Hidalgo Francisco J, León M Mercedes, Zamora Rosario
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Seville, Spain.
J Agric Food Chem. 2007 May 30;55(11):4436-42. doi: 10.1021/jf070119s. Epub 2007 May 8.
Phosphatidylethanolamine (PE), phosphatidylcholine (PC), lysine (Lys), and mixtures of them were tested for antioxidative activity in a tocopherol-stripped olive oil (TSO) and the same oil after addition of 250 microg of alpha-tocopherol g of oil/(tocopherol-added olive oil, TAO) to evaluate the role of tocopherol in the antioxidant activity of oxidized lipid-amine products. Neither PE nor PC nor Lys protected TSO when tested alone, but both PE and Lys increased the induction period (IP) of TAO. On the contrary, PE/Lys and PC/Lys mixtures, but not PC/PE mixtures, protected both TSO and TAO. These results were a consequence of both the formation of oxidized lipid-amine products, which were determined by gas chromatography-mass spectrometry after their conversion into volatile derivatives, and a synergism between alpha-tocopherol and the produced compounds. These results were confirmed by analyzing the antioxidative activity of two of the produced carbonyl-amine products: 6-amino-2-(1H-pyrrol-1-yl)hexanoic acid (1) and 2,3-dipalmitoylpropyl 2-(1H-pyrrol-1-yl)ethyl phosphate (2). The hydrophilic compound 1 was more antioxidant than the analogous lipophilic compound 2, and this antioxidative activity was observed in TAO and not in TSO. All these results suggested that antioxidative activity of carbonyl-amine products may be greatly increased with the addition of tocopherols, and those products derived from Lys are more antioxidant in bulk oils than those derived from PE.
对磷脂酰乙醇胺（PE）、磷脂酰胆碱（PC）、赖氨酸（Lys）及其混合物在脱生育酚橄榄油（TSO）中以及在每克油添加250微克α-生育酚后的同一油样（添加生育酚的橄榄油，TAO）中进行抗氧化活性测试，以评估生育酚在氧化脂质-胺产物抗氧化活性中的作用。单独测试时，PE、PC和Lys均不能保护TSO，但PE和Lys均可延长TAO的诱导期（IP）。相反，PE/Lys和PC/Lys混合物（而非PC/PE混合物）可同时保护TSO和TAO。这些结果是氧化脂质-胺产物形成的结果（在转化为挥发性衍生物后通过气相色谱-质谱法测定）以及α-生育酚与生成化合物之间协同作用的结果。通过分析所生成的两种羰基-胺产物：6-氨基-2-(1H-吡咯-1-基)己酸（1）和2,3-二棕榈酰丙基2-(1H-吡咯-1-基)乙基磷酸酯（2）的抗氧化活性，证实了这些结果。亲水性化合物1比类似的亲脂性化合物2具有更强的抗氧化性，并且这种抗氧化活性在TAO中观察到，而在TSO中未观察到。所有这些结果表明，添加生育酚可大大提高羰基-胺产物的抗氧化活性，并且在散装油中，源自Lys的产物比源自PE的产物具有更强的抗氧化性。
