熊果苷十一碳烯酸酯的酶促合成及其对黑色素合成的抑制作用。
Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.
作者信息
Tokiwa Yutaka, Kitagawa Masaru, Raku Takao, Yanagitani Shusaku, Yoshino Kenji
机构信息
National Institute of Advanced Industrial Science and Technology, Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan.
出版信息
Bioorg Med Chem Lett. 2007 Jun 1;17(11):3105-8. doi: 10.1016/j.bmcl.2007.03.039. Epub 2007 Mar 16.
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.
在二甲基甲酰胺中，碱性蛋白酶Bioprase催化熊果苷与十一碳烯酸乙烯酯发生酯交换反应，得到在葡萄糖部分6位带有十一碳烯酸的熊果苷衍生物，即6-O-十一碳烯酰对羟基苯基β-D-吡喃葡萄糖苷。反应速率随熊果苷浓度的增加而提高，当熊果苷浓度为0.9 M时，在加入2 M十一碳烯酸乙烯酯的情况下转化率超过90%。所得到的熊果苷酯显著抑制小鼠B16黑色素瘤细胞中的黑色素生成。
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