(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Chemical Properties

Melting point:

208-210°

alpha 

D24 -72.0 ±1.5° (c = 1.48 in methanol)

Boiling point:

1035.6±65.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

-20°C

pka

12.79±0.70(Predicted)

form 

solid

Safety Information

WGK Germany 

3

(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Usage And Synthesis

Originator

Thevetin A,SigmaAldrich

Uses

Thevetin A is a cardiac glycoside that can lead to intoxication and poisoning.

Definition

ChEBI: Thevetin A is a trisaccharide derivative and a gentiobiosylthevetoside. It is functionally related to a cannogenin.

Manufacturing Process

A mixture of Thevetins A and B was prepared by extraction from seeds of Thevetia neriifolia.
100 g of this mixture are dissolved in 1500 ml of aqueous ethanol at 96°C. Then 50 ml of a 30% solution of sodium bisulfite is added. The solution is left for about 1 hour and is then diluted with 3 L of water. The resulting solution is extracted 3 times in reflux extraction apparatus with 4 L of n-butanol as the extraction solvent. Thevetin A passes into said n-butanol which is then washed with distilled water and evaporated to dryness. The crude thevetin A is recrystallized in absolute ethanol (100 ml) and precipitating with 10 volumes of isopropyl oxide. The residual thevetin B of the bisulfite solution also may be prepared.

Therapeutic Function

Cardiotonic

Biological Activity

Cardiac glycosides found in yellow oleander including thevetin A, have potential to tre at patients with heart failure and atrial fibrillation.

Purification Methods

Crystallise thevetin A from H2O. The acetyl derivative crystallises from MeOH/Et2O at -15o with m 145-149o, and [] D -54.2o (c 1.86, CHCl3). [Block et al. Helv Chim Acta 43 652 1960, 13C NMR: Tori et al. Tetrahedron Lett 717 1977, Beilstein 18 III/IV 2552, 18/4 V 439.]