Biotransformation of Hydroxychalcones as a Method of Obtaining Novel and Unpredictable Products Using Whole Cells of Bacteria
Joanna Kozłowska , Bartłomiej Potaniec , Mirosław Anioł
AbstractThe 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.
|Journal series||Catalysts, ISSN 2073-4344, (N/A 100 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||biotransformation; biologically active compounds; chalcone; dihydrochalcone|
|License||Journal (articles only); published final; ; with publication|
|Score||= 100.0, 08-12-2020, ArticleFromJournal|
|Publication indicators||= 0; : 2018 = 0.912; : 2018 = 3.444 (2) - 2018=3.808 (5)|
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