6-Acetamidoflavone obtained by microbiological and chemical methods and its antioxidant activity.

Monika Stompor
Author Information
  1. Monika Stompor: 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.

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 (H, C, H-H, H-C, 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.

Keywords

MeSH Term

Acetic Anhydrides
Acetylation
Actinomycetales
Antioxidants
Arylamine N-Acetyltransferase
Biotransformation
Flavonoids
Rhodococcus
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet

Chemicals

Acetic Anhydrides
Antioxidants
Flavonoids
6-hydroxyflavone
acetic anhydride
aminoflavone
Arylamine N-Acetyltransferase

Word Cloud

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