Diacetylverrucarol
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| Category | Antibiotics |
| Catalog number | BBF-03026 |
| CAS | 2198-94-9 |
| Molecular Weight | 350.41 |
| Molecular Formula | C19H26O6 |
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Description
It is a terpenoid antibiotic produced by the strain of Myrothecium verrucaria. It mainly has anti-fungal effect and has high activity against Trichophyton purpureatum.
Specification
| Synonyms | Antibiotic A2; Trichothec-9-ene-4,15-diol,12,13-epoxy-diacetate; 4,15-Diacetylverrucarol; (-)-12,13-Epoxytrichothec-9-ene-4β,15-diol diacetate; (-)-Diacetylverrucarol; Di-O-acetylverrucarol |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,2R,7R,9R,11R,12S)-11-acetyloxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-2-yl]methyl acetate |
| Canonical SMILES | CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)OC(=O)C)C)COC(=O)C |
| InChI | InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-8-14(24-13(3)21)17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3/t14-,15-,16-,17-,18-,19+/m1/s1 |
| InChI Key | CVJVDRZXGYXIET-UPGMHYFXSA-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 prismatic Crystal |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 429.1°C at 760 mmHg |
| Melting Point | 148-150°C |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in Methanol, Ether |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Diacetylverrucarol is a natural trichothecene. 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. Toxicity of trichothecenes, moniliformin, zearalenone/ol, griseofulvin, patulin, PR toxin and rubratoxin B on protozoan tetrahymena pyriformis
K Nishie, H G Cutler, R J Cole Res Commun Chem Pathol Pharmacol. 1989 Aug;65(2):197-210.
The inhibitory effects of some fungal products from Fusarium, Trichothecium, Myrothecium and Penicillium were investigated on the protozoan Tetrahymena pyriformis. The dose of mycotoxin which decreased the protozoa growth by 50% in 24 h was defined as inhibitory dose 50 (ID50). The order of toxicity according to the ID50 values were: T-2 toxin greater than trichothecin greater than 4, 15-diacetylverrucarol greater than patulin greater than trichothecolone greater than verrucarol greater than zearalenone greater than PR toxin greater than 3 alpha-acetyldiacetoxyscirpenol greater than zearalenol greater than griseofulvin greater than acetyl T-2 greater than iso T-2 greater than T-2 triol greater than scirpentriol greater than rubratoxin B greater than T-2 tetraol greater than moniliformin. In analogous pairs of trichothecenes their toxicities depended upon the substituents at certain positions of the molecules. Thus, the order of toxicity by the substituents was: at C3 position, H greater than OH greater than OAc [e.g., verrucarol (H at C3) greater than scirpentriol (OH at C3); T-2 toxin (OH at C3) greater than acetyl T-2 (OAc at C3); 4,15-diacetylverrucarol (H at C3) greater than 3 alpha-acetyldiacetoxyscirpenol (OAc at C3)]; at C4 position, OAc greater than OH, and isocrotonyl greater than OH [e.g., acetyl T-2 (OAc at C4) greater than iso T-2 (OH at C4); trichothecin (isocrotonoyl at C4) greater than trichothecolone (OH at C4)]; at C8 position, H greater than isovaleryl greater than OH [e.g., 3 alpha-acetyldiacetoxyscirpenol (H at C8) greater than acetyl T-2 (isovaleryl at C8); T-2 triol isovaleryl at C8) greater than T-2 tetraol (OH at C8); scirpentriol (H at C8) greater than T-2 tetraol (OH at C8)]. Among trichothecenes (without ester groups) with H and OH substituents, the toxicity was inversely related to the number of OH groups in the molecule: verrucarol (2 OHs) greater than scirpentriol (3 OHs) greater than T-2 tetraol (4 OHs). Zearalenone was about 3 times more toxic than its analogue zearalenol. The Tetrahymena cultures exposed 1 d to mycotoxins had protozoa counts/microliters inversely related to doses, and the % transmittance and pH values were directly related to doses.
