Instituto de la Grasa, CSIC, Carretera de Utrera Km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
Instituto de la Grasa, CSIC, Carretera de Utrera Km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
Food Chem. 2023 Aug 15;417:135915. doi: 10.1016/j.foodchem.2023.135915. Epub 2023 Mar 8.
The reactions between malondialdehyde and 2,5-dimethylresorcinol, orcinol, olivetol, and alkylresocinols were studied in an attempt to investigate both if this lipid oxidation product is trapped by phenolics analogously to other reactive carbonyls and to elucidate the chemical structures of the produced adducts. After being formed, malondialdehyde is both partially fractionated to acetaldehyde and oligomerized into dimers and trimers. All these compounds react with phenolics producing three main kinds of derivatives: 5(or 7)-alkyl-7(or 5)-hydroxy-4-methyl-4H-chromene-3-carbaldehydes, 7-alkyl-9-hydroxy-6H-2,6-methanobenzo[d][1,3]dioxocine-5-carbaldehydes, and 4-(3-formylphenyl)-7-hydroxy-4H-chromene-3-carbaldehydes. A total of twenty-four adducts were isolated by semipreparative high-performance liquid chromatography (HPLC) and characterized by mono- and bi-dimensional nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). Reaction pathways to explain the formation of all these compounds are proposed. Obtained results show that phenolics can trap malondialdehyde producing stable derivatives. The function(s) that such derivatives can play in foods remain(s) to be elucidated.
研究了丙二醛与 2,5-二甲基间苯二酚、间苯三酚、橄榄醇和烷基间苯二酚的反应，试图探讨这种脂质氧化产物是否能像其他反应性羰基一样被酚类捕获，并阐明产生的加合物的化学结构。丙二醛形成后，部分会分馏为乙醛，并且会二聚和三聚。所有这些化合物都会与酚类反应生成三种主要的衍生物：5（或 7）-烷基-7（或 5）-羟基-4-甲基-4H-色烯-3-甲醛、7-烷基-9-羟基-6H-2,6-亚甲二氧基苯并[d][1,3]二恶嗪-5-甲醛和 4-(3-甲酰基苯基）-7-羟基-4H-色烯-3-甲醛。通过半制备高效液相色谱（HPLC）共分离出二十四种加合物，并通过单维和二维核磁共振（NMR）光谱和质谱（MS）进行了表征。提出了解释所有这些化合物形成的反应途径。研究结果表明，酚类可以捕获丙二醛生成稳定的衍生物。这些衍生物在食品中可以发挥的功能仍有待阐明。
