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The effects of nitrogen moieties on the autoxidation of phospatidylethanolamine (PE) and phosphatidylcholine (PC) were studied in Tween 20 micelles at 37°C under air. When the oxidation was initiated by a water-soluble azo compound, the rate of oxidation of PE and PC was proportional to the number of bisallylic hydrogens and to the square root of azo-initiator concentration, and independent of difference in nitrogen moieties of PE and PC. When oxidation was induced by copper (II) ion, the kinetic order in the concentration of copper (II) ion was 0.5, suggesting that the oxidation may thus be initiated by radicals formed in the copper (II) ion-catalyzed decomposition of phospholipid hydroperoxides. The rate of oxidation per the number of bisallylic hydrogens of PE was 6.5-times larger than that of PC, possively due to the formation of the PE-copper (II) ion complex. The accelerating effect of the ethanolamine moiety on oxidation induced by copper (II) ion was confirmed by the finding that the oxidation of PC was promoted by the addition of non-oxidizable dimyristoyl-PE but not dimyristoyl-PC.

Effects of the Nitrogen Moieties of Phosphatidylethanolamine and Phosphatidylcholine on the Autoxidation of These Phospholipids in Aqueous Dispersions