Three acylated saponins and a related compound from Pithecellobium dulce

J Nat Prod. 1997 Dec;60(12):1269-74. doi: 10.1021/np9703555.

Abstract

Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1 -->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl and alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1-3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-beta-D-xylopyranosyl- (1-->2)-alpha-L-arabinopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1 -->2)]- beta-D-glucopyranoside.

MeSH terms

  • Carbohydrate Sequence
  • Hydrolysis
  • India
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Plants, Medicinal / chemistry*
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Seeds / chemistry
  • Spectrometry, Mass, Fast Atom Bombardment
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification

Substances

  • Saponins
  • Triterpenes