应用化学 ›› 2016, Vol. 33 ›› Issue (7): 780-791.DOI: 10.11944/j.issn.1000-0518.2016.07.160031

• 研究论文 • 上一篇    下一篇

酚类糖苷缀合物的合成、表征及美白活性

李常a,孙竞阳a,支德福c,田甜a,陈艳华a,赵龙铉ab*(),赵春晖b*()   

  1. a 辽宁师范大学 化学化工学院 辽宁 大连 116029
    b 辽宁师范大学 生物技术与分子药物研发辽宁省重点实验室 辽宁 大连 116029
    c 大连民族大学生命科学院 辽宁 大连 116600
  • 收稿日期:2016-01-19 接受日期:2016-05-11 出版日期:2016-06-30 发布日期:2016-06-30
  • 通讯作者: 赵龙铉,赵春晖
  • 基金资助:
    国家自然科学基金资助项目(21101067)

Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates

LI Changa,SUN Jingyanga,ZHI Defuc,TIAN Tiana,CHEN Yanhuaa,ZHAO Longxuanab*(),ZHAO Chunhuib*()   

  1. a School of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China
    b Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery,Liaoning Normal University,Dalian,Liaoning 116029,China
    c Dalian Nationalities University College of Life Science,Dalian,Liaoning 116600,China
  • Received:2016-01-19 Accepted:2016-05-11 Published:2016-06-30 Online:2016-06-30
  • Contact: ZHAO Longxuan,ZHAO Chunhui
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21101067)

摘要:

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。

关键词: 熊果苷, 糖苷, 美白

Abstract:

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.

Key words: arbutin, glycoside, whitening activity