Clearing up the photochemistry of resveratrol: Effect of the solvent

Abstract Polyphenolic substances synthesized by plants are generally involved in protection against UV radiation and the attack of pathogenic microorganisms. Resveratrol (3,5,4′-trihydroxystilbene, RSV) is synthesized in its <i>trans-form</i> (<i>trans</i>-RSV) in plants unde...

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Autores: Gaspar Tosato, Maira, Vicendo, Patricia, Thomas, Andrés Héctor, Lorente, Carolina
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:Argentina
Institución:Universidad Nacional de La Plata
Repositorio:SEDICI (UNLP)
Idioma:inglés
OAI Identifier:oai:sedici.unlp.edu.ar:10915/124874
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/124874
Access Level:acceso abierto
Palabra clave:Ciencias Exactas
Química
Resveratrol
Photochemistry
UV radiation
Photoproducts
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spelling Clearing up the photochemistry of resveratrol: Effect of the solventGaspar Tosato, MairaVicendo, PatriciaThomas, Andrés HéctorLorente, CarolinaCiencias ExactasQuímicaResveratrolPhotochemistryUV radiationPhotoproductsAbstract Polyphenolic substances synthesized by plants are generally involved in protection against UV radiation and the attack of pathogenic microorganisms. Resveratrol (3,5,4′-trihydroxystilbene, RSV) is synthesized in its <i>trans-form</i> (<i>trans</i>-RSV) in plants under stress conditions like infections or UV exposure and has attracted attention as an antioxidant agent. <i>Trans</i>-RSV was irradiated with both UV-A (λ<sub>MAX</sub> = 365 nm) and UV-B (λ<sub>MAX</sub> = 300 nm) radiation in aqueous and ethanolic solutions at room temperature. The reactions were followed by UV–Vis spectrophotometry, HPLC with UV and fluorescence detection, and UPLC coupled to mass spectrometry detection. In both solvents the irradiation caused the fast isomerization of <i>trans</i>-RSV to cis-RSV. In ethanolic solutions, a strong fluorescent compound, identified as resveratrone (RSVT) was detected independently on the irradiation wavelength. In aqueous solutions, RSVT was not detected in both irradiation conditions. However, in aqueous/ethanol mixtures the amount RSVT was found to be proportional to the amount of ethanol in the solution. Under UV-B irradiation, both in ethanolic or water solutions other products were detected. Our results demonstrated that RSV is photosensitive and its photochemistry depends on the solvent nature and on the irradiation wavelength.Facultad de Ciencias ExactasInstituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas2018-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf327-331http://sedici.unlp.edu.ar/handle/10915/124874enginfo:eu-repo/semantics/altIdentifier/issn/1010-6030info:eu-repo/semantics/altIdentifier/issn/1873-2666info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2018.08.050info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2024-05-08T13:07:59Zoai:sedici.unlp.edu.ar:10915/124874Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292024-05-08 13:07:59.727SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Clearing up the photochemistry of resveratrol: Effect of the solvent
title Clearing up the photochemistry of resveratrol: Effect of the solvent
spellingShingle Clearing up the photochemistry of resveratrol: Effect of the solvent
Gaspar Tosato, Maira
Ciencias Exactas
Química
Resveratrol
Photochemistry
UV radiation
Photoproducts
title_short Clearing up the photochemistry of resveratrol: Effect of the solvent
title_full Clearing up the photochemistry of resveratrol: Effect of the solvent
title_fullStr Clearing up the photochemistry of resveratrol: Effect of the solvent
title_full_unstemmed Clearing up the photochemistry of resveratrol: Effect of the solvent
title_sort Clearing up the photochemistry of resveratrol: Effect of the solvent
dc.creator.none.fl_str_mv Gaspar Tosato, Maira
Vicendo, Patricia
Thomas, Andrés Héctor
Lorente, Carolina
author Gaspar Tosato, Maira
author_facet Gaspar Tosato, Maira
Vicendo, Patricia
Thomas, Andrés Héctor
Lorente, Carolina
author_role author
author2 Vicendo, Patricia
Thomas, Andrés Héctor
Lorente, Carolina
author2_role author
author
author
dc.subject.none.fl_str_mv Ciencias Exactas
Química
Resveratrol
Photochemistry
UV radiation
Photoproducts
topic Ciencias Exactas
Química
Resveratrol
Photochemistry
UV radiation
Photoproducts
description Abstract Polyphenolic substances synthesized by plants are generally involved in protection against UV radiation and the attack of pathogenic microorganisms. Resveratrol (3,5,4′-trihydroxystilbene, RSV) is synthesized in its <i>trans-form</i> (<i>trans</i>-RSV) in plants under stress conditions like infections or UV exposure and has attracted attention as an antioxidant agent. <i>Trans</i>-RSV was irradiated with both UV-A (λ<sub>MAX</sub> = 365 nm) and UV-B (λ<sub>MAX</sub> = 300 nm) radiation in aqueous and ethanolic solutions at room temperature. The reactions were followed by UV–Vis spectrophotometry, HPLC with UV and fluorescence detection, and UPLC coupled to mass spectrometry detection. In both solvents the irradiation caused the fast isomerization of <i>trans</i>-RSV to cis-RSV. In ethanolic solutions, a strong fluorescent compound, identified as resveratrone (RSVT) was detected independently on the irradiation wavelength. In aqueous solutions, RSVT was not detected in both irradiation conditions. However, in aqueous/ethanol mixtures the amount RSVT was found to be proportional to the amount of ethanol in the solution. Under UV-B irradiation, both in ethanolic or water solutions other products were detected. Our results demonstrated that RSV is photosensitive and its photochemistry depends on the solvent nature and on the irradiation wavelength.
publishDate 2018
dc.date.none.fl_str_mv 2018-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/124874
url http://sedici.unlp.edu.ar/handle/10915/124874
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1010-6030
info:eu-repo/semantics/altIdentifier/issn/1873-2666
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2018.08.050
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
327-331
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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