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Preservation of polyunsaturated fatty acyl glycerides via intramolecular antioxidant coupling.

Permanent URL:
http://handle.nal.usda.gov/10113/57564
File:
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Abstract:
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.
Author(s):
Joseph A. Laszlo , Kervin O. Evans , David L. Compton
Subject(s):
acylglycerols , antioxidant activity , antioxidants , ferulic acid , lipid bilayers , oxidation , oxidative stability , phospholipids , polyunsaturated fatty acids
Source:
Chemistry and Physics of Lipids 2012 v.165
Language:
English
Year:
2012
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
Rights:
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.