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 |
|
| Effects of trichothecene structure on cytokine secretion and gene expression in murine CD4+ T-cells. | 1995 Dec 15 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Alteration of blood brain barrier permeability by T-2 toxin: Role of MMP-9 and inflammatory cytokines. | 2011 Feb 4 |
|
| Effects of T-2 toxin and selenium on chondrocyte expression of matrix metalloproteinases (MMP-1, MMP-13), α2-macroglobulin (α2M) and TIMPs. | 2011 Mar |
|
| An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins. | 2012 Nov 15 |
|
| T-2 toxin inhibits gene expression and activity of key steroidogenesis enzymes in mouse Leydig cells. | 2015 Aug |
|
| 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 |
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
by
admin
on
Edited
Fri Dec 15 19:44:36 GMT 2023
by
admin
on
Fri Dec 15 19:44:36 GMT 2023
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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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