Studies on Cardiac Ingredients of Plants. III. Structural Confirmation and Biological Activity of Reduced Proscillaridins(Organic,Chemical)

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Catalytic hydrogenation of proscillaridin (I) gave five compounds (II-VI) which were successfully separated by reversed-phase high performance liquid chromatography. The structures of II-VI were determined on the basis of the proton, carbon-13 and two dimensional nuclear magnetic resonance (^1H-, ^<13>C- and 2D-NMR) spectra. The configurations of IV and V were determined by circular dichroism spectral analyses. Relationships between the chemical structures and biological activities of I-VI were studied by the use of isolated guinea-pig papillary muscle and an Na^+, K^+-adenosine triphosphatase preparation from dog kidney. The biological activity of each compound was evaluated in terms of pD_2 and pIC_<50> values, while the inotropic speed of each compound was evaluated in terms of T_<50> value. The activities of the reduced compounds (II-VI) were weaker than that of proscillaridin (I), but the inotropic speeds were faster. A significant correlation was obtained between the ^<13>C-NMR chemical shifts of C-24 and the pD_2 values of I-VI (r=0.95,p<0.01), The T_<50> values and ^<13>C-NMR chemical shifts of C-18 also showed a remarkable correlation (r=0.96, p<0.01).
社団法人日本薬学会の論文
1987-05-25