Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis

Detalhes bibliográficos
Autor(a) principal: Camuri, Isamara Julia
Data de Publicação: 2018
Outros Autores: Costa, Adriano Batista, Ito, Amando Siuiti, Pazin, Wallance Moreira [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.saa.2018.02.059
http://hdl.handle.net/11449/170738
Resumo: The bioactivity of propolis against several pathogens is well established, leading to the extensive consumption of that bee product to prevent diseases. Brazilian green propolis, collected by the species Apis mellifera, is one of the most consumed in the world. The chemical composition of green propolis is complex and it has been shown that it displays antioxidant, antimicrobial, anti-inflammatory and antitumor activities, especially due to the high content of Artepillin C. The molecule is a derivative of cinnamic acid with two prenylated groups, responsible for the improvement of the affinity of the compound for lipophilic environment. A carboxylic group (COOH) is also present in the molecule, making it a pH-sensitive compound and the pH-dependent structure of Artepillin C, may modulate its biological activity related to interactions with the cellular membrane of organisms and tissues. Molecular properties of Artepillin C on aqueous solution were examined by optical absorption, steady state and time-resolved fluorescence spectroscopies. Acid-base titration based on the spectral position of the near UV absorption band, resulted in the pKa value of 4.65 for the carboxylic group in Artepillin C. In acidic pH, below the pKa value, an absorption band raised around 350 nm at Artepillin C concentration above 50 μM, due to aggregation of the molecule. In neutral pH, with excitation at 310 nm, Artepillin C presents dual emission at 400 and 450 nm. In pH close to the pKa, the optical spectra show contribution from both protonated and deprotonated species. A three-exponential function was necessary to fit the intensity decays at the different pHs, dominated by a very short lifetime component, around 0.060 ns. The fast decay resulted in emission before fluorescence depolarization, and in values of fluorescence anisotropy higher than could be expected for monomeric forms of the compound. The results give fundamental knowledge about the protonation-deprotonation state of the molecule, that may be relevant in processes mediated by biological membranes.
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spelling Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolisAggregation propertiesArtepillin CGreen propolisOptical spectroscopypH effectsThe bioactivity of propolis against several pathogens is well established, leading to the extensive consumption of that bee product to prevent diseases. Brazilian green propolis, collected by the species Apis mellifera, is one of the most consumed in the world. The chemical composition of green propolis is complex and it has been shown that it displays antioxidant, antimicrobial, anti-inflammatory and antitumor activities, especially due to the high content of Artepillin C. The molecule is a derivative of cinnamic acid with two prenylated groups, responsible for the improvement of the affinity of the compound for lipophilic environment. A carboxylic group (COOH) is also present in the molecule, making it a pH-sensitive compound and the pH-dependent structure of Artepillin C, may modulate its biological activity related to interactions with the cellular membrane of organisms and tissues. Molecular properties of Artepillin C on aqueous solution were examined by optical absorption, steady state and time-resolved fluorescence spectroscopies. Acid-base titration based on the spectral position of the near UV absorption band, resulted in the pKa value of 4.65 for the carboxylic group in Artepillin C. In acidic pH, below the pKa value, an absorption band raised around 350 nm at Artepillin C concentration above 50 μM, due to aggregation of the molecule. In neutral pH, with excitation at 310 nm, Artepillin C presents dual emission at 400 and 450 nm. In pH close to the pKa, the optical spectra show contribution from both protonated and deprotonated species. A three-exponential function was necessary to fit the intensity decays at the different pHs, dominated by a very short lifetime component, around 0.060 ns. The fast decay resulted in emission before fluorescence depolarization, and in values of fluorescence anisotropy higher than could be expected for monomeric forms of the compound. The results give fundamental knowledge about the protonation-deprotonation state of the molecule, that may be relevant in processes mediated by biological membranes.