Constituents

The cardioactive glycoside content of D. purpurea leaves is 0.15% to 0.4% consisting of about 30 different structures. The fresh leaves contain purpurea glycoside A (50% of the glycoside mixture), purpurea glycoside B and glucogitaloxin. These possess at the C-3 position of the aglycone a linear chain of three digitoxose sugar moieties terminated by glucose. On drying, due to enzymatic degradation, the terminal glucose is lost forming digitoxin, gitoxin and gitaloxin respectively. The aglycone gitaloxigenin is less stable and hence digitoxin and gitoxin are the main active components of the drug. Careless storage leads to further hydrolysis resulting in the loss of the three digitoxose sugars leaving the inactive aglycones. Other glycosides present in small quantities involving sugar digitalose and glucose with the same aglycones are present as monoglycosides and diglycosides. Glycosides of gitoxigenin are less active than the corresponding digitoxigenin-derived series. D. purpurea leaves also contain anthraquinone derivatives and some saponins. The total cardenolide content of D. lanata is upto 1% which is 2–3 times that of D. purpurea. The primary glycosides of D. lanata resemble those of D. purpurea, but are acetylated at the digitoxose moiety next to terminal glucose. This acetyl group makes the compounds easier to isolate from the plant material as they crystallize readily. During drying and storage, deacetylation leads to the same products as of D. purpurea. In addition to the three aglycone-based glycosides two additional series of compounds formed on digoxigenin and diginatigenin are found in D. lanata. The primary glycosides containing the acetylated tetrasaccharide unit, glucose-(digitoxose)3, are called lanatosides. Lanatosides A and C based on aglycones digitoxigenin and digoxigenin respectively constitute the major components (50%–70%) of the fresh leaf. Some anthraquinone and flavonoid glycosides have also been characterized in D. lanata.


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