Antitrypanosomal triterpenoid with an ε-lactone E-ring from Salvia urmiensis

J Nat Prod. 2013 Sep 27;76(9):1806-9. doi: 10.1021/np400337a. Epub 2013 Sep 5.

Abstract

A new triterpenoid, urmiensolide (1), was isolated from Salvia urmiensis. The structure was elucidated by a combination of 1D and 2D NMR, HRESIMS, and X-ray crystallographic analyses. The absolute configuration was established by comparison of experimental and simulated ECD spectra. Urmiensolide is the first pentacyclic triterpenoid bearing a ε-lactone E-ring. The compound showed in vitro antitrypanosoal activity with an IC₅₀ value of 5.6 μM against the Trypanosoma brucei rhodesiense STIB 900 strain and a selectivity index of 33. A possible biosynthetic pathway of 1 from α-amyrin is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Inhibitory Concentration 50
  • Iran
  • Lactones / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / metabolism
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects
  • Salvia / chemistry*
  • Stereoisomerism
  • Triterpenes* / chemistry
  • Triterpenes* / isolation & purification
  • Triterpenes* / pharmacology
  • Trypanosoma brucei rhodesiense / drug effects

Substances

  • Lactones
  • Triterpenes
  • urmiensolide
  • Oleanolic Acid
  • beta-amyrin