Iloneoside: a cytotoxic ditigloylated pregnane glycoside from the leaves of Gongronema latifolium Benth

Nat Prod Res. 2018 Dec;32(24):2882-2886. doi: 10.1080/14786419.2017.1385019. Epub 2017 Oct 16.

Abstract

Gongronema latifolium Benth (Asclepiadaceae) is an edible-green-leafy vegetable with known medicinal value. A chemical investigation of the 80% methanolic extract of the leaves led to the isolation of a new pregnane glycoside: iloneoside (3-O-[6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→14)-β-D-oleandropyranosyl]-11,12-di-O-tigloyl-17β-marsdenin), together with four known constituents. Their chemical structures were determined by spectroscopic analysis. The isolates were tested for their in vitro growth inhibitory activity against human leukemia HL-60 cells. Iloneoside was the most active and gave apoptotic response. Molecular docking analysis demonstrated that iloneoside could be accommodated within hot spots of anti-apoptotic protein Bcl-2. These results suggest G. latifolium as a reliable source of potent anticancer compounds.

Keywords: Benth; antileukemic activity; iloneoside; pregnane glycoside; tigloyl group.

MeSH terms

  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Apocynaceae / chemistry*
  • Apoptosis / drug effects
  • Glycosides / isolation & purification*
  • HL-60 Cells / drug effects
  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*
  • Pregnanes / isolation & purification*

Substances

  • Antineoplastic Agents
  • Glycosides
  • Plant Extracts
  • Pregnanes
  • pregnane glycoside