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Cerberin

Cerberin
Chemical structure of 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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[2] Cerberin can be used as a treatment for heart failure and arrhythmia.[3]

Overconsumption of cerberin results in poisoning. Symptoms include nausea, vomiting, and bradycardia, often leading to death.[4] Cerberin containing plants such as Cerbera odollam have historically been used for suicide and homicide in their growth regions due to their high toxicity.

  1. ^ "cerberin | 25633-33-4". ChemicalBook. Retrieved 5 May 2024.
  2. ^ Botelho, Ana Flávia M.; Pierezan, Felipe; Soto-Blanco, Benito; Melo, Marília Martins (February 2019). "A review of cardiac glycosides: Structure, toxicokinetics, clinical signs, diagnosis and antineoplastic potential". Toxicon. 158: 63–68. doi:10.1016/j.toxicon.2018.11.429. PMID 30529380.
  3. ^ "Cardiac glycoside overdose: MedlinePlus Medical Encyclopedia". medlineplus.gov. Retrieved 5 May 2024.
  4. ^ Gaillard, Yvan; Krishnamoorthy, Ananthasankaran; Bevalot, Fabien (December 2004). "Cerbera odollam: a 'suicide tree' and cause of death in the state of Kerala, India". Journal of Ethnopharmacology. 95 (2–3): 123–126. doi:10.1016/j.jep.2004.08.004. PMID 15507323.

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