Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , , , , , |
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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Repositório Institucional da UNESP |
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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 |
|
_version_ |
1799965266239553536 |