15-Acetyl-DON
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Category | Mycotoxins |
Catalog number | BBF-05792 |
CAS | 88337-96-6 |
Molecular Weight | 338.35 |
Molecular Formula | C17H22O7 |
Purity | ≥98% |
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Description
15-Acetyl-DON is a mycotoxin produced by the fungi Fusarium culmorum and Fusarium graminearum. It can inhibit protein synthesis.
Specification
Synonyms | (3α,7α)-15-(Acetyloxy)-12,13-epoxy-3,7-dihydroxy-trichothec-9-en-8-one; 15-Acetylvomitoxin; 15-O-Acetyl-4-deoxynivalenol; Deoxynivalenol 15-Acetate; 15-Acetyl Deoxynivalenol; 15-Acetoxy-3alpha,7alpha-dihydroxy-12,13-epoxytrichothec-9-en-8-one; (3alpha,7alpha)-15-(acetyloxy)-12,13-epoxy-3,7-dihydroxytrichothec-9-en-8-one |
Storage | Store at -20°C |
IUPAC Name | [(1R,2R,3S,7R,9R,10R,12S)-3,10-dihydroxy-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate |
Canonical SMILES | CC1=CC2C(C(C1=O)O)(C3(CC(C(C34CO4)O2)O)C)COC(=O)C |
InChI | InChI=1S/C17H22O7/c1-8-4-11-16(6-22-9(2)18,13(21)12(8)20)15(3)5-10(19)14(24-11)17(15)7-23-17/h4,10-11,13-14,19,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1 |
InChI Key | IDGRYIRJIFKTAN-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
Appearance | White to Off-white Solid |
Boiling Point | 538.6±50.0°C (Predicted) |
Melting Point | >130°C (dec.) |
Density | 1.42±0.1 g/cm3 (Predicted) |
Solubility | Soluble in Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | 15-Acetyl-DON is a member of type B 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
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
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