Dereplication of sclerotiorin-like azaphilones produced by Penicillium meliponae using LC-MS/MS analysis and molecular networking.
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , , , , , , , , , , |
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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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 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice) instname:Empresa Brasileira de Pesquisa Agropecuária (Embrapa) instacron:EMBRAPA |
instname_str |
Empresa Brasileira de Pesquisa Agropecuária (Embrapa) |
instacron_str |
EMBRAPA |
institution |
EMBRAPA |
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) |
repository.mail.fl_str_mv |
cg-riaa@embrapa.br |
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1794503547901968384 |