Chemoenzymatic synthesis and some biological properties of O-phosphoryl derivatives of (E)-resveratrol

Abstract

3-O-, 3,5-di-O- and 4′-O-phosphoryl derivatives of (E)-resveratrol have been obtained following a chemoenzymatic strategy. Variedly acylated resveratrol derivatives have been obtained first by exploiting regioselective properties of Pseudomonas cepacea or Candida antarctica lipases in organic solvents. Each acyl-resveratrol was then phosphorylated by the phosphoramidite chemistry protocol and in sequence freed of protective groups, affording the desired O-phosphoryl derivative. Following UV-absorption spectroscopic investigation on the interaction of the newly synthesized compounds with DNA, 4′-O-phosphorylresveratrol exhibited the best binding affinity. As a result of cytotoxicity tests, 3-O-phosphorylresveratrol was more active than resveratrol against DU 145 prostate cancer cells.