Moniliformin
{{chembox
| verifiedrevid = 412682209
| ImageFile=Moniliformin sodium.png
| ImageSize=120px
| IUPACName=Sodium 3,4-dioxo-1-cyclobuten-1-olate
| OtherNames={{ubl|3-Hydroxycyclobut-3-ene-1,2-dione sodium salt|Moniliformin|Semisquaric acid sodium salt|Sodium semisquarate}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 36957
| InChI = 1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
| InChIKey = KGPQKNJSZNXOPV-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KGPQKNJSZNXOPV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 31876-38-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G5JMQ8SDF8
| PubChem = 40452
| SMILES = O=C1C(\O)=C/C1=O
}}
|Section2={{Chembox Properties
| Formula={{chem2|NaC4HO3}}
| C=4|H=1|Na=1|O=3
| Appearance=Yellow crystalline solid
| Density=
| MeltingPt=Decomposes at 345-355 °C without melting
| Solubility=very good
}}
|Section7={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
|Section9={{Chembox Related
| OtherCompounds=Squaric acid
}}
}}
Moniliformin is the organic compound with the formula {{chem2|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.{{cite journal |doi=10.1021/ja00814a055 |title=Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin |date=1974 |last1=Springer |first1=James P. |last2=Clardy |first2=Jon |last3=Cole |first3=Richard J. |last4=Kirksey |first4=Jerry W. |last5=Hill |first5=Richard K. |last6=Carlson |first6=Robert M. |last7=Isidor |first7=John L. |journal=Journal of the American Chemical Society |volume=96 |issue=7 |pages=2267–2268 |pmid=4833647 }} It is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.
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
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.{{cite journal|title=A molecular mechanism for the toxic action of moniliformin, a mycotoxin produced by fusarium moniliforme|journal=Biochemical Pharmacology|volume=27|issue=4|pages=483–6|doi=10.1016/0006-2952(78)90381-7|pmid=629807|year=1978|last1=Thiel|first1=Pieter G}}[https://fermentek.com/node/621 Moniliformin ] product page from Fermentek[http://www.romerlabs.com/downloads/Mycotoxins/Moniliformin.pdf Moniliformin information leaflet] by Romerlab 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.{{cln|reason=What is "Ultrastructural examination"??? Please someone clarify this jargon!|date=August 2023}} Minks are considered most sensitive mammals to the toxicity of moniliformin.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
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.