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Digitonin is produced from seeds of Digitalis pupurea and other Digitalis species. It is a steroid glycoside consisting of the aglycone digitogenin linked to five sugar residues. Reaction of naturally occurring steroids carrying a 3b-hydroxyl group with digitonin results in an insoluble precipitate. Digitonin has hemolytic activity and is toxic to humans. It permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated beta-hydroxysterols. Digitonin is frequently used for solubilization of membrane proteins and permeabilization of cellular and nuclear membranes. Due to the complexing interactions it can be used for the determination of cholesterol and ergosterol.
