Melampolides from the leaves of Smallanthus sonchifolius and their inhibitory activity of lps-induced nitric oxide production

Chem Pharm Bull (Tokyo). 2008 Feb;56(2):199-202. doi: 10.1248/cpb.56.199.

Abstract

Two new melampolide-type sesquiterpene lactones, 8beta-epoxyangeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide (1) and 8beta-angeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8beta-angeloyloxy-9alpha-acetoxy-14-oxo-acanthospermolide (7), 8beta-angeloyloxy-14-oxo-acanthospermolide (8), 8beta-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8beta-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Asteraceae / chemistry*
  • Cell Line
  • Cell Survival / drug effects
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Lactones / chemistry*
  • Lactones / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors*
  • Lipopolysaccharides / pharmacology*
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Models, Molecular
  • Nitric Oxide / biosynthesis*
  • Plant Extracts / analysis
  • Plant Leaves / chemistry
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • 8beta-angeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide
  • 8beta-epoxyangeloyloxy-9alpha-ethoxy-14-oxo-acanthospermolide
  • Lactones
  • Lipopolysaccharides
  • Plant Extracts
  • Sesquiterpenes
  • Nitric Oxide