T-2 Tetraol
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| Category | Mycotoxins |
| Catalog number | BBF-04196 |
| CAS | 34114-99-3 |
| Molecular Weight | 298.33 |
| Molecular Formula | C15H22O6 |
| Purity | ≥95% |
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Description
It is a kind of nature type-A trichothecene mycotoxin, could be used as a reference standard in quantitative analysis of food stuffs.
Specification
| Synonyms | Trichothec-9-ene-3α,4β,8α,15-tetrol, 12,13-epoxy-; (3α,4β,8α)-12,13-Epoxytrichothec-9-ene-3,4,8,15-tetrol; T 2 toxin tetraol; Toxin T 2 tetraol; Toxin T 4 |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (1S,2R,4S,7R,9R,10R,11S,12S)-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4,10,11-triol |
| Canonical SMILES | CC1=CC2C(CC1O)(C3(C(C(C(C34CO4)O2)O)O)C)CO |
| InChI | InChI=1S/C15H22O6/c1-7-3-9-14(5-16,4-8(7)17)13(2)11(19)10(18)12(21-9)15(13)6-20-15/h3,8-12,16-19H,4-6H2,1-2H3/t8-,9+,10+,11+,12+,13+,14+,15-/m0/s1 |
| InChI Key | ZAXZBJSXSOISTF-LYFQSNBGSA-N |
| Source | Trichothecenes are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. |
Properties
| Appearance | White to Off-white Solid |
| Boiling Point | 515.2±50.0°C (Predicted) |
| Melting Point | 197-200°C |
| Density | 1.48±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Acetonitrile, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | T-2 Tetraol is a group A trichothecene mycotoxin. Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. |
Reference Reading
1. Stability of T-2, HT-2, and T-2 tetraol in biological fluids
J G Pace, C F Matson J Anal Toxicol . 1988 Jan-Feb;12(1):48-50. doi: 10.1093/jat/12.1.48.
The stabilities of tritium-labeled T-2, HT-2, and T-2 tetraol were studied in blood and urine at -70 degrees, 4 degrees, and 23 degrees C for 6 months in the presence of EDTA or NaF. Samples were counted with a radiochromatographic scanner and results indicated the stability of T-2 tetraol greater than T-2 greater than HT-2. Toxins were most stable when stored at -70 degrees C, in the presence of NaF, and in urine (pH 6). They were less stable in saline (control, pH 7) and least stable in blood (pH 8). These results suggest that urine and T-2 tetraol are the biological fluid and metabolite of choice for diagnostic purposes.
2. Differential association of T-2 and T-2 tetraol with mammalian cells
J L Middlebrook, D L Leatherman J Pharmacol Exp Ther . 1989 Sep;250(3):860-6.
The interactions of T-2 and its metabolite T-2 tetraol (hereafter tetraol) with CHO (Chinese hamster ovary cells) and CHO ribosomes were studied. T-2 was about 300-fold more potent at inhibiting protein synthesis in CHO than was tetraol. Association of T-2 with CHO was highly specific and achieved a maximum at a concentration producing complete inhibition of protein synthesis. Association of tetraol with CHO was of low specificity, but the specific fraction did correlate with the dose-response curve for protein synthesis inhibition. Binding of both T-2 and tetraol to isolated CHO ribosomes was quantitatively similar and highly specific. With isolated ribosomes, each toxin competed effectively for the binding of the other. Using intact cells, tetraol competed for T-2 cell association, but not the converse. The kinetics at physiological temperature for total and specific T-2 cell association were much more rapid than those for tetraol. Furthermore, the rate of tetraol-cell association was indistinguishable from the rate for cellular uptake of tritiated water. At 0 degrees C, there was a substantial association of T-2 with cells, whereas none was observed with tetraol. The kinetics of dissociation of both toxins from CHO were similar. We conclude that T-2 rapidly crosses the cell membrane of cells and binds to the intracellular target, the ribosomes. In contrast, tetraol is taken up by the cell much more slowly, and many more toxin molecules are found in the cell than there are ribosomes. It would appear that the main physical property of the toxins that brings about these results is the relative hydrophobicities of the molecules.(ABSTRACT TRUNCATED AT 250 WORDS)
3. Distribution of T-2 toxin and HT-2 toxin during experimental feeding of yellow mealworm (Tenebrio molitor)
Florian Kaltner, Manfred Gareis, Nicolo Piacenza, Christoph Gottschalk, Ronald Maul, Karin Schwaiger Mycotoxin Res . 2021 Feb;37(1):11-21. doi: 10.1007/s12550-020-00411-x.
Within the European Union (EU), edible insects need to be approved as "Novel Food" according to Regulation (EU) 2015/2283 and must comply with the requirements of European food law with regard to microbiological and chemical food safety. Substrates used for feeding insects are susceptible to the growth of Fusarium spp. and consequently to contamination with trichothecene mycotoxins. Therefore, the current study aimed to investigate the influence of T-2 and HT-2 toxins on the larval life cycle of yellow mealworm (Tenebrio molitor (L.)) and to study the transfer of T-2, HT-2, T-2 triol and T-2 tetraol in the larvae. In a 4-week feeding study, T. molitor larvae were kept either on naturally (oat flakes moulded with Fusarium sporotrichioides) or artificially contaminated oat flakes, each at two levels (approximately 100 and 250 μg/kg total T-2 and HT-2). Weight gain and survival rates were monitored, and mycotoxins in the feeding substrates, larvae and residues were determined using LC-MS/MS. Larval development varied between the diets and was 44% higher for larvae fed artificially contaminated diets. However, the artificially contaminated diets had a 16% lower survival rate. No trichothecenes were detected in the surviving larvae after harvest, but T-2 and HT-2 were found both in the dead larvae and in the residues of naturally and artificially contaminated diets.
Spectrum
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
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
1H NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 1H
Frequency: 100
Nucleus: 1H
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
