In Vitro Antioxidant and Anti-Glycation Activity of Resveratrol and Its Novel Triester with Trolox

Resveratrol (RSV) is well known for its many beneficial activities, but its unfavorable physicochemical properties impair its effectiveness after systemic and topical administration; thus, several strategies have been investigated to improve RSV efficacy. With this aim, in this work, we synthesized a novel RSV triester with trolox, an analogue of vitamin E with strong antioxidant activity. The new RSV derivative (RSVTR) was assayed in vitro to evaluate its antioxidant and anti-glycation activity compared to RSV. RSVTR chemical stability was assessed at pH 2.0, 6.8, and 7.2 and different storage temperatures (5 degrees C, 22 degrees C, and 37 degrees C). An influence of pH stronger than that of temperature on RSVTR half-life values was pointed out, and RSVTR greatest stability was observed at pH 7.2 and 5 degrees C. RSVTR showed a lower antioxidant ability compared to RSV (determined by the oxygen radical absorbance capacity assay) while its anti-glycation activity (evaluated using the Maillard reaction) was significantly greater than that of RSV. The improved ability to inhibit the glycation process was attributed to a better interaction of RSVTR with albumin owing to its increased topological polar surface area value and H-bond acceptor number compared to RSV. Therefore, RSVTR could be regarded as a promising anti-glycation agent worthy of further investigations.

Automated summary

A novel resveratrol triester derivative, RSVTR, was synthesized by combining resveratrol with trolox, exhibiting improved anti-glycation activity compared to resveratrol. RSVTR showed good chemical stability under various pHs and temperatures, with the greatest stability observed at pH 7.2 and 5 degrees C. The enhanced ability to inhibit the glycation process was attributed to RSVTR's better interaction with albumin due to increased topological polar surface area values and H-bond acceptor numbers.