Bufadienolide

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]

Bufadienolide

Names
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
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:83977
ChemSpider	26286947
PubChem CID	3035030
CompTox Dashboard (EPA)	DTXSID70276154
InChI InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 Key: YBPMPRDOWHIVNA-JTSGVHQASA-N InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 Key: YBPMPRDOWHIVNA-JTSGVHQASA-N
SMILES CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5
Properties
Chemical formula	C24H34O2
Molar mass	354.534 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2]

Bufanolide

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:[3][4]

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

References

1. Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 534, 538. ISBN 3-8047-1763-2.
2. IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
3. Bufadienolides at the US National Library of Medicine Medical Subject Headings (MeSH)
4. Cardenolides at the US National Library of Medicine Medical Subject Headings (MeSH)

Further reading

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