Moniliformin

Moniliformin is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.

Moniliformin
Names
IUPAC name
Sodium 3,4-dioxo-1-cyclobuten-1-olate
Other names
  • 3-Hydroxycyclobut-3-ene-1,2-dione sodium salt
  • Moniliformin
  • Semisquaric acid sodium salt
  • Sodium semisquarate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H checkY
    Key: KGPQKNJSZNXOPV-UHFFFAOYSA-N checkY
  • InChI=1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
    Key: KGPQKNJSZNXOPV-UHFFFAOYAJ
  • O=C1C(\O)=C/C1=O
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
 Squaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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. Moniliformin 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.[1][2][3] 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. Minks are considered most sensitive mammals to the toxicity of moniliformin.[4] Chemically speaking, it is the sodium salt of deoxysquaric acid (the other name of that acid is semisquaric acid).

Physicochemical information

Moniliformin is soluble in water and polar solvents, such as methanol.

λmax: 226 nm and 259 nm in methanol.

See also

Sources and references
  1. 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.
  2. Moniliformin product page from Fermentek
  3. Moniliformin information leaflet by Romerlab
  4. 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
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