Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario-Edificio 46, 41013 Seville, Spain.
J Agric Food Chem. 2020 Jul 15;68(28):7474-7481. doi: 10.1021/acs.jafc.0c02869. Epub 2020 Jul 1.
Food processing is responsible for the destruction of some health hazards, but it is responsible for the formation of new ones. Among them, the formation of heterocyclic aromatic amines (HAAs) has received a considerable attention because of their carcinogenicity. In spite of this, HAA formation is still poorly understood. This study was undertaken to identify precursors and formation pathways for 2-amino-3-methylimidazo(4,5-)quinoline (IQ). IQ was produced by reaction of acrolein, crotonaldehyde, creatinine, and ammonia. Reaction conditions were studied, and its activation energy () was determined to be 77.0 ± 1.3 kJ/mol. IQ formation was always accompanied by the formation of the HAA 2-amino-3,4-dimethylimidazo(4,5-)quinoline (MeIQ), which was produced with an of 72.2 ± 0.4 kJ/mol. A reaction pathway for the competitive formation of IQ and MeIQ is proposed. Obtained results demonstrate the significant role of reactive carbonyls (the food carbonylome) in HAA formation and provide evidences for designing HAA mitigation strategies.
食品加工既能破坏一些健康危害物，也能形成新的危害物。其中，杂环芳香胺（HAAs）的形成引起了相当大的关注，因为它们具有致癌性。尽管如此，HAAs 的形成仍未被充分理解。本研究旨在确定 2-氨基-3-甲基咪唑并[4,5-f]喹啉（IQ）的前体和形成途径。IQ 是由丙烯醛、巴豆醛、肌酸和氨反应生成的。研究了反应条件，并确定其活化能（）为 77.0 ± 1.3 kJ/mol。IQ 的形成总是伴随着 HAA 2-氨基-3,4-二甲基咪唑并[4,5-f]喹啉（MeIQ）的形成，其形成的活化能为 72.2 ± 0.4 kJ/mol。提出了一个 IQ 和 MeIQ 竞争形成的反应途径。所得结果表明，反应性羰基（食品羰基组）在 HAA 形成中起重要作用，并为设计 HAA 缓解策略提供了证据。
