Authors:
Chapla, Vanessa M. [1] ; Honorio, Alana E. [2] ; Gubiani, Juliana R. [3] ; Vilela, Adriana F. L. [4] ; Young, Maria C. M. [5] ; Cardoso, Carmen L. [4] ; Pavan, Fernando R. [6] ; Cicarelli, Regina M. [6] ; Pinheiro Ferreira, Paulo Michel [7] ; Bolzani, Vanderlan da S. [2] ; Araujo, Angela R. [2]
Abstract:
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.
1 Environmental Chemistry, Federal University of Tocantins, UFT, Gurupi, TO, 77402-970, Brazil
2 Chemistry Institute, Department of Organic Chemistry, São Paulo State University, UNESP, Araraquara, SP, 14800-900, Brazil
3 São Carlos Institute of Chemistry, University of São Paulo, USP, CP 780, São Carlos, SP, 13560-970, Brazil
4 Departamento de Química, Grupo de Cromatografa de Bioafnidade e Produtos Naturais, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, USP, Ribeirão Preto, SP, 14040-901, Brazil
5 Institute of Botany – Plant Biochemistry and Physiology Section, São Paulo, SP, 01061-970, Brazil
6 Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista, UNESP, Araraquara, SP, 14800-903, Brazil
7 Departamento de Biofísica e Fisiologia, Laboratório de Cancerologia Experimental,Universidade Federal do Piauí, UFPI, Teresina, PI, 64049-550, Brazil
Link to article: https://www.sciencedirect.com/science/article/abs/pii/S1874390019308122?via%3Dihub
