Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations

Autores
Marrassini, Carla; Idrissi, Abdenacer; de Waele, Isabelle; Smail, Khadidja; Tchouar, Noureddine; Moreau, Myriam; Mezzetti Alberto
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The interactions of luteolin with three alcohols (methanol, 1-propanol, 1-butanol) and dimethylsulfoxide (DMSO) were studied by FT-Raman, Vis-Raman and UV-Raman spectroscopies, coupled to density functional theory calculations. No large shift was observed for the bands in the spectra of luteolin in alcohols or DMSO in the 1700–1550 cm− 1 region. This is possibly related to the presence of a strong intramolecular hydrogen bond involving the 5-OH and the carbonyl of luteolin, as suggested by literature data [V. Exarchou, A. Troganis, I.P. Gerothanassis, M. Tsimidou, D. Boskou, Tetrahedron 2002, 58, 7423–7429] and DFT calculations. Furthermore, DFT calculations suggest that the CO stretching of luteolin is implicated in several vibrational modes, whereas the most upshifted band in the 1700–1550 cm− 1 can be interpreted as arising mainly from a 5-OH bending. The results are discussed in the framework of vibrational spectroscopy studies on flavonoids, of the photophysical properties of luteolin, and of the reported literature of vibrational spectra of luteolin under different conditions, in particular when interacting with biomolecules.
Fil: Marrassini, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Farmacología. Cátedra de Farmacognosia; Argentina
Fil: Idrissi, Abdenacer. Université Lille 1; Francia
Fil: de Waele, Isabelle. Université Lille 1; Francia
Fil: Smail, Khadidja. Université des Sciences et de la Technologie d’Oran Mohamed Boudiaf; Argelia
Fil: Tchouar, Noureddine. Oran University of Science and Technology - Mohamed Boudiaf; Argelia
Fil: Moreau, Myriam. Université Lille 1; Francia
Fil: Mezzetti Alberto. Université Lille 1; Francia
Materia
Luteolin
Vis-Raman
Ft-Raman
Uv-Raman
Dft
Hydrogen Bond
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/18458
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/18458
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculationsMarrassini, CarlaIdrissi, Abdenacerde Waele, IsabelleSmail, KhadidjaTchouar, NoureddineMoreau, MyriamMezzetti AlbertoLuteolinVis-RamanFt-RamanUv-RamanDftHydrogen Bondhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The interactions of luteolin with three alcohols (methanol, 1-propanol, 1-butanol) and dimethylsulfoxide (DMSO) were studied by FT-Raman, Vis-Raman and UV-Raman spectroscopies, coupled to density functional theory calculations. No large shift was observed for the bands in the spectra of luteolin in alcohols or DMSO in the 1700–1550 cm− 1 region. This is possibly related to the presence of a strong intramolecular hydrogen bond involving the 5-OH and the carbonyl of luteolin, as suggested by literature data [V. Exarchou, A. Troganis, I.P. Gerothanassis, M. Tsimidou, D. Boskou, Tetrahedron 2002, 58, 7423–7429] and DFT calculations. Furthermore, DFT calculations suggest that the CO stretching of luteolin is implicated in several vibrational modes, whereas the most upshifted band in the 1700–1550 cm− 1 can be interpreted as arising mainly from a 5-OH bending. The results are discussed in the framework of vibrational spectroscopy studies on flavonoids, of the photophysical properties of luteolin, and of the reported literature of vibrational spectra of luteolin under different conditions, in particular when interacting with biomolecules.Fil: Marrassini, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Farmacología. Cátedra de Farmacognosia; ArgentinaFil: Idrissi, Abdenacer. Université Lille 1; FranciaFil: de Waele, Isabelle. Université Lille 1; FranciaFil: Smail, Khadidja. Université des Sciences et de la Technologie d’Oran Mohamed Boudiaf; ArgeliaFil: Tchouar, Noureddine. Oran University of Science and Technology - Mohamed Boudiaf; ArgeliaFil: Moreau, Myriam. Université Lille 1; FranciaFil: Mezzetti Alberto. Université Lille 1; FranciaElsevier Science2015-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/18458Marrassini, Carla; Idrissi, Abdenacer; de Waele, Isabelle; Smail, Khadidja; Tchouar, Noureddine; et al.; Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations; Elsevier Science; Journal of Molecular Liquids; 205; 5-2015; 2-80167-7322CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0167732214003729info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molliq.2014.08.014info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:03:21Zoai:ri.conicet.gov.ar:11336/18458instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 10:03:21.688CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
title Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
spellingShingle Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
Marrassini, Carla
Luteolin
Vis-Raman
Ft-Raman
Uv-Raman
Dft
