) | |
| Names | |
|---|---|
| IUPAC name (1β,3β,5β,11α)-1,3,5-(ethylidynetris(oxy)-11,14-dihydroxy-12,19-dioxobufa-20,22-dienolide | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
SMILES
| |
| Properties | |
| C26H30O9 | |
| Molar mass | 486.517 g·mol−1 |
| Density | 1.49 g/mL |
| Boiling point | 695.2 °C (1,283.4 °F; 968.4 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones (meaning that they bind with carbohydrates to form cardiac glycosides) that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice.[1][2] It is one of five bufadienolides that have been isolated from Kalanchoe daigremontiana.
Toxicity
Crassulaceans are one of the prime sources of bufadienolide cardiac glycosides (including daigremontianin) responsible for an estimated 33% of cattle mortalities related to plant poisoning in South Africa. Crassulacean bufadienolides cause cardiac poisoning, but repeated small doses cause a condition called cotyledonosis,[3] an intoxication affecting nervous and muscular systems of small animals, particularly, sheep in the Karoo area of South Africa.
References
- ^ Wagner, H.; Fischer, M.; Lotter, H. (1985). "Neue Bufadienolide von Kalanchoe daigremontiana Hamet et Perr. (Crassulaceae)" [New Bufadienolides from Kalanchoe daigremontiana Hamet et Perr. (Crassulaceae)]. Zeitschrift für Naturforschung B (in German). 40 (9): 1226–1227. doi:10.1515/znb-1985-0920.
- ^ Wagner, H.; Lotter, H.; Fischer, M. (1986). "Die toxischen und sedierend wirkenden Bufadienolide von Kalanchoe daigremontiana Hamet et Perr" [The Toxic and Sedative Bufadienolides of Kalanchoe daigremontiana Hamet et Perr.]. Helvetica Chimica Acta (in German). 69 (2): 359–367. doi:10.1002/hlca.19860690215.
- ^ Botha, Christo (2016-03-16). "Potential Health Risks Posed by Plant-Derived Cumulative Neurotoxic Bufadienolides in South Africa". Molecules (Basel, Switzerland). 21 (3): 348. doi:10.3390/molecules21030348. ISSN 1420-3049. PMC 6273117. PMID 27102163.