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
CAS Number	29565-35-3 N[EPA]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:83977 Y
ChemSpider	26286947 Y
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 Y Key: YBPMPRDOWHIVNA-JTSGVHQASA-N Y 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). N verify (what is YN ?) Infobox references

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]

Bufanolide

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:^[4][5]

• 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. Glitsch, H. G.; Pusch, H.; Zylka, Ch. (1990). "The action of 22,23-dihydrobufalin and other cardioactive steroids on contraction and active sodium/potassium transport of sheep cardiac Purkinje fibres". Naunyn-Schmiedeberg's Archives of Pharmacology. 342 (5): 598–604. doi:10.1007/BF00169051. PMID 2090954. S2CID 21474014.
3. IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
4. Bufadienolides at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
5. Cardenolides at the U.S. 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.