| 词条 | Vomitoxin |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 470631708 | ImageFile = Vomitoxin2DCSD.svg | ImageSize = | IUPACName = (3α,7α)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one | OtherNames = Deoxynivalenol (DON) Vomitoxin |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 36584 | 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 | EINECS = | 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 | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = |Section2={{Chembox Properties | C=15 | H=20 | O=6 | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = | IsoelectricPt = | SpecRotation = | RefractIndex = | Viscosity = | Dipole = }} |Section3={{Chembox Structure | CrystalStruct = | Coordination = | MolShape = | Dipole = }} |Section5={{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = }} |Section6={{Chembox Pharmacology | AdminRoutes = | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_US = }} |Section7={{Chembox Hazards | ExternalSDS = External MSDS | EUClass = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | RPhrases = | SPhrases = | RSPhrases = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = }} }}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. A direct relationship between the incidence of fusarium head blight and contamination of wheat with deoxynivalenol has been established.[1] 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.[2] Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use.[3] It occurs abundantly in grains in Norway due to heavy rainfall.[4] 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 actionVomitoxin belongs to a class of mycotoxins (trichothecenes) which are strong inhibitors of protein synthesis[5]; 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 feed intake, and may also partially explain the high incidence of paraesophageal stomach ulcers observed in sows during feed refusal. In humans DON is extensively glucuronidated and excreted via urine[6]. In foodWhen 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.
Biosynthesis{{clear}}References1. ^ Gautam, P. and Dill-Macky, R. 2011. Type I host resistance and Trichothecene Accumulation in Fusarium-infected Wheat Heads. American Journal of Agricultural and Animal Sciences 6(2):231-241. 2. ^ 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}} 3. ^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. 4. ^http://www.vkm.no/dav/eee04d10c4.pdf 5. ^{{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}} 6. ^{{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}} External links
6 : Mycotoxins|Epoxides|Spiro compounds|Alcohols|Ketones|Trichothecenes |
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