What is the Difference Between Cardenolides and Bufadienolides?

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Cardenolides and bufadienolides are two types of chemical compounds with steroid structures, known as cardiac glycosides, which are found in plants and have various medicinal uses. The key difference between cardenolides and bufadienolides lies in their chemical structure:

  • Cardenolides contain an "enolide," which is a five-membered ring with a single double bond, at the lactone end.
  • Bufadienolides contain a "dienolide," which is a six-membered ring with two double bonds, at the lactone end.

Cardenolides are produced only by plants, while bufadienolides are produced by both plants and animals. Some examples of plants containing cardenolides include Convallaria majalis (Lily of the Valley), Antiaris toxicaria (upas tree), Strophanthus kombe (Strophanthus vine), Digitalis lanata (purple foxglove), and Nerium oleander (oleander tree). Bufadienolides, on the other hand, have been derived from the venom of the cane toad Rhinella marina.

Both cardenolides and bufadienolides have been used in medicine. Cardenolides, for example, are commonly used for the treatment of congestive heart failure and other heart-related conditions. Meanwhile, bufadienolides have been used in Chinese medicine for topical anesthetic effects and as an antiarrhythmic drug.

Comparative Table: Cardenolides vs Bufadienolides

Cardenolides and bufadienolides are two types of chemical compounds with steroid structures, known as cardiac glycosides. They are derived from a parent compound called cardiac glycoside and are found in plants, with bufadienolides also present in animals. Here is a table highlighting the differences between cardenolides and bufadienolides:

Feature Cardenolides Bufadienolides
Origin Produced only by plants Produced by both plants and animals
Steroid Structure Yes Yes
Cardiac Glycoside Derived from cardiac glycoside Derived from cardiac glycoside
Aglycone Types Contain a five- or six-membered lactone ring Contain a five- or six-membered lactone ring
Therapeutic Use Cardenolides are therapeutically more useful than bufadienolides Bufadienolides are less available and cause mortality rates that are five times higher than cardenolides
Toxicity Both are toxic and can cause cardiac arrest Both are toxic and can cause cardiac arrest

In summary, the key difference between cardenolides and bufadienolides is their origin, with cardenolides being produced only by plants, while bufadienolides are produced by both plants and animals.