熊果苷类似物的合成、表征及美白活性

Synthesis,characterization and whitening activity of arbutin analogues

目的设计合成一系列熊果苷类似物,并评价其酪氨酸酶抑制活性。方法以邻苯二酚、间苯二酚、对苯二酚为原料,通过一侧酚羟基的苄基保护,与溴乙酰基半乳糖、葡萄糖、木糖、阿拉伯糖进行偶联并脱除保护基,得到11个未见报道的熊果苷类似物。通过~1H-NMR、^(13)C-NMR、HRMS等波谱分析方法对所合成的11个目标化合物进行结构表征。以α-熊果苷为阳性对照,对目标化合物及中间体进行抗酪氨酸酶活性测试。结果与结论目标化合物具有良好的酪氨酸酶抑制活性。其中,化合物p-5a、o-5a、p-4d、m-4d、m-5d的活性与阳性对照物α-熊果苷相当,化合物p-5d的活性优于阳性对照物α-熊果苷。

A series of arbutin analogues were designed and synthesized. Three kinds of hydroquinones with mono-protection of phenolic hydroxyl group were directly coupled with bromoacetylgalactose,glucose,xylose and arabinose,then removed the protecting groups to get eleven target compounds. The target compounds were characterized by ^1H-NMR,^13C-NMR and HRMS. The results of whitening activity of these analogues indicated p-5a,o-5a,p-4d,m-4d and m-5d had significant inhibition against tyrosinase,and the inhibition activity of p-5d against tyrosinase was obviously better than that of positive control α-arbutin.