Novel Bioactive Multifunctional Polyphenols: A Chemo-Enzymatic Approach

Stilbenes, such as resveratrol, possess numerous biological activities desirable in various industrial sectors (e.g., pharmaceutical, nutraceutical, and cosmetic). However, these activities are counteracted by their low bioavailability. In order to achieve an optimal hydrophylic/lipophilic balance (HLB) and thus maximize bioavailability, alkyl glucoside dimers of resveratrol (i.e., C2 to C12 alkyl oxystilbenin diglucosides (C8-O4' linkage) and δ-Viniferin diglucoside (C3-C8' linkage)) were synthesized from piceid-a β-glucoside of resveratrol-in one or two steps using a silver acetate-mediated oxidative coupling in various alcoholic solvents as the key step. δ-Viniferin diglucoside was functionalized by lauric acid using an enzyme-mediated esterification. HLB values, determined from Log P (the partition coefficient between water and octan-1-ol), were calculated for the nine synthesized compounds, revealing that four exhibited values within the range considered favorable for bioabsorption. Finally, antiradical and antioxidant activities were assessed using DPPH and ORAC tests, respectively, prior to anti-inflammatory testing on dermal human cells. These assays have shown very promising results with some activities overpassing that of resveratrol.