Effects of phosphatidylcholines containing furan fatty acid on oxidation in multilamellar liposomes.

Several phosphatidylcholines (PCs) containing furan fatty acid (10, 13-epoxy-11, 12-dimethyloctadeca-10, 12-dienoic acid, F acid) were synthesized, and their antioxidant activities were studied in the oxidation of soybean PC. The rate of oxidation in soybean PC liposomes initiated with 2, 2'-azobis(2, 4-dimethylvaleronitrile) (AMVN), a lipophilic azoinitiator, was measured by following the oxygen uptake, the accumulation of conjugated diene, and the disappearance of unsaturated fatty acid moieties. These PCs containing F acid were found to retard the rate of oxidation in soybean PC liposomes, and the retarding effect increased in the following order : 1/2 mol of di-furanoacyl PC (di-F PC)<1 mol of 1-furanoacyl-2-linoleoyl PC (F-18 : 2 PC)<1 mol of 1-furanoacyl-2-arachidonyl PC (F-20 : 4 PC)<1 mol of di-F PC (1 : 1 : 1 : 2, as molar ratios of F acid residue). This is the first report showing that the naturally occurring F acid has a retarding effect on lipid peroxidation.