[关键词]
[摘要]
目的 研究窝儿七(中华山荷叶Diphylleia sinensis干燥根茎)中的化学成分。方法 运用硅胶、AB-8大孔吸附树脂、ODS、MCI和Sephadex LH-20等柱色谱和半制备高效液相色谱对其化学成分进行分离纯化,通过IR、UV、MS、NMR等波谱分析技术,结合理化性质分析,鉴定化合物结构。采用DPPH自由基清除实验,测试化合物1、4、10、11、20的抗氧化活性。结果 从窝儿七95%乙醇和50%乙醇提取物中分离得到21个化合物,分别鉴定为 [4,5-二羟基-2-(1-羟基乙基)苯基] [(4-羟基)苯基]甲酮(1)、(+)-7'-甲氧基落叶松树脂醇(2)、7'R-羟基落叶松树脂醇(3)、3-甲氧基槲皮素(4)、二氢槲皮素(5)、二氢山柰酚(6)、山柰酚(7)、槲皮素(8)、podoverine B(9)、大黄酚-1-O-β-D-葡萄糖苷(10)、大黄酚-8-O-β-D-葡萄糖苷(11)、尿嘧啶(12)、胸腺嘧啶核苷(13)、uridine-5'α-hydroxypropanoate(14)、对甲氧基苯甲醛(15)、对羟基苯甲酸(16)、香草醛(17)、3,4-二羟基苯甲酸(18)、羟基酪醇(19)、3',5'-二羟基苯基-4-羟基苯甲酸酯(20)、5-羟甲基糠醛(21)。结论 化合物1为新化合物,命名为山荷叶甲酮。化合物20为新的天然产物,并首次对其氢谱和碳谱数据进行归属。化合物2、3、5、6、9~11、13、14、17和19~21为首次从山荷叶属植物中分离得到。首次从该属植物中发现了生物碱类和蒽醌类化合物的存在。DPPH自由基清除实验结果显示,化合物1对DPPH自由基具有较强的清除能力,半数抑制浓度(median inhibition concentration,IC50)值为8.52 μmol/L,且强于阳性药水溶性维生素E(trolox,14.95 μmol/L)。
[Key word]
[Abstract]
Objective To investigate the chemical constituents in the dried rhizomes of Diphylleia sinensis. Methods The compounds were isolated and purified by silica gel, diaion AB-8 macroporous adsorption resin,, ODS, MCI, Sephadex LH-20 column chromatography and semi-preparative HPLC, and their structures were identified by physicochemical properties, IR, UV, MS and NMR. The antioxidant activities of compounds 1, 4, 10, 11 and 20 were examined by DPPH radical scavenging assay. Results A total of 21 compounds were isolated from the 95% and 50% ethanol extract of D. sinensis, and their structures were identified as [4,5-dihydroxy-2-(1-hydroxyethyl)phenyl] [(4-hydroxy)phenyl]methanone (1), (+)-7'-methoxylariciresinol (2), 7'R-hydroxylariciresinol (3), 3-methoxy-quercetin (4), dihydroquercetin (5), dihydrokaempferol (6), kaempferol (7), quercetin (8), podoverine B (9), chrysophanol-1-O-β-D-glucopyranoside (10), chrysophanol-8-O-β-D-glucopyranoside (11), uracil (12), thymidine (13), uridine-5'α-hydroxypropanoate (14), p-anisaldehyde (15), p-hydroxybenzoic acid (16), vanillin (17), 3,4-dihydroxybenzoic acid (18), hydroxytyrosol (19), 3',5'-dihydroxyphenyl-4-hydroxybenzoate (20) and 5-hydromethyl furaldehyde (21). Conclusion Among them, Compound 1 is a new compound that has not been reported in literature and named diphymethanone A. Compound 20 is a new natural compound and its 1H and 13C NMR spectra are assigned for the first time. Compounds 2, 3, 5,6, 9-11, 13, 14, 17 and 19-21 were isolated from the genus of D. sinensis for the first time. Alkaloids and anthraquinones were found in this genus for the first time. Compound 1 had a strong DPPH radical scavenging ability, with a median inhibition concentration (IC50) of 8.52 μmol/L, which was stronger than that of positive drug trolox (14.95 μmol/L).
[中图分类号]
R284.1
[基金项目]
河南中医药大学省属高校基本科研业务专项(2014KYYWF-QN26);河南中医药大学科技创新人才(2016XCXRC01);河南省科技攻关项目(192102310438);河南省中医药科学研究专项(20-21ZY1039);河南省高校科技创新团队支持计划资助(24IRTSTHN039);河南省高等学校重点科研项目(24A360015)