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Department of Physics Faculty of Philosophy Sciences and Letters of Ribeirão Preto University of São Paulo (USP)Department of Physics School of Sciences and Technology São Paulo State University (UNESP)Department of Physics School of Sciences and Technology São Paulo State University (UNESP)FAPESP: 2016/09633-4CNPq: 305771/2016-7Universidade de São Paulo (USP)Universidade Estadual Paulista (Unesp)Camuri, Isamara JuliaCosta, Adriano BatistaIto, Amando SiuitiPazin, Wallance Moreira [UNESP]2018-12-11T16:52:14Z2018-12-11T16:52:14Z2018-06-05info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article71-77application/pdfhttp://dx.doi.org/10.1016/j.saa.2018.02.059Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, v. 198, p. 71-77.1386-1425http://hdl.handle.net/11449/17073810.1016/j.saa.2018.02.0592-s2.0-850429262182-s2.0-85042926218.pdfScopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy0,648info:eu-repo/semantics/openAccess2024-01-02T06:15:48Zoai:repositorio.unesp.br:11449/170738Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:53:51.374083Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
title Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
spellingShingle Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
Camuri, Isamara Julia
Aggregation properties
Artepillin C
Green propolis
Optical spectroscopy
pH effects
title_short Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
title_full Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
title_fullStr Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
title_full_unstemmed Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
title_sort Optical absorption and fluorescence spectroscopy studies of Artepillin C, the major component of green propolis
author Camuri, Isamara Julia
author_facet Camuri, Isamara Julia
Costa, Adriano Batista
Ito, Amando Siuiti
Pazin, Wallance Moreira [UNESP]
author_role author
author2 Costa, Adriano Batista
Ito, Amando Siuiti
Pazin, Wallance Moreira [UNESP]
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade de São Paulo (USP)
Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Camuri, Isamara Julia
Costa, Adriano Batista
Ito, Amando Siuiti
Pazin, Wallance Moreira [UNESP]
dc.subject.por.fl_str_mv Aggregation properties
Artepillin C
Green propolis
Optical spectroscopy
pH effects
topic Aggregation properties
Artepillin C
Green propolis
Optical spectroscopy
pH effects
description The bioactivity of propolis against several pathogens is well established, leading to the extensive consumption of that bee product to prevent diseases. Brazilian green propolis, collected by the species Apis mellifera, is one of the most consumed in the world. The chemical composition of green propolis is complex and it has been shown that it displays antioxidant, antimicrobial, anti-inflammatory and antitumor activities, especially due to the high content of Artepillin C. The molecule is a derivative of cinnamic acid with two prenylated groups, responsible for the improvement of the affinity of the compound for lipophilic environment. A carboxylic group (COOH) is also present in the molecule, making it a pH-sensitive compound and the pH-dependent structure of Artepillin C, may modulate its biological activity related to interactions with the cellular membrane of organisms and tissues. Molecular properties of Artepillin C on aqueous solution were examined by optical absorption, steady state and time-resolved fluorescence spectroscopies. Acid-base titration based on the spectral position of the near UV absorption band, resulted in the pKa value of 4.65 for the carboxylic group in Artepillin C. In acidic pH, below the pKa value, an absorption band raised around 350 nm at Artepillin C concentration above 50 μM, due to aggregation of the molecule. In neutral pH, with excitation at 310 nm, Artepillin C presents dual emission at 400 and 450 nm. In pH close to the pKa, the optical spectra show contribution from both protonated and deprotonated species. A three-exponential function was necessary to fit the intensity decays at the different pHs, dominated by a very short lifetime component, around 0.060 ns. The fast decay resulted in emission before fluorescence depolarization, and in values of fluorescence anisotropy higher than could be expected for monomeric forms of the compound. The results give fundamental knowledge about the protonation-deprotonation state of the molecule, that may be relevant in processes mediated by biological membranes.
publishDate 2018
dc.date.none.fl_str_mv 2018-12-11T16:52:14Z
2018-12-11T16:52:14Z
2018-06-05
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://dx.doi.org/10.1016/j.saa.2018.02.059
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, v. 198, p. 71-77.
1386-1425
http://hdl.handle.net/11449/170738
10.1016/j.saa.2018.02.059
2-s2.0-85042926218
2-s2.0-85042926218.pdf
url http://dx.doi.org/10.1016/j.saa.2018.02.059
http://hdl.handle.net/11449/170738
identifier_str_mv Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, v. 198, p. 71-77.
1386-1425
10.1016/j.saa.2018.02.059
2-s2.0-85042926218
2-s2.0-85042926218.pdf
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
0,648
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 71-77
application/pdf
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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