Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics

Autores
Salum, Maria Laura; Arroyo Mañez, Pau; Luque, F. Javier; Erra Balsells, Rosa
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Cinnamic acids are present in all kinds of plant tissues and hence in herbs and derived medicines, cosmetics and foods. The interest in their role in plants and their therapeutic applications has grown exponentially. Because of their molecular structure they can exist in E- and Z-forms, which are both found in plants. However, since only the E-forms are commercially available, very few in vitro and in vivo studies of the Z-form have been reported. In this work the physico-chemical properties of Z-cinnamic acids in solution have been examined by means of UV-absorption spectroscopy and high-level quantum mechanical computations. For each isomer similar absorption spectra were obtained in methanol and acetonitrile. However, distinct trends were found for Z- and E forms of cinnamic acids in water, where a higher hypsochromic shift of the Z-isomer relative to the E-form was observed. In general the wavelength of maximal absorption of the Z-form is dramatically blue shifted (−30 to −40 nm) to λ < 280 nm, while a slightly blue shift of the absorption maxima for the corresponding E-form (+3 to −4 nm) was observed. This difference is associated with the non-planar, largely distorted, Z-structure and to the almost complete flat structure of the E-form. The results provide a basis for the study of functional and biotechnological roles of cinnamic acids and for the analysis of samples containing mixture of both geometric isomers.
Fil: Salum, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Arroyo Mañez, Pau. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Luque, F. Javier. Universidad de Barcelona; España
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
Maldi
Ms
Maldi-Matrix
Cinnamic Acids
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:11336/29368
Acceder
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spelling Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamicsSalum, Maria LauraArroyo Mañez, PauLuque, F. JavierErra Balsells, RosaMaldiMsMaldi-MatrixCinnamic Acidshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Cinnamic acids are present in all kinds of plant tissues and hence in herbs and derived medicines, cosmetics and foods. The interest in their role in plants and their therapeutic applications has grown exponentially. Because of their molecular structure they can exist in E- and Z-forms, which are both found in plants. However, since only the E-forms are commercially available, very few in vitro and in vivo studies of the Z-form have been reported. In this work the physico-chemical properties of Z-cinnamic acids in solution have been examined by means of UV-absorption spectroscopy and high-level quantum mechanical computations. For each isomer similar absorption spectra were obtained in methanol and acetonitrile. However, distinct trends were found for Z- and E forms of cinnamic acids in water, where a higher hypsochromic shift of the Z-isomer relative to the E-form was observed. In general the wavelength of maximal absorption of the Z-form is dramatically blue shifted (−30 to −40 nm) to λ < 280 nm, while a slightly blue shift of the absorption maxima for the corresponding E-form (+3 to −4 nm) was observed. This difference is associated with the non-planar, largely distorted, Z-structure and to the almost complete flat structure of the E-form. The results provide a basis for the study of functional and biotechnological roles of cinnamic acids and for the analysis of samples containing mixture of both geometric isomers.Fil: Salum, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Arroyo Mañez, Pau. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Luque, F. Javier. Universidad de Barcelona; EspañaFil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaElsevier Science2015-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/29368Salum, Maria Laura; Arroyo Mañez, Pau; Luque, F. Javier ; Erra Balsells, Rosa; Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics; Elsevier Science; Journal Of Photochemistry And Photobiology B: Biology; 148; 5; 4-2015; 128-1351011-1344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1011134415001165info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2015.03.032info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:07:26Zoai:ri.conicet.gov.ar:11336/29368instacron: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:34982025-09-10 13:07:26.651CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
title Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
spellingShingle Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
Salum, Maria Laura
Maldi
Ms
Maldi-Matrix
Cinnamic Acids
title_short Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
title_full Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
