Sustainable Synthesis of Novel Bioactive Lipophilic Stilbene Glycosides: A Chemo-Enzymatic Approach glycosylated stilbenes

GlycoStil project financed by ANR aims to produce new functionalized stilbenic compounds. 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 hydrophobic/lipophilic balance (HLB) and thus maximize bioavailability, alkyl glucoside dimers of resveratrol (i.e., C2 to C12 alkyl oxystilbenin diglucosides (C8-O4’ linkage) and diglucoside δ-viniferin (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 key step. Diglucoside δ-viniferin was functionalized by lauric acid using an enzyme-mediated esterification. HLB values, determined from Log P (the partition coefficient between water and octanol), 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 shown very promising results with some activities overpassing that of resveratrol. This dataset grouped for each molecule data relative to their structural characterization, as well as their intrinsic properties such as UV absorption, antiradical scavenging activities.