蓍草化学成分研究

Study on the chemical constituents from Achillea alpine

研究蓍草Achillea alpine L.全草的化学成分。采用大孔树脂、ODS、Sephadex LH-20凝胶柱色谱和pre-HPLC等方法分离与纯化,运用NMR、MS等波谱技术鉴定化合物结构。从蓍草95%乙醇提取物中分离得到16个化合物,分别是(2 E,4 E)-N-(2-methylbutyl)deca-2,4-dienamide(1)、墙草碱(2)、(E,E,Z)-2,4,8-decatrienoicacid isobutylamide-8,9-dehydropellitorine(3)、N-2′-methylbutyl-(E,E)-2,4-decadienam(4)、methyl-(E,E)-2,4,9-oxooctadeca-10,12-dienoate(5)、(S)-14-(E,E)-10,12-methyl 14-hydroxy-9-oxo-octadeca-10,12-dienoate(6)、(E,E)-2,4-undecadiene-8,10-diynamide-N-(2-methylpropyl)(7)、(E,E)-2,4-decadienoic acid p-hydroxyphenethylamide(8)、sinapyl alcohol diisovalerate(9)、(S)-13-hydroxyoctadeca-(Z,E)-9,11-dienoic acid(10)、(E,E)-2,4-decadienamide acid p-methoxyphenethylamide(11)、erythro-N-isobutyl-4,5-dihydroxy-2-(E)-decenamide(12)、3-O-阿魏酰-奎宁酸(13)、肉桂酸(14)、绿原酸(15)、3-O-咖啡酰-5-O-阿魏酰奎宁酸(16)。化合物1是一个新的酰胺类化合物;化合物4~6、9、10、12、13、16为首次从该属植物中分离得到;化合物8、11为首次从蓍草中分离得到。化合物1~11在四种不同的胃癌细胞株上进行细胞毒活性筛选,结果显示化合物2、5与9在50μM时对MGC-803细胞株具有较弱抑制活性,其抑制率依次为38.7%、34.7%、31.5%。

To study the chemical constituents from the whole plant of Achillea alpine L..Various column chromatography, such as macroporous resin, ODS,Sephadex LH-20 and preparative HPLC were adopted to isolate and purify the compounds, and the structures of compounds 1-16 were identified by NMR,MS and other spectroscopic techniques.Sixteen compounds have been isolated from the 95% ethanol extract of A.alpine,and they were identified as(2E, 4E)-N-(2-methylbutyl) deca-2,4-dienamide(1),pellitorine(2),(E,E,Z)-2,4,8-decatrienoicacid isobutylamide-8,9-dehydropellitorine(3),N-2′-methylbutyl-(E,E)-2,4-decadienam(4),methyl-(E, E)-2,4,9-oxooctadeca-10,12-dienoate(5),(S)-14-(E, E)-10,12-methyl 14-hydroxy-9-oxo-octadeca-10,12-dienoate(6),(E,E)-2,4-undecadiene-8,10-diynamide-N-(2-methylpropyl)(7),(E, E)-2,4-decadienoic acid p-hydroxyphenethylamide(8),sinapyl alcohol diisovalerate(9),(S)-13-hydroxyoctadeca-(Z,E)-9,11-dienoic acid(10),(E,E)-2,4-decadienamide acid p-methoxyphenethylamide(11),erythro-N-isobutyl-4,5-dihydroxy-2-(E)-decenamide(12),3-O-feruloylquinic acid(13),cinnamic acid(14),chlorogenic acid(15),3-O-caffeoyl-5-O-feruloylquinic acid(16).Compound 1 was a new amide.Compounds 4-6,9,10,12,13,16 were isolated from the Achillea genus for the first time.Compounds 8 and 11 were isolated from this plant for the first time.Cytotoxic effects of compounds 1-11 were screened on four different gastric cancer cell lines, and the results showed that compounds 2,5 and 9 had weak activities on MGC-803 cell line at 50 μM with the inhibitory rates at 38.7%,34.7%,31.5%,respectively.