Bufadienolide Explained

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest.^[1]

Etymology

See also: Diene. The term derives from the toad genus Bufo that contains bufadienolide glycosides, the suffix -adien- that refers to the two double bonds in the lactone ring, and the ending -olide that denotes the lactone structure. Consequently, related structures with only one double bond are called bufenolides,^[2] and the saturated equivalent is bufanolide.^[3]

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:

• Polycyclic compounds
  • Steroids
    • Cardanolides
      • Cardiac glycosides
        • Bufanolides (includes bufenolides, bufadienolides, bufatrienolides)
          • Proscillaridin
          • Daigremontianin
        • Cardenolides

Further reading

• Steyn, PS; Heerden, FR van (1998). Bufadienolides of plant and animal origin, Natural Product Reports, 15(4):397-413.

Notes and References

1. Book: Mutschler. Ernst. Schäfer-Korting. Monika. Arzneimittelwirkungen. German. Stuttgart. Wissenschaftliche Verlagsgesellschaft. 2001. 8. 534, 538. 3-8047-1763-2.
2. The action of 22,23-dihydrobufalin and other cardioactive steroids on contraction and active sodium/potassium transport of sheep cardiac Purkinje fibres . H. G. . Glitsch . H. . Pusch . Ch. . Zylka . Naunyn-Schmiedeberg's Archives of Pharmacology . 342 . 598–604 . 1990 . 5 . 10.1007/BF00169051 . 2090954 . 21474014 .
3. [IUPAC]