New Hydroxylactones and Chloro-Hydroxylactones Obtained by Biotransformation of Bicyclic Halolactones and Their Antibacterial Activity

• Published in: Molecules (Basel, Switzerland) Vol. 29; no. 12; p. 2820
• Main Authors: Grabarczyk, Małgorzata, Duda-Madej, Anna, Romanenko, Fedor, Maciejewska, Gabriela, Mączka, Wanda, Białońska, Agata, Wińska, Katarzyna
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.06.2024; MDPI
• Subjects: Absidia - metabolism; Acids; Alcohol; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; antibacterial activity; Antibacterial agents; antifungal activity; Antifungal agents; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antimicrobial agents; Biotransformation; biotransformations; Candida albicans - drug effects; Carbon; Chemical synthesis; Fusarium - drug effects; halolactones; hydrolytic dehalogenation; hydroxylation; Lactones; Lactones - chemistry; Lactones - metabolism; Lactones - pharmacology; Methicillin-Resistant Staphylococcus aureus - drug effects; Microbial Sensitivity Tests; Molecular Structure; Poland; United Kingdom; antibacterial activity; multidrug resistance; biotransformations; halolactones; hydroxylation; hydrolytic dehalogenation; antifungal activity
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules29122820

The aim of this study was to obtain new halolactones with a gem-dimethyl group in the cyclohexane ring (at the C-3 or C-5 carbon) and a methyl group in the lactone ring and then subject them to biotransformations using filamentous fungi. Halolactones in the form of mixtures of two diasteroisomers were subjected to screening biotransformations, which showed that only compounds with a gem-dimethyl group located at the C-5 carbon were transformed. Strains from the genus Fusarium carried out hydrolytic dehalogenation, while strains from the genus Absidia carried out hydroxylation of the C-7 carbon. Both substrates and biotransformation products were then tested for antimicrobial activity against multidrug-resistant strains of both bacteria and yeast-like fungi. The highest antifungal activity against C. dubliniensis and C. albicans strains was obtained for compound 5b, while antimicrobial activity against S. aureus MRSA was obtained for compound 4a.