Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities

Detalhes bibliográficos
Autor(a) principal: Hilario, Felipe [UNESP]
Data de Publicação: 2020
Outros Autores: Polinário, Giulia [UNESP], de Amorim, Marcelo Rodrigues [UNESP], de Sousa Batista, Victor [UNESP], do Nascimento Júnior, Nailton Monteiro [UNESP], Araújo, Angela Regina [UNESP], Bauab, Taís Maria [UNESP], dos Santos, Lourdes Campaner [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.fitote.2019.104466
http://hdl.handle.net/11449/201444
Resumo: Curvularia lunata, isolated from the capitula of Paepalanthus chiquitensis (Eriocaulaceae), was cultured in potato dextrose broth (PDB) medium. The ethyl acetate extract yielded two new spirocyclic γ-lactams (3 and 4), and five known compounds, namely: triticones E (1) and F (2), 5-O-methylcurvulinic acid (5), curvulinic acid (6) and curvulin (7). Their structures were elucidated by spectroscopic analysis and by the comparison with literature data. Besides, a computational study was used to elucidate the absolute configuration of the C − 3′ in the compounds (3) and (4). The extract and the compounds (1 and 2), (6) and (7) were assayed against gram-positive and gram-negative bacteria and fluconazole-resistant yeast. The triticones (1) and (2) showed good antibacterial activity for Escherichia coli, with a minimum inhibitory concentration of 62.5 μg/mL.
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spelling Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activitiesAntibacterial activityCurvularia lunataCurvulinic acidPaepalanthus chiquitensisSpirocyclic lactamsCurvularia lunata, isolated from the capitula of Paepalanthus chiquitensis (Eriocaulaceae), was cultured in potato dextrose broth (PDB) medium. The ethyl acetate extract yielded two new spirocyclic γ-lactams (3 and 4), and five known compounds, namely: triticones E (1) and F (2), 5-O-methylcurvulinic acid (5), curvulinic acid (6) and curvulin (7). Their structures were elucidated by spectroscopic analysis and by the comparison with literature data. Besides, a computational study was used to elucidate the absolute configuration of the C − 3′ in the compounds (3) and (4). The extract and the compounds (1 and 2), (6) and (7) were assayed against gram-positive and gram-negative bacteria and fluconazole-resistant yeast. The triticones (1) and (2) showed good antibacterial activity for Escherichia coli, with a minimum inhibitory concentration of 62.5 μg/mL.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)São Paulo State University (UNESP) School of Pharmaceutical Sciences, Road Araraquara-Jaú km1São Paulo State University (UNESP) Institute of Chemistry, Av. Prof. Francisco Degni n.55São Paulo State University (UNESP) School of Pharmaceutical Sciences, Road Araraquara-Jaú km1São Paulo State University (UNESP) Institute of Chemistry, Av. Prof. Francisco Degni n.55FAPESP: 2016/05480-6Universidade Estadual Paulista (Unesp)Hilario, Felipe [UNESP]Polinário, Giulia [UNESP]de Amorim, Marcelo Rodrigues [UNESP]de Sousa Batista, Victor [UNESP]do Nascimento Júnior, Nailton Monteiro [UNESP]Araújo, Angela Regina [UNESP]Bauab, Taís Maria [UNESP]dos Santos, Lourdes Campaner [UNESP]2020-12-12T02:32:42Z2020-12-12T02:32:42Z2020-03-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.fitote.2019.104466Fitoterapia, v. 141.1873-69710367-326Xhttp://hdl.handle.net/11449/20144410.1016/j.fitote.2019.1044662-s2.0-85077359051Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengFitoterapiainfo:eu-repo/semantics/openAccess2024-06-24T13:08:25Zoai:repositorio.unesp.br:11449/201444Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T23:05:28.723274Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
title Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
spellingShingle Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
Hilario, Felipe [UNESP]
Antibacterial activity
Curvularia lunata
Curvulinic acid
Paepalanthus chiquitensis
Spirocyclic lactams
title_short Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
title_full Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
title_fullStr Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
title_full_unstemmed Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
title_sort Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
author Hilario, Felipe [UNESP]
author_facet Hilario, Felipe [UNESP]
Polinário, Giulia [UNESP]
de Amorim, Marcelo Rodrigues [UNESP]
de Sousa Batista, Victor [UNESP]
do Nascimento Júnior, Nailton Monteiro [UNESP]
Araújo, Angela Regina [UNESP]
Bauab, Taís Maria [UNESP]
dos Santos, Lourdes Campaner [UNESP]
author_role author
author2 Polinário, Giulia [UNESP]
de Amorim, Marcelo Rodrigues [UNESP]
de Sousa Batista, Victor [UNESP]
do Nascimento Júnior, Nailton Monteiro [UNESP]
Araújo, Angela Regina [UNESP]
Bauab, Taís Maria [UNESP]
dos Santos, Lourdes Campaner [UNESP]
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Hilario, Felipe [UNESP]
Polinário, Giulia [UNESP]
de Amorim, Marcelo Rodrigues [UNESP]
de Sousa Batista, Victor [UNESP]
do Nascimento Júnior, Nailton Monteiro [UNESP]
Araújo, Angela Regina [UNESP]
Bauab, Taís Maria [UNESP]
dos Santos, Lourdes Campaner [UNESP]
dc.subject.por.fl_str_mv Antibacterial activity
Curvularia lunata
Curvulinic acid
Paepalanthus chiquitensis
Spirocyclic lactams
topic Antibacterial activity
Curvularia lunata
Curvulinic acid
Paepalanthus chiquitensis
Spirocyclic lactams
description Curvularia lunata, isolated from the capitula of Paepalanthus chiquitensis (Eriocaulaceae), was cultured in potato dextrose broth (PDB) medium. The ethyl acetate extract yielded two new spirocyclic γ-lactams (3 and 4), and five known compounds, namely: triticones E (1) and F (2), 5-O-methylcurvulinic acid (5), curvulinic acid (6) and curvulin (7). Their structures were elucidated by spectroscopic analysis and by the comparison with literature data. Besides, a computational study was used to elucidate the absolute configuration of the C − 3′ in the compounds (3) and (4). The extract and the compounds (1 and 2), (6) and (7) were assayed against gram-positive and gram-negative bacteria and fluconazole-resistant yeast. The triticones (1) and (2) showed good antibacterial activity for Escherichia coli, with a minimum inhibitory concentration of 62.5 μg/mL.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-12T02:32:42Z
2020-12-12T02:32:42Z
2020-03-01
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/10.1016/j.fitote.2019.104466
Fitoterapia, v. 141.
1873-6971
0367-326X
http://hdl.handle.net/11449/201444
10.1016/j.fitote.2019.104466
2-s2.0-85077359051
url http://dx.doi.org/10.1016/j.fitote.2019.104466
http://hdl.handle.net/11449/201444
identifier_str_mv Fitoterapia, v. 141.
1873-6971
0367-326X
10.1016/j.fitote.2019.104466
2-s2.0-85077359051
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Fitoterapia
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
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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