Acylated glycosides of hydroxy fatty acid methyl esters generated from the crude resin glycoside (pharbitin) of seeds of Pharbitis nil by treatment with indium(III) chloride in methanol

J Nat Prod. 2010 Nov 29;73(11):1846-52. doi: 10.1021/np1004888. Epub 2010 Oct 12.

Abstract

Treatment of the crude ether-insoluble resin glycoside (convolvulin) from seeds of Pharbitis nil (Pharbitis Semen), called pharbitin, with indium(III) chloride in methanol provided seven oligoglycosides of hydroxy fatty acid methyl esters partially acylated by 2-methyl-3-hydroxybutyric (nilic) and 2S-methylbutyric acids. Their structures were elucidated on the basis of NMR and MS data and chemical conversions.

MeSH terms

  • Esters
  • Fatty Acids / chemistry
  • Fatty Acids / isolation & purification*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Indium / pharmacology
  • Ipomoea nil / chemistry*
  • Methanol
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal
  • Resins, Plant / chemistry
  • Resins, Plant / isolation & purification*
  • Seeds / chemistry

Substances

  • Esters
  • Fatty Acids
  • Glycosides
  • Resins, Plant
  • pharbitin
  • Indium
  • indium trichloride
  • Methanol