Structure and electronic properties of (+)-catechin: Aqueous solvent effects

Autores
Bentz, Erika Natalia; Pomilio, Alicia Beatriz; Lobayan, Rosana Maria
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols-one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mechanisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6″, 2α→O→1″)-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure.
Fil: Bentz, Erika Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina. Universidad de la Cuenca del Plata. Facultad de Ingeniería; Argentina
Fil: Pomilio, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Bioquímica y Medicina Molecular. Universidad de Buenos Aires. Facultad Medicina. Instituto de Bioquímica y Medicina Molecular; Argentina
Fil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería; Argentina. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; Argentina
Materia
Antioxidants
Aqueous Solvent Effect
Atoms in Molecules
Density Functional Theory
Molecular Polarizability
Natural Bond Orbital Analysis
Pcm Model
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/83910
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/83910
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Structure and electronic properties of (+)-catechin: Aqueous solvent effectsBentz, Erika NataliaPomilio, Alicia BeatrizLobayan, Rosana MariaAntioxidantsAqueous Solvent EffectAtoms in MoleculesDensity Functional TheoryMolecular PolarizabilityNatural Bond Orbital AnalysisPcm Modelhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols-one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mechanisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6″, 2α→O→1″)-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure.Fil: Bentz, Erika Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina. Universidad de la Cuenca del Plata. Facultad de Ingeniería; ArgentinaFil: Pomilio, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Bioquímica y Medicina Molecular. Universidad de Buenos Aires. Facultad Medicina. Instituto de Bioquímica y Medicina Molecular; ArgentinaFil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería; Argentina. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; ArgentinaSpringer2014-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/83910Bentz, Erika Natalia; Pomilio, Alicia Beatriz; Lobayan, Rosana Maria; Structure and electronic properties of (+)-catechin: Aqueous solvent effects; Springer; Journal of Molecular Modeling; 20; 2; 2-2014; 1-130948-50231610-2940CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-014-2105-zinfo:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00894-014-2105-z#citeasinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:38:26Zoai:ri.conicet.gov.ar:11336/83910instacron: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:34982025-09-29 09:38:27.237CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure and electronic properties of (+)-catechin: Aqueous solvent effects
title Structure and electronic properties of (+)-catechin: Aqueous solvent effects
spellingShingle Structure and electronic properties of (+)-catechin: Aqueous solvent effects
Bentz, Erika Natalia
Antioxidants
Aqueous Solvent Effect
Atoms in Molecules
Density Functional Theory
Molecular Polarizability
Natural Bond Orbital Analysis
Pcm Model
title_short Structure and electronic properties of (+)-catechin: Aqueous solvent effects
title_full Structure and electronic properties of (+)-catechin: Aqueous solvent effects
title_fullStr Structure and electronic properties of (+)-catechin: Aqueous solvent effects
title_full_unstemmed Structure and electronic properties of (+)-catechin: Aqueous solvent effects
title_sort Structure and electronic properties of (+)-catechin: Aqueous solvent effects
dc.creator.none.fl_str_mv Bentz, Erika Natalia
Pomilio, Alicia Beatriz
Lobayan, Rosana Maria
author Bentz, Erika Natalia
author_facet Bentz, Erika Natalia
Pomilio, Alicia Beatriz
Lobayan, Rosana Maria
author_role author
author2 Pomilio, Alicia Beatriz
Lobayan, Rosana Maria
author2_role author
author
dc.subject.none.fl_str_mv Antioxidants
Aqueous Solvent Effect
Atoms in Molecules
Density Functional Theory
Molecular Polarizability
Natural Bond Orbital Analysis
Pcm Model
topic Antioxidants
Aqueous Solvent Effect
Atoms in Molecules
Density Functional Theory
Molecular Polarizability
Natural Bond Orbital Analysis
Pcm Model
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols-one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mechanisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6″, 2α→O→1″)-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure.
Fil: Bentz, Erika Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina. Universidad de la Cuenca del Plata. Facultad de Ingeniería; Argentina
Fil: Pomilio, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Bioquímica y Medicina Molecular. Universidad de Buenos Aires. Facultad Medicina. Instituto de Bioquímica y Medicina Molecular; Argentina
Fil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería; Argentina. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; Argentina
description We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols-one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mechanisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6″, 2α→O→1″)-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure.
publishDate 2014
dc.date.none.fl_str_mv 2014-02
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/11336/83910
Bentz, Erika Natalia; Pomilio, Alicia Beatriz; Lobayan, Rosana Maria; Structure and electronic properties of (+)-catechin: Aqueous solvent effects; Springer; Journal of Molecular Modeling; 20; 2; 2-2014; 1-13
0948-5023
1610-2940
CONICET Digital
CONICET
url http://hdl.handle.net/11336/83910
identifier_str_mv Bentz, Erika Natalia; Pomilio, Alicia Beatriz; Lobayan, Rosana Maria; Structure and electronic properties of (+)-catechin: Aqueous solvent effects; Springer; Journal of Molecular Modeling; 20; 2; 2-2014; 1-13
0948-5023
1610-2940
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-014-2105-z
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00894-014-2105-z#citeas
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
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
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score 13.070432

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