Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013-Seville, Spain.
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013-Seville, Spain.
Food Chem. 2020 Sep 15;324:126898. doi: 10.1016/j.foodchem.2020.126898. Epub 2020 Apr 23.
Reactions involving reactive carbonyls, creatinine, and ammonia-producing compounds were investigated in order to clarify the formation of the heterocyclic aromatic amine (HAA) 2-amino-3,4-dimethylimidazo(4,5-f)quinoline (MeIQ). Obtained results showed that MeIQ was only produced when 2-butenal (crotonaldehyde) was present. Reaction yields depended on the pH, with a maximum around pH 6.5, and on concentrations of crotonaldehyde and creatinine. Ammonia was also required for MeIQ formation, but ammonia was produced by creatinine decomposition. The amount of MeIQ formed increased with reaction time, temperature, and oxygen content in the reaction atmosphere. Activation energy for MeIQ formation from crotonaldehyde, creatinine, and glutamine was 72.2 ± 0.4 kJ·mol. A reaction pathway that explains MeIQ formation is proposed. Obtained results suggest a main role of reactive carbonyls formed in foods (the food carbonylome) on HAA formation. In addition, they provide scientific basis for the understanding of how HAAs are formed and could be mitigated.
为了阐明杂环芳香胺（HAA）2-氨基-3,4-二甲基咪唑并[4,5-f]喹啉（MeIQ）的形成，研究了涉及反应性羰基、肌酸和生成氨的化合物的反应。结果表明，只有当 2-丁烯醛（巴豆醛）存在时才会生成 MeIQ。反应产率取决于 pH 值，在 pH 值约为 6.5 时达到最大值，还取决于巴豆醛和肌酸的浓度。MeIQ 的形成也需要氨，但氨是由肌酸分解产生的。随着反应时间、温度和反应气氛中氧气含量的增加，MeIQ 的形成量增加。从巴豆醛、肌酸和谷氨酰胺形成 MeIQ 的活化能为 72.2±0.4 kJ·mol。提出了一种解释 MeIQ 形成的反应途径。研究结果表明，食物中形成的反应性羰基（食物羰基组）在 HAA 形成中起主要作用。此外，这些结果为理解 HAA 的形成方式及其可以被减轻提供了科学依据。
