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Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation

trans-Resveratrol is a natural bioactive compound with well-recognized health promoting effects. When exposed to UV light, this compound can undergo a photochemically induced trans/cis isomerization and a 6π electrochemical cyclization with the subsequent formation of 2,4,6-trihydroxyphenanthrene (T...

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Autores principales: Mattioli, Roberto, Di Risola, Daniel, Federico, Rodolfo, Ciogli, Alessia, Gasparrini, Francesco, Villani, Claudio, Fontana, Mario, Maggiore, Anna, d’Erme, Maria, Mosca, Luciana, Francioso, Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000676/
https://www.ncbi.nlm.nih.gov/pubmed/35408747
http://dx.doi.org/10.3390/molecules27072348
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author Mattioli, Roberto
Di Risola, Daniel
Federico, Rodolfo
Ciogli, Alessia
Gasparrini, Francesco
Villani, Claudio
Fontana, Mario
Maggiore, Anna
d’Erme, Maria
Mosca, Luciana
Francioso, Antonio
author_facet Mattioli, Roberto
Di Risola, Daniel
Federico, Rodolfo
Ciogli, Alessia
Gasparrini, Francesco
Villani, Claudio
Fontana, Mario
Maggiore, Anna
d’Erme, Maria
Mosca, Luciana
Francioso, Antonio
author_sort Mattioli, Roberto
collection PubMed
description trans-Resveratrol is a natural bioactive compound with well-recognized health promoting effects. When exposed to UV light, this compound can undergo a photochemically induced trans/cis isomerization and a 6π electrochemical cyclization with the subsequent formation of 2,4,6-trihydroxyphenanthrene (THP). THP is a potentially harmful compound which can exert genotoxic effects. In this work we improved the chromatographic separation and determination of the two resveratrol isomers and of THP by using a non-commercial pentafluorophenyl stationary phase. We assessed the effect of natural deep eutectic solvents (NaDES) as possible photo-protective agents by evaluating cis-resveratrol isomer and THP formation under different UV-light exposure conditions with the aim of enhancing resveratrol photostability and inhibiting THP production. Our results demonstrate a marked photoprotective effect exerted by glycerol-containing NaDES, and in particular by proline/glycerol NaDES, which exerts a strong inhibitory effect on the photochemical isomerization of resveratrol and significantly limits the formation of the toxic derivative THP. Considering the presence of resveratrol in various commercial products, these results are of note in view of the potential genotoxic risk associated with its photochemical degradation products and in view of the need for the development of green, eco-sustainable and biocompatible resveratrol photo-stable formulations.
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spelling pubmed-90006762022-04-12 Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation Mattioli, Roberto Di Risola, Daniel Federico, Rodolfo Ciogli, Alessia Gasparrini, Francesco Villani, Claudio Fontana, Mario Maggiore, Anna d’Erme, Maria Mosca, Luciana Francioso, Antonio Molecules Article trans-Resveratrol is a natural bioactive compound with well-recognized health promoting effects. When exposed to UV light, this compound can undergo a photochemically induced trans/cis isomerization and a 6π electrochemical cyclization with the subsequent formation of 2,4,6-trihydroxyphenanthrene (THP). THP is a potentially harmful compound which can exert genotoxic effects. In this work we improved the chromatographic separation and determination of the two resveratrol isomers and of THP by using a non-commercial pentafluorophenyl stationary phase. We assessed the effect of natural deep eutectic solvents (NaDES) as possible photo-protective agents by evaluating cis-resveratrol isomer and THP formation under different UV-light exposure conditions with the aim of enhancing resveratrol photostability and inhibiting THP production. Our results demonstrate a marked photoprotective effect exerted by glycerol-containing NaDES, and in particular by proline/glycerol NaDES, which exerts a strong inhibitory effect on the photochemical isomerization of resveratrol and significantly limits the formation of the toxic derivative THP. Considering the presence of resveratrol in various commercial products, these results are of note in view of the potential genotoxic risk associated with its photochemical degradation products and in view of the need for the development of green, eco-sustainable and biocompatible resveratrol photo-stable formulations. MDPI 2022-04-06 /pmc/articles/PMC9000676/ /pubmed/35408747 http://dx.doi.org/10.3390/molecules27072348 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Mattioli, Roberto
Di Risola, Daniel
Federico, Rodolfo
Ciogli, Alessia
Gasparrini, Francesco
Villani, Claudio
Fontana, Mario
Maggiore, Anna
d’Erme, Maria
Mosca, Luciana
Francioso, Antonio
Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title_full Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title_fullStr Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title_full_unstemmed Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title_short Effect of Natural Deep Eutectic Solvents on trans-Resveratrol Photo-Chemical Induced Isomerization and 2,4,6-Trihydroxyphenanthrene Electro-Cyclic Formation
title_sort effect of natural deep eutectic solvents on trans-resveratrol photo-chemical induced isomerization and 2,4,6-trihydroxyphenanthrene electro-cyclic formation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000676/
https://www.ncbi.nlm.nih.gov/pubmed/35408747
http://dx.doi.org/10.3390/molecules27072348
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