Microbial transformation of deoxyandrographolide and their inhibitory activity on LPS-induced NO production in RAW 264.7 macrophages

Bioorg Med Chem Lett. 2012 Feb 15;22(4):1615-8. doi: 10.1016/j.bmcl.2011.12.122. Epub 2012 Jan 4.

Abstract

A series of analogues of deoxyandrographolide (1) transformed by Cunninghamella blakesleana AS 3.2004 were isolated and identified by spectral methods including 2D NMR. Among them, 3-oxo-17,19-dihydroxy-7,13-ent-labdadien-15,16-olide (9), 3-oxo-19-hydroxy-1,13-ent-labdadien-15,16-olide (16), 3-oxo-1β-hydroxy-14-deoxy-andrographolide (17) and 3-oxo-2β-hydroxy-14-deoxyandrographolide (18) are new compounds. And their structure-activity relationships (SAR) of inhibitory activity on LPS-induced NO production in RAW 264.7 macrophage cells were also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cunninghamella / enzymology
  • Cunninghamella / metabolism
  • Diterpenes / chemistry
  • Diterpenes / metabolism*
  • Diterpenes / pharmacology*
  • Lipopolysaccharides
  • Macrophages / drug effects*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Structure-Activity Relationship

Substances

  • 14-deoxyandrographolide
  • Diterpenes
  • Lipopolysaccharides
  • Nitric Oxide