Resin glycosides from the flowers of Ipomoea murucoides

J Nat Prod. 2006 Apr;69(4):595-9. doi: 10.1021/np0504457.

Abstract

The CHCl(3)-soluble extract from the flowers of the Mexican medicinal plant Ipomoea murucoides, through preparative-scale recycling HPLC, yielded murucoidins I-V (1-5), which are new pentasaccharides of jalapinolic acid, as well as the known stoloniferin I (6). Saponification of the crude resin glycoside mixture yielded two glycosidic acids, simonic acid B (9) and operculinic acid A (10), and their esterifying residues were composed of the two short-chain fatty acids, 2-methylpropanoic and (2S)-methylbutyric acids. All the isolated compounds (1-6) were characterized through high-field NMR spectroscopy. Compound 4 exhibited marginal cytotoxicity against Hep-2 cells (ED(50) 4 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carbohydrate Sequence
  • Drug Screening Assays, Antitumor
  • Flowers / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Humans
  • Ipomoea / chemistry*
  • Mexico
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Resins, Plant / chemistry
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Glycosides
  • Resins, Plant
  • operculinic acid