数字农科院2.0

Stereoselectivity during enzymatic oxidation of catechins and their products' characteristic in taste receptors and color properties

文献类型： 外文期刊

作者： Zekai Wang;Qing Qing Cao;Mingchun Wen;Yahui Li;Yuqing Cui;Zisheng Han;Xiaochun Wan;Chi Tang Ho;Yong Quan Xu;Liang Zhang

作者机构：

关键词： Black tea;Enzymatic oxidation;Taste receptors;Theaflavin;Through-space substituent effects

期刊名称： Food Chemistry

ISSN： 0308-8146

年卷期： 2025 年 495 卷

页码：

收录情况： SCIE（2025版） ; ; EI（2025版）

摘要： Black tea is one of the most widely consumed beverages globally, renowned for its rich flavor and vibrant color. However, the chemical mechanisms underlying its taste and color formation remain poorly understood. Here we systematically synthesized four theaflavin isomers (TF1s: TF1a, TF1b, TF1c and TF1d), the major pigments in black tea containing a benzotropolone moiety, through the enzymatic oxidation of (2R,3S)/(2R,3R)-catechin and (2R,3S)/(2R,3R)-gallocatechin pairs and elucidated their absolute configurations for the first time. Our results demonstrated that catechins configuration significantly influenced the synthesis, color, and taste properties of theaflavins. Specifically, the absolute configuration of hydroxyl groups at C-3 and C-3* of catechins affects the content of theaflavins, hence the color of oxidation systems. Furthermore, taste receptors screening revealed that different theaflavin configurations at C-3 and C-3* selectively activated distinct sweet and bitter receptors, providing novel insights into the relationship between taste perception and molecular structure. Finally, quantum chemistry was used in the properties and mechanisms of theaflavins.

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