Biotransformation of Hydroxychalcones as a Method of Obtaining Novel and Unpredictable Products Using Whole Cells of Bacteria

• Published in: Catalysts Vol. 10; no. 10; p. 1167
• Main Authors: Kozłowska, Joanna, Potaniec, Bartłomiej, Anioł, Mirosław
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01.10.2020
• Subjects: Alcohol; Alzheimer's disease; Analysis; Bacteria; Bioflavonoids; biologically active compounds; Biotransformation; Carbon; Carbonyl groups; Carbonyls; Catalysts; chalcone; Chemical reactions; Chemical synthesis; Chromatography; dihydrochalcone; Diketones; Enzymes; Flavones; Flavonoids; Fungi; Hydrogenation; Hydroxylation; Identification and classification; Ketones; Metabolites; Methods; Microorganisms; NMR; Nuclear magnetic resonance; Reduction; Rhodococcus; Structure; Poland
• ISSN: 2073-4344; 2073-4344
• DOI: 10.3390/catal10101167

The aim of our study was the evaluation of the biotransformation capacity of hydroxychalcones—2-hydroxy-4′-methylchalcone (1) and 4-hydroxy-4′-methylchalcone (4) using two strains of aerobic bacteria. The microbial reduction of the α,β-unsaturated bond of 2-hydroxy-4′-methylchalcone (1) in Gordonia sp. DSM 44456 and Rhodococcus sp. DSM 364 cultures resulted in isolation the 2-hydroxy-4′-methyldihydrochalcone (2) as a main product with yields of up to 35%. Additionally, both bacterial strains transformed compound 1 to the second, unexpected product of reduction and simultaneous hydroxylation at C-4 position—2,4-dihydroxy-4′-methyldihydrochalcone (3) (isolated yields 12.7–16.4%). During biotransformation of 4-hydroxy-4′-methylchalcone (4) we observed the formation of three products: reduction of C=C bond—4-hydroxy-4′-methyldihydrochalcone (5), reduction of C=C bond and carbonyl group—3-(4-hydroxyphenyl)-1-(4-methylphenyl)propan-1-ol (6) and also unpredictable 3-(4-hydroxyphenyl)-1,5-di-(4-methylphenyl)pentane-1,5-dione (7). As far as our knowledge is concerned, compounds 3, 6 and 7 have never been described in the scientific literature.