2. Detection of airborne Stachybotrys chartarum macrocyclic trichothecene mycotoxins on particulates smaller than conidia
T L Brasel, D R Douglas, S C Wilson, D C Straus Appl Environ Microbiol. 2005 Jan;71(1):114-22. doi: 10.1128/AEM.71.1.114-122.2005.
Highly respirable particles (diameter, <1 microm) constitute the majority of particulate matter found in indoor air. It is hypothesized that these particles serve as carriers for toxic compounds, specifically the compounds produced by molds in water-damaged buildings. The presence of airborne Stachybotrys chartarum trichothecene mycotoxins on particles smaller than conidia (e.g., fungal fragments) was therefore investigated. Cellulose ceiling tiles with confluent Stachybotrys growth were placed in gas-drying containers through which filtered air was passed. Exiting particulates were collected by using a series of polycarbonate membrane filters with decreasing pore sizes. Scanning electron microscopy was employed to determine the presence of conidia on the filters. A competitive enzyme-linked immunosorbent assay (ELISA) specific for macrocyclic trichothecenes was used to analyze filter extracts. Cross-reactivity to various mycotoxins was examined to confirm the specificity. Statistically significant (P < 0.05) ELISA binding was observed primarily for macrocyclic trichothecenes at concentrations of 50 and 5 ng/ml and 500 pg/ml (58.4 to 83.5% inhibition). Of the remaining toxins tested, only verrucarol and diacetylverrucarol (nonmacrocyclic trichothecenes) demonstrated significant binding (18.2 and 51.7% inhibition, respectively) and then only at high concentrations. The results showed that extracts from conidium-free filters demonstrated statistically significant (P < 0.05) antibody binding that increased with sampling time (38.4 to 71.9% inhibition, representing a range of 0.5 to 4.0 ng/ml). High-performance liquid chromatography analysis suggested the presence of satratoxin H in conidium-free filter extracts. These data show that S. chartarum trichothecene mycotoxins can become airborne in association with intact conidia or smaller particles. These findings may have important implications for indoor air quality assessment.
3. Occurrence of type A, B and D trichothecenes in barley and barley products from the Bavarian market
Jörg Barthel, Christoph Gottschalk, Martin Rapp, Matthias Berger, Johann Bauer, Karsten Meyer Mycotoxin Res. 2012 May;28(2):97-106. doi: 10.1007/s12550-012-0123-1. Epub 2012 Feb 24.
Fifty-nine samples of barley and barley products were analysed for 18 trichothecene mycotoxins by a sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method (detection limits 0.062-0.70 μg/kg) after sample extract clean-up on MycoSep®-226 columns. The samples were collected in 2009 from barley processing facilities (mills and malt houses) and at wholesale and retail stage from the Bavarian market. The predominant toxins were T-2 toxin (T-2), HT-2 toxin (HT-2) and deoxynivalenol (DON). For all samples, the mean levels of T-2 and HT-2 were 3.0 μg/kg and 6.8 μg/kg with rates of contamination of 63% and 71%, respectively. The maximum values were 40 μg/kg for T-2 and 47 μg/kg for HT-2. The rate of contamination with DON was high (95%) with a low mean level of 23 μg/kg. The DON levels ranged between 3.4 to 420 μg/kg. For T-2 tetraol, a mean level of 9.2 μg/kg and a maximum level of 51 μg/kg with a rate of contamination of 71% were determined. NIV was detected in 69% of the samples with a mean level of 11 μg/kg and a maximum level of 72 μg/kg. Other type A and B trichothecenes were detected only in traces. Type D trichothecenes, fusarenon-X, verrucarol and 4,15-diacetylverrucarol were not detected in any sample. Winter barley and malting barley were the most contaminated groups of all samples in this study. In malting barley, the highest levels of contamination with type A trichothecenes were found. In contrast, winter barley showed the highest contamination with type B trichothecenes. The lowest mycotoxin concentrations were found in de-hulled and naked barley and in pearl barley.
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
Molecular Formula: C19H26O6
Molecular Weight (Monoisotopic Mass): 350.1729 Da
Molecular Weight (Avergae Mass): 350.4061 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C19H26O6
Molecular Weight (Monoisotopic Mass): 350.1729 Da
Molecular Weight (Avergae Mass): 350.4061 Da
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
