本课题对两种具有抗糖尿病功能作用的中药-郁金(Curcuma wenyujin)和华泽兰(Eupatorium chinense)的抗糖尿病化学成分进行了研究。对郁金根茎的95%乙醇提取物进行了较系统的化学成分分离及鉴定,从中得到三十四个化合物,包括三十二个倍半萜,其中有两个新的杜松烷型倍半萜,即curcujinone A(1)和 curcujinone B(2),三十个已知倍半萜,即 curcumol(3),curcumenol(4),7α,11 α-epoxy-5β-hydroxy-9-guaiaen-8-one(5),zedoarondiol(6),1 S,4S,5S,10R-isozedoarondiol(7),procurcumadiol(8),phaeocaulisin E(9),12-hydroxycurcumenol(10),6-guaiene-4α,10α-diol(11),procurcumenol(12),4,10-epizedoarondiol(13),zedoarolide B(14),zedoalactone A(15),trans,trans-germacrone(16),curdione(17),1S,10S',4S,5S-germacrone(18),13-hydroxygermacrone(19),zederone(20),furanodienone(21),1(10)Z,4Z-furanodiene-6-one(22),curdionolide A(23),curcumalactone(24),curcumanolide A(25),curcumanolide B(26),gajutsulactone B(27),gajutsulactone A(28),curcuzedoalide(29),wenyujinin C(30),curzerenone(31),cyperusol C(32),一个带糖单萜(1R,2S,4S,5R)-angelicoidenol-2-O-β-D-glucopyranoside(33),一 个双萜 amoxanthin A(34)。从 中可以看出倍 半萜为其主要成分。对华泽兰根茎的95%乙醇提取物石油醚和乙酸乙酯萃取部位进行了化学成分分离及鉴定,从中得到二十个化合物,其中十个为新的苯并呋喃类化合物,即dieupachinin G(35),dieupachinin H(36),dieupachinin I(37),dieupachinin J(38),dieupachinin K(39),1-(6-hydroxy-2-(1-hydroxyethyl)benzofuran-5-yl)ethenone(40),8-acetyl-7-hydroxy-4-methyldibenzo[b,d]furan-2-carboxylic acid(41),1-(3,6-dihydroxy-3-methyl-2,3,3a,8b-tetrahydrofuro[3,2-b]benzofuran-7-yl)ethenone(42),8-acetyl-4,7-dihydroxy-1,4-dimethyl-1,2,3,4-tetrahydro-4a,9b-epoxydibenzo[b,d]furan-1-carboxylic acid(43),4-(acetoxymethyl)-8-acetyl-4,7-dihydroxy-1-methyl-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-carboxylic acid(44),十个已知的苯并呋喃类化合物,即泽兰素(45),2,5-二乙酰基-6-羟基-苯并呋喃(46),ruscodibenzofuran(47),(2R,3S)-5-乙酰基-6-羟基-2-异丙烯基-3-乙氧基-苯并呋喃(48),6-hydroxy-3β-methoxytrematone(49),2',4'-dihydroxy-5'-(3-methyl-3-buten-1-yl)acetophenone(50),12,13-dihydroxyeuparin(51),3α-tiglinoyfoxy-2,3-dihydroeupar(52),ethanone(53),gymnastone(54)。从中可以看出苯并呋喃类为其主要成分。对上述化合物通过多种波谱技术(NMR,ESI,IR等)进行了结构鉴定,并对这两味中药的特征性成分倍半萜和苯并呋喃类化合物进行了体外抗糖尿病活性研究,发现一些化合物如 curcumenol(4),7α,11α-epoxy-5β-hydroxy-9-guaiaen-8-one(5),莪术二酮(17),(1S,4S,5S,10S)-germacrone(18),zederone(20),a mixture of curcumanolide A(25)and curcumanolide B(26),gajutsulactone B(27),and wenyujinin C(30)能明显增加HepG2细胞葡萄糖消耗量;化合物dieupachinin G(35),dieupachinin H(36),dieupachinin J(38),dieupachinin K(39),8-acetyl-7-hydroxy-4-methyldibenzo[b,d]furan-2-carboxylic acid(41),8-acetyl-4,7-dihydroxy-1,4-dimethyl-1,2,3,4-tetrahydro-4a,9b-epoxydibenzo[b,d]furan-1-carboxylic acid(43)能显著增加C2C12细胞的葡萄糖转运量。本文的研究工作基本上阐明了这两味药材的抗糖尿病物质基础,探讨了两类化合物抗糖尿病的构效关系,发现了可作为抗糖尿病先导化合物的分子,为进一步开发新型抗糖尿病药物打下了坚实的基础。
