Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.

Detalhes bibliográficos
Autor(a) principal: PERES, E. G.
Data de Publicação: 2023
Outros Autores: SOUZA, M. P., SOUSA, T. F., SILVA, C. V. A. da, BARROS, A. L., SILVA, F. M. A. da, COSTA, E. V., MEDEIROS, L. S. de, FORIM, M. R., SOUZA, A. D. L. de, PAZ, W. H. P., SILVA, G. F. da, SOUZA, A. Q. L. de, KOOLEN, H. H. F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice)
Texto Completo: http://www.alice.cnptia.embrapa.br/alice/handle/doc/1153604
https://dx.doi.org/10.21577/0103-5053.20230027
Resumo: Penicillium meliponae, a recently described and rare species, was isolated as an endophytic fungus from the Amazonian plant Duguetia sthelechantha, and has been proven to be a pigment producer. Considering the high productivity of this species and the lack of data on its chemical composition, the present study aimed to characterize the chemical profile of P. meliponae and evaluate the influence of agitation and the use of different culture media. For this purpose, liquid chromatography coupled with mass spectrometry (LC-MS/MS) and molecular networking were used, allowing the identification of 17 azaphilone molecules with sclerotiorin-like skeletons, becoming the first chemical report of this species. In addition, the different production patterns in the tested culture media were indicative that this species is sensitive to changes in the composition of the carbon source and to the presence of agitation. Furthermore, this work contributes to the fragmentation mechanisms of the different possible structural arrangements for azaphilones of the sclerotiorin type and serves as a repository of information on the gas-phase behavior of this type of metabolite in mass spectrometry experiments and will assist future studies aimed at the discovery of azaphilones.
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spelling Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.Penicillium meliponaeAzaphilonesMolecular networkingPenicillium meliponae, a recently described and rare species, was isolated as an endophytic fungus from the Amazonian plant Duguetia sthelechantha, and has been proven to be a pigment producer. Considering the high productivity of this species and the lack of data on its chemical composition, the present study aimed to characterize the chemical profile of P. meliponae and evaluate the influence of agitation and the use of different culture media. For this purpose, liquid chromatography coupled with mass spectrometry (LC-MS/MS) and molecular networking were used, allowing the identification of 17 azaphilone molecules with sclerotiorin-like skeletons, becoming the first chemical report of this species. In addition, the different production patterns in the tested culture media were indicative that this species is sensitive to changes in the composition of the carbon source and to the presence of agitation. Furthermore, this work contributes to the fragmentation mechanisms of the different possible structural arrangements for azaphilones of the sclerotiorin type and serves as a repository of information on the gas-phase behavior of this type of metabolite in mass spectrometry experiments and will assist future studies aimed at the discovery of azaphilones.ELDRINEI G. PERES, UNIVERSIDADE DO ESTADO DO AMAZONAS; MAYANE P. SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; THIAGO F. SOUSA, UNIVERSIDADE DO ESTADO DO AMAZONAS; CARLOS V. A. DA SILVA, UNIVERSIDADE DO ESTADO DO AMAZONAS; ANDRÉ L. BARROS, UNIVERSIDADE DO ESTADO DO AMAZONAS; FELIPE M. A. DA SILVA, UNIVERSIDADE FEDERAL DO AMAZONAS; EMMANOEL V. COSTA, UNIVERSIDADE FEDERAL DO AMAZONAS; LÍVIA S. DE MEDEIROS, UNIVERSIDADE FEDERAL DE SÃO PAULO; MOACIR R. FORIM, UNIVERSIDADE FEDERAL DE SÃO CARLOS; AFONSO D. L. DE SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; WEIDER H. P. PAZ, UNIVERSIDADE DO ESTADO DO AMAZONAS; GILVAN FERREIRA DA SILVA, CPAA; ANTONIA Q. L. DE SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; HECTOR H. F. KOOLEN, UNIVERSIDADE DO ESTADO DO AMAZONAS.PERES, E. G.SOUZA, M. P.SOUSA, T. F.SILVA, C. V. A. daBARROS, A. L.SILVA, F. M. A. daCOSTA, E. V.MEDEIROS, L. S. deFORIM, M. R.SOUZA, A. D. L. dePAZ, W. H. P.SILVA, G. F. daSOUZA, A. Q. L. deKOOLEN, H. H. F.2023-08-02T10:23:49Z2023-08-02T10:23:49Z2023-05-092023info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleJournal of the Brazilian Chemical Society, v. 34, n. 8, p. 1139-1153, 2023.http://www.alice.cnptia.embrapa.br/alice/handle/doc/1153604https://dx.doi.org/10.21577/0103-5053.20230027enginfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice)instname:Empresa Brasileira de Pesquisa Agropecuária (Embrapa)instacron:EMBRAPA2023-08-02T10:23:49Zoai:www.alice.cnptia.embrapa.br:doc/1153604Repositório InstitucionalPUBhttps://www.alice.cnptia.embrapa.br/oai/requestopendoar:21542023-08-02T10:23:49falseRepositório InstitucionalPUBhttps://www.alice.cnptia.embrapa.br/oai/requestcg-riaa@embrapa.bropendoar:21542023-08-02T10:23:49Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice) - Empresa Brasileira de Pesquisa Agropecuária (Embrapa)false
dc.title.none.fl_str_mv Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
title Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
spellingShingle Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
PERES, E. G.
