Secondary metabolites from Triclisia gilletii (De Wild) Staner (Menispermaceae) with antimycobacterial activity against Mycobacterium tuberculosis

Nat Prod Res. 2019 Mar;33(5):642-650. doi: 10.1080/14786419.2017.1402324. Epub 2017 Nov 16.

Abstract

Triclisinone (2), a new ochnaflavone derivative, was isolated from the aerial parts of Triclisia gilletii, along with known drypemolundein B (1) and eight other known compounds. The chemical shifts of drypemolundein B (1) have been partially revised based on reinterpretation of NMR spectroscopic data. The eight other secondary metabolites are composed of: (+)-nonacosan-10-ol (3); stigmasterol (4), 3-O-β-D-glucopyranosylsitosterol (5), 3-O-β-D-glucopyranosylstigmasterol (6); oleanic acid (7); myricetin (8), quercetin (9) and 3-methoxyquercetin (10). Their structures were elucidated using IR, MS, NMR 1D and 2D, 1H and 13C and comparison with literature data. Furthermore, compounds 1, 2, 5, 6, 8, 9 and the crude extract were tested against Mycobacterium tuberculosis. Compounds 1, 2, 8 and 9 displayed moderate to very good activity against resistant strain (codified AC 45) of M. tuberculosis with minimum inhibitory concentrations MICs ranging from 3.90 to 62.5 μg/mL.

Keywords: Menispermaceae; NMR chemical shift analysis; antimycobacterial activity; ochnaflavone derivative.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Cameroon
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology*
  • Menispermaceae / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • Secondary Metabolism

Substances

  • Anti-Bacterial Agents
  • Flavonoids
  • Phytochemicals
  • Plant Extracts
  • ochnaflavone