Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)

Detalhes bibliográficos
Autor(a) principal: Grecco, Simone dos S. [UNIFESP]
Data de Publicação: 2014
Outros Autores: Dorigueto, Antonio C., Landre, Iara M., Soares, Marisi G., Martho, Kevin [UNIFESP], Lima, Ricardo [UNIFESP], Pascon, Renata Castiglioni [UNIFESP], Vallim, Marcelo Afonso [UNIFESP], Capello, Tabata M. [UNIFESP], Romoff, Paulete, Sartorelli, Patricia [UNIFESP], Lago, Joao Henrique Ghilardi [UNIFESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://dx.doi.org/10.3390/molecules19067528
http://repositorio.unifesp.br/handle/11600/37812
Resumo: Bioactivity-guided fractionation of an antimicrobial active extract from twigs of Baccharis retusa C. DC. (Asteraceae) yielded the flavanone 5,4'-dihydroxy-7-methoxy-flavanone (sakuranetin) as responsible for the detected activity. the structure of the bioactive compound was established on the basis of spectroscopic data analysis, including NMR and MS. Additionally, the structure of a new crystal form of sakuranetin was confirmed by X-ray diffratometry. the minimum inhibitory concentrations (MIC) of isolated compound were determined against pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background) and ranged from 0.32 to 0.63 mu g/mu L. Our results showed that sakuranetin, which structure was fully characterized, could be used as a tool for the design of novel and more efficacious antifungal agents.
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spelling Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)Baccharis retusasakuranetinX-ray diffratometryantimicrobial activityBioactivity-guided fractionation of an antimicrobial active extract from twigs of Baccharis retusa C. DC. (Asteraceae) yielded the flavanone 5,4'-dihydroxy-7-methoxy-flavanone (sakuranetin) as responsible for the detected activity. the structure of the bioactive compound was established on the basis of spectroscopic data analysis, including NMR and MS. Additionally, the structure of a new crystal form of sakuranetin was confirmed by X-ray diffratometry. the minimum inhibitory concentrations (MIC) of isolated compound were determined against pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background) and ranged from 0.32 to 0.63 mu g/mu L. Our results showed that sakuranetin, which structure was fully characterized, could be used as a tool for the design of novel and more efficacious antifungal agents.Universidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilUniv Fed ABC, Ctr Ciencias Nat & Humanas, BR-09090400 Santo Andre, SP, BrazilUniv Fed Alfenas, Inst Quim, BR-37130000 Alfenas, MG, BrazilUniv Presbiteriana Mackenzie, Escola Engn, BR-01302090 São Paulo, BrazilUniversidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilWeb of ScienceFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Fundacao de Amparo Pesquisa do Estado de Minas GeraisConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)FAPESP: FAPESP-2006/57626-5FAPESP: 2011/51739-0FAPESP: 2011/51298-4Fundacao de Amparo Pesquisa do Estado de Minas Gerais: FAPEMIG-APQ-02600-12Fundacao de Amparo Pesquisa do Estado de Minas Gerais: PPM-00524-12Mdpi AgUniversidade Federal de São Paulo (UNIFESP)Universidade Federal do ABC (UFABC)Univ Fed AlfenasUniv Presbiteriana MackenzieGrecco, Simone dos S. [UNIFESP]Dorigueto, Antonio C.Landre, Iara M.Soares, Marisi G.Martho, Kevin [UNIFESP]Lima, Ricardo [UNIFESP]Pascon, Renata Castiglioni [UNIFESP]Vallim, Marcelo Afonso [UNIFESP]Capello, Tabata M. [UNIFESP]Romoff, PauleteSartorelli, Patricia [UNIFESP]Lago, Joao Henrique Ghilardi [UNIFESP]2016-01-24T14:37:21Z2016-01-24T14:37:21Z2014-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion7528-7542application/pdfhttp://dx.doi.org/10.3390/molecules19067528Molecules. Basel: Mdpi Ag, v. 19, n. 6, p. 7528-7542, 2014.10.3390/molecules19067528WOS000338586700038.pdf1420-3049http://repositorio.unifesp.br/handle/11600/37812WOS:000338586700038engMoleculesinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-07-31T23:33:12Zoai:repositorio.unifesp.br/:11600/37812Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-07-31T23:33:12Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.none.fl_str_mv Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
title Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
spellingShingle Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
Grecco, Simone dos S. [UNIFESP]
Baccharis retusa
sakuranetin
X-ray diffratometry
antimicrobial activity
title_short Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
title_full Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
title_fullStr Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
title_full_unstemmed Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
title_sort Structural Crystalline Characterization of Sakuranetin - An Antimicrobial Flavanone from Twigs of Baccharis retusa (Asteraceae)
author Grecco, Simone dos S. [UNIFESP]
author_facet Grecco, Simone dos S. [UNIFESP]
Dorigueto, Antonio C.
