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
[H][C@@]12O[C@]3([H])C=C(C)C(=O)[C@@H](O)[C@]3(CO)[C@@](C)(C[C@H]1O)[C@]24CO4
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21217881Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20861219
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21217881
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21217881
Curator's Comment: Known to be CNS penetrant in mouse, pigs. Human data not available
Approval Year
PubMed
Title | Date | PubMed |
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The mycotoxin deoxynivalenol promotes uptake of Salmonella Typhimurium in porcine macrophages, associated with ERK1/2 induced cytoskeleton reorganization. | 2009 Nov-Dec |
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Induction of suppressors of cytokine signaling by the trichothecene deoxynivalenol in the mouse. | 2009 Oct |
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Pathway of deoxynivalenol-induced apoptosis in human colon carcinoma cells. | 2009 Oct 1 |
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HuR/ELAVL1 RNA binding protein modulates interleukin-8 induction by muco-active ribotoxin deoxynivalenol. | 2009 Oct 1 |
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Interactions of deoxynivalenol and lipopolysaccharides on cytokine excretion and mRNA expression in porcine hepatocytes and Kupffer cell enriched hepatocyte cultures. | 2009 Oct 8 |
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Suppression of insulin-like growth factor acid-labile subunit expression--a novel mechanism for deoxynivalenol-induced growth retardation. | 2010 Feb |
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Deoxynivalenol and nivalenol inhibit lipopolysaccharide-induced nitric oxide production by mouse macrophage cells. | 2010 Feb 1 |
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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 Jul 1 |
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Hematopoietic cell kinase associates with the 40S ribosomal subunit and mediates the ribotoxic stress response to deoxynivalenol in mononuclear phagocytes. | 2010 Jun |
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Deoxynivalenol affects in vitro intestinal epithelial cell barrier integrity through inhibition of protein synthesis. | 2010 Jun 15 |
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Transcriptomic profile indicative of immunotoxic exposure: in vitro studies in peripheral blood mononuclear cells. | 2010 Nov |
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Impact of DUSP1 on the apoptotic potential of deoxynivalenol in the epithelial cell line HepG2. | 2010 Nov 10 |
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Physio-pathological parameters affect the activation of inflammatory pathways by deoxynivalenol in Caco-2 cells. | 2010 Oct |
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Mechanism-based alternative monitoring of endoplasmic reticulum stress by 8-keto-trichothecene mycotoxins using human intestinal epithelial cell line. | 2010 Oct 20 |
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The effects of deoxynivalenol on gene expression in the murine thymus. | 2011 Feb 1 |
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Mycotoxin deoxynivalenol (DON) mediates biphasic cellular response in intestinal porcine epithelial cell lines IPEC-1 and IPEC-J2. | 2011 Jan 15 |
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Central inflammation and sickness-like behavior induced by the food contaminant deoxynivalenol: a PGE2-independent mechanism. | 2011 Nov |
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A mitochondria-mediated apoptotic pathway induced by deoxynivalenol in human colon cancer cells. | 2012 Apr |
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Zebrafish (Danio rerio) as a model for investigating dietary toxic effects of deoxynivalenol contamination in aquaculture feeds. | 2012 Dec |
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Anorexia induction by the trichothecene deoxynivalenol (vomitoxin) is mediated by the release of the gut satiety hormone peptide YY. | 2012 Dec |
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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 Jan |
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Targets and intracellular signaling mechanisms for deoxynivalenol-induced ribosomal RNA cleavage. | 2012 Jun |
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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 |
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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 Nov |
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An in vitro investigation of endocrine disrupting effects of trichothecenes deoxynivalenol (DON), T-2 and HT-2 toxins. | 2012 Nov 15 |
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Transcriptome analysis of the human T lymphocyte cell line Jurkat and human peripheral blood mononuclear cells exposed to deoxynivalenol (DON): New mechanistic insights. | 2012 Oct 1 |
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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 |
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Toxic effects of T-2 toxin and deoxynivalenol on the mitochondrial electron transport system of cardiomyocytes in rats. | 2013 |
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Deoxynivalenol as a new factor in the persistence of intestinal inflammatory diseases: an emerging hypothesis through possible modulation of Th17-mediated response. | 2013 |
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Global protein phosphorylation dynamics during deoxynivalenol-induced ribotoxic stress response in the macrophage. | 2013 Apr 15 |
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Assessment of the usefulness of the murine cytotoxic T cell line CTLL-2 for immunotoxicity screening by transcriptomics. | 2013 Feb 13 |
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Evaluation of insulin-like growth factor acid-labile subunit as a potential biomarker of effect for deoxynivalenol-induced proinflammatory cytokine expression. | 2013 Feb 8 |
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Comparison of emetic potencies of the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. | 2013 Jan |
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Modulation of inflammatory gene expression by the ribotoxin deoxynivalenol involves coordinate regulation of the transcriptome and translatome. | 2013 Jan |
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Individual and combined effects of Fusarium toxins on the mRNA expression of pro-inflammatory cytokines in swine jejunal epithelial cells. | 2013 Jul 18 |
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Deoxynivalenol-induced weight loss in the diet-induced obese mouse is reversible and PKR-independent. | 2013 Jul 31 |
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Early phosphoproteomic changes in the mouse spleen during deoxynivalenol-induced ribotoxic stress. | 2013 Sep |
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Comparative study of deoxynivalenol, 3-acetyldeoxynivalenol, and 15-acetyldeoxynivalenol on intestinal transport and IL-8 secretion in the human cell line Caco-2. | 2013 Sep |
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Role of tumor necrosis factor-α and interleukin-1β in anorexia induction following oral exposure to the trichothecene deoxynivalenol (vomitoxin) in the mouse. | 2014 |
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Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. | 2014 Apr |
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Hepatotoxic effects of mycotoxin combinations in mice. | 2014 Dec |
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Deoxynivalenol induced oxidative stress and genotoxicity in human peripheral blood lymphocytes. | 2014 Feb |
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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 Jan 30 |
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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 Jul 15 |
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In vitro effect of deoxynivalenol (DON) mycotoxin on porcine reproductive and respiratory syndrome virus replication. | 2014 Mar |
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Transcriptome-based functional classifiers for direct immunotoxicity. | 2014 Mar |
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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 May |
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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 Nov |
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Deoxynivalenol induced mouse skin cell proliferation and inflammation via MAPK pathway. | 2014 Sep 1 |
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In vitro glucuronidation kinetics of deoxynivalenol by human and animal microsomes and recombinant human UGT enzymes. | 2015 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21217881
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25717015
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
by
admin
on
Edited
Sat Dec 16 09:04:03 UTC 2023
by
admin
on
Sat Dec 16 09:04:03 UTC 2023
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Record UNII |
JT37HYP23V
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Record Status |
Validated (UNII)
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Record Version |
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m11499
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10022
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JT37HYP23V
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Deoxynivalenol
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