Synthesis and antifungal activity of aromatic bis-g-lactones analogous to avenaciolide
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Outros Autores: | , , , , , , |
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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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 |
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openAccess |
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Chemistry & Biodiversity |
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Chemistry & Biodiversity |
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