Hydrogen Bond
title_short Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
title_full Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
title_fullStr Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
title_full_unstemmed Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
title_sort Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations
dc.creator.none.fl_str_mv Marrassini, Carla
Idrissi, Abdenacer
de Waele, Isabelle
Smail, Khadidja
Tchouar, Noureddine
Moreau, Myriam
Mezzetti Alberto
author Marrassini, Carla
author_facet Marrassini, Carla
Idrissi, Abdenacer
de Waele, Isabelle
Smail, Khadidja
Tchouar, Noureddine
Moreau, Myriam
Mezzetti Alberto
author_role author
author2 Idrissi, Abdenacer
de Waele, Isabelle
Smail, Khadidja
Tchouar, Noureddine
Moreau, Myriam
Mezzetti Alberto
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Luteolin
Vis-Raman
Ft-Raman
Uv-Raman
Dft
Hydrogen Bond
topic Luteolin
Vis-Raman
Ft-Raman
Uv-Raman
Dft
Hydrogen Bond
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The interactions of luteolin with three alcohols (methanol, 1-propanol, 1-butanol) and dimethylsulfoxide (DMSO) were studied by FT-Raman, Vis-Raman and UV-Raman spectroscopies, coupled to density functional theory calculations. No large shift was observed for the bands in the spectra of luteolin in alcohols or DMSO in the 1700–1550 cm− 1 region. This is possibly related to the presence of a strong intramolecular hydrogen bond involving the 5-OH and the carbonyl of luteolin, as suggested by literature data [V. Exarchou, A. Troganis, I.P. Gerothanassis, M. Tsimidou, D. Boskou, Tetrahedron 2002, 58, 7423–7429] and DFT calculations. Furthermore, DFT calculations suggest that the CO stretching of luteolin is implicated in several vibrational modes, whereas the most upshifted band in the 1700–1550 cm− 1 can be interpreted as arising mainly from a 5-OH bending. The results are discussed in the framework of vibrational spectroscopy studies on flavonoids, of the photophysical properties of luteolin, and of the reported literature of vibrational spectra of luteolin under different conditions, in particular when interacting with biomolecules.
Fil: Marrassini, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Farmacología. Cátedra de Farmacognosia; Argentina
Fil: Idrissi, Abdenacer. Université Lille 1; Francia
Fil: de Waele, Isabelle. Université Lille 1; Francia
Fil: Smail, Khadidja. Université des Sciences et de la Technologie d’Oran Mohamed Boudiaf; Argelia
Fil: Tchouar, Noureddine. Oran University of Science and Technology - Mohamed Boudiaf; Argelia
Fil: Moreau, Myriam. Université Lille 1; Francia
Fil: Mezzetti Alberto. Université Lille 1; Francia
description The interactions of luteolin with three alcohols (methanol, 1-propanol, 1-butanol) and dimethylsulfoxide (DMSO) were studied by FT-Raman, Vis-Raman and UV-Raman spectroscopies, coupled to density functional theory calculations. No large shift was observed for the bands in the spectra of luteolin in alcohols or DMSO in the 1700–1550 cm− 1 region. This is possibly related to the presence of a strong intramolecular hydrogen bond involving the 5-OH and the carbonyl of luteolin, as suggested by literature data [V. Exarchou, A. Troganis, I.P. Gerothanassis, M. Tsimidou, D. Boskou, Tetrahedron 2002, 58, 7423–7429] and DFT calculations. Furthermore, DFT calculations suggest that the CO stretching of luteolin is implicated in several vibrational modes, whereas the most upshifted band in the 1700–1550 cm− 1 can be interpreted as arising mainly from a 5-OH bending. The results are discussed in the framework of vibrational spectroscopy studies on flavonoids, of the photophysical properties of luteolin, and of the reported literature of vibrational spectra of luteolin under different conditions, in particular when interacting with biomolecules.
publishDate 2015
dc.date.none.fl_str_mv 2015-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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://hdl.handle.net/11336/18458
Marrassini, Carla; Idrissi, Abdenacer; de Waele, Isabelle; Smail, Khadidja; Tchouar, Noureddine; et al.; Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations; Elsevier Science; Journal of Molecular Liquids; 205; 5-2015; 2-8
0167-7322
CONICET Digital
CONICET
url http://hdl.handle.net/11336/18458
identifier_str_mv Marrassini, Carla; Idrissi, Abdenacer; de Waele, Isabelle; Smail, Khadidja; Tchouar, Noureddine; et al.; Organic solvent–luteolin interactions studied by FT-Raman, Vis-Raman, UV-Raman spectroscopy and DFT calculations; Elsevier Science; Journal of Molecular Liquids; 205; 5-2015; 2-8
0167-7322
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0167732214003729
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molliq.2014.08.014
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842269798805798912
score 13.13397

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