Yajing Qi, Jiahao Cheng, Wangmin Ding, Li Wang, Haifeng Qian, Xiguang Qi, Gangcheng Wu, Ling Zhu, Tianyi Yang, Bin Xu and Hui Zhang*,
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引用次数: 0
摘要
在马氏反应中,热生成的 3-氨基丙酰胺是丙烯酰胺形成的中间体,其作用已得到证实。本文研究了表儿茶素在 160-220 °C 氧化条件下对 3-氨基丙酰胺转化为丙烯酰胺的影响。表儿茶素促进了丙烯酰胺的生成和3-氨基丙酰胺的降解。稳定同位素标记技术结合超高效液相色谱-轨道rap-MS/MS分析表明,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。这种最初形成的希夫碱可以直接降解为丙烯酰胺,也可以还原或脱水为其他中间体,然后生成丙烯酰胺。根据精确的质量分析,初步确定了五个具有完整或脱水 C 环的中间体。此外,根据加热过程中形成的加合物含量的变化,提出了反应途径。据作者所知,这项研究首次揭示了黄烷醇在马氏反应中促进丙烯酰胺形成的途径。
Epicatechin-Promoted Formation of Acrylamide from 3-Aminopropionamide Via Postoxidative Reaction of B-Ring
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.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.