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Effect of Acrolein, a Lipid Oxidation Product, on the Formation of the Heterocyclic Aromatic Amine 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in Model Systems and Roast Salmon Patties
Journal of Agricultural and Food Chemistry ( IF 6.1 ) Pub Date : 2022-05-03 , DOI: 10.1021/acs.jafc.2c00970
Ya Jiang 1, 2 , Qingqing Jiang 1, 2 , Daming Fan 3 , Mingfu Wang 4 , Yueliang Zhao 1, 2
Affiliation  

The effect of acrolein, a lipid oxidation product, on the formation of the heterocyclic aromatic amine 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) was investigated in a chemical model containing glycine, creatinine, and glucose. Acrolein addition at 0.02–0.2 mmol increased MeIQx formation, while high levels of acrolein (>0.2 mmol) did not further increase MeIQx formation. Moreover, acrolein addition decreased the residue of glycine and creatinine but increased the residue of glucose; it also increased the formation of volatile intermediates in the MeIQx-producing chemical model. Further analysis indicated that acrolein can react with glycine, creatinine, and MeIQx to eliminate them. These results revealed that acrolein was able to contribute to MeIQx formation as a consequence of the comprehensive ability of acrolein to facilitate Strecker degradation of glycine, increase the formation of volatile intermediates, and react with glycine, creatinine, and MeIQx. In addition, the oxidation of minced salmon increased the content of MeIQx in the roasted salmon patties, further supporting the potential contribution role of lipid oxidation products in the formation of MeIQx.

中文翻译:

丙烯醛(一种脂质氧化产物)对模型系统和烤鲑鱼肉饼中杂环芳胺 2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉 (MeIQx) 形成的影响

脂质氧化产物丙烯醛对杂环芳胺 2-氨基-3,8-二甲基咪唑[4,5- f ]形成的影响] 喹喔啉 (MeIQx) 在含有甘氨酸、肌酐和葡萄糖的化学模型中进行了研究。添加 0.02-0.2 mmol 的丙烯醛会增加 MeIQx 的形成,而高水平的丙烯醛 (>0.2 mmol) 不会进一步增加 MeIQx 的形成。此外,丙烯醛的添加降低了甘氨酸和肌酐的残留,但增加了葡萄糖的残留;它还增加了产生 MeIQx 的化学模型中挥发性中间体的形成。进一步分析表明,丙烯醛可以与甘氨酸、肌酐和 MeIQx 反应以消除它们。这些结果表明,丙烯醛能够促进 MeIQx 的形成,这是因为丙烯醛具有促进 Strecker 降解甘氨酸、增加挥发性中间体的形成以及与甘氨酸、肌酐和 MeIQx 反应的综合能力。
更新日期:2022-05-03
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