Cardiac Glycosides. 1.1 A Systematic Study of Digitoxigenin d-Glycosides

Dwight S. Fullerton, Masaru Kihara, Tamboue Deffo, Eitaro Kitatsuji, Khalil Ahmed, Bruce Simat, Arthur H.L. From, Douglas C. Rohrer

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22 Scopus citations

Abstract

A series of digitoxigenin glycosides was studied: five with β-D-sugars varying stepwise in sugar structure from β-D-digitoxose to β-D-galactose, including one β-D/α-D pair. I50 values for these glycosides and digitoxigenin were determined with hog kidney Na+,K+-ATPase. These data suggest a major and unexpected role for 4'-OH conformation in the sugar. All the glycosides with an equatorial 4'-OH were more active than the two with the 4'-OH axial [digitoxigenin β-D-galactoside (6) I50 = 6.45 X 10-8 M; digitoxigenin 2'-deoxy-α-D-rtbo-hexopyranoside (α-3a) I50 = 9.33 X 10-8M; digitoxigenin I50 = 1.17 X 10-7 M], Stereochemistry of the 3'-OH had much less of an activity role than that of the 4',-OH, in contrast to existing models of “sugar-site”binding.

Original languageEnglish (US)
Pages (from-to)256-261
Number of pages6
JournalJournal of medicinal chemistry
Volume27
Issue number3
DOIs
StatePublished - Jun 1984

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