Antioxidant activity and spectroscopic data of isoxanthohomol oxime and related compounds

•The new compound isoxanthohumol oxime is synthetised.•IR, UV, NMR spectra in comparison to oximes of naringenin and flavanone are studied.•Isoxanthohumol oxime antioxidant activity is comparable to the ascorbic acid.•Synergistic antioxidant activity of prenyl group and oxime group is observed. Oxim...

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Published inSpectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 118; pp. 716 - 723
Main Authors Potaniec, Bartłomiej, Grabarczyk, Małgorzata, Stompor, Monika, Szumny, Antoni, Zieliński, Paweł, Żołnierczyk, Anna Katarzyna, Anioł, Mirosław
Format Journal Article
LanguageEnglish
Published England Elsevier B.V 24.01.2014
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Summary:•The new compound isoxanthohumol oxime is synthetised.•IR, UV, NMR spectra in comparison to oximes of naringenin and flavanone are studied.•Isoxanthohumol oxime antioxidant activity is comparable to the ascorbic acid.•Synergistic antioxidant activity of prenyl group and oxime group is observed. Oximes of isoxanthohumol (IXN), naringenin (N) and flavanone (FL) were synthesized with yields of 88–95% and their antioxidant activity was evaluated using the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) method. Although naringenin oxime (NOX) and flavanone oxime (FLOX) did not have any significant antioxidant effect (EC50=2.21mM and 78.7mM, respectively), isoxanthohumol oxime (IXNOX) showed a strong antioxidant activity (EC50=0.0411mM), comparable to the activity of ascorbic acid (EC50=0.0181mM). The structure of new compound IXNOX was established using 1H NMR, 13C NMR, IR and UV–VIS spectroscopy, by comparison to IXN, NOX and FLOX.
ISSN:1386-1425
1873-3557
DOI:10.1016/j.saa.2013.09.018