熊果苷酯的全细胞生物催化剂催化的抗酪氨酸酶机制和抗黑色素生成作用。

Antityrosinase Mechanism and Antimelanogenic Effect of Arbutin Esters Synthesis Catalyzed by Whole-Cell Biocatalyst.

机构信息

School of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China.

State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510641, China.

出版信息

J Agric Food Chem. 2021 Apr 14;69(14):4243-4252. doi: 10.1021/acs.jafc.0c07379. Epub 2021 Apr 6.

DOI:10.1021/acs.jafc.0c07379

PMID:33821640

Abstract

Tyrosinase is a key enzyme responsible for enzymatic browning of fruits and vegetables and skin disorders due to overproduction of melanin. Arbutin is an inhibitor of tyrosinase; however, its high polarity and weak transdermal absorption capacity limit its applications. In this paper, a green solvent system was developed to successfully synthesize arbutin esters with improved liposolubilities (Clog values = 0.27-5.03). Among the obtained esters, arbutin undecenoate (AU) showed the strongest tyrosinase-inhibiting activity (15.6%), which was 9.0 times higher than that of arbutin. An enzyme kinetics study indicated that AU was a competitive inhibitor with reversible inhibition. The esters inhibited tyrosinase by making the secondary structure of tyrosinase looser and less stable; moreover, the interactions between tyrosinase and AU driven by metal interactions and hydrogen bonds also offered a mechanism for inhibition of AU on tyrosinase. In addition, AU (100 μM) reduced the melanin content of B16 mouse melanoma cells to 61.3% of the control group.

摘要

酪氨酸酶是一种关键的酶，负责水果和蔬菜的酶促褐变以及由于黑色素过度产生而导致的皮肤紊乱。熊果苷是一种酪氨酸酶抑制剂；然而，其高极性和弱透皮吸收能力限制了它的应用。在本文中，开发了一种绿色溶剂体系，成功合成了具有改善脂溶性的熊果苷酯（Clog 值= 0.27-5.03）。在所得到的酯中，熊果苷十一烯酸酯（AU）表现出最强的酪氨酸酶抑制活性（15.6%），比熊果苷高 9.0 倍。酶动力学研究表明，AU 是一种竞争性抑制剂，具有可逆抑制作用。这些酯通过使酪氨酸酶的二级结构更加松散和不稳定来抑制酪氨酸酶；此外，酪氨酸酶和 AU 之间的相互作用由金属相互作用和氢键驱动，这也为 AU 对酪氨酸酶的抑制作用提供了一种机制。此外，AU（100 μM）将 B16 小鼠黑素瘤细胞中的黑色素含量降低至对照组的 61.3%。