A new prenylated flavone from Pleione bulbocodioides

J Asian Nat Prod Res. 2017 Jul;19(7):738-743. doi: 10.1080/10286020.2017.1311871. Epub 2017 Apr 12.

Abstract

A new prenylated flavone, 3,5,7,3'-tetrahydroxy-8,4'-dimethoxy-6-(3-methylbut-2- enyl)flavone (1), together with three known flavone derivatives (2-4), two known dihydrophenanthrenes (5-6), two known lignin derivatives (7-8), and three known phenolic glycoside compounds (9-11) were isolated from the n-BuOH extract of Pleione bulbocodioides. High-resolution electrospray ionization mass spectroscopy (HRESIMS), FTIR spectroscopy, and NMR techniques were used to elucidate the structures of these compounds. Biological investigations showed that compound 5, 4,7-dihydroxy-2-methoxy-9,10-dihydrophenanthrene, exhibited potent anti-inflammatory activity on LPS-stimulated NO production in BV-2 microglial cells, with IC50 value of 5.44 μM.

Keywords: Orchidaceae; Pleione bulbocodioides; anti-inflammatory activity; prenylated flavone.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Flavones / chemistry
  • Flavones / isolation & purification*
  • Flavones / pharmacology
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Orchidaceae / chemistry*
  • Phenanthrenes / chemistry
  • Prenylation
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • 3,5,7,3'-tetrahydroxy-8,4'-dimethoxy-6-(3-methylbut-2-enyl)flavone
  • Anti-Inflammatory Agents
  • Drugs, Chinese Herbal
  • Flavones
  • Lipopolysaccharides
  • Phenanthrenes
  • lusianthridin
  • Nitric Oxide