Chemoenzymatic Synthesis and Some Biological Properties of O -phosphoryl Derivatives of ( E )-resveratrol

• Published in: Natural Product Communications
• Main Authors: Aleo, Danilo, Cardile, Venera, Chillemi, Rosa, Granata, Giuseppe, Sciuto, Sebastiano
• Format: Article in Journal/Newspaper
• Language: English
• Published: SAGE Publications 2008
• Subjects: Complementary and alternative medicine; Plant Science; Drug Discovery; Pharmacology; General Medicine; Freed; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1177/1934578x0800301023; http://journals.sagepub.com/doi/pdf/10.1177/1934578X0800301023

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.