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-Dimethylimidazo [4,5-f] Quinoxaline (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:

为了解脂质氧化产物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，本研究采用含甘氨酸、肌酐和葡萄糖的化学模型及烤罗非鱼鱼糜体系，结合超高效液相色谱-质谱联用(UHPLC-MS)技术和固相微萃取-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，2-甲基丙烯醛对MeIQx生成的影响呈浓度依赖性，添加0.02-0.20 mmol/L的2-甲基丙烯醛可显著促进MeIQx生成，浓度高于0.20 mmol/L时促进作用消失，0.80 mmol/L浓度显著抑制MeIQx生成；2-甲基丙烯醛可降低化学模型中甘氨酸和肌酐的含量，增加葡萄糖的含量，并促进乙二醛(GO)、甲基乙二醛(MGO)及2,5-二甲基吡嗪等挥发性中间体的形成；进一步验证发现，2-甲基丙烯醛可与甘氨酸、肌酐及MeIQx发生反应，并导致其消耗。综上，2-甲基丙烯醛通过促进甘氨酸的Strecker降解，促进挥发性中间体的形成，以及与MeIQx前体和产物发生反应，综合影响MeIQx的生成。此外，轻度至中度氧化(0-4 d)的罗非鱼糜能够促进MeIQx的形成，高度氧化(10 d)的罗非鱼鱼糜则相反。本研究明确了2-甲基丙烯醛对MeIQx形成的调控规律及作用机制，为脂质氧化产物作为MeIQx形成的标志物提供了科学依据，对优化食品加工工艺、降低食源性杂环芳香胺(Heterocyclic Aromatic Amines,HAAs)风险具有重要参考价值。

Abstract:

To investigate the effect of 2-methyl acrolein,a lipid oxidation product,on the formation of heterocyclic aromactic amines 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline (MeIQx),a chemical model containing glycine,creatinine and glucose as well as a roasted tilapia surimi system were used to systematically analyze the mechanism of 2-methyl acrolein by Ultra-High Performance Liquid Chromatography-Mass Spectrometry (UHPLC-MS) and Solid Phase Micro-Extraction Gas Chromatography-Mass Spectrometry (SPME-GC-MS).The results showed that the effect of 2-methyl acrolein on the formation of MeIQx was concentration-dependent.The addition of 0.02-0.20 mmol/L 2-methyl acrolein could significantly promote the formation of MeIQx,and the promotion effect disappeared when the concentration was higher than 0.20 mmol/L.The concentration of 0.80 mmol/L significantly inhibited the formation of MeIQx.2-Methyl acrolein can reduce the residues of glycine and creatinine in the chemical model,increase the residue of glucose,and promote the formation of volatile intermediates such as glyoxal (GO),methylglyoxal (MGO) and 2,5-dimethylpyrazine.Further verification found that 2-methyl acrolein could react with glycine,creatinine and MeIQx,and leaded to its consumption.In summary,2-methyl acrolein comprehensively affects the formation of MeIQx by promoting the Strecker degradation of glycine,promoting the formation of volatile intermediates,and reacting with MeIQx precursors and products. In addition,mild to moderate oxidation (within 4 d) of tilapia surimi could promote the formation of MeIQx,while highly oxidized (within 10 d) of tilapia surimi was the opposite.This study clarifies the regulation rule and mechanism of 2-methyl acrolein on the formation of MeIQx,provides a scientific basis for lipid oxidation products as a marker of MeIQx formation process,and has important reference value for optimizing food processing technology and reducing the risk of food-borne heterocyclic aromatic amines.