Penicillium meliponae
Azaphilones
Molecular networking
title_short Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
title_full Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
title_fullStr Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
title_full_unstemmed Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
title_sort Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
author PERES, E. G.
author_facet PERES, E. G.
SOUZA, M. P.
SOUSA, T. F.
SILVA, C. V. A. da
BARROS, A. L.
SILVA, F. M. A. da
COSTA, E. V.
MEDEIROS, L. S. de
FORIM, M. R.
SOUZA, A. D. L. de
PAZ, W. H. P.
SILVA, G. F. da
SOUZA, A. Q. L. de
KOOLEN, H. H. F.
author_role author
author2 SOUZA, M. P.
SOUSA, T. F.
SILVA, C. V. A. da
BARROS, A. L.
SILVA, F. M. A. da
COSTA, E. V.
MEDEIROS, L. S. de
FORIM, M. R.
SOUZA, A. D. L. de
PAZ, W. H. P.
SILVA, G. F. da
SOUZA, A. Q. L. de
KOOLEN, H. H. F.
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv ELDRINEI G. PERES, UNIVERSIDADE DO ESTADO DO AMAZONAS; MAYANE P. SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; THIAGO F. SOUSA, UNIVERSIDADE DO ESTADO DO AMAZONAS; CARLOS V. A. DA SILVA, UNIVERSIDADE DO ESTADO DO AMAZONAS; ANDRÉ L. BARROS, UNIVERSIDADE DO ESTADO DO AMAZONAS; FELIPE M. A. DA SILVA, UNIVERSIDADE FEDERAL DO AMAZONAS; EMMANOEL V. COSTA, UNIVERSIDADE FEDERAL DO AMAZONAS; LÍVIA S. DE MEDEIROS, UNIVERSIDADE FEDERAL DE SÃO PAULO; MOACIR R. FORIM, UNIVERSIDADE FEDERAL DE SÃO CARLOS; AFONSO D. L. DE SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; WEIDER H. P. PAZ, UNIVERSIDADE DO ESTADO DO AMAZONAS; GILVAN FERREIRA DA SILVA, CPAA; ANTONIA Q. L. DE SOUZA, UNIVERSIDADE FEDERAL DO AMAZONAS; HECTOR H. F. KOOLEN, UNIVERSIDADE DO ESTADO DO AMAZONAS.
dc.contributor.author.fl_str_mv PERES, E. G.
SOUZA, M. P.
SOUSA, T. F.
SILVA, C. V. A. da
BARROS, A. L.
SILVA, F. M. A. da
COSTA, E. V.
MEDEIROS, L. S. de
FORIM, M. R.
SOUZA, A. D. L. de
PAZ, W. H. P.
SILVA, G. F. da
SOUZA, A. Q. L. de
KOOLEN, H. H. F.
dc.subject.por.fl_str_mv Penicillium meliponae
Azaphilones
Molecular networking
topic Penicillium meliponae
Azaphilones
Molecular networking
description Penicillium meliponae, a recently described and rare species, was isolated as an endophytic fungus from the Amazonian plant Duguetia sthelechantha, and has been proven to be a pigment producer. Considering the high productivity of this species and the lack of data on its chemical composition, the present study aimed to characterize the chemical profile of P. meliponae and evaluate the influence of agitation and the use of different culture media. For this purpose, liquid chromatography coupled with mass spectrometry (LC-MS/MS) and molecular networking were used, allowing the identification of 17 azaphilone molecules with sclerotiorin-like skeletons, becoming the first chemical report of this species. In addition, the different production patterns in the tested culture media were indicative that this species is sensitive to changes in the composition of the carbon source and to the presence of agitation. Furthermore, this work contributes to the fragmentation mechanisms of the different possible structural arrangements for azaphilones of the sclerotiorin type and serves as a repository of information on the gas-phase behavior of this type of metabolite in mass spectrometry experiments and will assist future studies aimed at the discovery of azaphilones.
publishDate 2023
dc.date.none.fl_str_mv 2023-08-02T10:23:49Z
2023-08-02T10:23:49Z
2023-05-09
2023
dc.type.driver.fl_str_mv info:eu-repo/semantics/publishedVersion
info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv Journal of the Brazilian Chemical Society, v. 34, n. 8, p. 1139-1153, 2023.
http://www.alice.cnptia.embrapa.br/alice/handle/doc/1153604
https://dx.doi.org/10.21577/0103-5053.20230027
identifier_str_mv Journal of the Brazilian Chemical Society, v. 34, n. 8, p. 1139-1153, 2023.
url http://www.alice.cnptia.embrapa.br/alice/handle/doc/1153604
https://dx.doi.org/10.21577/0103-5053.20230027
dc.language.iso.fl_str_mv eng
language eng
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eu_rights_str_mv openAccess
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instname:Empresa Brasileira de Pesquisa Agropecuária (Embrapa)
instacron:EMBRAPA
instname_str Empresa Brasileira de Pesquisa Agropecuária (Embrapa)
instacron_str EMBRAPA
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reponame_str Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice)
collection Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice)
repository.name.fl_str_mv Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice) - Empresa Brasileira de Pesquisa Agropecuária (Embrapa)
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