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

Detalhes bibliográficos
Autor(a) principal: Castelo-Branco, Pedro A.
Data de Publicação: 2007
Outros Autores: Rubinger, Mayura M. M., Alves, Leandro de C., Barros, Pauline M. de, Pereira, Sinval G., Melo, Vanessa J. de, Pilo-Veloso, Dorila, Zambolim, Laércio
Tipo de documento: Artigo
Idioma: eng
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: http://dx.doi.org/10.1002/cbdv.200790223
http://www.locus.ufv.br/handle/123456789/14862
Resumo: Avenaciolide is a bis-γ-lactone isolated from Aspergillus avenaceus and possesses antifungal activity. Here, we describe the total syntheses and characterization by elemental analyses, and IR and NMR spectroscopy of three new bis-γ-lactones analogous to avenaciolide, where the octyl group of the natural product was replaced by aromatic groups. The effects of the avenaciolide, the novel compounds, and their synthetic precursors on the mycelia development and conidia germination of Colletotrichum gloeosporioides were evaluated in vitro. The new compounds were as active as avenaciolide in the tested conditions, while the synthetic precursors were inactive. The preparation and characterization of 15 new synthetic intermediates are also described.
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spelling Castelo-Branco, Pedro A.Rubinger, Mayura M. M.Alves, Leandro de C.Barros, Pauline M. dePereira, Sinval G.Melo, Vanessa J. dePilo-Veloso, DorilaZambolim, Laércio2017-12-12T17:17:34Z2017-12-12T17:17:34Z2007-02-131612-1880http://dx.doi.org/10.1002/cbdv.200790223http://www.locus.ufv.br/handle/123456789/14862Avenaciolide is a bis-γ-lactone isolated from Aspergillus avenaceus and possesses antifungal activity. Here, we describe the total syntheses and characterization by elemental analyses, and IR and NMR spectroscopy of three new bis-γ-lactones analogous to avenaciolide, where the octyl group of the natural product was replaced by aromatic groups. The effects of the avenaciolide, the novel compounds, and their synthetic precursors on the mycelia development and conidia germination of Colletotrichum gloeosporioides were evaluated in vitro. The new compounds were as active as avenaciolide in the tested conditions, while the synthetic precursors were inactive. The preparation and characterization of 15 new synthetic intermediates are also described.engChemistry & Biodiversity4(12), p. 2745-54, Dec. 2007Synthesis and antifungal activityBis-gamma-lactonesSynthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolideinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALCastelo-Branco_et_al-2007-Chemistry_&_Biodiversity.pdfCastelo-Branco_et_al-2007-Chemistry_&_Biodiversity.pdftexto completoapplication/pdf210821https://locus.ufv.br//bitstream/123456789/14862/1/Castelo-Branco_et_al-2007-Chemistry_%26_Biodiversity.pdf282ed5644226ff9c8cb3e272bd050b2bMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/14862/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILCastelo-Branco_et_al-2007-Chemistry_&_Biodiversity.pdf.jpgCastelo-Branco_et_al-2007-Chemistry_&_Biodiversity.pdf.jpgIM Thumbnailimage/jpeg4229https://locus.ufv.br//bitstream/123456789/14862/3/Castelo-Branco_et_al-2007-Chemistry_%26_Biodiversity.pdf.jpgbd19ca19768df260c2418ee60e91741cMD53123456789/148622017-12-12 22:00:54.707oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452017-12-13T01:00:54LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.en.fl_str_mv Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
title Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
spellingShingle Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
Castelo-Branco, Pedro A.
Synthesis and antifungal activity
Bis-gamma-lactones
title_short Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
title_full Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
title_fullStr Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
title_full_unstemmed Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
title_sort Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
author Castelo-Branco, Pedro A.
author_facet Castelo-Branco, Pedro A.
Rubinger, Mayura M. M.
Alves, Leandro de C.
Barros, Pauline M. de
Pereira, Sinval G.
Melo, Vanessa J. de
Pilo-Veloso, Dorila
Zambolim, Laércio
author_role author
author2 Rubinger, Mayura M. M.
Alves, Leandro de C.
Barros, Pauline M. de
Pereira, Sinval G.
Melo, Vanessa J. de
Pilo-Veloso, Dorila
Zambolim, Laércio
author2_role 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.
Barros, Pauline M. de
Pereira, Sinval G.
Melo, Vanessa J. de
Pilo-Veloso, Dorila
Zambolim, Laércio
dc.subject.pt-BR.fl_str_mv Synthesis and antifungal activity
Bis-gamma-lactones
topic Synthesis and antifungal activity
Bis-gamma-lactones
description Avenaciolide is a bis-γ-lactone isolated from Aspergillus avenaceus and possesses antifungal activity. Here, we describe the total syntheses and characterization by elemental analyses, and IR and NMR spectroscopy of three new bis-γ-lactones analogous to avenaciolide, where the octyl group of the natural product was replaced by aromatic groups. The effects of the avenaciolide, the novel compounds, and their synthetic precursors on the mycelia development and conidia germination of Colletotrichum gloeosporioides were evaluated in vitro. The new compounds were as active as avenaciolide in the tested conditions, while the synthetic precursors were inactive. The preparation and characterization of 15 new synthetic intermediates are also described.
publishDate 2007
dc.date.issued.fl_str_mv 2007-02-13
dc.date.accessioned.fl_str_mv 2017-12-12T17:17:34Z
dc.date.available.fl_str_mv 2017-12-12T17:17:34Z
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/10.1002/cbdv.200790223
http://www.locus.ufv.br/handle/123456789/14862
dc.identifier.issn.none.fl_str_mv 1612-1880
identifier_str_mv 1612-1880
url http://dx.doi.org/10.1002/cbdv.200790223
http://www.locus.ufv.br/handle/123456789/14862
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartofseries.pt-BR.fl_str_mv 4(12), p. 2745-54, Dec. 2007
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Chemistry & Biodiversity
publisher.none.fl_str_mv Chemistry & Biodiversity
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