Cerberin
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IUPAC name
(3β,5β)-3-[(2-O-acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
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| Other names
2'-Acetylneriifolin
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C32H48O9 | |
| Molar mass | 576.73 g·mol−1 |
| Melting point | 191 °C (376 °F) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Cerberin is a type of cardiac glycoside, a steroidal class found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree (Cerbera odollam) and the sea mango (Cerbera manghas). This class includes digitalis-like agents, channel-blockers that as a group have found historic uses as cardiac treatments, but which at higher doses are extremely toxic; in the case of cerberin, consumption of the C. odollam results in poisoning with presenting nausea, vomiting, and abdominal pain, often leading to death. The natural product has been structurally characterized, its toxicity is clear—it is often used as an intentional human poison in third-world countries, and accidental poisonings with fatalities have resulted from individuals even indirectly consuming the agent—but its potentially therapeutic pharmacologic properties are very poorly described.
Cerberin, like all cardiac glycosides, has as its core a steroid-type set of four carbocycles (all-carbon rings). In cerberin, this steroid core is connected, first, to a separate oxygen-containing lactone ring (shown here, upper right of box), and second, to a sugar substituent (shown in infobox structure, left of image).[subscription required]
There are two types of cardiac glycosides depending on the characteristics of the lactone moiety. Cerberin, with its five-membered ring, belongs to the cardenolide class;[subscription required] cardenolides are 23-carbon steroids with methyl groups at positions 10 and 13 of the steroid ring system, and the appended five-membered butenolide-type of lactone at C-17.
Many types of sugars can be attached to cardiac glycosides; in the case of cerberin, it is an O-acetylated derivative of α-L-thevetose, which is itself a derivative of L-glucose (6-deoxy-3-O-methyl-α-L-glucopyranose). The cardenolide substructure to which the sugar is attached has also been independently characterised, and can be referred to as digitoxigenin (see image), hence, cerberin is, synonymously, (L-2'-O-acetylthevetosyl)digitoxigenin. As well, the non-acetylated structure was independently discovered and named neriifolin, and so cerberin is, synonymously, 2'-acetylneriifolin.
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