Inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophage cells by lignans isolated from Euonymus alatus leaves and twigs

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2283-6. doi: 10.1016/j.bmcl.2011.02.102. Epub 2011 Mar 2.

Abstract

The 80% methanolic extract of Euonymus alatus leaves and twigs afforded three new lignans, (-)-threo-4,9,4',9'-tetrahydroxy-3,7,3',5'-tetramethoxy-8-O-8'-neolignan (1), (-)-threo-4,9,4',9'-tetrahydroxy-3,5,7,3'-tetramethoxy-8-O-8'-neolignan (2), (7R,8R,7'R)-(+)-lyoniresinol (3), together with seventeen known lignans (4-20). The structures of 1-20 were elucidated by extensive 1D and 2D spectroscopic methods including (1)H NMR, (13)C NMR, (1)H-(1)H COSY, HMQC, HMBC and NOESY. All the isolated compounds except for dilignans (19 and 20) significantly inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anisoles / chemistry*
  • Anisoles / isolation & purification
  • Anisoles / pharmacology
  • Cell Line
  • Euonymus / chemistry*
  • Lignans / chemistry*
  • Lignans / isolation & purification
  • Lignans / pharmacology
  • Lipopolysaccharides / toxicity
  • Macrophages / cytology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Naphthalenes / chemistry*
  • Naphthalenes / isolation & purification
  • Naphthalenes / pharmacology
  • Nitric Oxide / metabolism*
  • Plant Leaves / chemistry

Substances

  • Anisoles
  • Lignans
  • Lipopolysaccharides
  • Naphthalenes
  • lyoniresinol
  • threo-4,9,4',9'-tetrahydroxy-3,5,7,3'-tetramethoxy-8-O-8'-neolignan
  • threo-4,9,4',9'-tetrahydroxy-3,7,3',5'-tetramethoxy-8-O-8'-neolignan
  • Nitric Oxide