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Vomitoxin

Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum (Gibberella zeae) and F. culmorum, both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or 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.[1] Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use.[2] It occurs abundantly in grains in Norway due to heavy rainfall.[3]

Vomitoxin
Names
IUPAC name
3α,7α,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
Systematic IUPAC name
(2R,2′S,3R,5R,5aR,6S,9aR)-3,8-Dihydroxy-5a-(hydroxymethyl)-5,6-dimethylspiro[[2,5]methano[1]benzoxepine-10,2′-oxiran]-7(6H)-one
Other names

Deoxynivalenol (DON)
Vomitoxin
Identifiers
  • 51481-10-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:10022
ChEMBL
  • ChEMBL513300 Y
ChemSpider
  • 36584 Y
ECHA InfoCard 100.129.971
KEGG
  • C09747 N
  • 40024
UNII
  • JT37HYP23V N
  • DTXSID3020382
  • 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 Y
    Key: LINOMUASTDIRTM-QGRHZQQGSA-N Y
  • 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
    Key: LINOMUASTDIRTM-QGRHZQQGBF
  • CC1=C[C@H]2O[C@@H]3[C@H](O)C[C@]([C@]2([C@H](O)C1=O)CO)([C@]13OC1)C
Properties
C15H20O6
Molar mass 296.319 g·mol−1
Related compounds
Related compounds
nivalenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

F. graminearum grows optimally at a temperature of 25 °C and at a water activity above 0.88. F. culmorum grows optimally at 21 °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 edit

Vomitoxin belongs to a class of mycotoxins (trichothecenes) which are strong inhibitors of protein synthesis;[4] exposure to vomitoxin causes the brain to decrease its uptake of the amino acid tryptophan and, in turn, its synthesis of 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 and excreted via urine.[5]

In food edit

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 producers will likely encounter. This response to vomitoxin appears to occur through the central nervous system.

  • Human foods: Vomitoxin is not a known carcinogen, unlike 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 has established a level of 1 ppm (parts per million) restriction of vomitoxin.[citation needed]
  • Companion animals: Dogs and cats are restricted to 5 ppm and of grains and grain byproducts 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 and ruminating beef and feedlot cattle older than four months. Ingredients may not exceed 50% of the animal's diet. Dairy cow feed limits are set at 2 ppm.

Biosynthesis edit

 
Biosynthesis of vomitoxin

References edit

  1. ^ 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 [1]
  2. ^ 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. [2]
  3. ^ (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2015-03-29.{{cite web}}: CS1 maint: archived copy as title (link)
  4. ^ Pestka, James J. (27 August 2010). "Deoxynivalenol: mechanisms of action, human exposure, and toxicological relevance". Archives of Toxicology. 84 (9): 663–679. doi:10.1007/s00204-010-0579-8. PMID 20798930. S2CID 36072340.
  5. ^ Warth, Benedikt; Sulyok, Michael; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf (June 2013). "New insights into the human metabolism of the Fusarium mycotoxins deoxynivalenol and zearalenone". Toxicology Letters. 220 (1): 88–94. doi:10.1016/j.toxlet.2013.04.012. PMID 23623764.

External links edit

  • A comprehensive review on vomitoxin
  • Microbiology of Animal Feeds 2013-06-12 at the Wayback Machine

vomitoxin, also, known, deoxynivalenol, type, trichothecene, epoxy, sesquiterpenoid, this, mycotoxin, occurs, predominantly, grains, such, wheat, barley, oats, corn, less, often, rice, sorghum, triticale, occurrence, deoxynivalenol, associated, primarily, with. Vomitoxin also known as deoxynivalenol DON is a type B trichothecene an epoxy sesquiterpenoid This mycotoxin occurs predominantly in grains such as wheat barley oats rye and corn and less often in rice sorghum and triticale The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum Gibberella zeae and F culmorum both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or 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 1 Furthermore deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species previous crop tillage practices and fungicide use 2 It occurs abundantly in grains in Norway due to heavy rainfall 3 Vomitoxin NamesIUPAC name 3a 7a 15 Trihydroxy 12 13 epoxytrichothec 9 en 8 oneSystematic IUPAC name 2R 2 S 3R 5R 5aR 6S 9aR 3 8 Dihydroxy 5a hydroxymethyl 5 6 dimethylspiro 2 5 methano 1 benzoxepine 10 2 oxiran 7 6H oneOther names Deoxynivalenol DON VomitoxinIdentifiersCAS Number 51481 10 8 Y3D model JSmol Interactive imageChEBI CHEBI 10022ChEMBL ChEMBL513300 YChemSpider 36584 YECHA InfoCard 100 129 971KEGG C09747 NPubChem CID 40024UNII JT37HYP23V NCompTox Dashboard EPA DTXSID3020382InChI 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 YKey LINOMUASTDIRTM QGRHZQQGSA N YInChI 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 s1Key LINOMUASTDIRTM QGRHZQQGBFSMILES CC1 C C H 2O C H 3 C H O C C C 2 C H O C1 O CO C 13OC1 CPropertiesChemical formula C 15H 20O 6Molar mass 296 319 g mol 1Related compoundsRelated compounds nivalenolExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references F graminearum grows optimally at a temperature of 25 C and at a water activity above 0 88 F culmorum grows optimally at 21 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 Contents 1 Mechanism of action 2 In food 3 Biosynthesis 4 References 5 External linksMechanism of action editVomitoxin belongs to a class of mycotoxins trichothecenes which are strong inhibitors of protein synthesis 4 exposure to vomitoxin causes the brain to decrease its uptake of the amino acid tryptophan and in turn its synthesis of 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 and excreted via urine 5 In food editWhen 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 producers will likely encounter This response to vomitoxin appears to occur through the central nervous system Human foods Vomitoxin is not a known carcinogen unlike 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 has established a level of 1 ppm parts per million restriction of vomitoxin citation needed Companion animals Dogs and cats are restricted to 5 ppm and of grains and grain byproducts 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 and ruminating beef and feedlot cattle older than four months Ingredients may not exceed 50 of the animal s diet Dairy cow feed limits are set at 2 ppm Biosynthesis edit nbsp Biosynthesis of vomitoxinReferences edit 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 1 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 2 Archived copy PDF Archived from the original PDF on 2016 03 03 Retrieved 2015 03 29 a href Template Cite web html title Template Cite web cite web a CS1 maint archived copy as title link Pestka James J 27 August 2010 Deoxynivalenol mechanisms of action human exposure and toxicological relevance Archives of Toxicology 84 9 663 679 doi 10 1007 s00204 010 0579 8 PMID 20798930 S2CID 36072340 Warth Benedikt Sulyok Michael Berthiller Franz Schuhmacher Rainer Krska Rudolf June 2013 New insights into the human metabolism of the Fusarium mycotoxins deoxynivalenol and zearalenone Toxicology Letters 220 1 88 94 doi 10 1016 j toxlet 2013 04 012 PMID 23623764 External links editA comprehensive review on vomitoxin Microbiology of Animal Feeds Archived 2013 06 12 at the Wayback Machine Retrieved from https en wikipedia org w index php title Vomitoxin amp oldid 1178717544, wikipedia, wiki, book, 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