Moniliformin
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| Category | Mycotoxins |
| Catalog number | BBF-03836 |
| CAS | 71376-34-6 |
| Molecular Weight | 120.00 |
| Molecular Formula | C4HO3Na |
| Purity | >98% |
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Description
Moniliformin, a kind of water-soluble mycotoxin, could be obtained from sorts of Fusarium and has been found to exhibit toxicity to splenocytes, cardiac and skeletal myocytes.
Specification
| Related CAS | 39284-13-4 (free acid) |
| Synonyms | 1-Hydroxycyclobut-1-ene-3,4-dione |
| Storage | Store at 2-8°C |
| IUPAC Name | sodium;3,4-dioxocyclobuten-1-olate |
| Canonical SMILES | C1=C(C(=O)C1=O)[O-].[Na+] |
| InChI | InChI=1S/C4H2O3.Na/c5-2-1-3(6)4(2)7;/h1,5H;/q;+1/p-1 |
| InChI Key | FERDNJVXTWPNSA-UHFFFAOYSA-M |
| Source | Moniliformin is produced by a number of fungi of the Fusarium species. It can by found in contaminated cereal crops. |
Properties
| Appearance | Yellow Crystalline Solid |
| Boiling Point | 239.6°C at 760 mmHg |
| Melting Point | 340-356°C (dec.) |
| Solubility | Soluble in Metanol, Water |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Lethal Dose | LD50: 20.9 mg/kg (Mouse, Intraperitoneal). |
| Mechanism Of Toxicity | Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate. Moniliformin has also been shown to interfere with carbohydrate metabolism by inhibiting transketolase and aldose reductase. Moniliformin is also known to cause DNA damage, inducing chromatid breaks, chromosome breaks, and chromatid exchanges. |
Reference Reading
1. Mycotoxins: occurrence, toxicology, and exposure assessment
A J Ramos, S Marin, V Sanchis, G Cano-Sancho Food Chem Toxicol . 2013 Oct;60:218-37. doi: 10.1016/j.fct.2013.07.047.
Mycotoxins are abiotic hazards produced by certain fungi that can grow on a variety of crops. Consequently, their prevalence in plant raw materials may be relatively high. The concentration of mycotoxins in finished products is usually lower than in raw materials. In this review, occurrence and toxicology of the main mycotoxins are summarised. Furthermore, methodological approaches for exposure assessment are described. Existing exposure assessments, both through contamination and consumption data and biomarkers of exposure, for the main mycotoxins are also discussed.
2. Survey of moniliformin in wheat- and corn-based products using a straightforward analytical method
Ruud van Dam, Martien Spanjer, Joyce de Stoppelaar, Patricia López, Hans Mol, Monique de Nijs, Marta Herrera Mycotoxin Res . 2017 Nov;33(4):333-341. doi: 10.1007/s12550-017-0287-9.
A straightforward analytical method was developed and validated to determine the mycotoxin moniliformin in cereal-based foods. Moniliformin is extracted with water and quantified with liquid chromatography tandem mass spectrometry, and its presence confirmed with liquid chromatography-Orbitrap-high-resolution mass spectrometry. The method was validated for flour, bread, pasta and maize samples in terms of linearity, matrix effect, recovery, repeatability and limit of quantification. Quantification was conducted by matrix-matched calibration. Positive samples were confirmed by standard addition. Recovery ranged from 77 to 114% and repeatability from 1 to 14%. The limit of quantification, defined as the lowest concentration tested at which the validation criteria of recovery and repeatability were fulfilled, was 10 μg/kg. The method was applied to 102 cereal-based food samples collected in the Netherlands and Germany. Moniliformin was not detected in bread samples. One of 22 flour samples contained moniliformin at 10.6 μg/kg. Moniliformin occurred in seven out of 25 pasta samples at levels around 10 μg/kg. Moniliformin (MON) was present in eight out of 23 maize products at levels ranging from 12 to 207 μg/kg.
3. Moniliformin in Norwegian grain
S Uhlig, J Jarp, A C Gutleb, A Parich, M Torp, R Krska Food Addit Contam . 2004 Jun;21(6):598-606. doi: 10.1080/02652030410001704258.
Norwegian grain samples (73 oats, 75 barley, 83 wheat) from the 2000-02 growing seasons were examined for contamination with moniliformin, and the association between the fungal metabolite and the number of kernels infected with common Fusaria was investigated. Before quantification of moniliformin using ion pairing reversed-phase high-performance liquid chromatography with diode array ultraviolet light detection, all samples were extracted using acetonitrile/water (84/16) and disposable strong anion exchange columns used for clean up. The limit of detection was 40 microg kg(-1). Moniliformin was found in 25, 32 and 76% of the barley, oats and wheat samples, respectively. The maximum concentrations of moniliformin in barley, oats and wheat were 380, 210 and 950 microg kg(-1), respectively. At the same time, the prevalence and infection level of the moniliformin-producing F. avenaceum/arthrosporioides was as high as 100 and >53% on average, respectively. Moniliformin concentrations were significantly correlated to the variables grain species, growing season and infection with F. avenaceum/arthrosporioides and F. culmorum. The survey indicates that the prevalence of moniliformin in Norwegian grain is high, especially in wheat. On the other hand, field conditions in Norway do not seem to favour contamination of grain with high levels of moniliformin.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C4H2O3
Molecular Weight (Monoisotopic Mass): 98.0004 Da
Molecular Weight (Avergae Mass): 98.0569 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C4H2O3
Molecular Weight (Monoisotopic Mass): 98.0004 Da
Molecular Weight (Avergae Mass): 98.0569 Da
LC-MS/MS Spectrum - 35V, Negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C4H2O3
Molecular Weight (Monoisotopic Mass): 98.0004 Da
Molecular Weight (Avergae Mass): 98.0569 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C4H2O3
Molecular Weight (Monoisotopic Mass): 98.0004 Da
Molecular Weight (Avergae Mass): 98.0569 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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