高山蓍中的萜类成分及其降糖活性研究

Study on the terpenoids from Achillea alpina L.and their hypoglycemic activity

研究高山蓍Achillea alpina L.全草中萜类成分及其降糖活性。采用ODS、Sephadex LH-20柱色谱和pre-HPLC等方法分离纯化,采用NMR、MS等波谱技术鉴定化合物的结构。从高山蓍的二氯甲烷部位中分离纯化得到13个单体化合物,分别是[3S-[3α,3aα,4α(Z),6α,6aα,9α,9aα,9bβ]],2-butenoic acid,2-methyl-2,3,3a,4,5,6,6a,9,9a,9b-decahydro-6,6a,9-trihydroxy-3,6,9-trimethyl-2-oxoazuleno[4,5-b]furan-4-yl ester(1)、10β-hydroxyisodauc-6-en-14-al(2)、isodauc-6-ene-10β,14-diol(3)、aphanamol II(4)、ent-4(15)-eudesmene-1β,6α-diol(5)、12-羟基-α-香附酮(6)、1β-羟基-α-香附酮(7)、(E)-3,7,11-trimethyl-1,6,10-dodecatriene-3,5-diol(8)、2,6,10-trimethyl-3,6,11-dodecatriene-2,8,10-triol(9)、黑麦草内酯(10)、8-hydroxyphellandral(11)、(3R,6R,7E)-3-hydroxy-4,7-megastigmadien-9-one(12)、saniculamoid D(13)。化合物1~4、6、8和10~13为首次从该属植物中分离得到,化合物5、7和9为首次从植物高山蓍中分离得到。将化合物1~13在棕榈酸诱导的HepG2胰岛素抵抗细胞模型上进行细胞耗糖量的活性筛选,结果显示化合物5、9和10(50μmol/L)具有良好的逆转胰岛素抵抗活性。

To study the terpenoids constituents and their hypoglycemic activities from Achillea alpina L..The extract was separated and purified by column chromatography on ODS,Sephadex LH-20 column chromatography and pre-HPLC.The structures of the compounds 1-13 were identified by NMR,MS and other spectroscopic techniques.Thirteen compounds have been isolated and purified from dichloromethane extract of A.alpina,and they were identified as[3S-[3α,3aα,4α(Z),6α,6aα,9α,9aα,9bβ]],2-butenoic acid,2-methyl-2,3,3a,4,5,6,6a,9,9a,9b-decahydro-6,6a,9-trihydroxy-3,6,9-trimethyl-2-oxoazuleno[4,5-b]furan-4-yl ester(1),10β-hydroxyisodauc-6-en-14-al(2),isodauc-6-ene-10β,14-diol(3),aphanamol II(4),ent-4(15)-eudesmene-1β,6α-diol(5),12-hydroxy-α-cyperone(6),lβ-hydroxy-α-cyperone(7),(E)-3,7,11-trimethyl-1,6,10-dodecatriene-3,5-diol(8),2,6,10-trimethyl-3,6,11-dodecatriene-2,8,10-triol(9),loliolide(10),8-hydroxyphellandral(11),(3R,6R,7E)-3-hydroxy-4,7-megastigmadien-9-one(12),saniculamoid D(13).Compounds 1-4,6,8 and 10-13 were isolated from the Achillea genus for the first time.Compounds 5,7 and 9 were isolated from this plant for the first time.Glucose consumption was analyzed to investigate the effect of compounds 1-13 in palmitic acid-mediated HepG2-insulin resistance cell.The result showed that compounds 5,9 and 10(50μmol/L)exhibited strong reversal IR activity.