An inelastic neutron scattering study of dietary phenolic acids
Autor(a) principal: | |
---|---|
Data de Publicação: | 2014 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/25640 https://doi.org/10.1039/c4cp00338a |
Resumo: | The conformational preferences and hydrogen-bonding motifs of several potential chemopreventive hydroxycinnamic derivatives were determined by inelastic neutron scattering spectroscopy. The aim is to understand their recognized beneficial activity and establish reliable structure–activity relationships for these types of dietary phytochemicals. A series of phenolic acids with different hydroxyl/methoxyl ring substitution patterns were studied: trans-cinnamic, p-coumaric, m-coumaric, trans-caffeic and ferulic acids. Their INS spectra were completely assigned by theoretical calculations performed at the Density Functional Theory level, for the isolated molecule, dimeric centrosymmetric species and the solid (using plane-wave expansion approaches). Access to the low energy vibrational region of the spectra enabled the identification of particular modes associated with intermolecular hydrogen-bonding interactions, which are the determinants of the main conformational preferences and antioxidant capacity of these systems. |
id |
RCAP_47e7b7cd4a1c3e87b7a43229cffcf4ad |
---|---|
oai_identifier_str |
oai:estudogeral.uc.pt:10316/25640 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
An inelastic neutron scattering study of dietary phenolic acidsAntioxidantsHydrogen BondingHydroxybenzoatesNeutron DiffractionQuantum TheoryThe conformational preferences and hydrogen-bonding motifs of several potential chemopreventive hydroxycinnamic derivatives were determined by inelastic neutron scattering spectroscopy. The aim is to understand their recognized beneficial activity and establish reliable structure–activity relationships for these types of dietary phytochemicals. A series of phenolic acids with different hydroxyl/methoxyl ring substitution patterns were studied: trans-cinnamic, p-coumaric, m-coumaric, trans-caffeic and ferulic acids. Their INS spectra were completely assigned by theoretical calculations performed at the Density Functional Theory level, for the isolated molecule, dimeric centrosymmetric species and the solid (using plane-wave expansion approaches). Access to the low energy vibrational region of the spectra enabled the identification of particular modes associated with intermolecular hydrogen-bonding interactions, which are the determinants of the main conformational preferences and antioxidant capacity of these systems.The authors are thankful for financial support from the Portuguese Foundation for Science and Technology – PEst-OE/QUI/UI0070/ 2014. The INS work was supported by the European Commission under the 7th Framework Programme through the Key Action: Strengthening the European Research Area, Research Infrastructures. Contract no. CP-CSA_INFRA-2008-1.1.1 Number 226507- NMI3.the Owner Societies2014info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/25640http://hdl.handle.net/10316/25640https://doi.org/10.1039/c4cp00338aenghttp://pubs.rsc.org/en/Content/ArticleLanding/2014/CP/c4cp00338a#!divAbstractMarques, M. P. M.Carvalho, Luís A. E. Batista deValero, RosendoMachado, Nelson F. L.Parker, Stewart F.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-08-24T13:21:21Zoai:estudogeral.uc.pt:10316/25640Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:56:06.391484Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
An inelastic neutron scattering study of dietary phenolic acids |
title |
An inelastic neutron scattering study of dietary phenolic acids |
spellingShingle |
An inelastic neutron scattering study of dietary phenolic acids Marques, M. P. M. Antioxidants Hydrogen Bonding Hydroxybenzoates Neutron Diffraction Quantum Theory |
title_short |
An inelastic neutron scattering study of dietary phenolic acids |
title_full |
An inelastic neutron scattering study of dietary phenolic acids |
title_fullStr |
An inelastic neutron scattering study of dietary phenolic acids |
title_full_unstemmed |
An inelastic neutron scattering study of dietary phenolic acids |
title_sort |
An inelastic neutron scattering study of dietary phenolic acids |
author |
Marques, M. P. M. |
author_facet |
Marques, M. P. M. Carvalho, Luís A. E. Batista de Valero, Rosendo Machado, Nelson F. L. Parker, Stewart F. |
author_role |
author |
author2 |
Carvalho, Luís A. E. Batista de Valero, Rosendo Machado, Nelson F. L. Parker, Stewart F. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Marques, M. P. M. Carvalho, Luís A. E. Batista de Valero, Rosendo Machado, Nelson F. L. Parker, Stewart F. |
dc.subject.por.fl_str_mv |
Antioxidants Hydrogen Bonding Hydroxybenzoates Neutron Diffraction Quantum Theory |
topic |
Antioxidants Hydrogen Bonding Hydroxybenzoates Neutron Diffraction Quantum Theory |
description |
The conformational preferences and hydrogen-bonding motifs of several potential chemopreventive hydroxycinnamic derivatives were determined by inelastic neutron scattering spectroscopy. The aim is to understand their recognized beneficial activity and establish reliable structure–activity relationships for these types of dietary phytochemicals. A series of phenolic acids with different hydroxyl/methoxyl ring substitution patterns were studied: trans-cinnamic, p-coumaric, m-coumaric, trans-caffeic and ferulic acids. Their INS spectra were completely assigned by theoretical calculations performed at the Density Functional Theory level, for the isolated molecule, dimeric centrosymmetric species and the solid (using plane-wave expansion approaches). Access to the low energy vibrational region of the spectra enabled the identification of particular modes associated with intermolecular hydrogen-bonding interactions, which are the determinants of the main conformational preferences and antioxidant capacity of these systems. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10316/25640 http://hdl.handle.net/10316/25640 https://doi.org/10.1039/c4cp00338a |
url |
http://hdl.handle.net/10316/25640 https://doi.org/10.1039/c4cp00338a |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
http://pubs.rsc.org/en/Content/ArticleLanding/2014/CP/c4cp00338a#!divAbstract |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
the Owner Societies |
publisher.none.fl_str_mv |
the Owner Societies |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
|
_version_ |
1799133846145335296 |