A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE
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Publication Date: | 2016 |
Other Authors: | , , , , , , , , , , , , |
Format: | Article |
Language: | eng |
Source: | Repositório Institucional da UNESP |
Download full: | http://dx.doi.org/10.5935/0100-4042.20160092 http://hdl.handle.net/11449/161938 |
Summary: | The isolation and identification of bioactive metabolites from complex extracts obtained from microbial growth media is a time consuming, costly, and labor-intensive task. A strategy to rapidly identify secondary metabolites isolated from extracts obtained from the culture media of marine-derived and endophytic fungal strains is described. Identification was achieved by HPLC-UV-MS and H-1 NMR analyses in combination with data obtained from the Dictionary of Natural Products. Among the compounds identified, (-)-naphthoquinoneimine, citreorosein, emodin, pyrenocine A and harzianopyridone displayed moderate to potent antiviral activity. (-)-Naphthoquinoneimine was isolated as the enantiomer of its previously reported dextrorotatory congener, while 6,7-dihydroxy-2,2- dimethyl-4-chromanone is herein reported for the first time as a natural product. |
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A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONEfungal metabolitesrapid identificationdereplicationantiviralThe isolation and identification of bioactive metabolites from complex extracts obtained from microbial growth media is a time consuming, costly, and labor-intensive task. A strategy to rapidly identify secondary metabolites isolated from extracts obtained from the culture media of marine-derived and endophytic fungal strains is described. Identification was achieved by HPLC-UV-MS and H-1 NMR analyses in combination with data obtained from the Dictionary of Natural Products. Among the compounds identified, (-)-naphthoquinoneimine, citreorosein, emodin, pyrenocine A and harzianopyridone displayed moderate to potent antiviral activity. (-)-Naphthoquinoneimine was isolated as the enantiomer of its previously reported dextrorotatory congener, while 6,7-dihydroxy-2,2- dimethyl-4-chromanone is herein reported for the first time as a natural product.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, BrazilUniv Michigan, Life Sci Inst, Ann Arbor, MI 48109 USAUniv Sao Francisco, BR-13045510 Campinas, SP, BrazilUniv Estadual Campinas, Lab Virol, Inst Biol, CP 6109, BR-13083970 Campinas, SP, BrazilUniv Estadual Paulista, Dept Bioquim & Microbiol, Inst Biociencias, BR-13506900 Rio Claro, SP, BrazilUniv Estadual Paulista, Dept Bioquim & Microbiol, Inst Biociencias, BR-13506900 Rio Claro, SP, BrazilFAPESP: 2010/50190-2FAPESP: 2013/50228-8FAPESP: 2011/08064-2FAPESP: 2008/00331-9FAPESP: 2013/23153-7CAPES: BEX 4498-14-3Soc Brasileira QuimicaUniversidade de São Paulo (USP)Univ MichiganUniv Sao FranciscoUniversidade Estadual de Campinas (UNICAMP)Universidade Estadual Paulista (Unesp)Ioca, Laura P.Romminger, StelamarSantos, Mario F. C.Bandeira, Karin F.Rodrigues, Fabiana T.Kossuga, Miriam H.Nicacio, Karen J.Ferreira, Everton L. F.Morais-Urano, Raquel P.Passos, Messias S.Kohn, Luciana K.Arns, Clarice W.Sette, Lara D. [UNESP]Berlinck, Roberto G. S.2018-11-26T17:06:15Z2018-11-26T17:06:15Z2016-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article720-731application/pdfhttp://dx.doi.org/10.5935/0100-4042.20160092Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 39, n. 6, p. 720-731, 2016.0100-4042http://hdl.handle.net/11449/16193810.5935/0100-4042.20160092S0100-40422016000600720WOS:000383618200011S0100-40422016000600720.pdfWeb of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengQuimica Nova0,255info:eu-repo/semantics/openAccess2023-10-05T06:06:27Zoai:repositorio.unesp.br:11449/161938Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-10-05T06:06:27Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
