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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crsagepubl:10.1177/1934578x0800301023 2023-05-15T14:07:18+02:00 Chemoenzymatic Synthesis and Some Biological Properties of O -phosphoryl Derivatives of ( E )-resveratrol Aleo, Danilo Cardile, Venera Chillemi, Rosa Granata, Giuseppe Sciuto, Sebastiano 2008 http://dx.doi.org/10.1177/1934578x0800301023 http://journals.sagepub.com/doi/pdf/10.1177/1934578X0800301023 en eng SAGE Publications http://journals.sagepub.com/page/policies/text-and-data-mining-license Natural Product Communications volume 3, issue 10, page 1934578X0800301 ISSN 1934-578X 1555-9475 Complementary and alternative medicine Plant Science Drug Discovery Pharmacology General Medicine journal-article 2008 crsagepubl https://doi.org/10.1177/1934578x0800301023 2022-04-14T04:46:28Z 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 SAGE Publications (via Crossref) Freed ENVELOPE(164.333,164.333,-71.483,-71.483) Natural Product Communications 3 10 1934578X0800301 |
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Open Polar |
collection |
SAGE Publications (via Crossref) |
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crsagepubl |
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 Aleo, Danilo Cardile, Venera Chillemi, Rosa Granata, Giuseppe Sciuto, Sebastiano 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 |
Aleo, Danilo Cardile, Venera Chillemi, Rosa Granata, Giuseppe Sciuto, Sebastiano |
author_facet |
Aleo, Danilo Cardile, Venera Chillemi, Rosa Granata, Giuseppe Sciuto, Sebastiano |
author_sort |
Aleo, Danilo |
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 |
publisher |
SAGE Publications |
publishDate |
2008 |
url |
http://dx.doi.org/10.1177/1934578x0800301023 http://journals.sagepub.com/doi/pdf/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_source |
Natural Product Communications volume 3, issue 10, page 1934578X0800301 ISSN 1934-578X 1555-9475 |
op_rights |
http://journals.sagepub.com/page/policies/text-and-data-mining-license |
op_doi |
https://doi.org/10.1177/1934578x0800301023 |
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Natural Product Communications |
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3 |
container_issue |
10 |
container_start_page |
1934578X0800301 |
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1766279190733127680 |