Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

Detalhes bibliográficos
Autor(a) principal: Chapla, Vanessa Mara [UNESP]
Data de Publicação: 2014
Outros Autores: Zeraik, Maria Luiza [UNESP], Ximenes, Valdecir F. [UNESP], Zanardi, Lisineia Maria [UNESP], Lopes, Márcia Nasser [UNESP], Cavalheiro, Alberto José [UNESP], Silva, Dulce Helena Siqueira [UNESP], Young, Maria Claudia M., Fonseca, Luiz Marcos da [UNESP], Bolzani, Vanderlan da Silva [UNESP], Araújo, Angela Regina [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.3390/molecules19056597
http://hdl.handle.net/11449/113198
Resumo: Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.
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spelling Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilissecondary metabolitesbioactivitiesendophytic fungiPhomopsis sp.Senna spectabilisChemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Univ Estadual Paulista, UNESP, NuBBE Nucleo Bioensaios Biossintese & Ecofisiol, Inst Quim Organ,Inst Quim, BR-14800900 Araraquara, SP, BrazilUniv Estadual Paulista, UNESP, Dept Quim, Fac Ciencias, BR-17033360 Bauru, SP, BrazilNucleo Pesquisa Fisiol & Bioquim, Inst Bot, BR-04301902 Sao Paulo, BrazilUniv Estadual Paulista, UNESP, Fac Ciencias Farmaceut Araraquara, Dept Anal Clin, BR-14801902 Araraquara, SP, BrazilUniv Estadual Paulista, UNESP, NuBBE Nucleo Bioensaios Biossintese & Ecofisiol, Inst Quim Organ,Inst Quim, BR-14800900 Araraquara, SP, BrazilUniv Estadual Paulista, UNESP, Dept Quim, Fac Ciencias, BR-17033360 Bauru, SP, BrazilUniv Estadual Paulista, UNESP, Fac Ciencias Farmaceut Araraquara, Dept Anal Clin, BR-14801902 Araraquara, SP, BrazilFAPESP: 10/52327-5FAPESP: 13/07600-3Mdpi AgUniversidade Estadual Paulista (Unesp)Nucleo Pesquisa Fisiol & BioquimChapla, Vanessa Mara [UNESP]Zeraik, Maria Luiza [UNESP]Ximenes, Valdecir F. [UNESP]Zanardi, Lisineia Maria [UNESP]Lopes, Márcia Nasser [UNESP]Cavalheiro, Alberto José [UNESP]Silva, Dulce Helena Siqueira [UNESP]Young, Maria Claudia M.Fonseca, Luiz Marcos da [UNESP]Bolzani, Vanderlan da Silva [UNESP]Araújo, Angela Regina [UNESP]2014-12-03T13:11:29Z2014-12-03T13:11:29Z2014-05-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article6597-6608application/pdfhttp://dx.doi.org/10.3390/molecules19056597Molecules. Basel: Mdpi Ag, v. 19, n. 5, p. 6597-6608, 2014.1420-3049http://hdl.handle.net/11449/11319810.3390/molecules19056597WOS:000337113000070WOS000337113000070.pdf47020049042312480000-0001-7616-96520000-0002-1516-7765Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengMolecules3.0980,855info:eu-repo/semantics/openAccess2024-04-29T18:17:11Zoai:repositorio.unesp.br:11449/113198Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-04-29T18:17:11Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
title Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
spellingShingle Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
Chapla, Vanessa Mara [UNESP]
secondary metabolites
bioactivities
endophytic fungi
Phomopsis sp.
Senna spectabilis
title_short Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
title_full Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
title_fullStr Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
title_full_unstemmed Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
title_sort Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
author Chapla, Vanessa Mara [UNESP]
author_facet Chapla, Vanessa Mara [UNESP]
Zeraik, Maria Luiza [UNESP]
Ximenes, Valdecir F. [UNESP]
Zanardi, Lisineia Maria [UNESP]
Lopes, Márcia Nasser [UNESP]
Cavalheiro, Alberto José [UNESP]
Silva, Dulce Helena Siqueira [UNESP]
Young, Maria Claudia M.
Fonseca, Luiz Marcos da [UNESP]
Bolzani, Vanderlan da Silva [UNESP]
Araújo, Angela Regina [UNESP]
author_role author
author2 Zeraik, Maria Luiza [UNESP]
Ximenes, Valdecir F. [UNESP]
Zanardi, Lisineia Maria [UNESP]
Lopes, Márcia Nasser [UNESP]
Cavalheiro, Alberto José [UNESP]
Silva, Dulce Helena Siqueira [UNESP]
Young, Maria Claudia M.
Fonseca, Luiz Marcos da [UNESP]
Bolzani, Vanderlan da Silva [UNESP]
Araújo, Angela Regina [UNESP]
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
Nucleo Pesquisa Fisiol & Bioquim
dc.contributor.author.fl_str_mv Chapla, Vanessa Mara [UNESP]
Zeraik, Maria Luiza [UNESP]
Ximenes, Valdecir F. [UNESP]
Zanardi, Lisineia Maria [UNESP]
Lopes, Márcia Nasser [UNESP]
Cavalheiro, Alberto José [UNESP]
Silva, Dulce Helena Siqueira [UNESP]
Young, Maria Claudia M.
Fonseca, Luiz Marcos da [UNESP]
Bolzani, Vanderlan da Silva [UNESP]
Araújo, Angela Regina [UNESP]
dc.subject.por.fl_str_mv secondary metabolites
bioactivities
endophytic fungi
Phomopsis sp.
Senna spectabilis
topic secondary metabolites
bioactivities
endophytic fungi
Phomopsis sp.
Senna spectabilis
description Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.
publishDate 2014
dc.date.none.fl_str_mv 2014-12-03T13:11:29Z
2014-12-03T13:11:29Z
2014-05-01
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/10.3390/molecules19056597
Molecules. Basel: Mdpi Ag, v. 19, n. 5, p. 6597-6608, 2014.
1420-3049
http://hdl.handle.net/11449/113198
10.3390/molecules19056597
WOS:000337113000070
WOS000337113000070.pdf
4702004904231248
0000-0001-7616-9652
0000-0002-1516-7765
url http://dx.doi.org/10.3390/molecules19056597
http://hdl.handle.net/11449/113198
identifier_str_mv Molecules. Basel: Mdpi Ag, v. 19, n. 5, p. 6597-6608, 2014.
1420-3049
10.3390/molecules19056597
WOS:000337113000070
WOS000337113000070.pdf
4702004904231248
0000-0001-7616-9652
0000-0002-1516-7765
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Molecules
3.098
0,855
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 6597-6608
application/pdf
dc.publisher.none.fl_str_mv Mdpi Ag
publisher.none.fl_str_mv Mdpi Ag
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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