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

• Autor(a) principal: Chapla, Vanessa M.
• Data de Publicação: 2020
• Outros Autores: 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 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
• topic: AchE inhibitory activity; Cyclohexanoids; Endophytic fungi; Eugenia jambolana; Saccharicola sp.; Speciosins

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.