3-Acetyl-DON
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| Category | Mycotoxins |
| Catalog number | BBF-04066 |
| CAS | 50722-38-8 |
| Molecular Weight | 338.35 |
| Molecular Formula | C17H22O7 |
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Description
3-Acetyl-DON is a mycotoxin that has been found in F. graminearum.
Specification
| Synonyms | 3-Acetyldeoxynivalenol |
| Storage | Store at -20°C |
| IUPAC Name | [(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate |
| Canonical SMILES | CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)OC(=O)C)C)CO |
| InChI | InChI=1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1 |
| InChI Key | ADFIQZBYNGPCGY-HTJQZXIKSA-N |
| Source | Trichothecenes are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. |
Properties
| Boiling Point | 518.8°C |
| Melting Point | 185.5-186°C |
| Density | 1.42 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 3-Acetyl-DON is a trichothecene mycotoxin. Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. |
Reference Reading
1.Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in cereals.
Habler K1, Rychlik M2. Anal Bioanal Chem. 2016 Jan;408(1):307-17. doi: 10.1007/s00216-015-9110-7. Epub 2015 Oct 29.
A multi-mycotoxin stable isotope dilution LC-MS/MS method was developed for 14 Fusarium toxins including modified mycotoxins in cereals (deoxynivalenol, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, HT2-toxin, T2-toxin, enniatin B, enniatin B1, enniatin A1, enniatin A, beauvericin, fusarenone X, nivalenol, deoxynivalenol-3-glucoside, and zearalenone). The chromatographic separation of the toxins with particular focus on deoxynivalenol and deoxynivalenol-3-glucoside was achieved using a C18-hydrosphere column. An expedient sample preparation method was developed that uses solid-phase extraction for the purification of trichothecenes combined with zearalenone, enniatins, and beauvericin and provides excellent validation data. Linearity, intra-day precision, inter-day precision, and recoveries were ≥0.9982, 1-6 %, 5-12 %, and 79-117 %, respectively. Method accuracy was verified by analyzing certified reference materials for deoxynivalenol, HT2-toxin, and T2-toxin with deviations below 7 %.
2.Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: New insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals.
Gauthier L1, Bonnin-Verdal MN2, Marchegay G3, Pinson-Gadais L4, Ducos C5, Richard-Forget F6, Atanasova-Penichon V7. Int J Food Microbiol. 2016 Mar 16;221:61-8. doi: 10.1016/j.ijfoodmicro.2016.01.005. Epub 2016 Jan 12.
Fusarium Head Blight and Gibberella Ear Rot, mainly caused by the fungi Fusarium graminearum and Fusarium culmorum, are two of the most devastating diseases of small-grain cereals and maize. In addition to yield loss, these diseases frequently result in contamination of kernels with toxic type B trichothecenes. The potential involvement of chlorogenic acid in cereal resistance to Fusarium Head Blight and Gibberella Ear Rot and to trichothecene accumulation was the focus of this study. The effects of chlorogenic acid and one of its hydrolyzed products, caffeic acid, on fungal growth and type B trichothecenes biosynthesis were studied using concentrations close to physiological amounts quantified in kernels and a set of F. graminearum and F. culmorum strains. Both chlorogenic and caffeic acids negatively impact fungal growth and mycotoxin production, with caffeic acid being significantly more toxic. Inhibitory efficiencies of both phenolic acids were strain-dependent.
3.[Dietary exposure assessment of deoxynivalenol and its acetylate & derivatives in wheat flour in Shanghai].
Yin F, Tian M, Wang L, Chen B, Wu M, He G. Wei Sheng Yan Jiu. 2015 Jul;44(4):661-5.
OBJECTIVE: To assess the dietary exposure of Shanghai residents to a compound of deoxynivalenol (DON) and its acetylated derivatives, 3-acetyl-deoxynivalenol (3-Ac-DON) and 15-acetyl-deoxynivalenol (15-Ac-DON) through wheat flour.
4.Plant-microbe rhizosphere interactions mediated by Rehmannia glutinosa root exudates under consecutive monoculture.
Wu L1,2, Wang J1,2, Huang W1,2, Wu H1,2, Chen J1,2, Yang Y1,2, Zhang Z3, Lin W1,3. Sci Rep. 2015 Oct 30;5:15871. doi: 10.1038/srep15871.
Under consecutive monoculture, the biomass and quality of Rehmannia glutinosa declines significantly. Consecutive monoculture of R. glutinosa in a four-year field trial led to significant growth inhibition. Most phenolic acids in root exudates had cumulative effects over time under sterile conditions, but these effects were not observed in the rhizosphere under monoculture conditions. It suggested soil microbes might be involved in the degradation and conversion of phenolic acids from the monocultured plants. T-RFLP and qPCR analysis demonstrated differences in both soil bacterial and fungal communities during monoculture. Prolonged monoculture significantly increased levels of Fusarium oxysporum, but decreased levels of Pseudomonas spp. Abundance of beneficial Pseudomonas spp. with antagonistic activity against F. oxysporum was lower in extended monoculture soils. Phenolic acid mixture at a ratio similar to that found in the rhizosphere could promote mycelial growth, sporulation, and toxin (3-Acetyldeoxynivalenol, 15-O-Acetyl-4-deoxynivalenol) production of pathogenic F.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
