酚类糖苷缀合物的合成、表征及美白活性

根据拼合原理,以对苯二酚(p-HQ)、间苯二酚(m-HQ)及邻苯二酚(o-HQ)为先导化合物,通过一侧酚羟基的苄基保护、引入溴乙酸甲酯、还原、与3种糖元偶联、脱除保护基得到9种目标化合物。 同样以3-(4-羟基苯基)-1-丙醇为起始物质,通过苄基保护、与3种糖元偶联、脱除保护基得到3种目标化合物。 通过IR、¹H NMR、¹³C NMR、HRMS等波谱分析方法对所合成的12种目标化合物进行了结构表征。 对合成的酚类糖苷缀合物进行了美白活性研究。 结果表明,化合物p-HQ-6a、m-HQ-7a、p-HQ-6b、m-HQ-6b、o-HQ-6b、p-HQ-6c、m-HQ-7c、L-3a和L-4b对酪氨酸酶有抑制作用,其中o-HQ-6b和p-HQ-6c对酪氨酸酶的抑制作用优于阳性对照物α-熊果苷。

Synthesis,Characterization and Whitening Activity of Glucoside-phenols Conjugates

Three alcohol intermediates were synthesized through protection of one side phenolic hydroxyl group, coupling with methyl bromoacetate, and reduction using p-dihydroxybenzene, m-dihydroxybenzene and o-dihydroxybenzene as lead compounds. These three intermediates coupled with three different glycogens to get nine targeting compounds. Similarly, we protected phenolic hydroxyl of 3-(4-hydroxyphenyl)-1-propanol, and then coupled it with three different glycogens to yield three target compounds. The twelve target compounds were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. The study of whitening activity of these conjugates shows that compounds p-HQ-6a, m-HQ-7a, p-HQ-6b, m-HQ-6b, o-HQ-6b, p-HQ-6c, m-HQ-7c, L-3a and L-4b have significant inhibition to tyrosinase, among of them compounds o-HQ-6b and p-HQ-6c against tyrosinase are obviously better than the positive control of α-Abutin.