2-甲基丙烯醛对杂环芳香胺2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）形成的影响

Effect of 2-methyl acrolein on the formation of heterocyclic aromatic amine 2-amino-3,8-dimethylimidazole [4,5-f] quinolorel (MeIQx)

关键词:  2-甲基丙烯醛  MeIQx  前体  中间体  罗非鱼

Key words:  2-methyl acrolein  MeIQx  precursor  intermediate  tilapia

摘要:

本研究探讨了脂质氧化产物2-甲基丙烯醛对杂环芳香胺2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉（MeIQx）形成的影响。通过含甘氨酸、肌酐和葡萄糖的化学模型及烤罗非鱼糜体系，结合超高效液相色谱-质谱联用（UHPLC-MS）和固相微萃取-气相色谱-质谱联用（SPME-GC-MS）技术，系统分析2-甲基丙烯醛的作用机理。结果表明，添加0.02~0.2 mmol 2-甲基丙烯醛可显著促进MeIQx生成，但更高浓度则无促进作用。丙烯醛降低了甘氨酸和肌酐的残留量，但增加了葡萄糖残留量，并促进了MeIQx生成化学模型中挥发性中间体的形成。进一步分析发现，2-甲基丙烯醛可与甘氨酸、肌酐及MeIQx发生反应，导致其消耗。结果表明，2-甲基丙烯醛通过促进甘氨酸的Strecker降解、增加挥发性中间体的形成，以及与MeIQx前体及产物的反应，综合影响MeIQx的生成。此外，罗非鱼肉糜的氧化提高了罗非鱼糜中MeIQx的含量，为脂质氧化产物作为MeIQx形成过程标志物提供科学依据。

Abstract:

This study investigated the effect of the lipid oxidation product 2-methyl acrolein on the formation of the heterocyclic aromatic amine 2-amino-3,8-dimethylimidazole and [4,5-f] quinololine (MeIQx). The mechanism of action of 2-methacrylate was systematically analyzed by chemical models containing glycine, creatinine and glucose and roasted tilapia surimi system, combined with ultra-performance liquid chromatography-mass spectrometry (UHPLC-MS) and solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS). The results showed that the addition of 0.02-0.2 mmol/L 2-methyl acrolein significantly promoted MeIQx generation, but the higher concentration showed no further effect. 2-methyl acrylein reduced the residues of glycine and creatinine but increased glucose residues and facilitated the formation of volatile intermediates in the chemical model of MeIQx generation. Further analysis revealed that 2-methyl acrolein could react with glycine, creatinine, and MeIQx, leading to its depletion. These results suggest that 2-methyl acrolein comprehensively affects the generation of MeIQx by promoting the strek degradation of glycine, increasing the formation of volatile intermediates, and reaction with MeIQx precursors and products. Furthermore, oxidation of tilapia meat increased the MeIQx content in tilapia, further supporting the potential contribution of lipid oxidation products to MeIQx formation.