51481-10-8 Usage
Description
Deoxynivalenol, also known as Vomitoxin, is a type B trichothecene mycotoxin produced by certain species of the fungus Fusarium, particularly those found on cereal crops such as wheat, barley, oats, maize, and rye. It is cytotoxic and known to hinder macromolecular synthesis, including protein, RNA, and DNA synthesis. Deoxynivalenol can induce vomiting, diarrhea, weight loss, and other physiological and toxicological effects. It is also a potent immunosuppressant, which may predispose animals to other diseases.
Uses
Used in Analytical Chemistry:
Deoxynivalenol is used as an analytical reference standard for the quantification of the analyte in cornmeal and wheat meal matrices using high-performance liquid chromatography with UV detection (HPLC-UV). It is also used as an analytical standard in investigating its toxicity mechanism on human chondrocytes by microarray and bioinformatics analysis.
Used in Research and Development:
Deoxynivalenol exhibits cytotoxic activity in vivo via the ribotoxic stress response and is used in research to study its effects on various cell types, such as leukocytes. It induces p38-mediated gene expression and apoptosis in leukocytes, resulting in systemic expression of interleukin-6 (IL-6) and other proinflammatory cytokines. Additionally, it induces migration of NF-κB into the nucleus, which is crucial for understanding its mechanism of action and potential applications in therapeutics.
Used in Agriculture and Food Safety:
Deoxynivalenol is a significant concern in the agricultural industry due to its presence in cereal crops. It is essential to monitor and control the levels of this mycotoxin in the food supply to prevent health issues in both animals and humans. As a result, deoxynivalenol is used as a reference material for developing and validating methods to detect and quantify its presence in various food products.
Used in Toxicology Studies:
Due to its toxicological effects, deoxynivalenol is used in toxicology studies to understand the mechanisms of trichothecene toxicity and to develop strategies for mitigating their harmful effects. This includes research on the binding of deoxynivalenol to eukaryotic ribosomes and its impact on protein synthesis, as well as its immunosuppressive properties.
Biochem/physiol Actions
Deoxynivalenol (DON) is a trichothecene mycotoxin that inhibits the synthesis of DNA and RNA as well as protein synthesis at the ribosomal level. DON induces IL-6 mediated serum hyperelevation of IgA, as well as phosphorylation of extracellular signal regulated protein kinases 1 and 2 (ERK 1,2) and c-Jun N-terminal kinases 1 and 2 (JNK 1,2) in mice. An in vitro study with porcine ovarian granulosa cells suggests a dose dependent association of DON on porcine ovarian functions. It was also shown that LPS and its downstream mediators can interact with DON to modulate proliferative, cytotoxic and apoptotic outcomes in leukocytes in a tissue specific manner.
Check Digit Verification of cas no
The CAS Registry Mumber 51481-10-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,4,8 and 1 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 51481-10:
(7*5)+(6*1)+(5*4)+(4*8)+(3*1)+(2*1)+(1*0)=98
98 % 10 = 8
So 51481-10-8 is a valid CAS Registry Number.
InChI: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
51481-10-8Relevant articles and documents
Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin
Fruhmann, Philipp,Skrinjar, Philipp,Weber, Julia,Mikula, Hannes,Warth, Benedikt,Sulyok, Michael,Krska, Rudolf,Adam, Gerhard,Rosenberg, Erwin,Hametner, Christian,Fr?hlich, Johannes
, p. 5260 - 5266 (2014/07/08)
The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.
Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay
Desjardins, Anne E.,McCormick, Susan P.,Appell, Michael
, p. 6487 - 6492 (2008/09/19)
Many Fusarium species produce trichothecenes, sesquiterpene epoxides that differ in patterns of oxygenation and esterification at carbon positions C-3, C-4, C-7, C-8, and C-15. For the first comprehensive and quantitative comparison of the effects of oxygenation and esterification on trichothecene phytotoxicity, we tested 24 precursors, intermediates, and end products of the trichothecene biosynthetic pathway in an Arabidopsis thaliana detached leaf assay. At 100 μM, the highest concentration tested, only the trichothecene precursor trichodiene was nontoxic. Among trichothecenes, toxicity varied more than 200-fold. Oxygenation at C-4, C-8, C-7/8, or C-15 was, on average, as likely to decrease as to increase toxicity. Esterification at C-4, C-8, or C-15 generally increased toxicity. Esterification at C-3 increased toxicity in one case and decreased toxicity in three of eight cases tested. Thus, the increase in structural complexity along the trichothecene biosynthetic pathway in Fusarium is not necessarily associated with an increase in phytotoxicity.
Preparation of 10-g Quantities of 15-O-Acetyl-4-deoxynivalenol
Grove, John Frederick,McAlees, Alan J.,Taylor, Alan
, p. 3860 - 3862 (2007/10/02)
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