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Paper | Special issue | Vol 39, No. 2, 1994, pp.669-686
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)59
Digitalis-like Compounds of Toad Bile: Sulfation and Reduction of Bufadienolides Decrease Potency of Na+, K+- ATPase Inhibition

Shoei-sheng Lee, Fadila Derguini, Reimar C. Bruening, Koji Nakanishi,* Earl T. Wallick, Toshifumi Akizawa, Caryn S. Rosenbaum, and Vincent P. Butler, Jr.

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, U.S.A.

Abstract

The most abundant digitalis-like compound in the bile of the toad, Bufo marinus, was identified as 12β-hydroxytetrahydroresibufogenin-3-sulfate. Other digitalis-like compounds in toad bile had the properties of bufadienolide-3-sulfates, the most abundant of which was found to be marinobufagin-3-sulfate, a compound previously described only as a trace component in toad skin. Both compounds were less effective than unconjugated marinobufagin in the inhibition of Na+,K+-ATPase enzymatic activity and of Na+,K+-ATPase ouabain binding. This study suggests that sulfation of the A ring and reduction of the lactone ring may be responsible for bufadienolide inactivation in vivo.