Antitrypanosomal quinoline alkaloids from the roots of Waltheria indica

J Nat Prod. 2014 Oct 24;77(10):2304-11. doi: 10.1021/np5006554. Epub 2014 Oct 14.

Abstract

Chemical investigation of the dichloromethane root extract of Waltheria indica led to the isolation and characterization of 10 quinoline alkaloids, namely, 8-deoxoantidesmone (1), waltheriones E-L (2-9), and antidesmone (10). Among these, compounds 2-9 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C NMR, HSQC, HMBC, COSY, and NOESY experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by comparison of experimental and TDDFT-calculated ECD spectra. In addition, the isolated constituents were evaluated for their in vitro antitrypanosomal activity. Compounds 4, 5, and 8 showed potent and selective growth inhibition toward Trypanosoma cruzi with IC50 values between 0.02 and 0.04 μM. Cytotoxicity for mouse skeletal L-6 cells was also determined for these compounds.

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Animals
  • Inhibitory Concentration 50
  • Malvaceae / chemistry*
  • Mice
  • Molecular Structure
  • Niger
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Quinolines* / chemistry
  • Quinolines* / isolation & purification
  • Quinolines* / pharmacology
  • Trypanocidal Agents* / chemistry
  • Trypanocidal Agents* / isolation & purification
  • Trypanocidal Agents* / pharmacology
  • Trypanosoma / drug effects*

Substances

  • Alkaloids
  • Quinolines
  • Trypanocidal Agents