Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis

被引:41
作者
Tokiwa, Yutaka
Kitagawa, Masaru
Raku, Takao
Yanagitani, Shusaku
Yoshino, Kenji
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058566, Japan
[2] Toyobo Res Ctr, Otsu, Shiga 5200292, Japan
[3] Green Prod Lab Co, Tsukuba, Ibaraki 3058566, Japan
关键词
arbutin; tyrosinase; undecylenic acid; melanin; tyrosinase inhibitor;
D O I
10.1016/j.bmcl.2007.03.039
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Transesterification of arbutin and undecylenic acid vinyl ester was catalyzed by alkaline protease, Bioprase, in dimethylformamide to get arbutin derivative having undecylenic acid at 6-position of glucose moiety, 6-O-undecylenoyl p-hydroxyphenyl beta-D-glucopyranoside. The reaction rate increased with increase of arbutin concentration, and when its concentration was 0.9 M, the conversion rate was more than 90% under addition of 2 M undecylenic acid vinyl ester. The obtained arbutin ester significantly suppressed melanin production in murine B16 melanoma cells. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3105 / 3108
页数:4
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