Uncinoside A and B, two new antiviral chromone glycosides from Selaginella uncinata

Chem Pharm Bull (Tokyo). 2003 Nov;51(11):1264-7. doi: 10.1248/cpb.51.1264.

Abstract

Five compounds have been isolated from the dried whole plants of Selaginella uncinata, two of them were new chromone glycosides, 5-hydroxy-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside (uncinoside A) and 5-acetoxyl-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside (uncinoside B). Their structures were elucidated by spectroscopic methods including one- and two-dimensional NMR techniques. The other three compounds were identified as 8-methyl eugenitol, amentoflavone and hinokiflavone. Uncinoside A and B showed potent antiviral activities against respiratory syncytial virus (RSV) with IC(50) value of 6.9 and 1.3 microg/ml, moderate antiviral activities against parainfluenza type 3 virus (PIV 3) with IC(50) value of 13.8 and 20.8 microg/ml, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology*
  • Cell Survival / drug effects
  • Chromones / isolation & purification*
  • Chromones / pharmacology*
  • Crystallography, X-Ray
  • Cytopathogenic Effect, Viral / drug effects
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Parainfluenza Virus 3, Human / drug effects
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Respiratory Syncytial Viruses / drug effects
  • Selaginellaceae / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Virus Replication / drug effects

Substances

  • 5-acetoxyl-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside
  • 5-hydroxy-2,6,8-trimethylchromone 7-O-beta-D-glucopyranoside
  • Antiviral Agents
  • Chromones
  • Plant Extracts