6826. Oleandrin

Nomenclature

CAS number: 465-16-7
(3β,5β,16β)-16-(Acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-α-l-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide; neriolin; Corrigen; Folinerin.
C32H48O9; mol wt 576.72.
C 66.64%, H 8.39%, O 24.97%.

Description and references

Cytotoxic glycoside from the leaves of Nerium oleander L., Apocynaceae (Laurier rose). Component of the commercial oleander extract, Anvirzel. Isoln: Tanret, Compt. Rend. 194, 914 (1932); Neumann, Ber. 70, 1547 (1937). Prepn by enzymic hydrolysis of urechitoxin: Hassall, J. Chem. Soc. 1951, 3193. Structure: Tschesche, Ber. 70, 1554 (1937); Krasso et al., Helv. Chim. Acta 46, 1691 (1963). LC/MS/MS determn in tissues and biological fluids: E. R. Tor et al., J. Agric. Food Chem. 53, 4322 (2005). Apoptotic activity study: Y. Sreenivasan et al., Biochem. Pharmacol. 66, 2223 (2003). Pharmacology: D. Ni et al., J. Exp. Ther. Oncol. 2, 278 (2002). Review of toxicity: S. D. Langford, P. J. Boor, Toxicology 109, 1-13 (1996).

Chemical structure

Properties

Crystals from dil methanol, mp 250°. [α]D25 -48.0° (c = 1.3 in methanol). uv max: 220 nm (log ε 4.20). Practically insol in water. Sol in alcohol, chloroform.

Derivative

Desacetyloleandrin.

Nomenclature

CAS number: 36190-93-9
C30H46O8; mol wt 534.68.
C 67.39%, H 8.67%, O 23.94%.

Properties

Leaflets from alcohol, mp 238-240°. [α]D18 -24.9°.

Therapeutic Category

Cardiotonic; diuretic.

Keywords

Cardiotonic; Diuretic; Steroids