New acylated flavonoid glycosides from flowers of Aerva javanica

J Asian Nat Prod Res. 2013 Jul;15(7):708-16. doi: 10.1080/10286020.2013.795553. Epub 2013 Jun 14.

Abstract

Chromatographic purification of ethyl acetate soluble fraction of the methanolic extract of the flowers of Aerva javanica yielded three new acylated flavone glycosides: kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-galactoside (1), kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(3″-E-p-coumaroyl)galactoside (2), and kaempferol-3-O-β-d-[4‴-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(4″-E-p-coumaroyl)galactoside (3), along with p-coumaric acid (4), caffeic acid (5), gallic acid (6), eicosanyl-trans-p-coumarate (7), hexadecyl ferulate (8), and hexacosyl ferulate (9). The compounds 1-9 were characterized using 1D ((1)H, (13)C) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) and in comparison with the reported data in the literature. Compound 1 showed weak inhibitory activity against enzymes, such as acetylcholinesterase, butyrylcholinesterase, and lipoxygenase with IC50 values 205.1, 304.1, and 212.3 μM, respectively, whereas compounds 2 and 3 were only weakly active against the enzyme acetylcholinesterase.

MeSH terms

  • Amaranthaceae / chemistry*
  • Caffeic Acids / chemistry
  • Caffeic Acids / isolation & purification
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / pharmacology
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification
  • Flowers / chemistry
  • Galactosides / chemistry
  • Galactosides / isolation & purification*
  • Galactosides / pharmacology
  • Gallic Acid / chemistry
  • Gallic Acid / isolation & purification
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Inhibitory Concentration 50
  • Kaempferols / chemistry
  • Kaempferols / isolation & purification*
  • Kaempferols / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pakistan
  • Plants, Medicinal / chemistry*
  • Propionates

Substances

  • Caffeic Acids
  • Cholinesterase Inhibitors
  • Coumaric Acids
  • Galactosides
  • Glycosides
  • Kaempferols
  • Propionates
  • kaempferol-3-O-beta-D-(4'-E-p-coumaroyl-alpha-L-rhamnosyl(1-6))-(3'-E-p-coumaroyl)galactoside
  • kaempferol-3-O-beta-D-(4'-E-p-coumaroyl-alpha-L-rhamnosyl(1-6))-(4''-E-p-coumaroyl)galactoside
  • kaempferol-3-O-beta-D-(4'-E-p-coumaroyl-alpha-L-rhamnosyl(1-6))galactoside
  • Gallic Acid
  • p-coumaric acid
  • caffeic acid