Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp.
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.phytol.2020.07.016 http://hdl.handle.net/11449/200879 |
Resumo: | Three new oxygenated cyclohexanoids, namely, speciosin U (1), speciosin V (2) and speciosin W (3), along with four known compounds consisting of 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4), 4-hydroxy-3-prenyl-benzoic acid (5), 2,2-dimethyl-2H-chromene-6-carboxylic acid (6) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) were isolated from scale-up cultures of Saccharicola sp., an endophyte of Eugenia jambolana. The structures were established by analysis of spectroscopic data, including 1D and 2D NMR. The absolute configuration of 1 was determined using Mosher's method. Speciosin U (1) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) exhibited a potent acetylcholinesterase (AChE) inhibitory activity comparable to reference inhibitor galantamine. Furthermore, speciosin U (1) presented antifungal activity invitro against the phytopathogenic fungi Cladosporium cladosporioides, while compounds 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4) and 4-hydroxy-3-prenyl-benzoic acid (5) exhibited antifungal activity against C. sphaerospermum. |
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Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp.AchE inhibitory activityCyclohexanoidsEndophytic fungiEugenia jambolanaSaccharicola sp.SpeciosinsThree new oxygenated cyclohexanoids, namely, speciosin U (1), speciosin V (2) and speciosin W (3), along with four known compounds consisting of 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4), 4-hydroxy-3-prenyl-benzoic acid (5), 2,2-dimethyl-2H-chromene-6-carboxylic acid (6) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) were isolated from scale-up cultures of Saccharicola sp., an endophyte of Eugenia jambolana. The structures were established by analysis of spectroscopic data, including 1D and 2D NMR. The absolute configuration of 1 was determined using Mosher's method. Speciosin U (1) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) exhibited a potent acetylcholinesterase (AChE) inhibitory activity comparable to reference inhibitor galantamine. Furthermore, speciosin U (1) presented antifungal activity invitro against the phytopathogenic fungi Cladosporium cladosporioides, while compounds 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4) and 4-hydroxy-3-prenyl-benzoic acid (5) exhibited antifungal activity against C. sphaerospermum.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Environmental Chemistry Federal University of Tocantins UFTChemistry Institute Department of Organic Chemistry São Paulo State University UNESPSão Carlos Institute of Chemistry University of São Paulo USP CP 780Departamento de Química Grupo de Cromatografa de Bioafnidade e Produtos Naturais Faculdade de Filosofia Ciências e Letras de Ribeirão Preto Universidade de São Paulo, USPInstitute of Botany - Plant Biochemistry and Physiology SectionFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista UNESPDepartamento de Biofísica e Fisiologia Laboratório de Cancerologia Experimental Universidade Federal do Piauí UFPIChemistry Institute Department of Organic Chemistry São Paulo State University UNESPFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista UNESPUFTUniversidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Institute of Botany - Plant Biochemistry and Physiology SectionUFPIChapla, Vanessa M.Honório, Alana E. [UNESP]Gubiani, Juliana R.Vilela, Adriana F.L.Young, Maria C.M.Cardoso, Carmen L.Pavan, Fernando R. [UNESP]Cicarelli, Regina M. [UNESP]Michel Pinheiro Ferreira, PauloBolzani, Vanderlan da S. [UNESP]Araujo, Angela R. [UNESP]2020-12-12T02:18:32Z2020-12-12T02:18:32Z2020-10-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article116-123http://dx.doi.org/10.1016/j.phytol.2020.07.016Phytochemistry Letters, v. 39, p. 116-123.1876-74861874-3900http://hdl.handle.net/11449/20087910.1016/j.phytol.2020.07.0162-s2.0-85089242805Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengPhytochemistry Lettersinfo:eu-repo/semantics/openAccess2021-10-23T15:33:30Zoai:repositorio.unesp.br:11449/200879Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T18:37:28.956829Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
