Reactive oxygen species scavenging activity of flavone glycosides from Melilotus neapolitana

Molecules. 2007 Feb 28;12(2):263-70. doi: 10.3390/12020263.

Abstract

One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-beta-D-glucopyranosyloxy-4',5-dihydroxy-3-[O-alpha-L-rhamnopyranosyl-(1-->6)-3-O-beta-D-glucopyranosyloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin (4), quercetin-3-O-glucoside (5), isorhamnetin-3-O-rutinoside (6), and isorhamnetin-3-O-glucoside (7). The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker's synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3) and isorhamnetin derivatives (6,7) being less active than the corresponding quercetin derivatives 4,5.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Disaccharides / chemistry
  • Disaccharides / isolation & purification
  • Disaccharides / pharmacology*
  • Flavones / chemistry
  • Flavones / isolation & purification
  • Flavones / pharmacology*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Flavonols / chemistry
  • Flavonols / isolation & purification
  • Flavonols / pharmacology
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Kaempferols / chemistry
  • Kaempferols / isolation & purification
  • Kaempferols / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Melilotus / chemistry*
  • Monosaccharides / chemistry
  • Monosaccharides / isolation & purification
  • Monosaccharides / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Quercetin / analogs & derivatives*
  • Quercetin / chemistry
  • Quercetin / isolation & purification
  • Quercetin / pharmacology
  • Reactive Oxygen Species / metabolism*
  • Rutin / chemistry
  • Rutin / isolation & purification
  • Rutin / pharmacology

Substances

  • 7-O-glucopyranosyloxy-4',5-dihydroxy-3-(O-rhamnopyranosyl-(1-6)-3-O-glucopyranosyloxy)flavone
  • Antioxidants
  • Disaccharides
  • Flavones
  • Flavonoids
  • Flavonols
  • Free Radical Scavengers
  • Glycosides
  • Kaempferols
  • Monosaccharides
  • Plant Extracts
  • Reactive Oxygen Species
  • isorhamnetin 3-O-rutinoside
  • kaempferol-3-O-glucoside
  • isoquercitrin
  • kaempferol-3-O-rutinoside
  • Rutin
  • kaempferol
  • Quercetin
  • isorhamnetin 3-O-glucoside