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洋紫荆粉色花的化学成分及其酪氨酸酶抑制活性研究

Chemical Constituents and Tyrosinase Inhibitory Activities from the Pink Flowers of Bauhinia variegata L.

  • 摘要: 采用Sephadex LH-20、MCI gel CHP 20P、Toyopearl Butyl-650C等柱色谱层析和半制备高效液相色谱分离技术,对洋紫荆粉色花的甲醇提取物进行分离纯化,共得到14个化合物;运用核磁共振波谱技术对化合物进行结构鉴定,并运用酪氨酸酶催化左旋多巴氧化速率法筛选化合物的酪氨酸酶抑制活性。通过波谱数据分析并与文献数据对比,14个化合物分别鉴定为:邻苯二酚(1)、原儿茶酸(2)、对羟基苯甲酸(3)、2,5-二羟基苯乙酸甲酯(4)、反-对香豆酸(5)、顺-对香豆酸(6)、咖啡酸(7)、咖啡酸乙酯(8)、阿魏酸(9)、愈创木酚-β-D-吡喃葡萄糖苷(10)、对羟基苯甲酸葡萄糖酯(11)、2,3-二羟基环戊基-3-(3′, 4′-二羟基苯基)丙稀酸酯(12)、绿原酸(13)和异荭草苷(14)。其中,化合物56910111214为首次从该植物中分离得到。酪氨酸酶抑制活性测试结果表明:化合物27的酪氨酸酶抑制活性相对较好,半数抑制质量浓度(IC50)值分别为(4.804±0.939) g/L和(7.339±0.549) g/L,且其抑制活性随着化合物质量浓度的提高而增强,表现出正的量效关系。

     

    Abstract: The methanol extract of the pink flowers of Bauhinia variegata L. was isolated and purified by chromatography on Sephadex LH-20, MCI gel CHP 20P and Toyopearl Butyl-650C were used to isolate and purify, a total of 14 compounds were obtained. The structures of the compounds were identified by NMR spectroscopy, and their tyrosinase inhibitory activities were screened by the method of tyrosinase-catalyzed levodopa oxidation rate. Fourteen compounds isolated and purified from the pink flowers of B. variegata, were identified as pyrocatechol(1), protocatechuic acid(2), phydroybenzoic acid(3), 2, 5-dihydroxy methyl phenylacetate(4), trans-p-coumaric acid(5), cis-p-coumaric acid(6), caffeic acid(7), ethyl caffeic acid(8), trans ferulic acid(9), guaiacol β-D-glucopyranoside(10), p-hydroxybenzoic acid glucose ester(11), (E)-2, 3-dihydroxycyclopentyl-3-(3′, 4′-dihydroxyphenyl) acrylate(12), chlorogenic acid(13), and isoorientin(14) by spectral analysis and comparison with literature data. Compounds 5, 6, 9, 10, 11, 12, 14 were obtained from this plant for the first time. The results of tyrosinase inhibition activity test showed that, compounds 2 and 7 showed relatively good tyrosinase inhibitory activity with IC50 values of (4.804±0.939) g/L and (7.339±0.549) g/L, respectively. Their inhibitory activity increased with the increase of compound concentration, showing a positive dose-effect relationship.

     

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