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. 2018 Oct 15;263:89-95. doi: 10.1016/j.foodchem.2018.04.121. Epub 2018 Apr 28.
Phenolics can trap lipid-derived reactive carbonyls as a protective function that diminishes the broadcasting of the lipid oxidative damage to food macromolecules. In an attempt to clarify the trapping of 2,4-alkadienals by phenolics, this study analyzes the reactions of 2,4-hexadienal, 2,4-heptadienal, and 2,4-decadienal with 2-methylresorcinol. These reactions produced (E)-4-(alk-1-en-1-yl)-8-methyl-2,7-bis(prop-1-en-2-yloxy)chromanes, which were isolated and characterized by 1D and 2D NMR and MS. Carbonyl-phenol adduct formation was favored at pH > 7 and moderate temperatures (25-80 °C). Adducts were quantified and shown to be produced as a mixture of diastereomers. Diastereomers 2R,4S plus 2S,4R were formed to a higher extent than diastereomers 2R,4R plus 2S,4S under the different conditions assayed, although activation energies (E) for the formation of all of them was mostly the same (∼62 kJ·mol). These results show that phenolics can trap 2,4-alkadienals and provide the basis for the later detection of the formed adducts in food pro[ducts.
酚类可以作为一种保护功能，捕获脂质衍生的反应性羰基，从而减少脂质氧化损伤向食物大分子的传播。为了阐明酚类对 2,4-链烯醛的捕获作用，本研究分析了 2,4-己二烯醛、2,4-庚二烯醛和 2,4-癸二烯醛与 2-甲基间苯二酚的反应。这些反应产生了（E）-4-（1-烯-1-基）-8-甲基-2,7-双（1-丙烯-2-基氧基）色满，通过 1D 和 2D NMR 和 MS 对其进行了分离和表征。在 pH > 7 和中等温度（25-80°C）下，有利于形成羰基-酚加合物。定量了加合物，并表明它们是作为非对映异构体混合物产生的。在不同的测试条件下，2R,4S 加 2S,4R 非对映异构体的形成程度高于 2R,4R 加 2S,4S 非对映异构体，尽管它们形成的所有非对映异构体的活化能（E）大致相同（约 62 kJ·mol）。这些结果表明，酚类可以捕获 2,4-链烯醛，并为以后在食品产物中检测形成的加合物提供了基础。
