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...
Published in: | Natural Product Communications |
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Main Authors: | , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2008
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Subjects: | |
Online Access: | https://www.openaccessrepository.it/record/108607 https://doi.org/10.1177/1934578x0800301023 |
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. |
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