Synthesis and antifungal activity of halogenated aromatic bis-γ-lactones analogous to avenaciolide
Autor(a) principal: | |
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Data de Publicação: | 2011 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | LOCUS Repositório Institucional da UFV |
Texto Completo: | http://dx.doi.org/10.1590/S0100-40422012000500016 http://www.locus.ufv.br/handle/123456789/18057 |
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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Castelo-Branco, Pedro A.Rubinger, Mayura M. M.Alves, Leandro de C.Liberto, Natalia A.Nepel, Thayane C. M.Catrinck, MarianaGuilardi, SilvanaSilvério, Hudson A.Zambolim, LaércioPiló-Veloso, DorilaF. Neto, Wilson P.2018-03-05T13:41:21Z2018-03-05T13:41:21Z2011-11-0801004042http://dx.doi.org/10.1590/S0100-40422012000500016http://www.locus.ufv.br/handle/123456789/18057Here 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.engQuímica Novav. 35, n. 5, p. 948-955, 2012Avenaciolide analoguesAbsolute structural determinationAntifungal activitySynthesis and antifungal activity of halogenated aromatic bis-γ-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:UFVORIGINALartigo.pdfartigo.pdfTexto completoapplication/pdf571507https://locus.ufv.br//bitstream/123456789/18057/1/artigo.pdf809f3dff64e3d653752c19bf5ea478e4MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/18057/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILartigo.pdf.jpgartigo.pdf.jpgIM Thumbnailimage/jpeg5910https://locus.ufv.br//bitstream/123456789/18057/3/artigo.pdf.jpg61970745d52d82c013edc112b21a757dMD53123456789/180572018-03-05 23:00:46.538oai:locus.ufv.br:123456789/18057Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452018-03-06T02:00:46LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false |
dc.title.en.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. Zambolim, Laércio Piló-Veloso, Dorila F. Neto, Wilson P. |
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. Zambolim, Laércio Piló-Veloso, Dorila F. Neto, Wilson P. |
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. Zambolim, Laércio Piló-Veloso, Dorila F. Neto, Wilson P. |
dc.subject.pt-BR.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 |
2011 |
dc.date.issued.fl_str_mv |
2011-11-08 |
dc.date.accessioned.fl_str_mv |
2018-03-05T13:41:21Z |
dc.date.available.fl_str_mv |
2018-03-05T13:41:21Z |
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/10.1590/S0100-40422012000500016 http://www.locus.ufv.br/handle/123456789/18057 |
dc.identifier.issn.none.fl_str_mv |
01004042 |
identifier_str_mv |
01004042 |
url |
http://dx.doi.org/10.1590/S0100-40422012000500016 http://www.locus.ufv.br/handle/123456789/18057 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartofseries.pt-BR.fl_str_mv |
v. 35, n. 5, p. 948-955, 2012 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Química Nova |
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Química Nova |
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LOCUS Repositório Institucional da UFV |
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