Antioxidant activity and active sites of phospholipids as antioxidants

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Various compounds, representative of the major functional groups in phospholipids, phosphatidylethanolamine and phosphatidylcholine, were tested for antioxidant activity (AA) in a sardine oil system to determine the relationship between molecular structure and the AA of these compounds. AA was found to be attributable not only to the side-chain amino groups but also to the cooperative effect of the hydroxy group in the side chain. Choline and ethanolamine, side-chain moieties of phospholipids, strongly inhibited increases in peroxide values in a sardine oil mixture during storage; however, phosphatidic acid derivatives and glycerol, also major functional groups of phospholipids, did not show AA. Choline and ethanolamine have hydroxy amines as functional groups; therefore, several model reagents that contained amines and alcohols were assayed to compare the activity of the amino group with that of the hydroxy group. All basic alkylamines examined had AA as decomposers of hydroperoxides. The intramolecular hydroxy group in these amines complemented AA of the amino group. Only intramolecular alcohol, which can donate a proton, showed strong synergistic activity with AAof the basic amines, while protected groups, such as methyl ether and phosphate ester, did not show this effect.