Zearalenone
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| Category | Mycotoxins |
| Catalog number | BBF-03998 |
| CAS | 17924-92-4 |
| Molecular Weight | 318.37 |
| Molecular Formula | C18H22O5 |
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Description
Zearalenone is a mycotoxin produced by Fusarium. The 100 ppm acetonitrile solution of Zearalenone, a kind of natural estrogen, could be used as standard solution.
Specification
| Synonyms | (3S,11E)-3,4,5,6,9,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2 -benzoxacyclotetradecin-1,7(8H)-dione; (-)-Zearalenone; Mycotoxin F 2; Toxin F2; Zenone; trans-Zearalenone |
| Storage | Store at -20°C (dark) |
| IUPAC Name | (4S,12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione |
| Canonical SMILES | CC1CCCC(=O)CCCC=CC2=CC(=CC(=C2C(=O)O1)O)O |
| InChI | InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+/t12-/m0/s1 |
| InChI Key | MBMQEIFVQACCCH-QBODLPLBSA-N |
| Source | Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is produced by some Giberella species. Several Fusarium species also produce zearalenone as their primary toxin. It can be found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum, and also in bread. |
Properties
| Appearance | White to Pale Beige Solid |
| Application | Estrogens, Non-Steroidal |
| Boiling Point | 600.4°C at 760 mmHg |
| Melting Point | 160-161°C |
| Density | 1.168 g/cm3 |
| Solubility | less than 0.1 mg/mL at 64 °F |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. Zearalenone also has significant estrogenic activity, causing severe reproductive problems in animals. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. |
| Toxicity | LD50 > 2000 mg/kg (Oral, Mouse); LD50 > 500 mg/kg (Intraperitoneal, Mouse). |
Reference Reading
1.The potential effects of antioxidant feed additives in mitigating the adverse effects of corn naturally contaminated with Fusarium mycotoxins on antioxidant systems in the intestinal mucosa, plasma, and liver in weaned pigs.
Van Le Thanh B1, Lemay M1, Bastien A1, Lapointe J2, Lessard M2, Chorfi Y3, Guay F4. Mycotoxin Res. 2016 May;32(2):99-116. doi: 10.1007/s12550-016-0245-y. Epub 2016 Mar 29.
Seventy-two piglets (6.0 kg BW) were randomly distributed within six different dietary treatments to evaluate the effect of deoxynivalenol (DON) and the potential of four antioxidant feed additives in mitigating the adverse effects of DON on growth performances and oxidative status. Dietary treatments were as follows: control diet 0.8 mg/kg DON; contaminated diet (DON-contaminated diet) 3.1 mg/kg DON; and four contaminated diets, each supplemented with a different antioxidant feed additive, DON + vitamins, DON + organic selenium (Se)/glutathione (GSH), DON + quercetin, and DON + COMB (vitamins + Se/GSH + quercetin from the other treatments). Although DON was the main mycotoxin in the contaminated diet, this diet also contained 1.8 mg/kg of zearalenone (ZEN). The "mycotoxin" effects therefore included the combined effect of these two mycotoxins, DON, and ZEN. The DON-ZEN ingestion did not affect growth performances, average daily gain (ADG), average daily feed intake (ADFI), and feed efficiency (G:F ratio), but partially induced oxidative stress in weaned pigs as shown by increased malondialdehyde (MDA) content in the plasma and superoxide dismutase (SOD) activity in liver (P < 0.
2.High-throughput determination of multi-mycotoxins in Chinese yam and related products by ultra fast liquid chromatography coupled with tandem mass spectrometry after one-step extraction.
Li M1, Kong W2, Li Y3, Liu H2, Liu Q4, Dou X2, Ou-Yang Z5, Yang M6. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Apr 8;1022:118-125. doi: 10.1016/j.jchromb.2016.04.014. [Epub ahead of print]
A simple, accurate and sensitive ultra fast liquid chromatography coupled with tandem mass spectrometry (UFLC-MS/MS) method was developed for high-throughput determination of aflatoxins (AFB1, AFB2, AFG1 and AFG2), ochratoxin A (OTA), fumonisins (FB1 and FB2) and zearalenone (ZEA) in Chinese yam, yam flours and yam-derived products. Mycotoxins were extracted from the samples with methanol-water-formic acid (79:20:1, v/v/v) and no further cleanup step before analysis. After optimization of some crucial parameters including sample preparation, chromatographic separation and MS/MS conditions, the method was successfully validated to exhibit excellent performance in terms of satisfactory linearity (r≥0.9977), limits of detection (≤0.15ngmL-1) and quantification (≤0.5ngmL-1) with good precision (RSD for intra- and inter-day variations of ≤4.65% and 6.31%, respectively), good accuracy (recoveries of 71.0-106.0%) and robustness, together with short run time (8min/sample).
3.Molecular characterization, fitness and mycotoxin production of Fusarium graminearum laboratory strains resistant to benzimidazoles.
Sevastos A1, Markoglou A1, Labrou NE2, Flouri F1, Malandrakis A3. Pestic Biochem Physiol. 2016 Mar;128:1-9. doi: 10.1016/j.pestbp.2015.10.004. Epub 2015 Oct 9.
4.Effects of zearalenone-diet on expression of ghrelin and PCNA genes in ovaries of post-weaning piglets.
Dai M1, Jiang S1, Yuan X2, Yang W1, Yang Z3, Huang L4. Anim Reprod Sci. 2016 May;168:126-37. doi: 10.1016/j.anireprosci.2016.03.006. Epub 2016 Mar 17.
Numerous reports have provided evidence that zearalenone (ZEN) can increase the weight of genital organs. These findings have been confirmed by many studies in which the ghrelin gene was expressed in the ovary and was implicated in the control of cells in reproductive tissues. The proliferating cell nuclear antigen (PCNA) is an important marker of cell proliferation. The present study investigates the effects of a ZEN-treated diet on the development of ovaries in post-weaning piglets by the detection of ghrelin and PCNA protein and relative abundance of mRNA using optical microscopy, immunohistochemistry and quantitative real-time (qRT-PCR). A total of 20 piglets (Duroc×Landrace×Yorkshire) weaned at 28 d, with an average body weight of 8.74 ± 0.26 kg (P=0.919) were used in this study. Piglets in the control group (n=10) were fed a normal basal diet, and those in the treatment group (n=10) were fed a diet containing ZEN (1.04mg/kg), for 35 d.
Spectrum
LC-MS/MS Spectrum - 20V, Positive
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
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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 ╳
