Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide

Arch Pharm Res. 2010 Mar;33(3):381-5. doi: 10.1007/s12272-010-0306-2. Epub 2010 Mar 30.

Abstract

Bioassay-guided fractionation of a CH2Cl2-soluble fraction of the stems of Catalpa ovata led to isolation of a new naphthoquinone, 4-hydroxy-2-(2-methoxy-3-hydroxy-3-methyl-but-1-enyl)-4-hydro-1H-naphthalen-1-one (10), together with nine known compounds, catalponol (1), catalponone (2), catalpalactone (3), alpha-lapachone (4), 9-hydroxy-alpha-lapachone (5), 4,9-dihydroxy-alpha-lapachone (6), 9-methoxy-alpha-lapachone (7), 4-oxo-alpha-lapachone (8), and 9-methoxy-4-oxo-alpha-lapachone (9). The structures were elucidated on the basis of spectroscopic analyses. The inhibitory effects of these isolates on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells were evaluated. Among them, catapalactone (3), 9-hydroxy-alpha-lapachone (5) and 4,9-dihydroxy-alpha-lapachone (6) exhibited potent inhibitory effects, with IC(50) values of 9.80, 4.64 and 2.73 microM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bignoniaceae* / chemistry
  • Biological Assay
  • Cell Line
  • Chemical Fractionation
  • Chromatography, High Pressure Liquid
  • Down-Regulation
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology*
  • Nitric Oxide / metabolism*
  • Plant Stems
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship

Substances

  • Lipopolysaccharides
  • Naphthoquinones
  • Nitric Oxide