Cyanogenic and non-cyanogenic pyridone glucosides from Acalypha indica (Euphorbiaceae)

Phytochemistry. 2009 Jan;70(2):270-7. doi: 10.1016/j.phytochem.2008.12.011. Epub 2009 Jan 20.

Abstract

Seven cyanopyridone derivatives and one corresponding seco compound have been isolated from a methanolic extract of the inflorescences and leaves of Acalypha indica L. (Euphorbiaceae). The absolute configuration of the main cyanogenic glucoside acalyphin, (-)-(5R,6S)-5-cyano-5-beta-d-glucopyranosyloxy-6-hydroxy-4-methoxy-1-methyl-2(5,6-dihydro)-pyridone, was deduced from an X-ray crystallographic study. In addition, the 6R-epimer of acalyphin, epiacalyphin, and the corresponding pair of N-demethyl derivatives were isolated. The corresponding amide of acalyphin and a 1',2'-glucosyl-fused epiacalyphin amide were isolated from air-dried material. Structural elucidation was performed by means of (1)H and (13)C NMR-spectra, chiroptical methods such as CD-spectroscopy and optical rotation. Two further corresponding derivatives, an aromatized compound and an open-chain structure, were isolated from the aqueous phase.

MeSH terms

  • Amides / chemistry
  • Crystallography, X-Ray
  • Euphorbiaceae / chemistry*
  • Glucosides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nitriles / chemistry*
  • Pyridones / chemistry*

Substances

  • Amides
  • Glucosides
  • Nitriles
  • Pyridones
  • cyanogen