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

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

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)...

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Bibliographic Details
Published in:Fitoterapia Vol. 173; p. 105810
Main Authors: Teixeira, Maria V.S., Fernandes, Lívia M., de Paula, Vinícius S., Ferreira, Antonio G., Pires, Loren M., Santos, Raquel A., Furtado, Niege A.J.C.
Format: Journal Article
Language:English
Published: Netherlands Elsevier B.V 01-03-2024
Subjects:
Antifungal Agents
Antifungal compounds
Biotransformation
Candida
Candida glabrata
Candida krusei
Cunninghamella elegans
Diterpenes
Ent-hardwickiic acid
Fluconazole - pharmacology
Microbial Sensitivity Tests
Molecular Structure
Candida glabrata
Candida krusei
Antifungal compounds
Biotransformation
Ent-hardwickiic acid
Cunninghamella elegans
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Summary: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. [Display omitted] •Five ent-hardwickiic acid antifungal derivatives were produced by biotransformation.•Diterpene derivatives were more potent than fluconazole against Candida strains.•Regio- stereoselective hydroxylation of ent-hardwickiic acid increased the activity.
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2023.105810