Epicatechin-Promoted Formation of Acrylamide from 3-Aminopropionamide Via Postoxidative Reaction of B-Ring

美拉德反应 丙烯酰胺 化学 加合物 席夫碱 戒指(化学) 有机化学 高分子化学 聚合物 共聚物
作者
Yajing Qi,John B. Cheng,Weijun Ding,Li Wang,Haifeng Qian,Xiguang Qi,Gangcheng Wu,Linghua Zhu,Tianyi Yang,Bin Xu,Hui Zhang
出处
期刊:Journal of Agricultural and Food Chemistry [American Chemical Society]
标识
DOI:10.1021/acs.jafc.4c01116
摘要

The role of thermally generated 3-aminopropionamide as an intermediate in acrylamide formation in the Maillard reaction has been well established. Herein, the effect of epicatechin on the conversion of 3-aminopropionamide into acrylamide under oxidative conditions was investigated at 160–220 °C. Epicatechin promoted acrylamide generation and 3-aminopropionamide degradation. The stable isotope-labeling technique combined with UHPLC-Orbitrap-MS/MS analysis showed adduct formation between 3-aminopropionamide and the oxidized B ring of epicatechin to form a Schiff base. This initially formed Schiff base could directly degrade to acrylamide, undergo reduction or dehydration to other intermediates, and subsequently generate acrylamide. Based on accurate mass analysis, five intermediates with intact or dehydrated C rings were tentatively identified. Furthermore, reaction pathways were proposed that were supported by the changes in the levels of adducts formed during heating. To the authors' knowledge, this study is the first to reveal pathways through which flavanols promoted the formation of acrylamide in Maillard reactions.
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