Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H20O6 |
| Molecular Weight | 296.3157 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@@](C)([C@]34CO4)[C@@]2(CO)[C@H](O)C1=O
InChI
InChIKey=LINOMUASTDIRTM-QGRHZQQGSA-N
InChI=1S/C15H20O6/c1-7-3-9-14(5-16,11(19)10(7)18)13(2)4-8(17)12(21-9)15(13)6-20-15/h3,8-9,11-12,16-17,19H,4-6H2,1-2H3/t8-,9-,11-,12-,13-,14-,15+/m1/s1
| Molecular Formula | C15H20O6 |
| Molecular Weight | 296.3157 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20861219
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20861219
Deoxynivalenol (DON) is one of several mycotoxins produced by certain Fusarium species that frequently infect corn, wheat, oats, barley, rice, and other grains in the field or during storage. DON-induced activation of the p44/42 ERK signaling pathway inhibits the expression of claudin-4 protein, which leads to impaired intestinal barrier function. Given the high levels of DON in cereal grains, these observations of impaired barrier function have implications for human and animal health.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro glucuronidation kinetics of deoxynivalenol by human and animal microsomes and recombinant human UGT enzymes. | 2015-06 |
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| Hepatotoxic effects of mycotoxin combinations in mice. | 2014-12 |
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| Comparison of anorectic and emetic potencies of deoxynivalenol (vomitoxin) to the plant metabolite deoxynivalenol-3-glucoside and synthetic deoxynivalenol derivatives EN139528 and EN139544. | 2014-11 |
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| Deoxynivalenol induced mouse skin cell proliferation and inflammation via MAPK pathway. | 2014-09-01 |
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| Effects of oral exposure to naturally-occurring and synthetic deoxynivalenol congeners on proinflammatory cytokine and chemokine mRNA expression in the mouse. | 2014-07-15 |
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| Modulation of mucin mRNA (MUC5AC and MUC5B) expression and protein production and secretion in Caco-2/HT29-MTX co-cultures following exposure to individual and combined Fusarium mycotoxins. | 2014-05 |
|
| Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. | 2014-04 |
|
| In vitro effect of deoxynivalenol (DON) mycotoxin on porcine reproductive and respiratory syndrome virus replication. | 2014-03 |
|
| Transcriptome-based functional classifiers for direct immunotoxicity. | 2014-03 |
|
| Deoxynivalenol induced oxidative stress and genotoxicity in human peripheral blood lymphocytes. | 2014-02 |
|
| DON shares a similar mode of action as the ribotoxic stress inducer anisomycin while TBTO shares ER stress patterns with the ER stress inducer thapsigargin based on comparative gene expression profiling in Jurkat T cells. | 2014-01-30 |
|
| Role of tumor necrosis factor-α and interleukin-1β in anorexia induction following oral exposure to the trichothecene deoxynivalenol (vomitoxin) in the mouse. | 2014 |
|
| Early phosphoproteomic changes in the mouse spleen during deoxynivalenol-induced ribotoxic stress. | 2013-09 |
|
| Comparative study of deoxynivalenol, 3-acetyldeoxynivalenol, and 15-acetyldeoxynivalenol on intestinal transport and IL-8 secretion in the human cell line Caco-2. | 2013-09 |
|
| Deoxynivalenol-induced weight loss in the diet-induced obese mouse is reversible and PKR-independent. | 2013-07-31 |
|
| Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells. | 2013-07-18 |
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| Global protein phosphorylation dynamics during deoxynivalenol-induced ribotoxic stress response in the macrophage. | 2013-04-15 |
|
| Assessment of the usefulness of the murine cytotoxic T cell line CTLL-2 for immunotoxicity screening by transcriptomics. | 2013-02-13 |
|
| Evaluation of insulin-like growth factor acid-labile subunit as a potential biomarker of effect for deoxynivalenol-induced proinflammatory cytokine expression. | 2013-02-08 |
|
| Comparison of emetic potencies of the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. | 2013-01 |
|
| Modulation of inflammatory gene expression by the ribotoxin deoxynivalenol involves coordinate regulation of the transcriptome and translatome. | 2013-01 |
|
| Deoxynivalenol impairs hepatic and intestinal gene expression of selected oxidative stress, tight junction and inflammation proteins in broiler chickens, but addition of an adsorbing agent shifts the effects to the distal parts of the small intestine. | 2013 |
|
| Toxic effects of T-2 toxin and deoxynivalenol on the mitochondrial electron transport system of cardiomyocytes in rats. | 2013 |
|
| Deoxynivalenol as a new factor in the persistence of intestinal inflammatory diseases: an emerging hypothesis through possible modulation of Th17-mediated response. | 2013 |
|
| Zebrafish (Danio rerio) as a model for investigating dietary toxic effects of deoxynivalenol contamination in aquaculture feeds. | 2012-12 |
|
| Anorexia induction by the trichothecene deoxynivalenol (vomitoxin) is mediated by the release of the gut satiety hormone peptide YY. | 2012-12 |
|
| An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins. | 2012-11-15 |
|
