Production of new ent-hardwickiic acid derivatives by microbial transformation and their antifungal activity.

Autor: Teixeira MVS; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, s/n, Ribeirão Preto 14040-903, SP, Brazil., Fernandes LM; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, s/n, Ribeirão Preto 14040-903, SP, Brazil., de Paula VS; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, s/n, Ribeirão Preto 14040-903, SP, Brazil., Ferreira AG; Laboratory of Nuclear Magnetic Resonance, Chemistry Department, Federal University of São Carlos, São Carlos 13565-905, SP, Brazil., Pires LM; Nucleus of Research in Sciences and Technology, University of Franca, Franca 14404-600, SP, Brazil., Santos RA; Nucleus of Research in Sciences and Technology, University of Franca, Franca 14404-600, SP, Brazil., Furtado NAJC; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, s/n, Ribeirão Preto 14040-903, SP, Brazil. Electronic address: niege@fcfrp.usp.br.
Jazyk: angličtina
Zdroj: Fitoterapia [Fitoterapia] 2024 Mar; Vol. 173, pp. 105810. Date of Electronic Publication: 2023 Dec 30.
DOI: 10.1016/j.fitote.2023.105810
Abstrakt: Ent-hardwickiic acid is the major compound of Copaifera pubiflora Benth oleoresin traditionally used in Brazilian folk medicine as an antimicrobial agent. Microbial transformation of ent-hardwickiic by Cunninghamella elegans ATCC 10028b resulted in two and five antifungal derivatives (four new ones) produced in the Czapek modified and Koch's K1 media, respectively. The derivatives were isolated and their structures were determined by spectral analysis, namely 1D/2D NMR and HR-ESIMS. All compounds were tested for cytotoxic and antifungal activities and they were not cytotoxic to the tested cell lines, but all derivatives showed fungicidal activity against Candida glabrata and Candida krusei, which have emerged as resistant to fluconazole. One of the yet unreported biotransformation products displayed the strongest activity with minimum fungicidal concentration values smaller than the other compounds, including fluconazole.
Competing Interests: Declaration of competing interest There are no conflicts of interest to declare.
(Copyright © 2023 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: