6474. Neriifolin

Nomenclature

CAS number: 466-07-9
(3β,5β)-3-[(6-Deoxy-3-O-methyl-α-l-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide.
C30H46O8; mol wt 534.68.
C 67.39%, H 8.67%, O 23.94%.

Description and references

Cardiac glycoside isolated from Thevetia neriifolia Juss.: M. Frèrejacque, Compt. Rend. 221, 645 (1945); from Cerbera odollam Gaertn.: S. Rangaswami, E. V. Rao, J. Sci. Ind. Res. 16B, 209 (1957); from Thevetia thevetioides seeds: J. L. McLaughlin et al., J. Econ. Entomol. 73, 39 (1980). Pharmacology: K. Mezey, Arch. Int. Pharmacodyn. Ther. 84, 367 (1950); K. K. Chen et al., ibid. 81.

Chemical structure

Properties

Rhombic plates from methanol, mp 218-225°. Also reported as mp 208° (Frèrejacque). [α]D23 -50.2° (CH3OH). uv max (CH3OH): 217 nm (log ε 4.1).

Derivative

2′-Acetate.

Nomenclature

Cerberin; veneniferin; monoacetylneriifolin.
C32H48O9; mol wt 576.72.
C 66.64%, H 8.39%, O 24.97%.

Description and references

Identity of cerberin with monoacetylneriifolin: M. Frèrejacque, Compt. Rend. 226, 835 (1948); of cerberin with veneniferin: M. Frèrejacque, Durgeat, ibid. 228, 1310 (1949).

Properties

Coarse prisms from methanol + water, mp 212-215°. [α]D19 -82° (CHCl3). Sol in alc, CHCl3, acetic acid, ether. Practically insol in water.

Therapeutic Category

Cardiotonic.

Keywords

Cardiotonic