Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase

Chem Pharm Bull (Tokyo). 2002 Jul;50(7):972-5. doi: 10.1248/cpb.50.972.

Abstract

Two new flavanone glycosides, (2S)- and (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acids, and a new phenylbutanoid glycoside, (2S, 3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside, were isolated from the flowers of Chrysanthemum indicum L. cultivated in China together with eight flavonoids. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. Both of the new flavanone glycosides were found to show inhibitory activity for rat lens aldose reductase.

MeSH terms

  • Acetylation
  • Aldehyde Reductase / antagonists & inhibitors*
  • Animals
  • Chrysanthemum / chemistry*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Flavanones*
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology*
  • Flowers / chemistry
  • Hydrolysis
  • In Vitro Techniques
  • Lens, Crystalline / drug effects
  • Lens, Crystalline / enzymology*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Rats

Substances

  • 1-phenyl-2,3-butanediol 3-O-glucopyranoside
  • Enzyme Inhibitors
  • Flavanones
  • Flavonoids
  • eriodictyol 7-O-glucopyranosiduronic acid
  • Aldehyde Reductase