Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium

J Nat Prod. 1999 Aug;62(8):1101-5. doi: 10.1021/np9900674.

Abstract

(3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1-->6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.

MeSH terms

  • Carbohydrate Sequence
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Hydrolysis
  • Methylation
  • Molecular Sequence Data
  • Pentanoic Acids / chemistry*
  • Pentanoic Acids / isolation & purification
  • Plants, Medicinal / chemistry*
  • Polygonaceae / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared
  • Turkey

Substances

  • Flavonoids
  • Glycosides
  • Pentanoic Acids
  • 5-phenylvaleric acid