Cardiac glycosides are composed of two structural features: the sugar (glycone) and the nonsugar (aglycone–steroid) moieties.
Chemically, the aglycone part of cardiac glycosides is a steroidal moiety.
They are either C23 or C24 steroids, because of either five membered or six membered lactone ring respectively.
Those with five membered lactone ring are called as cardenolides, while with six membered lactone ring and two double bond which is attached at the 17 α-position are termed as bufadienolides.
The lactone of cardenolide contain only one double bond and is attached to steroidal nucleus through C - 17 α-position.
The term bufadienolide has been derived from bufalin, obtained from skin of toads.
The presence and attachment through a specific position to steroidal nucleus of the lactone is essential for proper cardiac activity.
The steroid nucleus has hydroxyls at 3- and 14-positions of which the sugar attachment uses the 3-OH group. 14-OH is normally unsubstituted.
Many genins have OH groups at 12- and 16-positions.
These additional hydroxyl groups influence the partitioning of the cardiac glycosides into the aqueous media and greatly affect the duration of action.
The size and degree of unsaturation varies with the source of the glycoside.
The sugar part is attached through C - 3, β OH-linkage. Various types of sugars have been reported to be present in cardiac glycosides, such as glucose, fucose, rhamnose, digitoxose, digitalose, cymarose, sarmentose, thevatose, etc.
Though, the sugars do not potentiate the medicinal activity of aglycone part, they are useful in solubilization of aglycone thereby, beneficial in absorption and distribution in the body.
These sugars predominantly exist in the cardiac glycosides in the β-conformation.
The presence of acetyl group on the sugar affects the lipophilic character and the kinetics of the entire glycoside.
It has been also shown that increase in number of OH groups on aglycone leads to quicker onset of action and enhanced metabolism.
Though, the number of plants contain cardiac glycosides, they are broadly restricted to angiosperms. Leguminosae, Sterculiaceae, Cruciferae, Scrophulariaceae, Euphorbiaceae etc. show presence of cardenolides.
Very few families like Liliaceae and Ranunculaceae contain bufadienolides.
The cardenolides have an unsaturated butyrolactone ring while the bufadienolides have a pyrone ring.
References:
1. Trease D. & Evans W.C.: Text Book of Pharmacognosy: W.B. Saunders.
2. Tyler V. E. Brady L. R. & Robbers J. E.: Pharmacognosy; Lea Feibger, USA.
3. Biren shah, A. K. Seth; Text Book of Pharmacognosy; Elsevier Publishers, Haryana.
4. Kokate C. K., Purohit A. P. & Gokhale S. B.: Pharmacognosy; Nirali Publications, Pune.
5. Harbone J. B.: Phytochemical Methods: A guide to modern techniques Analysis: Chapman & Hall, London.
6. Bruneton J.: Pharmacognosy, Phytochemistry, Medicinal Plants: Intercept Limited.