两种熊果甙同系物的合成及其对酪氨酸酶的影响  

The Synthesis of two Arbutin Derivatives and Inhibitory Effect of Them on Mushroom Tyrosinase

作　　者：郭华云[1] 宋康康[1] 陈清西[1] 

机构地区：[1]厦门大学生命科学学院细胞生物学和肿瘤细胞工程教育部重点实验室,福建厦门361005

出　　处：《厦门大学学报（自然科学版）》2004年第B08期1-4,共4页Journal of Xiamen University：Natural Science

基　　金：福建省科技攻关课题(2004N002);福建省自然科学基金(B0410003)资助

摘　　要：熊果甙作为化妆品添加剂具有增白效果,主要是由于它对皮肤酪氨酸酶有抑制作用.以葡萄糖为原料合成了两种熊果甙同系物:1 对异丙基苯基葡萄糖甙和1 对甲氧基苯基葡萄糖甙.并对其结构进行红外光谱分析.以熊果甙及上述其两种同系物为效应物,研究对酪氨酸酶酶活力的影响,以探讨抑制剂分子结构与其对酪氨酸酶抑制效果的关系.结果表明,这3种效应物对酪氨酸酶活性的抑制效果为:熊果甙>1 对异丙基苯基葡萄糖甙>1 对甲氧基苯基葡萄糖甙.Tyrosinase (1.14.18.1) is a metalloenzyme oxidase, known as a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Its abnormal expressing would contribute to various dermatological disorders, such as melasama, age spots, and sites of actinic damage. The inhibitors of tyrosinase can become potent whitening agents to meet the medical requirements for depigmenting agents. Arbutin is a cosmetic additive for whitening, according to that it can inhibit tyrosinase activity. In this paper, two kinds of arbutin derivatives were synthesized derived from D-glucose. The deritives were p-isopropylphenyl-D-glycopyranose and p- methoxyphenyl-D-glycopyranose. Adding to triethylamine and BF_3·ether, 1',2',3',4'6'-penta-O-acetyl-D-glycose was reacted with p- isopropylphenol and p- methoxyphenol to afford the target product, respectively. The structure of products were identified by IR spectra. Thesis three compounds acted as effector study the inhibit effect of them on mushroom tyrosinase when L-DOPA is substrate. It can help study deeply the relationship between the structure of inhibitors and the inhibitor capacity of them on the tyrosinase. The result elucidated the sequence of inhibitor capacity: arbutin>p-isopropylphenyl-D-glycopyranose>p-methoxyphenyl-D-glycopyranose. It showed that the hydroxy group on the benzene ring acted important effect on inhibitory capacity, which according with the result reported that arbutin was a competitive inhibitor.

关 键 词：酪氨酸酶 熊果甙 l-对异丙基苯基葡萄糖甙 l-对甲氧基苯基葡萄糖甙 抑制作用 化妆品添加剂 

分 类 号：TQ464.8[化学工程—制药化工]