# Vomitoxin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Vomitoxin
> Markdown URL: https://mediated.wiki/source/Vomitoxin.md
> Source: https://en.wikipedia.org/wiki/Vomitoxin
> Source revision: 1334831608
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{{Short description|Fungal toxic chemical in grains}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 470631708
| ImageFile = Vomitoxin2DCSD.svg
| ImageSize = 
| IUPACName = 3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
| SystematicName = (2''R'',2′''S'',3''R'',5''R'',5a''R'',6''S'',9a''R'')-3,8-Dihydroxy-5a-(hydroxymethyl)-5,6-dimethylspiro[<nowiki/>[2,5]methano[1]benzoxepine-10,2′-oxiran]-7(6''H'')-one
| OtherNames = <br />Deoxynivalenol (DON)<br />Vomitoxin
|Section1={{Chembox Identifiers
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 36584
| ChEBI = 10022
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 513300
| InChIKey = LINOMUASTDIRTM-QGRHZQQGBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LINOMUASTDIRTM-QGRHZQQGSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 51481-10-8
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| PubChem = 40024
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C09747
| SMILES = CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@]([C@]2([C@H](O)C1=O)CO)([C@]13OC1)C
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = JT37HYP23V
| InChI = 1/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
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|Section2={{Chembox Properties
| C=15 | H=20 | O=6
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|Section3={{Chembox Structure
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|Section5={{Chembox Thermochemistry
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|Section6={{Chembox Pharmacology
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|Section7={{Chembox Hazards
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|Section8={{Chembox Related
| OtherAnions = 
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| OtherCompounds = [nivalenol](/source/nivalenol)}}
}}

'''Vomitoxin''', also known as '''deoxynivalenol''' ('''DON'''), is a type B [trichothecene](/source/trichothecene), an [epoxy](/source/epoxy)-[sesquiterpenoid](/source/sesquiterpene). This [mycotoxin](/source/mycotoxin) occurs predominantly in grains such as [wheat](/source/wheat), [barley](/source/barley), [oat](/source/oat)s, [rye](/source/rye), and [corn](/source/maize), and less often in [rice](/source/rice), [sorghum](/source/sorghum), and [triticale](/source/triticale). The occurrence of deoxynivalenol is associated primarily with ''[Fusarium graminearum](/source/Fusarium_graminearum)'' (''Gibberella zeae'') and ''[F. culmorum](/source/Fusarium_culmorum)'', both of which are important plant [pathogens](/source/pathogens) which cause fusarium head blight in wheat and gibberella or [fusarium ear blight](/source/fusarium_ear_blight) in corn. The incidence of fusarium head blight is strongly associated with moisture at the time of flowering (anthesis), and the timing of rainfall, rather than the amount, is the most critical factor. However, increased amount of moisture towards harvest time has been associated with lower amount of vomitoxin in wheat grain due to leaching of toxins.<ref>Gautam, P. and Dill-Macky, R. 2012. Impact of moisture, host genetics and Fusarium graminearum isolates on Fusarium head blight development and trichothecene accumulation in spring wheat. Mycotoxin Research 28 (1) {{doi|10.1007/s12550-011-0115-6}} [https://doi.org/10.1007%2Fs12550-011-0115-6]</ref> Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards ''Fusarium'' species, previous crop, tillage practices, and fungicide use.<ref>Beyer M, Klix MB, Klink H, Verreet J-A (2006): Quantifying the effects of previous crop, tillage, cultivar and triazole fungicides on the deoxynivalenol content of wheat grain – a review. Journal of Plant Diseases and Protection 113: 241–246. [http://www.ulmer.de/Artikel.dll/Beyer_MTczNzcy.PDF]</ref>  It occurs abundantly in grains in [Norway](/source/Norway) due to heavy rainfall.<ref>{{Cite web |url=http://www.vkm.no/dav/eee04d10c4.pdf |title=Archived copy |access-date=2015-03-29 |archive-date=2016-03-03 |archive-url=https://web.archive.org/web/20160303190419/http://www.vkm.no/dav/eee04d10c4.pdf |url-status=dead }}</ref>

''F. graminearum'' grows optimally at a temperature of 25&nbsp;°C and at a [water activity](/source/water_activity) above 0.88. ''F. culmorum'' grows optimally at 21&nbsp;°C and at a water activity above 0.87. The geographical distribution of the two species appears to be related to temperature, ''F. graminearum'' being the more common species occurring in warmer climates. Deoxynivalenol has been implicated in incidents of mycotoxicoses in both humans and farm animals.

