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 Oct 30;328:127100. doi: 10.1016/j.foodchem.2020.127100. Epub 2020 May 20.
Pyridines are produced during food processing and are important flavor compounds. In spite of that, their formation pathways are still poorly understood, in particular those related to 3-hydroxypyridines. In an attempt to fill this gap, this study describes, for the first time, precursors and reaction pathways leading to 3-hydroxypyridine formation. 3-Hydroxypyridines are produced by reaction of lipid-derived reactive carbonyls and ammonia-producing compounds and were studied by using gas chromatography coupled to mass spectrometry. Their main precursors resulted to be 4,5-epoxy-2-alkenals and 2,4-alkadienals. 3-Hydroxypyridines were produced at temperatures higher than 100 °C, at slightly basic pH values, and with an activation energy of about 50 kJ/mol. A reaction pathway that explains their formation in the course of the lipid oxidation pathway is proposed. The role of lipid oxidation on the production of 3-hydroxypyridines was confirmed by studying their formation in oxidized linseed and menhaden oils heated in the presence of glutamine.
吡啶类化合物是在食品加工过程中产生的，它们是重要的风味化合物。尽管如此，它们的形成途径仍然知之甚少，特别是与 3-羟基吡啶有关的途径。为了填补这一空白，本研究首次描述了导致 3-羟基吡啶形成的前体和反应途径。3-羟基吡啶是由脂质衍生的反应性羰基化合物和产生氨的化合物反应生成的，并通过气相色谱-质谱联用进行了研究。它们的主要前体是 4,5-环氧-2-烯醛和 2,4-链烯醛。3-羟基吡啶在高于 100°C 的温度下、稍碱性 pH 值和大约 50 kJ/mol 的活化能下生成。提出了一种解释它们在脂质氧化途径中形成的反应途径。通过研究在存在谷氨酰胺的条件下加热氧化亚麻籽油和鲱鱼油时 3-羟基吡啶的形成，证实了脂质氧化在 3-羟基吡啶形成中的作用。