title |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
spellingShingle |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE Ioca, Laura P. fungal metabolites rapid identification dereplication antiviral |
title_short |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
title_full |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
title_fullStr |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
title_full_unstemmed |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
title_sort |
A STRATEGY FOR THE RAPID IDENTIFICATION OF FUNGAL METABOLITES AND THE DISCOVERY OF THE ANTIVIRAL ACTIVITY OF PYRENOCINE A AND HARZIANOPYRIDONE |
author |
Ioca, Laura P. |
author_facet |
Ioca, Laura P. Romminger, Stelamar Santos, Mario F. C. Bandeira, Karin F. Rodrigues, Fabiana T. Kossuga, Miriam H. Nicacio, Karen J. Ferreira, Everton L. F. Morais-Urano, Raquel P. Passos, Messias S. Kohn, Luciana K. Arns, Clarice W. Sette, Lara D. [UNESP] Berlinck, Roberto G. S. |
author_role |
author |
author2 |
Romminger, Stelamar Santos, Mario F. C. Bandeira, Karin F. Rodrigues, Fabiana T. Kossuga, Miriam H. Nicacio, Karen J. Ferreira, Everton L. F. Morais-Urano, Raquel P. Passos, Messias S. Kohn, Luciana K. Arns, Clarice W. Sette, Lara D. [UNESP] Berlinck, Roberto G. S. |
author2_role |
author author author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade de São Paulo (USP) Univ Michigan Univ Sao Francisco Universidade Estadual de Campinas (UNICAMP) Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
Ioca, Laura P. Romminger, Stelamar Santos, Mario F. C. Bandeira, Karin F. Rodrigues, Fabiana T. Kossuga, Miriam H. Nicacio, Karen J. Ferreira, Everton L. F. Morais-Urano, Raquel P. Passos, Messias S. Kohn, Luciana K. Arns, Clarice W. Sette, Lara D. [UNESP] Berlinck, Roberto G. S. |
dc.subject.por.fl_str_mv |
fungal metabolites rapid identification dereplication antiviral |
topic |
fungal metabolites rapid identification dereplication antiviral |
description |
The isolation and identification of bioactive metabolites from complex extracts obtained from microbial growth media is a time consuming, costly, and labor-intensive task. A strategy to rapidly identify secondary metabolites isolated from extracts obtained from the culture media of marine-derived and endophytic fungal strains is described. Identification was achieved by HPLC-UV-MS and H-1 NMR analyses in combination with data obtained from the Dictionary of Natural Products. Among the compounds identified, (-)-naphthoquinoneimine, citreorosein, emodin, pyrenocine A and harzianopyridone displayed moderate to potent antiviral activity. (-)-Naphthoquinoneimine was isolated as the enantiomer of its previously reported dextrorotatory congener, while 6,7-dihydroxy-2,2- dimethyl-4-chromanone is herein reported for the first time as a natural product. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-07-01 2018-11-26T17:06:15Z 2018-11-26T17:06:15Z |
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/10.5935/0100-4042.20160092 Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 39, n. 6, p. 720-731, 2016. 0100-4042 http://hdl.handle.net/11449/161938 10.5935/0100-4042.20160092 S0100-40422016000600720 WOS:000383618200011 S0100-40422016000600720.pdf |
url |
http://dx.doi.org/10.5935/0100-4042.20160092 http://hdl.handle.net/11449/161938 |
identifier_str_mv |
Quimica Nova. Sao Paulo: Soc Brasileira Quimica, v. 39, n. 6, p. 720-731, 2016. 0100-4042 10.5935/0100-4042.20160092 S0100-40422016000600720 WOS:000383618200011 S0100-40422016000600720.pdf |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Quimica Nova 0,255 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
720-731 application/pdf |
dc.publisher.none.fl_str_mv |
Soc Brasileira Quimica |
publisher.none.fl_str_mv |
Soc Brasileira Quimica |
dc.source.none.fl_str_mv |
Web of Science reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
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1799964444169601024 |