G4烯G3G酮一致(王夕红等,
1993),故鉴定化合物9为[24S]G豆甾G4烯G3G酮.
化合物10 无色油状物,易溶于石油醚、氯仿、
乙酸乙酯,不溶于水,分子式为C20H38O,ESIGMS:
m/z294[M]+.1HGNMR(600MHz,CDCl3)δ:0.84
(3H,d,J=7.5Hz,HG19),0.85(3H,d,J=6.5Hz,
HG19),0.87(3H,d,J=6.5Hz,HG20),0.87(3H,d,J
=6.5Hz,HG16),2.19(3H,s,HG17),5.89(1H,d,J
=6.8,HG2),9.99(1H,d,J=8.1Hz,HG1);13CG
NMR(150 MHz,CDCl3)δ:17.7(CG17),19.8(CG
18),19.9(CG19),22.8(CG20),22.9(CG16),24.6(CG
9),24.8(CG13),24.9(CG5),28.1(CG15),32.8(CG7),
33.9(CG11),36.7(CG6),36.9(CG12),37.4(CG10),
37.5(CG8),39.5(CG14),41.1(CG4),127.5(CG2),
164.6(CG3),191.5(CG1).上述数据与文献报道的
植物烯醛一致(袁兆慧等,2006),故鉴定化合物10
为植物烯醛.
化合物11 无色针晶(CHCl3),分子式为
C30H48O3,EIGMS:m/z456 [M]+.1HGNMR(600
MHz,CDCl3)δ:0.75(3H,s,HG24),0.82(3H,s,HG
25),0.93(3H,s,HG23),0.96(3H,s,HG26),0.97
(3H,s,HG27),1.69(3H,s,HG30),2.99(1H,ddd,J
=5.53,11.35,11.35Hz,HG19),3.19(1H,dd,J=
4.7,11.6Hz,HG3),4.60(1H,d,J=1.9Hz,HG29a),
4.74(1H,d,J=1.9 Hz,HG29b);13CGNMR(150
MHz,CDCl3)δ:14.9(CG27),15.5(CG24),16.2(CG
25),16.3(CG26),18.4(CG6),19.5(CG30),21.0(CG
11),25.7(CG12),27.6(CG2),28.1(CG23),29.9(CG
21),30.7(CG15),32.1(CG16),34.5(CG7),37.2(CG
22),37.2(CG10),38.5(CG13),38.5(CG1),38.8(CG
4),41.8(CG8),42.6(CG14),47.1(CG18),49.4(CG
19),50.56(CG9),55.5(CG5),56.5(CG17),79.2(CG
3),109.8(CG29),150.6(CG20),180.9(CG28).上述
数据与文献报道的白桦脂酸一致(陈家源等,2008),
故鉴定化合物11为白桦脂酸.
化合物12 白色固体,分子式为C18H30O3,EIG
MS:m/z294[M]+.1HGNMR(600MHz,CDCl3)δ:
0.90(3H,t,J=6.8Hz,HG18),1.31(14H,brs,HG3G
7,15G16),1.61(2H,m,HG17),2.30(2H,q,J=7.4
Hz,HG8),2.35(2H,t,J=7.4Hz,HG2),2.52(2H,t,
J=7.4Hz,HG14),5.96(1H,dt,J=7.6,11.1Hz,HG
9),6.12(1H,t,J=11.3Hz,HG10),6.18(1H,d,J=
15.4Hz,HG12),7.47(1H,dd,J=11.3,15.4Hz,HG
11);13CGNMR(150 MHz,CDCl3)δ:14.1(CG18),
22.7(CG17),24.3(CG15),24.8(CG3),28.5(CG4),29.1
(CG6),29.1(CG8),29.2(CG5),29.4(CG7),31.7(CG
16),34.2(CG2),41.4(CG14),127.2(CG10),129.5(CG
12),137.3(CG11),142.7(CG9),179.6(CG1),201.6
(CG13).上述数据与文献报道的13G羰基G十八碳二
烯酸一致(Meietal.,2000),故鉴定化合物12为
13G羰基G十八碳二烯酸.
化合物13 白色固体,分子式为C16H26O3,EIG
MS:m/z294[M]+.1HGNMR(600MHz,CDCl3)δ:
0.89(3H,t,J=7.1Hz,HG16),1.33(2H,m,HG15),
1.44(2H,br.s,HG5),1.63(2H,m,HG3),2.18(2H,
br.s,m,HG6),2.36(2H,t,J=7.7Hz,HG2),2.54
(2H,t,J=7.6Hz,HG12),6.09(1H,d,J=15.5Hz,
HG10),6.17(2H,m,HG7,8),7.14(1H,m,HG9);
13CGNMR(150MHz,CDCl3)δ:14.1(CG16),22.6(CG
15),24.3(CG13),24.8(CG3),28.8(CG5),29.1(CG4),
31.7(CG14),33.2(CG6),34.0(CG2),40.7(CG12),
128.1(CG8),129.1(CG10),143.0(CG9),145.45(CG
7),178.8(CG1),201.4(CG11).上述数据与文献报
道的EG7,9G11G羰基G棕榈酸一致(张喜萍,2010),故
鉴定化合物13为EG7,9G11G羰基G棕榈酸.
