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Structure Determination of Saponins with Cardiotonic Activity by Circular Dichroism

Endogenous Ouabain Saga

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Part of the book series: Proceedings of the Phythochemical Society of Europe ((PPSE,volume 45))

Abstract

Cardenolides including ouabain and digoxin are plant steroids that occur in nature as glycosides. They exhibit powerful cardiotonic activity by inhibiting Na+,K+-ATPase (the sodium pump) in mammalian and insect cells and as such have long been used for the treatment of certain cardiac disorders. The chemical structures of cardenolides are characterized by 3-β-OH (or 3β-O-sugar), C/D—cis-ring juncture, 14β-OH, and 17β-unsaturated lactone ring (Figure 1) [1,2]. Most of the sugars isolated after hydrolysis of cardiac glycosides are unique and have only rarely been found elsewhere in nature. Based on optical rotation data it was suggested that all natural cardiac glycosides of D(L) -sugars are β(α) glycosides at the aglycone-sugar linkage. Although the cardenolides have been mostly purified from plants and toads, their conserved and specific binding site located on the catalytic sub-unit of the mammalian plasma membrane sodium pump led to the speculation that there might exist the mammalian counterparts of cardenolides. that control the physiological functions of sodium pump[1,3].

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Dong, JG., Kawamura, A., Guo, J., Zanze, I.A., Nakanishi, K., Berova, N. (2000). Structure Determination of Saponins with Cardiotonic Activity by Circular Dichroism. In: Oleszek, W., Marston, A. (eds) Saponins in Food, Feedstuffs and Medicinal Plants. Proceedings of the Phythochemical Society of Europe, vol 45. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9339-7_9

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  • DOI: https://doi.org/10.1007/978-94-015-9339-7_9

  • Publisher Name: Springer, Dordrecht

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