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Molecules 2018, 23(4), 970; https://doi.org/10.3390/molecules23040970

Microbial Oxidation of the Fusidic Acid Side Chain by Cunninghamella echinulata

1
Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta 31527, Egypt
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta 31527, Egypt
3
Institute for Computational Molecular Science and Department of Chemistry, Temple University, Philadelphia, PA 19122, USA
4
Department of BioMolecular Sciences, Division of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677-1848, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Charles L. Cantrell
Received: 10 April 2018 / Revised: 17 April 2018 / Accepted: 20 April 2018 / Published: 21 April 2018
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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 24 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. View Full-Text
Keywords: fusidic acid; Cunninghamella echinulata; C-26-oxidation; C-27-oxidation fusidic acid; Cunninghamella echinulata; C-26-oxidation; C-27-oxidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ibrahim, A.-R.S.; Elokely, K.M.; Ferreira, D.; Ragab, A.E. Microbial Oxidation of the Fusidic Acid Side Chain by Cunninghamella echinulata. Molecules 2018, 23, 970.

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