Alepposides, cardenolide oligoglycosides from Adonis aleppica

J Nat Prod. 1993 Jan;56(1):67-75. doi: 10.1021/np50091a010.

Abstract

The structures of novel oligoglycosidic cardenolides, alepposide A (C55H86O23) [1] and alepposide B (C48H74O20) [2], have been deduced mainly by nmr methods. Based on homonuclear (1H and 13C nmr, 1H COSY) and proton-detected heteronuclear shift correlation experiments [HMQC both for 1J(C,H) and for long-range couplings], alepposide A [1] was shown to have the structure strophanthidin-3-O-beta-glucopyranosyl-(1-->4)-O-beta-diginopyranosyl -(1-->4)-O - beta-oleandropyranosyl-(1-->4)-O-beta-digitoxopyranosyl-(1-- >4)-O-beta- digitoxopyranoside. The structure of alepposide B [2] was established as strophanthidin-3-O-beta-glucopyranosyl-(1-->4)-O-beta-oleandropyranos yl- (1-->4)-O-beta-digitoxopyranosyl-(1-->4)-O-beta-digitoxopyranos ide.

MeSH terms

  • Carbohydrate Sequence
  • Cardenolides / analysis*
  • Glycosides / analysis*
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / analysis*
  • Plants / chemistry*

Substances

  • Cardenolides
  • Glycosides
  • Oligosaccharides
  • alepposide B
  • alepposide A