MEDICINAL CHEMISTRY
MEDICINAL CHEMISTRY
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