| Toxicity of deoxynivalenol and its acetylated derivatives on the intestine: differential effects on morphology, barrier function, tight junction proteins, and mitogen-activated protein kinases. | 2012-11 |
|
| Transcriptome analysis of the human T lymphocyte cell line Jurkat and human peripheral blood mononuclear cells exposed to deoxynivalenol (DON): New mechanistic insights. | 2012-10-01 |
|
| Targets and intracellular signaling mechanisms for deoxynivalenol-induced ribosomal RNA cleavage. | 2012-06 |
|
| 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. | 2012-06 |
|
| A mitochondria-mediated apoptotic pathway induced by deoxynivalenol in human colon cancer cells. | 2012-04 |
|
| Chronic Nod2 stimulation potentiates activating transcription factor 3 and paradoxical superinduction of epithelial proinflammatory chemokines by mucoactive ribotoxic stressors via RNA-binding protein human antigen R. | 2012-01 |
|
| Central inflammation and sickness-like behavior induced by the food contaminant deoxynivalenol: a PGE2-independent mechanism. | 2011-11 |
|
| The effects of deoxynivalenol on gene expression in the murine thymus. | 2011-02-01 |
|
| Mycotoxin deoxynivalenol (DON) mediates biphasic cellular response in intestinal porcine epithelial cell lines IPEC-1 and IPEC-J2. | 2011-01-15 |
|
| Impact of DUSP1 on the apoptotic potential of deoxynivalenol in the epithelial cell line HepG2. | 2010-11-10 |
|
| Transcriptomic profile indicative of immunotoxic exposure: in vitro studies in peripheral blood mononuclear cells. | 2010-11 |
|
| Mechanism-based alternative monitoring of endoplasmic reticulum stress by 8-keto-trichothecene mycotoxins using human intestinal epithelial cell line. | 2010-10-20 |
|
| Physio-pathological parameters affect the activation of inflammatory pathways by deoxynivalenol in Caco-2 cells. | 2010-10 |
|
| Lutein protects HT-29 cells against Deoxynivalenol-induced oxidative stress and apoptosis: prevention of NF-kappaB nuclear localization and down regulation of NF-kappaB and Cyclo-Oxygenase-2 expression. | 2010-07-01 |
|
| Deoxynivalenol affects in vitro intestinal epithelial cell barrier integrity through inhibition of protein synthesis. | 2010-06-15 |
|
| Hematopoietic cell kinase associates with the 40S ribosomal subunit and mediates the ribotoxic stress response to deoxynivalenol in mononuclear phagocytes. | 2010-06 |
|
| Deoxynivalenol and nivalenol inhibit lipopolysaccharide-induced nitric oxide production by mouse macrophage cells. | 2010-02-01 |
|
| Suppression of insulin-like growth factor acid-labile subunit expression--a novel mechanism for deoxynivalenol-induced growth retardation. | 2010-02 |
|
| Interactions of deoxynivalenol and lipopolysaccharides on cytokine excretion and mRNA expression in porcine hepatocytes and Kupffer cell enriched hepatocyte cultures. | 2009-10-08 |
|
| Pathway of deoxynivalenol-induced apoptosis in human colon carcinoma cells. | 2009-10-01 |
|
| HuR/ELAVL1 RNA binding protein modulates interleukin-8 induction by muco-active ribotoxin deoxynivalenol. | 2009-10-01 |
|
| Induction of suppressors of cytokine signaling by the trichothecene deoxynivalenol in the mouse. | 2009-10 |
|
| The mycotoxin deoxynivalenol promotes uptake of Salmonella Typhimurium in porcine macrophages, associated with ERK1/2 induced cytoskeleton reorganization. | 2009-01-15 |
Patents
Sample Use Guides
in animals:
Acute toxicity: Male B6C3F1 mice were orally administered deoxynivalenol (DON) (25 mg/kg [84 µmol/kg]) to assess the kinetics of DON distribution and clearance. DON was detectable in the plasma, liver, spleen, and brain from 5 minutes up to 24 hours post administration
chronic toxicity: Female B6C7F1 mice (7 weeks old) were fed experimental diets for 16 weeks that contained DON (20 mg/kg [67 µmol/kg]). DON reduced the mean daily food consumption (2.94 ± 0.66 g vs. 3.6 ± 0.48 g), the mean body weight gain (2.76 ± 0.84 g vs.12.94 ± 1.68 g), and total body weight, and increased serum immunoglobulin A (IgA) levels in treated vs. control mice starting 8 weeks after diet initiation.
Route of Administration:
Oral
Porcine circovirus type 2 (PCV2) is the main causative agent of several syndromes in weaning piglets collectively known as porcine circovirus-associated disease (PCVAD). The objectives of this study were to investigate the impact of deoxynivalenol (DON) on PCV2 replication in NPTr permissive cell line. Noninfected and infected cells with PCV2 were treated with increasing concentrations of DON (0, 70, 140, 280, 560, 1200 ng/mL) and cell survival and virus titer were evaluated 72 h postinfection. In vitro results showed that low concentrations of DON could potentially increase PCV2 replication depending on virus genotype.
| Substance Class |
Chemical
Created
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admin
on
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Mon Mar 31 22:27:58 GMT 2025
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admin
on
Mon Mar 31 22:27:58 GMT 2025
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| Record UNII |
JT37HYP23V
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| Record Status |
Validated (UNII)
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Deoxynivalenol
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Phosphorylates eukaryotic initiation factor 2 (eIF2), when activated thereby impeding translation.
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