title |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
spellingShingle |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. Chapla, Vanessa M. AchE inhibitory activity Cyclohexanoids Endophytic fungi Eugenia jambolana Saccharicola sp. Speciosins |
title_short |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
title_full |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
title_fullStr |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
title_full_unstemmed |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
title_sort |
Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp. |
author |
Chapla, Vanessa M. |
author_facet |
Chapla, Vanessa M. Honório, Alana E. [UNESP] Gubiani, Juliana R. Vilela, Adriana F.L. Young, Maria C.M. Cardoso, Carmen L. Pavan, Fernando R. [UNESP] Cicarelli, Regina M. [UNESP] Michel Pinheiro Ferreira, Paulo Bolzani, Vanderlan da S. [UNESP] Araujo, Angela R. [UNESP] |
author_role |
author |
author2 |
Honório, Alana E. [UNESP] Gubiani, Juliana R. Vilela, Adriana F.L. Young, Maria C.M. Cardoso, Carmen L. Pavan, Fernando R. [UNESP] Cicarelli, Regina M. [UNESP] Michel Pinheiro Ferreira, Paulo Bolzani, Vanderlan da S. [UNESP] Araujo, Angela R. [UNESP] |
author2_role |
author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
UFT Universidade Estadual Paulista (Unesp) Universidade de São Paulo (USP) Institute of Botany - Plant Biochemistry and Physiology Section UFPI |
dc.contributor.author.fl_str_mv |
Chapla, Vanessa M. Honório, Alana E. [UNESP] Gubiani, Juliana R. Vilela, Adriana F.L. Young, Maria C.M. Cardoso, Carmen L. Pavan, Fernando R. [UNESP] Cicarelli, Regina M. [UNESP] Michel Pinheiro Ferreira, Paulo Bolzani, Vanderlan da S. [UNESP] Araujo, Angela R. [UNESP] |
dc.subject.por.fl_str_mv |
AchE inhibitory activity Cyclohexanoids Endophytic fungi Eugenia jambolana Saccharicola sp. Speciosins |
topic |
AchE inhibitory activity Cyclohexanoids Endophytic fungi Eugenia jambolana Saccharicola sp. Speciosins |
description |
Three new oxygenated cyclohexanoids, namely, speciosin U (1), speciosin V (2) and speciosin W (3), along with four known compounds consisting of 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4), 4-hydroxy-3-prenyl-benzoic acid (5), 2,2-dimethyl-2H-chromene-6-carboxylic acid (6) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) were isolated from scale-up cultures of Saccharicola sp., an endophyte of Eugenia jambolana. The structures were established by analysis of spectroscopic data, including 1D and 2D NMR. The absolute configuration of 1 was determined using Mosher's method. Speciosin U (1) and trans-3,4-dihydro-3,4-dihydroxy-anofinic acid (7) exhibited a potent acetylcholinesterase (AChE) inhibitory activity comparable to reference inhibitor galantamine. Furthermore, speciosin U (1) presented antifungal activity invitro against the phytopathogenic fungi Cladosporium cladosporioides, while compounds 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid (4) and 4-hydroxy-3-prenyl-benzoic acid (5) exhibited antifungal activity against C. sphaerospermum. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-12T02:18:32Z 2020-12-12T02:18:32Z 2020-10-01 |
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.phytol.2020.07.016 Phytochemistry Letters, v. 39, p. 116-123. 1876-7486 1874-3900 http://hdl.handle.net/11449/200879 10.1016/j.phytol.2020.07.016 2-s2.0-85089242805 |
url |
http://dx.doi.org/10.1016/j.phytol.2020.07.016 http://hdl.handle.net/11449/200879 |
identifier_str_mv |
Phytochemistry Letters, v. 39, p. 116-123. 1876-7486 1874-3900 10.1016/j.phytol.2020.07.016 2-s2.0-85089242805 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Phytochemistry Letters |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
116-123 |
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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1808128955716206592 |