Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide

Detalhes bibliográficos
Autor(a) principal: Castelo-Branco,Pedro A.
Data de Publicação: 2012
Outros Autores: Rubinger,Mayura M. M., Alves,Leandro de C., Liberto,Natalia A., Nepel,Thayane C. M., Catrinck,Mariana, Guilardi,Silvana, Silvério,Hudson A., F. Neto,Wilson P., Zambolim,Laércio, Piló-Veloso,Dorila
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000500016
Resumo: Here we describe the total syntheses and characterization by elemental analyses, infrared and NMR spectroscopy of three new compounds analogous to avenaciolide, a bis-γ-lactone isolated from Aspergillus avenaceus that possesses antifungal activity, where the octyl group of the natural product was replaced by aromatic groups containing chlorine and fluorine atoms. The effects of the avenaciolide, the novel compounds and their synthetic precursors on mycelia development and conidia germination of Colletotrichum gloeosporioides and Fusarium solani were evaluated in vitro. The title compounds were almost as active as avenaciolide. The absolute structures of the chlorinated analogs were determined by X-ray diffraction analysis.
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spelling Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolideavenaciolide analoguesabsolute structural determinationantifungal activityHere we describe the total syntheses and characterization by elemental analyses, infrared and NMR spectroscopy of three new compounds analogous to avenaciolide, a bis-γ-lactone isolated from Aspergillus avenaceus that possesses antifungal activity, where the octyl group of the natural product was replaced by aromatic groups containing chlorine and fluorine atoms. The effects of the avenaciolide, the novel compounds and their synthetic precursors on mycelia development and conidia germination of Colletotrichum gloeosporioides and Fusarium solani were evaluated in vitro. The title compounds were almost as active as avenaciolide. The absolute structures of the chlorinated analogs were determined by X-ray diffraction analysis.Sociedade Brasileira de Química2012-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000500016Química Nova v.35 n.5 2012reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422012000500016info:eu-repo/semantics/openAccessCastelo-Branco,Pedro A.Rubinger,Mayura M. M.Alves,Leandro de C.Liberto,Natalia A.Nepel,Thayane C. M.Catrinck,MarianaGuilardi,SilvanaSilvério,Hudson A.F. Neto,Wilson P.Zambolim,LaércioPiló-Veloso,Dorilaeng2012-07-02T00:00:00Zoai:scielo:S0100-40422012000500016Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2012-07-02T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
title Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
spellingShingle Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
Castelo-Branco,Pedro A.
avenaciolide analogues
absolute structural determination
antifungal activity
title_short Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
title_full Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
title_fullStr Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
title_full_unstemmed Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
title_sort Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
author Castelo-Branco,Pedro A.
author_facet Castelo-Branco,Pedro A.
Rubinger,Mayura M. M.
Alves,Leandro de C.
Liberto,Natalia A.
Nepel,Thayane C. M.
Catrinck,Mariana
Guilardi,Silvana
Silvério,Hudson A.
F. Neto,Wilson P.
Zambolim,Laércio
Piló-Veloso,Dorila
author_role author
author2 Rubinger,Mayura M. M.
Alves,Leandro de C.
Liberto,Natalia A.
Nepel,Thayane C. M.
Catrinck,Mariana
Guilardi,Silvana
Silvério,Hudson A.
F. Neto,Wilson P.
Zambolim,Laércio
Piló-Veloso,Dorila
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Castelo-Branco,Pedro A.
Rubinger,Mayura M. M.
Alves,Leandro de C.
Liberto,Natalia A.
Nepel,Thayane C. M.
Catrinck,Mariana
Guilardi,Silvana
Silvério,Hudson A.
F. Neto,Wilson P.
Zambolim,Laércio
Piló-Veloso,Dorila
dc.subject.por.fl_str_mv avenaciolide analogues
absolute structural determination
antifungal activity
topic avenaciolide analogues
absolute structural determination
antifungal activity
description Here we describe the total syntheses and characterization by elemental analyses, infrared and NMR spectroscopy of three new compounds analogous to avenaciolide, a bis-γ-lactone isolated from Aspergillus avenaceus that possesses antifungal activity, where the octyl group of the natural product was replaced by aromatic groups containing chlorine and fluorine atoms. The effects of the avenaciolide, the novel compounds and their synthetic precursors on mycelia development and conidia germination of Colletotrichum gloeosporioides and Fusarium solani were evaluated in vitro. The title compounds were almost as active as avenaciolide. The absolute structures of the chlorinated analogs were determined by X-ray diffraction analysis.
publishDate 2012
dc.date.none.fl_str_mv 2012-01-01
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://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000500016
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000500016
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0100-40422012000500016
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Química Nova v.35 n.5 2012
reponame:Química Nova (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Química Nova (Online)
collection Química Nova (Online)
repository.name.fl_str_mv Química Nova (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv quimicanova@sbq.org.br
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