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]
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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
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3D model (JSmol)
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CompTox Dashboard (EPA)
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| 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).
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Etymology
editThe 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
editAccording to MeSH, bufadienolides and bufanolides are classified as follows:[4][5]
- Polycyclic compounds
- Steroids
- Cardanolides
- Cardiac glycosides
- Bufanolides (includes bufenolides, bufadienolides, bufatrienolides)
- Cardenolides
- Cardiac glycosides
- Cardanolides
- Steroids
References
edit- ^ Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 534, 538. ISBN 3-8047-1763-2.
- ^ 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.
- ^ IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
- ^ Bufadienolides at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
- ^ Cardenolides at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Further reading
edit- Steyn, PS; Heerden, FR van (1998). Bufadienolides of plant and animal origin, Natural Product Reports, 15(4):397-413.
