Acylated Glycosidic Acid Methyl Esters Generated from the Convolvulin Fraction of Rhizoma Jalapae Braziliensis by Treatment with Indium(III) Chloride in Methanol

Chem Pharm Bull (Tokyo). 2017;65(1):107-111. doi: 10.1248/cpb.c16-00673.

Abstract

Four hexaglycosides of methyl 3S,12S-dihydroxyhexadecanoate (1-4) were provided after treatment of the crude convolvulin fraction from Rhizoma Jalapae Braziliensis (the root of Ipomoea operculata (GOMES) MART., Convolvulaceae) with indium(III) chloride in methanol. The structures of 1-4 were elucidated on the basis of spectroscopic and chemical methods. Their sugar moieties were partially acylated with organic acids including (3S,9R)-3,6:6,9-diepoxydecanoic (exogonic) acid, (E)-2-methylbut-2-enoic (tiglic) acid, and isovaleric acid.

MeSH terms

  • Acids / chemical synthesis*
  • Acids / chemistry
  • Acylation
  • Convolvulaceae / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Indium / chemistry*
  • Methanol / chemistry*
  • Methyl Ethers / chemical synthesis*
  • Methyl Ethers / chemistry
  • Molecular Structure
  • Plant Roots / chemistry
  • Resins, Plant / chemistry*

Substances

  • Acids
  • Glycosides
  • Methyl Ethers
  • Resins, Plant
  • convolvulin
  • Indium
  • indium trichloride
  • Methanol