牡丹皮正丁醇部位化学成分研究

Chemical constituents from n-butyl alcohol extracts of Moutan Cortex

研究牡丹皮85%乙醇提取物正丁醇萃取部位化学成分及其抗炎、抗菌的活性。采用大孔树脂柱色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱结合反相中压柱色谱和半制备色谱技术,分离纯化牡丹皮的正丁醇萃取部位,并利用核磁共振波谱、质谱数据与文献比对鉴定化合物的结构。从牡丹皮乙醇提取部位的正丁醇萃取物中得到16个化合物,分别为5-hydroxy-3 S-hydroxymethyl-6-methyl-2,3-dihydrobenzofuran(1)、(S)-(6-methyl-2,3-dihydrobenzofuran-3-yl)methanol(2)、4-thujone-7-hydroxyl-8-O-β-D-glucopyranoside(3)、resacetophenone(4)、acetoisovanillone(5)、2,5-二羟基-4-甲氧基-苯乙酮(6)、3-(4-hydroxy-3-methoxy phenyl)propan-1,2-diol(7)、erythro-1-(3-methoxy-4-hydroxy-phenyl)-propan-1,2-diol(8)、thero-1-(3-methoxy-4-hydroxy-phenyl)-propan-1,2-diol(9)、(+)-儿茶素(10)、(+)-儿茶素-7-O-β-D-吡喃葡萄糖苷(11)、对羟基苯甲酸-β-D-吡喃葡萄糖苷(12)、苯甲酸-β-D-吡喃葡萄糖苷(13)、没食子酸乙酯(14)、没食子酸甲酯(15)、香草酸(16)。化合物2、7~9和11~16均首次从芍药属中分离得到。活性筛选发现化合物1能够抑制脂多糖诱导的RAW 264.7细胞中的炎症因子水平(NO、TNF-α和IL-6),其IC 50值分别为15.67±1.20、18.59±1.27和15.79±1.20μmol/L。

This study aims to investigate the chemical constitutes of n-butyl alcohol extracts from the 85%ethanol extract of the Moutan Cortex.Compounds were isolated and purified via combinative chromatographic techniques,including macroporous resin,silica gel,Sephadex LH-20 gel,along with mid-pressure and semi-preparative reversed-phase chromatography.The structures of monomeric compounds were elucidated by the data of NMR and MS.Sixteen compounds were obtained and identified as 5-hydroxy-3 S-hydroxymethyl-6-methyl-2,3-dihydrobenzofuran(1),(S)-(6-methyl-2,3-dihydrobenzofuran-3-yl)methanol(2),4-thujone-7-hydroxyl-8-O-β-D-glucopyranoside(3),resacetophenone(4),acetoisovanillone(5),2,5-dihydrox-4-methoxyacetophenone(6),3-(4-hydroxy-3-methoxy phenyl)propan-1,2-diol(7),erythro-1-(3-methoxy-4-hydroxy-phenyl)-propan-1,2-diol(8),thero-1-(3-methoxy-4-hydroxy-phenyl)-propan-1,2-diol(9),(+)-catechin(10),(+)-catechin-7-O-β-D-glucopyranoside(11),p-hydroxybenzoic acidβ-D-glucopyranoside(12),β-D-glucopyranosyl benzoate(13),ethyl gallate(14),gallicin(15)and vanillic acid(16),respectively.Among them,compounds 2,7-9 and 11-16 were obtained from the genus Paeonia for the first time.Activity screening showed that 1 inhibited the NO,TNF-αand IL-6 inflammatory cytokines levels with IC 50 of 15.67±1.20,18.59±1.27 and 15.79±1.20μmol/L in lipopolysaccharide-induced RAW 264.7 macrophages.