Deoxynivalenol
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| Category | Mycotoxins |
| Catalog number | BBF-01828 |
| CAS | 51481-10-8 |
| Molecular Weight | 296.319 |
| Molecular Formula | C15H20O6 |
| Purity | ≥ 98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-01828 | 5 mg | $349 | In stock |
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Add to cartDescription
Deoxynivalenol is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin can induce vomiting, diarrhea, and weight loss as well as other physiological and toxicological effects. It inhibits protein biosynthesis, binds to peptidyl transferase, and inhibits the synthesis of RNA and DNA, contributing to immunotoxicity.
Specification
| Synonyms | Vomitoxin; Dehydronivalenol; 4-Deoxynivalenol |
| Storage | Store at 2-8ºC |
| IUPAC Name | (1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one |
| Canonical SMILES | CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)CO |
| InChI | 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 |
| InChI Key | LINOMUASTDIRTM-QGRHZQQGSA-N |
| Source | Vomitoxin (deoxynivalenol) is a type B trichothecene, an epoxy-sesquiterpeneoid. Trichothecenes are produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. Vomitoxin occurs predominantly in grains such as wheat, barley, oats, rye, and maize, and less often in rice, sorghum, and triticale. |
Properties
| Appearance | White to Off-White Solid |
| Boiling Point | 543.9ºC at 760 mmHg |
| Melting Point | 151-153ºC |
| Density | 1.48 g/cm3 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Deoxynivalenol is a type B trichothecene. Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. |
| Toxicity | LD50: 70 mg/kg (Intraperitoneal, Mouse); LD50: 46 mg/kg (Oral, Mouse); LD50: 43 mg/kg (Subcutaneous, Mouse). |
Reference Reading
1. The Deoxynivalenol Challenge
Mark W Sumarah J Agric Food Chem . 2022 Aug 10;70(31):9619-9624. doi: 10.1021/acs.jafc.2c03690.
This perspective examines four of the primary challenges that the mycotoxin deoxynivalenol (DON) presents to farmers, producers, and consumers. DON is one of the big five agriculturally important mycotoxins, resulting fromFusariuminfection on grains, such as maize, barley, and wheat. In many countries, such as Canada, DON is the mycotoxin of principal concern because it can lead to major economic losses and stresses on food and feed security. The challenges discussed here include (1) understanding the different toxin profiles ofFusarium graminearumchemotypes/genotypes and the fate of these toxins upon interaction with the host crop, (2) the need for rapid analytical tests to measure DON and any masked or modified toxins in food and feed products, (3) DON exposure assessments in human populations to ensure health and safety, and (4) how contaminated food and feed products can be managed throughout the supply chain system. Despite decades of research, we are continuously learning new knowledge about DON and how best to manage it; however, there is still much work to be done. DON poses a very complex challenge that is being further exacerbated by climate change, evolving fungal populations, and the increased need for global food security.
2. Deoxynivalenol and Zearalenone-Synergistic or Antagonistic Agri-Food Chain Co-Contaminants?
Asmita Thapa, Dermot Walls, Blánaid White, Karina A Horgan Toxins (Basel) . 2021 Aug 11;13(8):561. doi: 10.3390/toxins13080561.
Deoxynivalenol (DON) and Zearalenone (ZEN) are two commonly co-occurring mycotoxins produced by members of the genusFusarium. As important food chain contaminants, these can adversely affect both human and animal health. Critically, as they are formed prior to harvesting, their occurrence cannot be eliminated during food production, leading to ongoing contamination challenges. DON is one of the most commonly occurring mycotoxins and is found as a contaminant of cereal grains that are consumed by humans and animals. Consumption of DON-contaminated feed can result in vomiting, diarrhoea, refusal of feed, and reduced weight gain in animals. ZEN is an oestrogenic mycotoxin that has been shown to have a negative effect on the reproductive function of animals. Individually, their mode of action and impacts have been well-studied; however, their co-occurrence is less well understood. This common co-occurrence of DON and ZEN makes it a critical issue for the Agri-Food industry, with a fundamental understanding required to develop mitigation strategies. To address this issue, in this targeted review, we appraise what is known of the mechanisms of action of DON and ZEN with particular attention to studies that have assessed their toxic effects when present together. We demonstrate that parameters that impact toxicity include species and cell type, relative concentration, exposure time and administration methods, and we highlight additional research required to further elucidate mechanisms of action and mitigation strategies.
3. Deoxynivalenol: Toxicology, Degradation by Bacteria, and Phylogenetic Analysis
Camilla Reginatto De Pierri, Fernando Bittencourt Luciano, Ana Silvia de Lara Pires Batista Gomes, Alberto Gonçalves Evangelista, Anne Caroline Schoch Marques Pinto Toxins (Basel) . 2022 Jan 25;14(2):90. doi: 10.3390/toxins14020090.
Deoxynivalenol (DON) is a toxic secondary metabolite produced by fungi that contaminates many crops, mainly wheat, maize, and barley. It affects animal health, causing intestinal barrier impairment and immunostimulatory effect in low doses and emesis, reduction in feed conversion rate, and immunosuppression in high doses. As it is very hard to completely avoid DON's production in the field, mitigatory methods have been developed. Biodegradation has become a promising method as new microorganisms are studied and new enzymatic routes are described. Understanding the common root of bacteria with DON degradation capability and the relationship with their place of isolation may bring insights for more effective ways to find DON-degrading microorganisms. The purpose of this review is to bring an overview of the occurrence, regulation, metabolism, and toxicology of DON as addressed in recent publications focusing on animal production, as well as to explore the enzymatic routes described for DON's degradation by microorganisms and the phylogenetic relationship among them.
Spectrum
LC-MS/MS Spectrum - 30V, Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
