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Daigremontianin

Names
IUPAC name (1β,3β,5β,11α)-1,3,5-(ethylidynetris(oxy)-11,14-dihydroxy-12,19-dioxobufa-20,22-dienolide
Identifiers
CAS Number	98205-50-6
3D model (JSmol)	Interactive image Interactive image
ChemSpider	112839
PubChem CID	127105
UNII	N5SG3A9FLM
CompTox Dashboard (EPA)	DTXSID40897532
InChI InChI=1S/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1Key: PHOLEJIIASOWOL-SQBSQXRJSA-N InChI=1/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1Key: PHOLEJIIASOWOL-SQBSQXRJBB
SMILES C12(CC2C(C=C3)=COC3=O)(O)4()CC5(OC6(C)O7)C7C(O6)5(C=O)4()(O)C1=O O=C\1O\C=C(/C=C/1)65(C(=O)(O)73(C=O)C4(OC2(O(CC3O2)C4)C)CC75(O)CC6)C
Properties
Chemical formula	C26H30O9
Molar mass	486.517 g·mol
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 , 100 kPa). Y verify (what is  ?) Infobox references

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. 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, an intoxication affecting nervous and muscular systems of small animals, particularly, sheep in the Karoo area of South Africa.

References

1. 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. S2CID 95146056.
2. 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.
3. 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.

External links

• Canadian Biodiversity Information Facility

• Bufanolides
• Diols
• Aldehydes
• Ketones