[关键词]
[摘要]
目的 对金桂花Osmanthus fragrans var. thunbergii的化学成分及其抗神经炎症活性进行研究。方法 采用大孔树脂、正反相硅胶、Sephadex LH-20柱色谱和半制备高效液相等多种色谱分离方法分离纯化,采用质谱、核磁共振和圆二色谱等波谱技术对分离得到的化合物进行结构鉴定。采用脂多糖诱导小鼠小胶质细胞(BV-2细胞)NO释放模型,评价化合物的抗炎活性。结果 从金桂花70%乙醇提取物中分离鉴定了13个化合物,分别为4-甲氧基苯乙基 (2S,3E,4R,5R)-2-O-β-D-吡喃葡萄糖基-3-乙烯基-5-甲氧羰基-四氢-2H-吡喃-4-乙酸酯(1)、(8E)-ligstroside(2)、橄榄苦苷(3)、10-acetoxyligustroside(4)、10-hydroxyligustroside(5)、连翘苷(6)、(+)-连翘脂素(7)、(+)-松脂素(8)、(+)-落叶松树脂醇二甲醚(9)、eutigoside A(10)、jasminoside O(11)、齐墩果酸(12)和对香豆酸乙酯(13)。抗神经炎活性评价结果表明,化合物1、2、4、5、9~11和13具有一定抗神经炎活性,其中化合物1、4和10对脂多糖诱导的BV-2细胞NO释放的半数抑制浓度(median inhibition concentration,IC50)分别为3.27、3.66、3.63 μmol/L。结论 化合物1为新的环烯醚萜苷类化合物,命名为金桂苷A;化合物8和9为首次从木犀属中分离得到,化合物1、4和10具有较强的抑制脂多糖诱导的BV-2细胞NO释放活性。
[Key word]
[Abstract]
Objective To study the chemical constituents of Osmanthus fragrans var. thunbergii and their anti-neuroinflammatory activities. Methods The chemical constituents were isolated and purified by macroporous resin, silica gel and reversed-phase silica gel, Sephadex LH-20 molecular exclusion column chromatography and semipreparative reversed-phase high performance liquid chromatography. And their structures were elucidated by nuclear magnetic resonance (NMR), mass spectrometry (MS) and circular dichroism spectroscopy (CD). The anti-neuroinflammatory activities were evaluated on NO release model in microglia (BV-2 cells) stimulated by lipopolysaccharide (LPS). Results A total of 13 compounds were isolated from 70% ethanol extract of O. fragrans var. thunbergii and identified as (4-methoxyphenylethyl) (2S,3E,4R,5R)-2-O-(β-D-glucopyranosyl)-3-vinyl-5-methoxycarbonyl-tetrahydro-2H-pyran-4-acetate (1), (8E)-ligstroside (2), oleuropein (3), 10-acetoxyligustroside (4), 10-hydroxyligustroside (5), phillyrin (6), phillygenin (7), pinoresinol (8), lariciresinol dimethyl ether (9), eutigoside A (10), jasminoside O (11), oleanolic acid (12) and p-coumaric acid ethyl ester (13), respectively. In anti-neuroinflammatory bioassay, compounds 1, 2, 4, 5, 9, 10, 11 and 13 inhibited the production of the inflammatory mediator NO on LPS-induced BV-2 microglial cells. Compounds 1, 4 and 10 exhibited inhibitory effects with IC50 values of 3.27, 3.66 and 3.63 μmol/L, respectively. Conclusion Compound 1 is a new secoiridoid, and compounds 8 and 9 were isolated from the genus Osmanthus for the first time. Compounds 1, 4 and 10 exhibited significant inhibitory effects on NO production in LPS-induced BV-2 microglial cells.
[中图分类号]
R284.1
[基金项目]