化合物14 无色固体,分子式为 C15H18O4,
ESIGMS:m/z285[M+Na]+.1HGNMR(600MHz,
CDCl3)δ:1.60(3H,s,HG15),2.15(1H,m,HG9α),
2.19(1H,m,HG8β),2.25(1H,m,HG3α),2.35(1H,
m,HG3β),2.56(1H,m,HG7),2.90(1H,m,HG9β),
3.38(1H,m,HG2β),4.58(1H,dd,J=9.0,10.0Hz,
HG6),4.91(1H,d,J=10.0,HG5),5.51(1H,d,J=
2.9Hz,HG13b),5.68(1H,dd,J=3.7,13.0Hz,HG
1),6.24(1H,d,J=3.4Hz,HG13a);13CGNMR(150
MHz,CDCl3)δ:17.0(CG15),26.7(CG2),30.1(CG8),
36.7(CG9),39.2(CG3),50.3(CG7),82.1(CG6),120.1
(CG13),126.0(CG5),130.3(CG10),139.8(CG4),
143.2(CG11),149.9(CG1),170.6(CG12),173.3(CG
14).上述数据与文献报道的蒲公英酸一致(KlauG
diaetal.,2010),故鉴定化合物14为蒲公英酸.
化合物15 白色粉末,分子式为C27H44O,EIG
MS:m/z387[M]+.1HGNMR(600MHz,CDCl3)δ:
0.67(3H,s,HG18),1.00(3H,s,HG19),3.52(1H,
m,HG3),5.34(1H,m,HG6);13CGNMR(150MHz,
604 广 西 植 物                  34卷
CDCl3)δ:12.1(CG18),18.9(CG21),19.2(CG19),21.2
(CG11),22.8(CG26),22.8(CG27),23.2(CG23),24.5
(CG15),28.4(CG16),28.4(CG25),29.9(CG22),31.8
(CG2),32.1(CG7),32.1(CG8),36.4(CG20),36.7(CG
10),37.4(CG1),39.9(CG12),39.9(CG24),42.5(CG
13),42.5(CG4),50.3(CG9),56.2(CG17),56.9(CG
14),72.0(CG3),121.9(CG6),140.9(CG5).上述数据
与文献报道的3βG羟基G胆甾G5G烯一致(刘涛等,
2012),故鉴定化合物15为3βG羟基G胆甾G5G烯.
化合物16 淡黄色油状物,分子式为C40H78O,
ESIGMS:m/z575 [M]+.1HGNMR(600 MHz,
CDCl3)δ:0.82G0.87(24H,br.s,HG1,32G35,38G40),
1.24(3H,s,HG36),1.65(3H,s,HG37),1.95(2H,t,J
=7.3Hz,HG20),2.15(2H,m,HG17),2.71(1H,t,J
=6.3Hz,HG15),5.39(1H,t,J=6.9Hz,HG18);
13CGNMR(150MHz,CDCl3)δ:14.3(CG37),16.4(CG
36),19.8(CG35),19.9(CG38),19.9(CG39),19.9(CG
34),22.8(CG1),22.8(CG32),22.9(CG40),22.9(CG
33),24.7(CG25),24.7(CG4),24.7(CG16),24.7(CG
8),24.7(CG29),25.0(CG12),25.4(CG21),28.2(CG
2),28.2(CG31),29.6(CG17),29.8(CG24),32.9(CG
10),33.1(CG6),33.1(CG23),33.1(CG27),36.9(CG
22),37.5(CG11),37.6(CG5),37.6(CG9),37.6(CG
28),37.7(CG7),37.7(CG26),39.6(CG3),39.6(CG
13),39.6(CG30),40.1(CG20),59.7(CG14),63.3(CG
15),123.3(CG18),140.5(CG19).上述数据与文献
报道的环氧树脂烯一致(Delahaisetal.,1997),故
鉴定化合物16为环氧树脂烯.
化合物17 白色粉末,分子式为 C41H70O3,
ESIGMS:m/z610 [M]+.1HGNMR(600 MHz,
CDCl3)δ:0.75(3H,s,HG26),0.83(3H,s,HG25),
0.93(3H,s,HG24),0.97(3H,s,HG27),1.25(4CH2,
br.s,HG4′G7′),1.69(3H,s,HG30),2.26(2H,t,J=
7.5Hz,HG2′),2.35(1H,m,HG19),3.80(1H,s,HG
28a),3.82(1H,s,HG28b),4.45(1H,dd,J=7.5,10.5
Hz,HG3),4.73,4.60(2H,brs,HG29);13CGNMR
(150MHz,CDCl3)δ:14.2(CG11′),14.8(CG27),15.5
(CG24),16.1(CG25),16.3(CG26),18.4(CG6),19.5
(CG30),21.0(CG11),22.8(CG10′),24.8(CG8′),25.6
(CG12),27.5(CG15),28.1(CG23),29.2(CG8′),29.4
(CG16),29.4(CG7′),29.5(CG6′),29.6(CG5′),29.8
(CG21),29.8(CG4′),30.6(CG9′),32.0(CG3′),32.7
(CG2′),34.0(CG7),34.5(CG22),37.2(CG10),37.8(CG
13),38.5(CG1),38.8(CG4),40.8(CG8),42.6(CG14),
47.0(CG17),48.4(CG18),49.4(CG19),50.7(CG9),
55.5(CG5),56.5(CG28),79.2(CG3),150.5(CG20),
109.8(CG29),181.2(CG1′).上述数据与文献报道的
28GOG月桂酸酯白桦醇一致(Harishetal.,2010),
故鉴定化合物17为28GOG月桂酸酯白桦醇.
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7043期            陈亚萍等:光叶兔儿风的化学成分研究