[关键词]
[摘要]
目的 研究瑞香狼毒Stellera chamaejasme花中黄酮和木脂素类化学成分及其抗氧化活性,分析构效关系。方法 利用大孔吸附树脂、正反相硅胶、Sephadex LH-20等色谱分离材料,通过柱色谱和高效液相色谱等分离方法进行分离纯化,运用核磁共振(NMR)、质谱(MS)等波谱技术鉴定化合物结构,并采用FRAP法、DPPH法和ABTS法对分离得到的化合物进行体外抗氧化活性测试。结果 从瑞香狼毒花甲醇提取物中分离鉴定了12个化合物,分别鉴定为艾黄素(1)、槲皮素(2)、isoscutellarein-8-O-β-D-glucuronopyranoside(3)、槲皮素-3-O-β-D-葡萄糖苷(4)、紫云英苷(5)、hypolaetin-8-O-β-D-glucuronopyranoside(6)、kaempferol 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-xylopyranoside(7)、rel-(3R,3'S,4R,4'S)-3,3',4,4'-tetrahydro-6,6'-dimethoxy[3,3'-bi-2H-benzopyran]-4,4'-diol(8)、马台树脂醇(9)、乌拉尔醇(10)、环黄芪醇(11)、松脂醇(12)。抗氧化活性实验表明,黄酮和木脂素类化合物均显示了较强的抗氧化活性。结论 化合物1、3、5~7和10为首次从该植物中分离得到;化合物2、4、5和10表现出显著的抗氧化活性,其中黄酮类化合物C-3或C-8位连有糖链会降低其抗氧化活性。
[Key word]
[Abstract]
Objective To investigate the flavonoids and lignans from the flowers of Stellera chamaejasme and their structure-activity relationship (SAR) of antioxidant activity. Methods The compounds were isolated by column chromatography and HPLC packed with macroporous resin, silica gel, and Sephadex LH-20. Their structures were elucidated by spectroscopic analysis. Their anti-oxidant activities in vitro were evaluated by DPPH, ABTS, and FRAP assays. Results Twelve compounds were isolated from the flowers of S. chamaejasme, and identified as artemisetin (1), quercetin (2), isoscutellarein-8-O-β-D-glucuronopyranoside (3), quercetin-3-O-β-D- glucopyranoside (4), astragalin (5), hypolaetin-8-O-β-D-glucuronopyranoside (6), kaempferol 3-O-β-D-glucopyranosyl-(1→2)-O-α- L-xylopyranoside (7), rel-(3R,3'S,4R,4'S)-3,3',4,4'-tetrahydro-6,6'-dimethoxy [3,3'-bi-2H-benzopyran]-4,4'-diol (8), matairesinol (9), uralenol (10), cycloastragenol (11), and (+)-pinoresinol (12). Conclusion Compounds 1, 3, 5-7, and 10 are isolated from this plant for the first time, and compounds 2, 4, 5, and 10 showed significant antioxidant activity, and the SAR analysis suggested that the glycosylation at the C-8 or C-3 position of flavonoids could weaken their 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(31870341);四川省青年科技创新研究团队专项计划项目(2016TD0006)