== Mechanism of action ==
Vomitoxin belongs to a class of mycotoxins ([trichothecenes](/source/trichothecenes)) which are strong inhibitors of protein synthesis;<ref>{{cite journal |last1=Pestka |first1=James J. |title=Deoxynivalenol: mechanisms of action, human exposure, and toxicological relevance |journal=Archives of Toxicology |date=27 August 2010 |volume=84 |issue=9 |pages=663–679 |doi=10.1007/s00204-010-0579-8|pmid=20798930 |bibcode=2010ArTox..84..663P |s2cid=36072340 }}</ref> exposure to vomitoxin causes the brain to decrease its uptake of the amino acid tryptophan and, in turn, its synthesis of [serotonin](/source/serotonin). Reduced levels of serotonin are believed to be responsible for the anorexic effects of DON and other trichothecenes. Irritation of the gastrointestinal tract may also play a role in reducing food intake, and may also partially explain the high incidence of paraesophageal stomach ulcers observed in sows during food refusal. In humans DON is extensively [glucuronidated](/source/Glucuronidation) and excreted via urine.<ref>{{cite journal |last1=Warth |first1=Benedikt |last2=Sulyok |first2=Michael |last3=Berthiller |first3=Franz |last4=Schuhmacher |first4=Rainer |last5=Krska |first5=Rudolf |title=New insights into the human metabolism of the Fusarium mycotoxins deoxynivalenol and zearalenone |journal=Toxicology Letters |date=June 2013 |volume=220 |issue=1 |pages=88–94 |doi=10.1016/j.toxlet.2013.04.012|pmid=23623764 |bibcode=2013ToxL..220...88W |doi-access=free }}</ref>

== In food ==
When compared to other trichothecene mycotoxins which can form in grains and forages, vomitoxin is relatively mild. Reduced feed intake, with its accompanying decrease in performance, is the only symptom of vomitoxin toxicity [livestock](/source/livestock) producers will likely encounter. This response to vomitoxin appears to occur through the [central nervous system](/source/central_nervous_system).

* Human foods: Vomitoxin is not a known [carcinogen](/source/carcinogen), unlike [aflatoxin](/source/aflatoxin). Large amounts of grain with vomitoxin would have to be consumed to pose acute toxicity in humans. Currently, the chronic effects of low-dose exposure are unknown. The [U.S. Food and Drug Administration](/source/Food_and_Drug_Administration_(United_States)) has established a level of 1 [ppm](/source/parts_per_million) (parts per million) restriction of vomitoxin.{{Citation needed|date=November 2022}}
* Companion animals: Dogs and cats are restricted to 5 ppm and of grains and grain [byproduct](/source/byproduct)s and the grains are not to exceed 40% percent of the diet.
* Livestock and farm animals: In animals and livestock, vomitoxin causes a refusal to feed and lack of weight gain when fed above advised levels. Restrictions are set at 10 ppm for [poultry](/source/poultry) and ruminating [beef](/source/beef) and feedlot cattle older than four months. Ingredients may not exceed 50% of the animal's diet. [Dairy cow](/source/Dairy_cow) feed limits are set at 2 ppm.

== Biosynthesis ==
thumb|770 px|left|Biosynthesis of vomitoxin
{{clear}}

== References ==
{{Reflist|30em}}

== External links ==
* [http://www.inchem.org/documents/jecfa/jecmono/v47je05.htm A comprehensive review on vomitoxin]
* [http://www.fao.org/DOCREP/ARTICLE/AGRIPPA/556_EN.HTM Microbiology of Animal Feeds] {{Webarchive|url=https://web.archive.org/web/20130612051936/http://www.fao.org/docrep/ARTICLE/AGRIPPA/556_EN.HTM |date=2013-06-12 }}

{{Toxins}}
{{Authority control}}

Category:Mycotoxins
Category:Epoxides
Category:Spiro compounds
Category:Alcohols
Category:Ketones
Category:Trichothecenes

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Adapted from the Wikipedia article [Vomitoxin](https://en.wikipedia.org/wiki/Vomitoxin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Vomitoxin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.