胭脂树醇提物中乙酸乙酯部位的化学成分

Chemical constituents from ethyl acetate fraction of Bixa orellana L.

目的:研究胭脂树(Bixa orellana L.)地上带果枝叶部分醇提物中乙酸乙酯部位的化学成分。方法:综合运用反复硅胶柱、ODS开放柱、凝胶柱色谱和反相半制备型HPLC,对胭脂树的90%乙醇提取物中乙酸乙酯极性部位的化学成分进行分离纯化,并通过HR-TOF-MS、NMR等光谱数据及X-ray单晶衍射鉴定化合物结构。结果:分离得到18个化合物,分别鉴定为isoshonanin(1)、(-)-3-羟基-β-紫罗兰酮(2)、己二烯二酸(3)、(S)-3-羟基-β-紫罗兰酮(4)、3-hydroxy-7,8-dehydro-β-ionol(5)、(6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one(6)、黑麦草内酯(7)、松脂素(8)、β-谷甾醇(9)、3-(3′-hydroxybutyl)-2,4,4-trimethylcyclohexa-2,5-dienone(10)、异黑麦草内酯(11)、单棕榈酸甘油酯(12)、桂皮酸(13)、(3β,22α)-stigmast-5-ene-3,22-diol(14)、表松脂酚(15)、去氢吐叶醇(16)、9-hydroxymegastigm-5-en-4-one(17)、牛蒡子苷元(18)。结论:除化合物9以外,其他化合物均为首次从该植物中分离得到。对分离得到的18个化合物进行抗炎活性筛选,活性分析表明化合物4具有抑制脂多糖(LPS)诱导RAW 264.7巨噬细胞释放NO的作用,其半数抑制浓度为(5.48±1.48)μmol/L。

Objective:To investigate the chemical constituents of the ethyl acetate fractions from 90%ethanol extract of aerial part of Bixa orellana L.Methods:The compounds were isolated and purified by repeated silica gel column,ODS open column,Sephadex LH-20 chromatography and semi-preparative HPLC.Based on HR-TOF-MS,NMR and other spectral data,their structures were identified.Results:Eighteen compounds were identified as isoshonanin(1),(-)-3-hydroxy-β-ionone(2),muconic acid(3),(S)-3-hydroxy-β-ionone(4),3-hydroxy-7,8-dehydro-β-ionol(5),(6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one(6),(+)-isololiolide(7),(+)-pinoresinol(8),β-sitosterol(9),3-(3′-hydroxybutyl)-2,4,4-trimethylcyclohexa-2,5-dienone(10),(-)-loliolide(11),glyceroyl monopalmitate(12),cinnami acid(13),(3β,22α)-stigmast-5-ene-3,22-diol(14),(+)-epipinoresinol(15),(+)-dehydrovomifoliol(16),9-hydroxymegastigm-5-en-4-one(17),arctigenin(18).Conclusion:All compounds were isolated from this plant for the first time except compound 9.All compounds were screened for anti-inflammatory activities and compound 4 has inhibitory effect on NO release in LPS-induced RAW 264.7 macrophage cells with IC50 value of(5.48±1.48)μmol/L.