Synthesis of acetates of gomphogenin and gomphoside and evaluation of structure-activity relationships
1995
Summary Acetates of gomphogenin and gomphoside have been synthesized and their structures established by NMR measurements, optical rotation, mass and infrared spectrometry. The kinetic and equilibrium parameters of the inhibitory interaction of the compounds with guinea-pig heart muscle Na + /K + -ATPase are presented and discussed. Acetylation of the 2α-OH group in gomphogenin or its 3β-acetate increases the binding affinity by 15- and 24-fold, respectively, whereas 3β- O -acetylation of gomphogenin and its 2α-acetate increases the affinity only two- and threefold. Acetylation of 4′-OH or 3′,4′-OH of gomphoside, instead, reduces the high affinity of gomphoside towards Na + /K + -ATPase.
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