(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

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

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.]