Moniliformin is the organic compound with the formula M[C4HO3] (M+ = K+ or Na+). Both the sodium and potassium salts are generally hydrated, e.g. . In terms of its structure, it is the alkali metal salt of the conjugate base of 3-hydroxy-1,2-cyclobutenedione (the enolate of 1,2,3-cyclobutanetrione), a planar molecule related to squaric acid.[1] It is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.
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| Names | |
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| IUPAC name
Sodium 3,4-dioxo-1-cyclobuten-1-olate
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| NaC4HO3 | |
| Molar mass | 120.039 g·mol−1 |
| Appearance | Yellow crystalline solid |
| Melting point | Decomposes at 345-355 °C without melting |
| very good | |
| Related compounds | |
Related compounds
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Squaric acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Moniliformin is formed in many cereals by a number of Fusarium species that include Fusarium moniliforme, Fusarium avenaceum, Fusarium subglutinans, Fusarium proliferatum, Fusarium fujikuroi and others. It is mainly cardiotoxic and causes ventricular hypertrophy.
Biochemistry
editMoniliformin actually causes competitive inhibition of the activity of pyruvate dehydrogenase complex of respiratory reaction, which prevents pyruvic acid, product of glycolysis, to convert to acetyl-CoA.[2][3][4] Ultrastructural examination of right ventricular wall of 9 month old female mink (Mustela vison) fed acute doses of moniliformin (2.2 and 2.8 mg/kg diet) and sub-acute doses (1.5 to 3.2 mg/kg diet) reveals significant damage to myofiber, mitochondria, Z and M lines and sarcoplasmic reticulum as well as increased extracellular collagen deposition.[clarification needed] Minks are considered most sensitive mammals to the toxicity of moniliformin.[5] Chemically speaking, it is the sodium salt of deoxysquaric acid (the other name of that acid is semisquaric acid).
Physicochemical information
editMoniliformin is soluble in water and polar solvents, such as methanol.
See also
editSources and references
edit- ^ Springer, James P.; Clardy, Jon; Cole, Richard J.; Kirksey, Jerry W.; Hill, Richard K.; Carlson, Robert M.; Isidor, John L. (1974). "Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin". Journal of the American Chemical Society. 96 (7): 2267–2268. doi:10.1021/ja00814a055. PMID 4833647.
- ^ Thiel, Pieter G (1978). "A molecular mechanism for the toxic action of moniliformin, a mycotoxin produced by fusarium moniliforme". Biochemical Pharmacology. 27 (4): 483–6. doi:10.1016/0006-2952(78)90381-7. PMID 629807.
- ^ Moniliformin product page from Fermentek
- ^ Moniliformin information leaflet by Romerlab
- ^ Morgan MK, Fitzgerald SD, Rottinghaus GE, Bursian SJ and Aulerich RJ. 1999. Toxic effects to mink of moniliformin extracted from Fusarium fujikuroi culture material. Veterinary and Human Toxicology 1(1):pp-1-5