title: 6-Acetamidoflavone obtained by microbiological and chemical methods and its antioxidant activity.
abstract: The aim of this research was to select microbial strains capable of transforming flavonoid compounds containing an amino group. 6-Aminoflavone (1) was used as a model compound. Biotransformation of 1 by the cultures of Rhodococcus sp. DSM 364 and Gordonia sp. DSM 44456 bacteria led to 6-acetamidoflavone (2) with the isolated yields in 86% and 93%, respectively. The structure of the product was determined on the basis of spectroscopic data, including NMR spectra (1H,13C,1H-1H,1H-13C, and DEPT 135°), a UV and IR spectrum and HR ESI-MS analysis. The developed method of microbial replacement of the amino group in 6-aminoflavone (1) by a acetamido one may find application in chemical industry, being an alternative to the reactions involving acetic anhydride. The antioxidant activity of flavone, and its C-6 substituted derivatives: 6-aminoflavone (1), 6-hydroxyflavone and isolated metabolite 6-acetamidoflavone (2) has been examined using the ABTS and DPPH methods.
authors.affiliation: Centre for Innovative Research in Medical and Natural Sciences, Faculty of Medicine, University of Rzeszów, Warzywna 1a, 35-310 Rzeszów, Poland; Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. Electronic address: monika.stompor@gmail.com.
authors.forename: Monika
authors.initials: M
authors.lastname: Stompor
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry; D000107:Acetylation; D000192:Actinomycetales / Q000201:enzymology / Q000378:metabolism; D000975:Antioxidants / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D001191:Arylamine N-Acetyltransferase / Q000378:metabolism; D001711:Biotransformation; D005419:Flavonoids / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D012240:Rhodococcus / Q000201:enzymology / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000089:Acetic Anhydrides; D000975:Antioxidants; D005419:Flavonoids; C529356:6-hydroxyflavone; C031800:acetic anhydride; C413760:aminoflavone; D001191:Arylamine N-Acetyltransferase
keywords: 6-Acetamidoflavone; 6-Aminoflavone; Arylamine N-acetyltransferase; Gordonia sp. DSM 44456; N-acetylation; Rhodococcus sp. DSM 364