Acetylcholinesterase inhibition and antifungal activity of cyclohexanoids from the endophytic fungus Saccharicola sp.

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,...

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Detalles Bibliográficos
Autores: 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]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2020
País:Brasil
Institución:Universidade Estadual Paulista (UNESP)
Repositorio:Repositório Institucional da UNESP
Idioma:inglés
OAI Identifier:oai:repositorio.unesp.br:11449/200879
Acceso en línea:http://dx.doi.org/10.1016/j.phytol.2020.07.016
http://hdl.handle.net/11449/200879
Access Level:acceso abierto
Palabra clave:AchE inhibitory activity
Cyclohexanoids
Endophytic fungi
Eugenia jambolana
Saccharicola sp.
Speciosins
Descripción
Sumario: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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