Antioxidant activity and spectroscopic data of isoxanthohomol oxime and related compounds

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 24:118:716-23. doi: 10.1016/j.saa.2013.09.018. Epub 2013 Sep 12.

Abstract

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=2.21 mM and 78.7 mM, respectively), isoxanthohumol oxime (IXNOX) showed a strong antioxidant activity (EC50=0.0411 mM), comparable to the activity of ascorbic acid (EC50=0.0181 mM). The structure of new compound IXNOX was established using (1)H NMR, (13)C NMR, IR and UV-VIS spectroscopy, by comparison to IXN, NOX and FLOX.

Keywords: Antioxidant activity; DPPH method; Isoxanthohumol oxime; NMR–IR–UV spectra; Synergism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Biphenyl Compounds / chemistry
  • Free Radicals / chemistry
  • Magnetic Resonance Spectroscopy
  • Oximes / chemistry*
  • Oximes / pharmacology
  • Picrates / chemistry
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Xanthones / chemistry*
  • Xanthones / pharmacology

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Free Radicals
  • Oximes
  • Picrates
  • Xanthones
  • isoxanthohumol
  • 1,1-diphenyl-2-picrylhydrazyl