Vomitoxin

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.129.971 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: LINOMUASTDIRTM-QGRHZQQGSA-N checkY
  • 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 checkY☒N ?)

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]

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.

  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. ^ "Archived copy" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2015-03-29.{{cite web}}: CS1 maint: archived copy as title (link)