Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H34O9 |
| Molecular Weight | 466.5214 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]24CO4)OC(=O)CC(C)C
InChI
InChIKey=BXFOFFBJRFZBQZ-QYWOHJEZSA-N
InChI=1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3/t16-,17+,19+,20+,21+,22+,23+,24-/m0/s1
Among the naturally occurring trichothecenes in food and feed, T-2 toxin is a cytotoxic fungal secondary metabolite produced by various species of Fusarium. Following ingestion, T-2 toxin causes acute and chronic toxicity and induces apoptosis in the immune system and fetal tissues. T-2 toxin is usually metabolized and eliminated after ingestion, yielding more than 20 metabolites. Consequently, there is a possibility of human consumption of animal products contaminated with T-2 toxin and its metabolites. The molecular mechanism of inhibition of protein synthesis may be the high affinity of T-2 toxin for the 60S ribosomal subunit.
CNS Activity
Curator's Comment: Known to be CNS penetrant in vitro in . Human data not available
In general the toxic effects on the BBB in vitro were detected at low nanomolar concentrations. However, when comparing the results to the situation in vivo, it has to be taken into account that the used model system does not include serum which can modify the availability of T-2 and HT-2 toxin under in vivo conditions.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| T-2 toxin production by Fusarium tricinctum on solid substrate. | 1971 Apr |
|
| Synthesis of DNA in human fibroblasts treated with T-2 toxin and HT-2 toxin (the trichothecene metabolites of Fusarium species) and the effects of hydroxyurea. | 1980 Feb |
|
| Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells. | 1995 Dec 15 |
|
| Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis. | 2009 Aug |
|
| Oxidative damage and gene expression profile of antioxidant enzymes after T-2 toxin exposure in mice. | 2009 May-Jun |
|
| Cytotoxicity and accumulation of ergot alkaloids in human primary cells. | 2011 Apr 11 |
|
| T-2 toxin is a cytochrome P450 1A1 inducer and leads to MAPK/p38- but not aryl hydrocarbon receptor-dependent interleukin-8 secretion in the human intestinal epithelial cell line Caco-2. | 2011 Jun 18 |
|
| Effects of T-2 toxin and selenium on chondrocyte expression of matrix metalloproteinases (MMP-1, MMP-13), α2-macroglobulin (α2M) and TIMPs. | 2011 Mar |
|
| T-2 toxin induces apoptosis in ovarian granulosa cells of rats through reactive oxygen species-mediated mitochondrial pathway. | 2011 May 10 |
|
| Toxic effects of HT-2 toxin on mouse oocytes and its possible mechanisms. | 2016 Jun |
Patents
Sample Use Guides
in mice toxic effect: Groups of 50 male and 50 female CD-1 mice, six weeks of age, were fed a semi-synthetic diet containing 0, 1.5 or 3.0 mg/kg T-2 toxin for 71 weeks.
in rats toxic effect: 40 weanling male and female Wistar- Porton rats were administered one to eight doses of 0.2-4 mg/kg bw T-2 toxin intragastrically at approximately monthly intervals (duration unspecified).
Route of Administration:
Other
Embryos were cultured in media supplemented with 0.5, 0.75 and 1 ng/ml T-2. Different exposure times were applied [96 h (treatment I) or 24 h following 72 h in toxin-free media (treatment II)]. Blastomere number, nuclear chromatin status and blastocoel formation were investigated in blastocysts. After 24 h of exposure applied following a 72-h culture, blastomeres had a higher level of chromatin damage, although their developmental potential was the same as in the control embryos. In both cases, decreased mitotic rate was found, which resulted in decreased blastomere number even at low toxin concentration.
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138780
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9381
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3544
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5284461
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T-2 mycotoxin
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21259-20-1
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D013605
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DTXSID6021298
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I3FL5NM3MO
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m11251
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PRIMARY | Merck Index |
SUBSTANCE RECORD
