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

Author(s):Show less -

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]

Affiliation

^[1] Fed Univ Tocantins, UFT, Environm Chem, BR-77402970 Gurupi, TO - Brazil

^[2] Sao Paulo State Univ, Chem Inst, Dept Organ Chem, UNESP, BR-14800900 Araraquara, SP - Brazil

^[3] Univ Sao Paulo, Sao Carlos Inst Chem, CP 780, BR-13560970 Sao Carlos, SP - Brazil

^[4] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Grp Cromatografa Bioafnidade & Prod Nat, BR-14040901 Ribeirao Preto, SP - Brazil

^[5] Inst Bot, Plant Biochem & Physiol Sect, BR-01061970 Sao Paulo, SP - Brazil

^[6] Univ Estadual Paulista, Fac Ciencias Farmaceut, UNESP, BR-14800903 Araraquara, SP - Brazil

^[7] Univ Fed Piaui, Dept Biofis & Fisiol, Lab Cancerol Expt, UFPI, BR-64049550 Teresina, PI - Brazil

• Document type: Journal article
• Source: PHYTOCHEMISTRY LETTERS; v. 39, p. 116-123, OCT 2020.
• Web of Science Citations: 1

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. (AU)

• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 17/06014-4 - New secondary metabolites of endophytic and marine organisms as proteasome inhibitors: a validated target against cancer
• Grantee: Juliana Regina Gubiani
• Support Opportunities: Scholarships in Brazil - Post-Doctoral