Cerberin

Cerberin
Names
IUPAC name
14-Hydroxy-5β-card-20(22)-enolid-3β-yl α-D-quinovopyranoside 2-acetate
Systematic IUPAC name
(2R,3S,4R,5S,6S)-5-Hydroxy-2-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]-4-methoxy-6-methyloxan-3-yl acetate
Other names
2′-Acetylneriifolin
(3β,5β)-3-[(2-O-Acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C32H48O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h14,17,20-24,26-29,35-36H,6-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,24+,26-,27+,28-,29-,30-,31+,32-/m0/s1
    Key: UYQMTWMXBKEHJQ-IVHDSYOHSA-N
  • CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
Properties
C32H48O9
Molar mass 576.727 g·mol−1
Melting point 212 °C (414 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cerberin is a type of cardiac glycoside, found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree (Cerbera odollam) and the sea mango (Cerbera manghas). As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase. Cerberin can be used as a treatment for heart failure and arrhythmia.

Overconsumption of cerberin results in poisoning. Symptoms include nausea, vomiting, and bradycardia, often leading to death. Cerberin containing plants such as Cerbera odollam have historically been used for suicide and homicide in their growth regions due to their high toxicity.