Abstract
Ferulic acid and its ester derivatives are known to be effective antioxidants and as such have been investigated as a potential antioxidant agent for cosmetic and pharmaceutical uses. Using immobilized Candida antarctica lipase B we synthesized ferulic acid lipophilic derivatives from vegetable oils. After synthesis we isolated the predominate species, feruloyl dioleoylglycerol (FDOG), and incorporated it into model phospholipid vesicles at 1 and 5 mol percent. Membrane leakage experiments showed that FDOG did not disturb the phospholipid membrane integrity. Fluorescence quenching experiments and molecular modeling determined that the feruloyl moiety rested within the hydrophobic/hydrophilic interface of the bilayer. This was further supported by NMR analysis that showed FDOG exists with its feruloyl moiety far away from its oleoyl groups. Lipid peroxidation inhibition and free-radical-scavenging analysis indicated that FDOG retained its inherent antioxidant capability, possibly by intercepting aqueous-phase free radicals as they penetrate the bilayer.
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