Lipophilization of Resveratrol and Effects on Antioxidant Activities

Resveratrol (R), a polyphenol, was structurally modified via esterification with selected fatty acids to expand its potential application in lipophilic foods, drugs, and cosmetics. The esterification was carried out using 12 different fatty acids with varying chain lengths and degrees of unsaturation (C3:0-C22:6). Two monoesters, two diesters, and one triester were identified by high-performance liquid chromatography mass spectrometry, and the monoesters (R-3-O-monodocosahexaenoate and R-4'-O-monodocosahexaenoate) were structurally confirmed by nuclear magnetic resonance. The lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging assay, whereas short-chain fatty acid (C3:0, C4:0, and C6:0) showed higher antioxidant activity in the ABTS radical cation scavenging assay. The results may imply that resveratrol derivatives could be used in lipophilic media as health beneficial antioxidants.