Abstract
Biotransformation of fusidic acid (1) was accomplished using a battery of microorganisms including Cunninghamella echinulata NRRL 1382, which converted fusidic acid (1) into three new metabolites 2–4 and the known metabolite 5. These metabolites were identified using 1D and 2D NMR and HRESI-FTMS data. Structural assignment of the compounds was supported via computation of 1H- and 13C-NMR chemical shifts. Compounds 2 and 3 were assigned as the 27-hydroxy and 26-hydroxy derivatives of fusidic acid, respectively. Subsequent oxidation of 3 afforded aldehyde 4 and the dicarboxylic acid 5. Compounds 2, 4 and 5 were screened for antimicrobial activity against different Gram positive and negative bacteria, Mycobacterium smegmatis, M. intercellulare and Candida albicans. The compounds showed lower activity compared to fusidic acid against the tested strains. Molecular docking studies were carried out to assist the structural assignments and predict the binding modes of the metabolites.
Highlights
IntroductionFusidic acid (1) is a natural antibacterial steroid-like compound without any steroidal activity [1,2]
Fusidic acid (1) is a natural antibacterial steroid-like compound without any steroidal activity [1,2].It was first isolated and identified from the fungus Fusidium coccineum [1,2] and introduced into the market in the 1960s as the corresponding sodium salt for clinical use
We explored the metabolic fate of fusidic acid using several organisms among which the fungus Cunninghamella echinulata was the most proficient in the biotransformation of this antibiotic
Summary
Fusidic acid (1) is a natural antibacterial steroid-like compound without any steroidal activity [1,2]. It was first isolated and identified from the fungus Fusidium coccineum [1,2] and introduced into the market in the 1960s as the corresponding sodium salt for clinical use. We explored the metabolic fate of fusidic acid using several organisms among which the fungus Cunninghamella echinulata was the most proficient in the biotransformation of this antibiotic. 16-De-O-acetyl-7β-hydroxyfusidic acid was isolated from the fungus Acremonium crotocinigenum [12]. Biotransformation of the side chain functionalities fusidic acid is rare. Biotransformation of the sideof chain functionalities of fusidic acid is rare.
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