title_fullStr Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
title_full_unstemmed Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
title_sort Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics
dc.creator.none.fl_str_mv Salum, Maria Laura
Arroyo Mañez, Pau
Luque, F. Javier
Erra Balsells, Rosa
author Salum, Maria Laura
author_facet Salum, Maria Laura
Arroyo Mañez, Pau
Luque, F. Javier
Erra Balsells, Rosa
author_role author
author2 Arroyo Mañez, Pau
Luque, F. Javier
Erra Balsells, Rosa
author2_role author
author
author
dc.subject.none.fl_str_mv Maldi
Ms
Maldi-Matrix
Cinnamic Acids
topic Maldi
Ms
Maldi-Matrix
Cinnamic Acids
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Cinnamic acids are present in all kinds of plant tissues and hence in herbs and derived medicines, cosmetics and foods. The interest in their role in plants and their therapeutic applications has grown exponentially. Because of their molecular structure they can exist in E- and Z-forms, which are both found in plants. However, since only the E-forms are commercially available, very few in vitro and in vivo studies of the Z-form have been reported. In this work the physico-chemical properties of Z-cinnamic acids in solution have been examined by means of UV-absorption spectroscopy and high-level quantum mechanical computations. For each isomer similar absorption spectra were obtained in methanol and acetonitrile. However, distinct trends were found for Z- and E forms of cinnamic acids in water, where a higher hypsochromic shift of the Z-isomer relative to the E-form was observed. In general the wavelength of maximal absorption of the Z-form is dramatically blue shifted (−30 to −40 nm) to λ < 280 nm, while a slightly blue shift of the absorption maxima for the corresponding E-form (+3 to −4 nm) was observed. This difference is associated with the non-planar, largely distorted, Z-structure and to the almost complete flat structure of the E-form. The results provide a basis for the study of functional and biotechnological roles of cinnamic acids and for the analysis of samples containing mixture of both geometric isomers.
Fil: Salum, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Arroyo Mañez, Pau. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Luque, F. Javier. Universidad de Barcelona; España
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description Cinnamic acids are present in all kinds of plant tissues and hence in herbs and derived medicines, cosmetics and foods. The interest in their role in plants and their therapeutic applications has grown exponentially. Because of their molecular structure they can exist in E- and Z-forms, which are both found in plants. However, since only the E-forms are commercially available, very few in vitro and in vivo studies of the Z-form have been reported. In this work the physico-chemical properties of Z-cinnamic acids in solution have been examined by means of UV-absorption spectroscopy and high-level quantum mechanical computations. For each isomer similar absorption spectra were obtained in methanol and acetonitrile. However, distinct trends were found for Z- and E forms of cinnamic acids in water, where a higher hypsochromic shift of the Z-isomer relative to the E-form was observed. In general the wavelength of maximal absorption of the Z-form is dramatically blue shifted (−30 to −40 nm) to λ < 280 nm, while a slightly blue shift of the absorption maxima for the corresponding E-form (+3 to −4 nm) was observed. This difference is associated with the non-planar, largely distorted, Z-structure and to the almost complete flat structure of the E-form. The results provide a basis for the study of functional and biotechnological roles of cinnamic acids and for the analysis of samples containing mixture of both geometric isomers.
publishDate 2015
dc.date.none.fl_str_mv 2015-04
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/11336/29368
Salum, Maria Laura; Arroyo Mañez, Pau; Luque, F. Javier ; Erra Balsells, Rosa; Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics; Elsevier Science; Journal Of Photochemistry And Photobiology B: Biology; 148; 5; 4-2015; 128-135
1011-1344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/29368
identifier_str_mv Salum, Maria Laura; Arroyo Mañez, Pau; Luque, F. Javier ; Erra Balsells, Rosa; Combined experimental and computational investigation of the absorption spectra of E- and Z-cinnamic acids in solution: the peculiarity of Z-cinnamics; Elsevier Science; Journal Of Photochemistry And Photobiology B: Biology; 148; 5; 4-2015; 128-135
1011-1344
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/S1011134415001165
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2015.03.032
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
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
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