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Preservation of polyunsaturated fatty acyl glycerides via intramolecular antioxidant coupling.

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Ferulic acid and its esters are known to be effective antioxidants. Feruloyl di-y-linolenoylglycerol was assessed for its ability to serve as an antioxidant for preventing the oxidation of its y- linolenoyl polyunsaturated fatty acyl groups in model membrane phospholipid vesicles. The molecule was incorporated into single-lamellar vesicles comprised of 1,2-dioleoyl-sn-glycero-3-phosphocholine. Feruloyl di-y-linolenoylglycerol was found to be highly resistant to 2,2'-azobis(2-amidinopropane) dihydrochloride-initiated oxidation in comparison to di-y-linolenoylglycerol. Analysis of the individual fatty acyl chains indicated that degradation of y-linolenoyl groups from feruloyl di-y-linolenoylglycerol proceeded much more slowly than loss of the entire molecule, indicating that the feruloyl moiety was preferentially oxidized. In vesicles incorporating di-y-linolenoylglycerol and an equal amount (5 mol% each) feruloyl dioleoylglycerol, the extent of y-linolenoyl protection was not as great as when the y- linolenoyl groups were molecularly combined with a ferulate group. These findings indicate that the ferulate group of feruloyl di-y-linolenoylglycerol expresses intramolecular antioxidant activity. Direct coupling of polyunsaturated fatty acids with phenolic antioxidants may improve the oxidative stability of sensitive fatty acids in food or topical uses.
Joseph A. Laszlo , Kervin O. Evans , David L. Compton
acylglycerols , antioxidant activity , antioxidants , ferulic acid , lipid bilayers , oxidation , oxidative stability , phospholipids , polyunsaturated fatty acids
Chemistry and Physics of Lipids 2012 v.165
Journal Articles, USDA Authors, Peer-Reviewed
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