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
| Molecular Formula | C24H34O9 |
| Molecular Weight | 466.5214 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|
| Direct and reflex cardiovascular effects of trichothecene mycotoxins. | 1987 |
|
| Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells. | 1995 Dec 15 |
|
| [Protective effect of selenium against T-2 toxin-induced inhibition of chondrocyte aggrecan and collagen II synthesis]. | 2006 Apr |
|
| T-2 toxin induces apoptosis, and selenium partly blocks, T-2 toxin induced apoptosis in chondrocytes through modulation of the Bax/Bcl-2 ratio. | 2006 Apr |
|
| Promotion of the articular cartilage proteoglycan degradation by T-2 toxin and selenium protective effect. | 2008 Jan |
|
| Metabolism and cytotoxic effects of T-2 toxin and its metabolites on human cells in primary culture. | 2009 Apr 28 |
|
| Fusarial toxin-induced toxicity in cultured cells and in isolated mitochondria involves PTPC-dependent activation of the mitochondrial pathway of apoptosis. | 2009 Aug |
|
| Oxidative stress induction by T-2 toxin causes DNA damage and triggers apoptosis via caspase pathway in human cervical cancer cells. | 2009 Aug 3 |
|
| Role of GRP78/BiP degradation and ER stress in deoxynivalenol-induced interleukin-6 upregulation in the macrophage. | 2009 Jun |
|
| Oxidative damage and gene expression profile of antioxidant enzymes after T-2 toxin exposure in mice. | 2009 May-Jun |
|
| Brain oxidative stress after dermal and subcutaneous exposure of T-2 toxin in mice. | 2010 Dec |
|
| Immunopathological effects of ochratoxin A and T-2 toxin combination on broilers. | 2010 Jun |
|
| DNA damage and DNA damage responses in THP-1 monocytes after exposure to spores of either Stachybotrys chartarum or Aspergillus versicolor or to T-2 toxin. | 2010 May |
|
| Cytotoxicity and accumulation of ergot alkaloids in human primary cells. | 2011 Apr 11 |
|
| Alteration of blood brain barrier permeability by T-2 toxin: Role of MMP-9 and inflammatory cytokines. | 2011 Feb 4 |
|
| 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 |
|
| T-2 toxin induced skin inflammation and cutaneous injury in mice. | 2012 Dec 16 |
|
| JAK/STAT pathway plays a critical role in the proinflammatory gene expression and apoptosis of RAW264.7 cells induced by trichothecenes as DON and T-2 toxin. | 2012 Jun |
|
| An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins. | 2012 Nov 15 |
|
| T-2 toxin enhances catabolic activity of hypertrophic chondrocytes through ROS-NF-κB-HIF-2α pathway. | 2012 Oct |
|
| Toxic effects of T-2 toxin and deoxynivalenol on the mitochondrial electron transport system of cardiomyocytes in rats. | 2013 |
|
| Toxic effects of dietary exposure to T-2 toxin on intestinal and hepatic biotransformation enzymes and drug transporter systems in broiler chickens. | 2013 May |
|
| Toxicity induced by F. poae-contaminated feed and the protective effect of Montmorillonite supplementation in broilers. | 2014 Dec |
|
| T-2 toxin inhibits gene expression and activity of key steroidogenesis enzymes in mouse Leydig cells. | 2015 Aug |
|
| T-2 toxin regulates steroid hormone secretion of rat ovarian granulosa cells through cAMP-PKA pathway. | 2015 Feb 3 |
|
| Differential effects of route of T-2 toxin exposure on hepatic oxidative damage in mice. | 2015 Jan |
|
| Delay of the onset of puberty in female rats by prepubertal exposure to T-2 toxin. | 2015 Nov 9 |
|
| Integrated Transcriptional and Proteomic Analysis of Growth Hormone Suppression Mediated by Trichothecene T-2 Toxin in Rat GH3 Cells. | 2015 Oct |
|
| Developmental exposure to T-2 toxin reversibly affects postnatal hippocampal neurogenesis and reduces neural stem cells and progenitor cells in mice. | 2016 Aug |
|
| Toxicity and oxidative stress induced by T-2 toxin and HT-2 toxin in broilers and broiler hepatocytes. | 2016 Jan |
|
| 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.
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
I3FL5NM3MO
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| Record Status |
Validated (UNII)
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| Record Version |
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