Resveratrol (3,5,4'-trihydroxy-stilbene), or its corresponding oligomers (e.g., viniferins), are stilbenoids of great interest on account of their many promising biological activities (e.g., anticancer, antioxidant, whitening). Moreover, due to their role as phytoalexins in many plants (e.g., Vitis vinifera, Fallopia japonica), stilbenoids play an important role in the defense against pathogens. Piceid, resveratrol-β-glucoside, is thought to aid in the storage and translocation of resveratrol within cell tissues as well as protect resveratrol from oxidation. Recent studies reported that resveratrol glycosides with an α bond configuration obtained by enzymatic glycosylation, exhibit not only significantly increased water solubility but also novel surfactant property, compared to the natural β-glycosides. In order to develop an efficient, sustainable and economic process allowing the production of α-glycosides of resveratrol, different conditions were evaluated for the enzyme-catalyzed glycosylation, by varying both the nature of the solvent (ionic liquid or water) and that of the glycosyl-donor. After optimization of the different parameters by DoE, resveratrol a-glycosylation was successfully achieved in a 35% yield (mol/mol) in only 2 hours. The various products were purified by Centrifugal Partition Chromatography and characterized by LC-NMR. DPPH analyses were performed in order to determine their antiradical properties. It is noteworthy to mention that the reaction was scaled-up from 4 mL to 2 L without loss of yield, thus showing the potentiality to perform it at pilot scale.

Enzymatic modification of resveratrol: Green strategies for α-glycosylation

254th National Meeting (2017)

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