Bufadienolide

Bufadienolide
File:Bufadienolide skeletal.svg
IUPAC name 5-[(5R, 8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
PubChem	3035030
SMILES
InChI
InChI key	YBPMPRDOWHIVNA-JTSGVHQASA-N
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C24H34O2
Molar mass	354.53 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bufadienolide is a type of steroid. 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 gylcosides. Both bufadienolides and their glycosides are toxic; specifically, they are heart-arresting.

Etymology

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, and the saturated equivalent is bufanolide.

Classification

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

• Polycyclic compounds

• Steroids

• Cardanolides

• Cardenolides
• Cardiac glycosides

• Bufanolides

• Bufenolides
• Bufadienolides

• Proscillaridin
• Daigremontianin

• Cardenolides

Note that cardenolides have been classified under cardanolides as well as cardiac glycosides in this classification.