Bufadienolide

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Bufadienolide
File:Bufadienolide skeletal.svg
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)
ChEBI
ChemSpider
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  • 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 checkY
    Key: YBPMPRDOWHIVNA-JTSGVHQASA-N checkY
  • 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
  • CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5
Properties
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).

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

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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]

File:Bufanolide structure.png
Bufanolide

Classification

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

References

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  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  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

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