Landre, Iara M.
Soares, Marisi G.
Martho, Kevin [UNIFESP]
Lima, Ricardo [UNIFESP]
Pascon, Renata Castiglioni [UNIFESP]
Vallim, Marcelo Afonso [UNIFESP]
Capello, Tabata M. [UNIFESP]
Romoff, Paulete
Sartorelli, Patricia [UNIFESP]
Lago, Joao Henrique Ghilardi [UNIFESP]
author_role author
author2 Dorigueto, Antonio C.
Landre, Iara M.
Soares, Marisi G.
Martho, Kevin [UNIFESP]
Lima, Ricardo [UNIFESP]
Pascon, Renata Castiglioni [UNIFESP]
Vallim, Marcelo Afonso [UNIFESP]
Capello, Tabata M. [UNIFESP]
Romoff, Paulete
Sartorelli, Patricia [UNIFESP]
Lago, Joao Henrique Ghilardi [UNIFESP]
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Federal de São Paulo (UNIFESP)
Universidade Federal do ABC (UFABC)
Univ Fed Alfenas
Univ Presbiteriana Mackenzie
dc.contributor.author.fl_str_mv Grecco, Simone dos S. [UNIFESP]
Dorigueto, Antonio C.
Landre, Iara M.
Soares, Marisi G.
Martho, Kevin [UNIFESP]
Lima, Ricardo [UNIFESP]
Pascon, Renata Castiglioni [UNIFESP]
Vallim, Marcelo Afonso [UNIFESP]
Capello, Tabata M. [UNIFESP]
Romoff, Paulete
Sartorelli, Patricia [UNIFESP]
Lago, Joao Henrique Ghilardi [UNIFESP]
dc.subject.por.fl_str_mv Baccharis retusa
sakuranetin
X-ray diffratometry
antimicrobial activity
topic Baccharis retusa
sakuranetin
X-ray diffratometry
antimicrobial activity
description Bioactivity-guided fractionation of an antimicrobial active extract from twigs of Baccharis retusa C. DC. (Asteraceae) yielded the flavanone 5,4'-dihydroxy-7-methoxy-flavanone (sakuranetin) as responsible for the detected activity. the structure of the bioactive compound was established on the basis of spectroscopic data analysis, including NMR and MS. Additionally, the structure of a new crystal form of sakuranetin was confirmed by X-ray diffratometry. the minimum inhibitory concentrations (MIC) of isolated compound were determined against pathogenic yeast belonging to the genus Candida (six species), Cryptococcus (two species/four serotypes) and S. cerevisiae BY 4742 (S288c background) and ranged from 0.32 to 0.63 mu g/mu L. Our results showed that sakuranetin, which structure was fully characterized, could be used as a tool for the design of novel and more efficacious antifungal agents.
publishDate 2014
dc.date.none.fl_str_mv 2014-06-01
2016-01-24T14:37:21Z
2016-01-24T14:37:21Z
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.3390/molecules19067528
Molecules. Basel: Mdpi Ag, v. 19, n. 6, p. 7528-7542, 2014.
10.3390/molecules19067528
WOS000338586700038.pdf
1420-3049
http://repositorio.unifesp.br/handle/11600/37812
WOS:000338586700038
url http://dx.doi.org/10.3390/molecules19067528
http://repositorio.unifesp.br/handle/11600/37812
identifier_str_mv Molecules. Basel: Mdpi Ag, v. 19, n. 6, p. 7528-7542, 2014.
10.3390/molecules19067528
WOS000338586700038.pdf
1420-3049
WOS:000338586700038
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 7528-7542
application/pdf
dc.publisher.none.fl_str_mv Mdpi Ag
publisher.none.fl_str_mv Mdpi Ag
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv biblioteca.csp@unifesp.br
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