A ternary system of α-tocopherol with phosphatidylethanolamine and l-ascorbyl palmitate in bulk oils provides antioxidant synergy through stabilization and regeneration of α-tocopherol. (15th October 2022)

• Record Type: Journal Article
• Authors: Doert, Martin; Grebenteuch, Sandra; Kroh, Lothar W.; Rohn, Sascha
• Is Part Of: Food chemistry. Volume 391(2022)
• Publication Date: 2022-10-15
• Subjects: Phospholipids -- Phosphatidylethanolamine -- α-Tocopherol -- Ascorbyl palmitate -- Synergistic antioxidant; AA ascorbic acid -- AA-N-DHA di(2-deoxy-2-l-ascorbyl)amine (oxidized form) -- AP ascorbyl palmitate -- α-Toc α-tocopherol -- a-TQ α-tocopherylquinone -- α-TP α-tocopherone -- T+ α-tocopherone ion -- BHA butylated hydroxyanisole -- BHT butylated hydroxytoluene -- CMC critical micelle concentration -- DHA dehydroascorbic acid -- DHAP dehydroascorbyl palmitate -- DPPH 2, 2-diphenyl-1-picrylhydrazyl radical -- EA activation energy -- Ext extinction -- ESI-HRMS electrospray ionization high-resolution mass spectrometry -- HOOR hydroperoxid -- OOR hydroperoxyl radical -- HPLC high performance liquid chromatography -- HPTLC high performance thin layer chromatography -- IFT interfacial tension -- IP induction period -- PA phosphatidic acid -- PA-Na 1, 2-dipalmitoyl-sn-glycero-3-phosphate monosodium salt -- PC phosphatidylcholine -- PE phosphoethanolamine -- PE(AA)2 1:2 condensate of PE and AA -- PE(AP)2 1:2 condensate of PE and AP -- PE-TP PE-tocopherone (condensate of PE and TQ) -- PL phospholipid -- SCAP scorbamic acid palmitate; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2022.133084
• Languages: English
• ISSNs: 0308-8146

Abstract

Graphical abstract: Highlights: α-Tocopherol in bulk oil is stabilized by phospholipids in mixture with ascorbate. The stabilization is based on the regeneration of the α-tocopherylquinone. The ascorbate reducible α-tocopherone ion is formed under acidic conditions. Phosphoethanolamine and ascorbyl palmitate establish a 1:2 condensation product. Amino reductones are developed between dehydroascorbate and phosphoethanolamine. Abstract: The stabilization of fats and oils against oxidative lipid deterioration is still a great challenge. The synergistic interaction between phospholipids, l -ascorbate, and tocopherols have not yet been comprehensively understood. The mechanism of the synergistic antioxidant effect of 1, 2-dipalmitoyl- sn -glycero-3-phosphoethanolamine (PE) in mixtures with l -ascorbyl palmitate (AP) and α-tocopherol (α-Toc) was investigated in an ethyl linoleate model and sunflower oil at 110 °C. The mixture of PE, AP, and α-Toc is stabilized through continuous regeneration of α-Toc from its oxidation product α-tocopherylquinone (α-TQ). This reaction is catalyzed by acids and proceeded through the formation of the α-tocopherone ion (T + ) as an intermediate product. In addition to the direct reduction of T + by AP, PE can also cause regeneration indirectly by reacting with dehydroascorbyl palmitate (DHAP) or other tricarbonyl compounds to form amino reductones. PE and AP undergo an amino-carbonyl reaction to form the condensate PE(AP)2 .