3155. Diginatigenin

Nomenclature

CAS number: 559-57-9
(3β,5β,12β,16β)-3,12,14,16-Tetrahydroxycard-20(22)-enolide; 12-hydroxygitoxigenin; 16-hydroxydigoxigenin.
C23H34O6; mol wt 406.51.
C 67.96%, H 8.43%, O 23.61%.

Description and references

Aglycone of diginatin from Digitalis lanata Ehrk., Scrophulariaceae: Murphy, J. Am. Pharm. Assoc. Sci. Ed. 44, 719 (1955). Aglycone of lanatoside D: Angliker et al., Ann. 607, 131 (1957). Obtained by microbiological conversion of gitoxigenin: Tamm, Gubler, Helv. Chim. Acta 41, 1762 (1958); Okado et al., Chem. Pharm. Bull. 8, 530 (1960). Structure: Linde et al., Helv. Chim. Acta 42, 2040 (1959); Okado et al., Chem. Pharm. Bull. 8, 535 (1960).

Chemical structure

Properties

Needles from water, mp 157°. [α]D20 +34° (methanol). Absorption max (ethanol): 318 nm (log ε 4.18); (98% w/w H2SO4): 230, 310, 390, 490 nm (E1%1cm 160, 130, 210, 85).