Uncarilic acid and secouncarilic acid, two new triterpenoids from Uucaria sessilifructus

Molecules. 2013 Aug 14;18(8):9727-34. doi: 10.3390/molecules18089727.

Abstract

Two new compounds, the 6-oxo oleanane-type triterpenoid uncarilic acid, and its 5,6-secotriterpenoid derivative, secouncarilic acid, were isolated from the hooks and stems of Uucaria sessilifructus together with seven known ursane-type triterpenoids. Uncarilic acid is the second 6-oxo oleanane-type triterpenoid ever reported, while secouncarilic acid is the first oleanane-type 5,6-secotriterpenoid. A plausible biosynthetic pathway from uncarilic acid to secouncarilic acid was also postulated. The inhibitory activities of all the nine compounds against LPS-induced nitric oxide production in RAW264.7 macrophages were evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Humans
  • Inflammation / chemically induced
  • Inflammation / drug therapy*
  • Lipopolysaccharides / toxicity
  • Macrophages / drug effects
  • Molecular Structure
  • Nitric Oxide / metabolism*
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Secosteroids / chemistry*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Uncaria / chemistry*

Substances

  • Lipopolysaccharides
  • Secosteroids
  • Triterpenes
  • Nitric Oxide
  • Oleanolic Acid