Antioxidant phenolic glycosides from Moricandia arvensis

J Nat Prod. 2005 Apr;68(4):517-22. doi: 10.1021/np049581m.

Abstract

The new phenolic glycosides quercetin 3,4'-di-O-beta-d-glucopyranoside-7-O-alpha-l-rhamnopyranoside (moricandin) (1), beta-d-glucopyranosyl 4-O-beta-d-glucopyranosylcaffeate (2), methyl 3-O-beta-d-glucopyranosyl-5-hydroxycinnamate (3), and beta-d-glucopyranosyl 4-O-beta-d-glucopyranosylbenzoate (4), together with the previously known beta-d-glucopyranosyl 4-hydroxybenzoate (5), methyl 4-O-beta-d-glucopyranosylcaffeate (6), 1-O-caffeoyl-beta-d-glucopyranoside (7), and 2-phenylethyl-beta-d-glucopyranoside (8), were isolated from the flowers of Moricandia arvensis. Their structures were elucidated by extensive spectroscopic analysis and chemical methods. Compounds 1-8 were evaluated for antioxidant activity using DPPH, TEAC, and reducing power assays, where the caffeic acid derivative 7 and the quercetin triglycoside 2 proved to possess the most potent scavenging activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology
  • Biphenyl Compounds
  • Brassicaceae / chemistry*
  • Caffeic Acids / chemistry
  • Caffeic Acids / pharmacology
  • Flowers / chemistry
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Picrates / pharmacology
  • Plants, Medicinal / chemistry*
  • Tunisia

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Caffeic Acids
  • Free Radical Scavengers
  • Glycosides
  • Picrates
  • beta-D-glucopyranosyl 4-O-beta-D-glucopyranosylcaffeate
  • moricandin
  • 1,1-diphenyl-2-picrylhydrazyl