Rearranged limonoids and chromones from Harrisonia perforata and their anti-inflammatory activity

Bioorg Med Chem Lett. 2013 Jul 1;23(13):3896-900. doi: 10.1016/j.bmcl.2013.04.064. Epub 2013 May 2.

Abstract

Two new rearranged limonoids, harperforatin (1) and harperfolide (2), and a new chromone, harperamone (3), were isolated from fruits and roots of Harrisonia perforata, together with eight known compounds. Their structures were elucidated on the basis of spectroscopic data. Harperfolide (2) exhibited potent anti-inflammatory activity by suppressing nitric oxide (NO) production from activated macrophages with IC50 value of 6.51 μM. Furthermore, its effect is mediated by reduction of iNOS protein expression, attributable to the inhibitory action of LPS-induced NO production.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Dose-Response Relationship, Drug
  • Limonins / chemistry
  • Limonins / isolation & purification
  • Limonins / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / biosynthesis
  • Simaroubaceae / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Chromones
  • Limonins
  • Lipopolysaccharides
  • Nitric Oxide
  • Nitric Oxide Synthase Type II