[关键词]
[摘要]
目的 研究覆盆子Rubi Fructus的化学成分及抗氧化活性。方法 采用大孔吸附树脂、正向硅胶柱、ODS柱、Sephadex LH-20葡聚糖凝胶柱、半制备HPLC等色谱方法进行分离纯化,并运用ESI-MS、NMR等现代谱学技术进行化合物结构鉴定。通过DPPH自由基的清除能力对单体化合物进行体外抗氧化活性评估。结果 从覆盆子20%正丁醇部位共分离得到16个化合物,分别鉴定为 (赤式,赤式)-1-[4-[2-羟基-2-(4-羟基)-1-(羟甲基)乙氧基]-3-甲氧基苯基]-1,2,3-丙三醇(1)、(+)-儿茶素-5-O-β-D-葡萄糖苷(2)、短叶苏木酚酸(3)、(1'R,3'S,5'R,8'S,2Z,4E)-二氢菜豆酸-3'-O-β-D-葡萄糖苷(4)、(—)-儿茶素(5)、3,4,5-三甲氧基苯基-β-D-吡喃葡萄糖苷(6)、2,4,6-三羟基苯乙酮-6-O-β-D-吡喃葡萄糖苷(7)、3,4'-二羟基苯丙酮-3-β-D-葡萄糖苷(8)、trans-vaginoside(9)、cis-vaginoside(10)、dichotomoside E(11)、二氢松柏醇(12)、2-苯乙基-β-D-吡喃葡萄糖苷(13)、二氢对香豆醇-γ-O-吡喃葡萄糖苷(14)、2-羟基柚皮素-5-O-β-D-吡喃葡萄糖苷(15)、香橙素-7-O-β-吡喃葡萄糖苷(16)。化合物3、5、16对DPPH自由基的半数清除能力分别为5.83、1.13、8.46 μmol/L。结论 化合物1为新的木脂素类化合物,命名为覆盆子脂素,化合物2、4~16均为首次从该植物中得到。化合物3、5、16清除DPPH自由基能力较强,具有明显的抗氧化活性。
[Key word]
[Abstract]
Objective To study the chemical constituents from Fupenzi (Rubi Fructus) and their antioxidant activities. Methods Chemical constituents were isolated and purified by chromatographic methods such as microporous adsorption resin, positive silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC. The structures were identified by modern spectrum technology such as ESI-MS, NMR. The antioxidant activity of monomer compounds was evaluated in vitro by the scavenging ability of DPPH radicals. Results A total of 16 compounds were isolated from the 20% n-butanol extract of Rubi Fructus and identified as (erythro,erythro)-1-[4-[2-hydroxy-2-(4-hydroxy)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol (1), (+)-catechin-5-O-β-D-glucoside (2), brevifolin carboxylic acid (3), (1'R,3'S,5'R,8'S,2Z,4E)-dihydrophaseic acid 3'-O-β-D- glucopyranoside (4), (−)-catechin (5), 3,4,5-trimethoxyphenyl-β-D-glucopyranoside (6), 2,4,6-trihydroxy-acetophenone-6-O-β-D-glucopyranoside (7), 3,4'-dihy-droxypropio- phenone-3-β-D-glucoside (8), trans-vaginoside (9), cis-vaginoside (10), dichotomoside E (11), dihydroconiferyl alcohol (12), 2-phenylethyl-β-D-glucopyranoside (13), dihydro-p-coumaryl alcohol γ-O-glucopyranoside (14), 2-hydroxynaringin-5-O-β-D-glucopyranoside (15), aromadendrin-7-O-β-glucopyranoside (16). The antioxidant activities of compounds 3, 5 and 16 were assessed through DPPH radical scavenging assay, with IC50 values determined to be 5.83, 1.13 and 8.46 μmol/L, respectively. Conclusion Among them, compound 1 is new lignan compound, named fupenzicmin, compounds 2, 4—16 are isolated from this plant for the first time. In vitro studies revealed that compounds 3, 5 and 16 display significant DPPH free radical scavenging capabilities and exhibit remarkable antioxidant activity.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(81973458);上海市科委科技创新行动计划(18401931100)