15-Acetoxyscirpenol
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| Category | Mycotoxins |
| Catalog number | BBF-04140 |
| CAS | 2623-22-5 |
| Molecular Weight | 324.37 |
| Molecular Formula | C17H24O6 |
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Description
15-Acetoxyscirpenol is a trichothecene mycotoxin isolated from predominantly.
Specification
| Synonyms | MAS; 15-Monoacetoxyscirpenol; 15-Deacetylanguidin; 4-Deacetylanguidin; YD0111000; 15-Mono-O-acetylscirpenol; Trichothec-9-ene-3-alpha,4-beta,15-triol, 12,13-epoxy-, 15-acetate |
| Storage | Store at -20°C |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(C(C(C34CO4)O2)O)O)C)COC(=O)C |
| InChI | InChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3/t11-,12-,13-,14-,15-,16-,17+/m1/s1 |
| InChI Key | IRXDUBNENLKYTC-DIRMQTSCSA-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 Powder |
| Boiling Point | 465.5°C at 760 mmHg |
| Melting Point | 165-167°C |
| Density | 1.34 g/cm3 |
| Solubility | Soluble in chloroform, diethyl ether, ethyl acetate, acetone |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 15-Acetoxyscirpenol 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. Fusarium Species Pathogenic to Barley and Their Associated Mycotoxins
L K Prom, B Tacke, B J Steffenson, T G Fetch Jr, P B Schwarz, B Salas, H H Casper Plant Dis . 1999 Jul;83(7):667-674. doi: 10.1094/PDIS.1999.83.7.667.
Epidemics of Fusarium head blight (FHB) occurred on barley in Minnesota, North Dakota, and South Dakota from 1993 to 1998. The Red River Valley region was most severely impacted by the disease based on assessments of FHB severity in grain samples harvested from commercial fields. Fusarium graminearum was the primary pathogen causing these FHB epidemics. It comprised from 62 to 64% of all Fusarium species isolated from infected kernels from 1994 to 1996. Fusarium poae (range of isolation 13 to 20%),F. sporotrichioides (10 to 17%), and F. avenaceum (6 to 10%) also were isolated from barley kernels and were likely involved in causing some FHB infection, but to a very limited extent. All four Fusarium species were pathogenic on barley in inoculation tests conducted in both the greenhouse and the field. Mycotoxin screens were performed on barley spikes inoculated with the respective species in the greenhouse. Spikes infected with F. graminearum contained deoxynivalenol and 15-acetyldeoxyni-valenol; those infected with F. sporotrichioides contained T-2 toxin, HT-2 toxin, and T-2 tetraol; and those infected with F. poae contained nivalenol. Some isolates of F. poae also produced 15-acetoxyscirpenol and scirpentriol. Although F. graminearum and DON are recognized as the primary FHB pathogen and mycotoxin, respectively, in barley, the possible presence of other Fusarium species and mycotoxins should not be overlooked.
2. Trichothecene structure and toxicity to the green alga Chlorella pyrenoidosa
C Carr, M Ikawa, T Tatsuno Toxicon . 1985;23(3):535-7. doi: 10.1016/0041-0101(85)90040-6.
Using the paper-disk method with Chlorella-seeded agar plates, 15-acetoxyscirpenol, HT-2 toxin, acetyl T-2 toxin and neosolaniol inhibited growth at a concentration of 1 mg/ml, whereas verrucarol, T-2 tetraol, nivalenol, fusarenon-X, deoxynivalenol and 3-acetyldeoxynivalenol were inactive. Taking into account that verrucarin A, roridin A, T-2 toxin and diacetoxyscirpenol had previously been found to strongly inhibit Chlorella growth, esterification at R15 appears to be important for growth inhibitory activity. The most active agents are also esterified at R4. Inhibition of protein synthesis appears to be involved in the toxicity.
3. Development of a sensitive enzyme-linked immunosorbent assay for the detection of diacetoxyscirpenol
U Klaffer, G Terplan, E Märtlbauer Int J Food Microbiol . 1988 Feb;6(1):9-17. doi: 10.1016/0168-1605(88)90079-7.
An enzyme-linked immunosorbent assay (ELISA) for the detection of diacetoxyscirpenol (DAS) was developed. Antibodies against DAS were obtained after immunization of rabbits with DAS-hemiglutarate-human serum albumin (DAS-HG-HSA). After an immunization period of 6 weeks a sufficient level of specific antibodies was reached. A DAS-hemisuccinate-horseradish peroxidase-conjugate (DAS-HS-HRP) was prepared by an ester method and used as enzyme-labelled toxin in the competitive assay. The detection limit for DAS was about 10 pg/ml. The relative cross reactivity of the assay was 597.5, 5.2, 100.0, 2.5, and 1.5% for 3 alpha-acetyl-DAS, DAS, T-2 toxin, neosolaniol, and 15-acetoxyscirpenol, respectively.
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
Mass Spectrum (Electron Ionization)
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 ╳
