Alepposides, cardenolide oligoglycosides from Adonis aleppica.
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.
Pauli
G F
GF
Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany.
Junior
P
P
Berger
S
S
Matthiesen
U
U
D002240:Carbohydrate Sequence; D002298:Cardenolides / Q000032:analysis*; D006027:Glycosides / Q000032:analysis*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000032:analysis*; D010944:Plants / Q000737:chemistry*
D002298:Cardenolides; D006027:Glycosides; D009844:Oligosaccharides; C080224:alepposide B; C080223:alepposide A