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MEDICINAL CHEMISTRY

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HO<br />

HO<br />

HO<br />

HO<br />

H 3C<br />

CH 3<br />

H<br />

Digitoxigenin (107)<br />

CH 3<br />

H<br />

Gitoxigenin (112)<br />

OH<br />

HO<br />

O<br />

O<br />

CH<br />

H<br />

CH 3<br />

OH<br />

CH 3<br />

OH<br />

Major Cardenolide Aglycones<br />

O<br />

OH<br />

Strophanthidin (114)<br />

O<br />

CH 3<br />

O<br />

O<br />

OH<br />

O<br />

O<br />

HO<br />

HO<br />

Selected Glycones of Cardiac Glycosides<br />

OH<br />

β−D−Digitoxose (115)<br />

H 3C<br />

HO<br />

O<br />

OH<br />

OH<br />

β−D−Rhamnose (117)<br />

HOH2C HO<br />

HO<br />

HO<br />

CH 3<br />

H<br />

Digoxigenin (111)<br />

OH<br />

OH<br />

HO<br />

CH2 H<br />

Oubagenin (113)<br />

O<br />

OH<br />

β−D−Glucose (116)<br />

H 3C<br />

OCH 3<br />

OH<br />

O<br />

OH<br />

β−D−Cymarose (118)<br />

In most cases, the cardiac glycosides of plant origin, the cardenolides, possess a fivemembered<br />

α, β-unsaturated lactone ring, whereas those derived from animal origin, the<br />

bufadienolides, possess a six-membered lactone ring with two conjugated double bonds<br />

(generally referred to as α-pyrone). Bufadienolides are commonly known as toad poison<br />

because several are found in the skin secretion of toad species.<br />

OH<br />

CH 3<br />

OH<br />

CH 3<br />

OH<br />

O<br />

O<br />

O<br />

O

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