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.

中文翻译：

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表儿茶素通过 B 环的后氧化反应促进 3-氨基丙酰胺形成丙烯酰胺


热生成的 3-氨基丙酰胺作为美拉德反应中丙烯酰胺形成的中间体的作用已得到充分证实。本文在 160-220 °C 的氧化条件下研究了表儿茶素对 3-氨基丙酰胺转化为丙烯酰胺的影响。表儿茶素促进丙烯酰胺的生成和3-氨基丙酰胺的降解。稳定同位素标记技术与 UHPLC-Orbitrap-MS/MS 分析相结合，显示 3-氨基丙酰胺与表儿茶素的氧化 B 环之间形成加合物，形成希夫碱。最初形成的希夫碱可以直接降解为丙烯酰胺，再还原或脱水为其他中间体，随后生成丙烯酰胺。基于精确质量分析，初步鉴定出五种具有完整或脱水C环的中间体。此外，还提出了由加热过程中形成的加合物水平变化支持的反应途径。据作者所知，这项研究首次揭示了黄烷醇在美拉德反应中促进丙烯酰胺形成的途径。