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...
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ftopenaccessrep:oai:zenodo.org:108607 2023-10-25T01:32:22+02:00 Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol Giuseppe Granata Venera Cardile Danilo Aleo Sebastiano Sciuto Rosa Chillemi 2008-10-01 https://www.openaccessrepository.it/record/108607 https://doi.org/10.1177/1934578x0800301023 eng eng url:https://www.openaccessrepository.it/communities/itmirror https://www.openaccessrepository.it/record/108607 doi:10.1177/1934578x0800301023 info:eu-repo/semantics/openAccess Complementary and alternative medicine Plant Science Drug Discovery Pharmacology General Medicine info:eu-repo/semantics/article publication-article 2008 ftopenaccessrep https://doi.org/10.1177/1934578x0800301023 2023-09-26T22:20:54Z 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. Article in Journal/Newspaper Antarc* Antarctica Istituto Nazionale di Fisica Nucleare (INFN): Open Access Repository Freed ENVELOPE(164.333,164.333,-71.483,-71.483) Natural Product Communications 3 10 1934578X0800301 |
institution |
Open Polar |
collection |
Istituto Nazionale di Fisica Nucleare (INFN): Open Access Repository |
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ftopenaccessrep |
language |
English |
topic |
Complementary and alternative medicine Plant Science Drug Discovery Pharmacology General Medicine |
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Complementary and alternative medicine Plant Science Drug Discovery Pharmacology General Medicine Giuseppe Granata Venera Cardile Danilo Aleo Sebastiano Sciuto Rosa Chillemi Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
topic_facet |
Complementary and alternative medicine Plant Science Drug Discovery Pharmacology General Medicine |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Giuseppe Granata Venera Cardile Danilo Aleo Sebastiano Sciuto Rosa Chillemi |
author_facet |
Giuseppe Granata Venera Cardile Danilo Aleo Sebastiano Sciuto Rosa Chillemi |
author_sort |
Giuseppe Granata |
title |
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
title_short |
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
title_full |
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
title_fullStr |
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
title_full_unstemmed |
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol |
title_sort |
chemoenzymatic synthesis and some biological properties of o-phosphoryl derivatives of (e)-resveratrol |
publishDate |
2008 |
url |
https://www.openaccessrepository.it/record/108607 https://doi.org/10.1177/1934578x0800301023 |
long_lat |
ENVELOPE(164.333,164.333,-71.483,-71.483) |
geographic |
Freed |
geographic_facet |
Freed |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
url:https://www.openaccessrepository.it/communities/itmirror https://www.openaccessrepository.it/record/108607 doi:10.1177/1934578x0800301023 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1177/1934578x0800301023 |
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Natural Product Communications |
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3 |
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10 |
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1934578X0800301 |
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1780728045186842624 |