洋金花果皮正丁醇层化学成分研究

Chemical Constituents from the n-Butanol Layer of the Pericarps of Datura metel

目的:研究洋金花果皮正丁醇层的化学成分。方法:以70%乙醇提取洋金花果皮,并依次采用石油醚、乙酸乙酯、正丁醇进行萃取,利用硅胶、ODS、Sephadex LH-20等柱色谱及制备型HPLC对其正丁醇层进行分离纯化,运用HR-ESI-MS和NMR等多种波谱技术鉴定化合物结构。结果:从洋金花果皮的正丁醇层中共分离得到13个化合物,分别鉴定为:(+)-puerol-B2-O-β-glucopyranoside(1)、大豆苷(2)、pueraria glycoside(PG)-1(3)、葛根素(4)、daidzein-4′,7-diglucoside(5)、6″-O-α-D-apiofranosylpuerarin(6)、pueraria glycolside(PG)-3(7)、(S)-methyl 2-amino-2-phenylacetate(8)、(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(9)、1H-pyrido[3,4-b]indol-1-one,2,3,4,9-tetrahydro-7-hydroxy(10)、(Z)-3-hexenyl-O-α-arabinopyranosyl-(1→6)-O-β-D-glucopyranoside(11)、phenethyl alcohol-8-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside(12)、phenylmethyl-7-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside(13)。结论:其中,化合物8、9、10为首次从茄科植物中分离得到,并首次得到化合物1的单晶X射线晶体结构数据,化合物10、13表现为较强的抗肿瘤活性。

Objective:To study the chemical constituents from the n-butanol layer of the pericarps of Datura metel.Methods:The pericarps of Datura metel was extracted by 70%ethanol,and extracted by petroleum ether,ethyl acetate,n-butanol.The n-butanol layer was isolated and purified by the process of silica gel,ODS,Sephadex LH-20,and preparative HPLC.Their structures were identified by HR-ESI-MS,NMR and other spectroscopic techniques.Results:Thirteen compounds were isolated from the n-butanol layer of the pericarps of Datura metel and identified as(+)-puerol-B2-O-β-glucopyranoside(1),daidzin(2),pueraria glycoside(PG)-1(3),puerarin(4),daidzein-4′,7-diglucoside(5),6″-O-α-D-apiofranosylpuerarin(6),pueraria glycolside(PG)-3(7),(S)-methyl 2-amino-2-phenylacetate(8),(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(9),1 H-pyrido[3,4-b]indol-1-one,2,3,4,9-tetrahydro-7-hydroxy(10),(Z)-3-hexenyl-O-α-arabinopyranosyl-(1→6)-O-β-D-glucopyranoside(11),phenethyl alcohol-8-O-β-D-glucopy-ranosyl-(1→2)-β-D-glucopyranoside(12),phenylmethyl-7-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside(13),respectively.Conclusion:Among them,Compounds 8 to 10 are isolated from the Solanaceae for the first time.The crystal structure data of compound 1 by single crystal X-ray diffraction are obtained for the first time.Compounds 10 and 13 show strong anti-tumor activity.