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

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 so...

Full description

Bibliographic Details
Published in:Natural Product Communications
Main Authors: Giuseppe Granata, Venera Cardile, Danilo Aleo, Sebastiano Sciuto, Rosa Chillemi
Format: Article in Journal/Newspaper
Language:English
Published: 2008
Subjects:
Complementary and alternative medicine
Plant Science
Drug Discovery
Pharmacology
General Medicine
Freed
Antarc*
Antarctica
Online Access:https://www.openaccessrepository.it/record/108607
https://doi.org/10.1177/1934578x0800301023
Description
Summary: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.

Similar Items