β-Zearalenol
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| Category | Mycotoxins |
| Catalog number | BBF-04352 |
| CAS | 71030-11-0 |
| Molecular Weight | 320.38 |
| Molecular Formula | C18H24O5 |
| Purity | > 99 % by HPLC |
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Description
A mycotoxin produced by several species of fusarium. It exhibits pronounced estrogenic activity, like other zearalenones. It is an important food quality issue for both human and animal health.
Specification
| Synonyms | 1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S-(3R*,7R*,11E))-; β-trans-Zearalenol; (-)-β-Zearalenol; (3S,7S,11E)-3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one |
| Storage | Store at -20 ℃ |
| IUPAC Name | (4S,8S,12E)-8,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraen-2-one |
| Canonical SMILES | CC1CCCC(CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1)O |
| InChI | InChI=1S/C18H24O5/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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3/b7-3+/t12-,14-/m0/s1 |
| InChI Key | FPQFYIAXQDXNOR-PMRAARRBSA-N |
| Source | Fusarium sp. |
Properties
| Appearance | White to pale beige solid |
| Boiling Point | 599 ℃ at 760 mmHg |
| Melting Point | 137-139 ℃ |
| Density | 1.174 g/cm3 |
| Solubility | Slightly soluble in Acetone, Methanol |
| LogP | 3.37140 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Mycotoxins, such as α-zearalenol (α-ZOL) and β-Zearalenol (β-ZOL), as contaminants of animal food can impair fertility and can cause abnormal fetal development in farm animals. The effects of mycotoxins on FSH receptor-dependent and receptor-independent pathways indicate that adenylate cyclase activity and/or regulatory pathways further downstream are targets of mycotoxin actions. The apparent dose-dependent reduction of p450scc and 3beta-HSD transcripts implies an effect of α- and β-ZOL on transcriptional regulation of these enzymes. The zearalenone metabolites induced loss of mitochondrial membrane potential (MMP), mitochondrial changes in Bcl-2 and Bax proteins, and cytoplasmic release of cytochrome c and apoptosis-inducing factor (AIF). Use of an inhibitor specific to c-Jun N-terminal kinase (JNK), p38 kinase or p53, but not pan-caspase or caspase-8, decreased the toxin-induced generation of reactive oxygen species (ROS) and also attenuated the α-ZOL- or β-ZOL-induced decrease of cell viability. |
Reference Reading
1. Effects of Panax ginseng, zearalenol, and estradiol on sperm function
William R Boone, Brett R Lackey, Sandra L Gray J Ginseng Res . 2016 Jul;40(3):251-9. doi: 10.1016/j.jgr.2015.08.004.
Background:Estrogen signaling pathways are modulated by exogenous factors. Panax ginseng exerts multiple activities in biological systems and is classified as an adaptogen. Zearalenol is a potent mycoestrogen that may be present in herbs and crops arising from contamination or endophytic association. The goal of this study was to investigate the impact of P. ginseng, zearalenol and estradiol in tests on spermatozoal function.Methods:The affinity of these compounds for estrogen receptor (ER)-alpha and beta (ERα and ERβ)-was assessed in receptor binding assays. Functional tests on boar spermatozoa motility, movement and kinematic parameters were conducted using a computer-assisted sperm analyzer. Tests for capacitation, acrosome reaction (AR), and chromatin decondensation in spermatozoa were performed using microscopic analysis.Results:Zearalenol-but not estradiol (E2)- or ginseng-treated spermatozoa-decreased the percentage of overall, progressive, and rapid motile cells. Zearalenol also decreased spontaneous AR and increased chromatin decondensation. Ginseng decreased chromatin decondensation in response to calcium ionophore and decreased AR in response to progesterone (P4) and ionophore.Conclusion:Zearalenol has adverse effects on sperm motility and function by targeting multiple signaling cascades, including P4, E2, and calcium pathways. Ginseng protects against chromatin damage and thus may be beneficial to reproductive fitness.
2. Understanding the Toxin Effects of β-Zearalenol and HT-2 on Bovine Granulosa Cells Using iTRAQ-Based Proteomics
Genlin Wang, Min Yang, Fangxiao Yang, Lian Li, Chengmin Li Animals (Basel) . 2020 Jan 13;10(1):130. doi: 10.3390/ani10010130.
Zearalenone (ZEA) and T-2 are the most common mycotoxins in grains and can enter the animal and human food-chain and cause many health disorders. To elucidate the toxic response profile, we stimulated bovine granulosa cells (GCs) with β-zearalenol or HT-2. Using isobaric tags for relative and absolute quantification (iTRAQ)-based proteomic, 178 and 291 differentially expressed proteins (DEPs, fold change ≥ 1.3 andp-value < 0.05) in β-zearalenol and HT-2 groups were identified, respectively. Among these DEPs, there were 66 common DEPs between β-zearalenol and HT-2 groups. These 66 DEPs were associated with 23 biological processes terms, 14 molecular functions terms, and 19 cellular components terms. Most heat shock proteins (HSPs) were involved in the toxic response. Reactive oxygen species accumulation, the endoplasmic reticulum (ER)-stress related marker molecule (GRP78), and apoptosis were activated. β-zearalenol and HT-2 inhibited oestradiol (E2) production. These results emphasized the important function of HSPs, clarified oxidative stress, and demonstrated the caspase-3 signaling cascade involved in mycotoxin-treated toxic response, along with decreased E2production. This study offers new insights into the toxicity of β-zearalenol and HT-2 on ovarian granulosa cells.
3. Zearalenone (ZEN) in Livestock and Poultry: Dose, Toxicokinetics, Toxicity and Estrogenicity
Jundi Liu, Todd Applegate Toxins (Basel) . 2020 Jun 7;12(6):377. doi: 10.3390/toxins12060377.
One of the concerns when using grain ingredients in feed formulation for livestock and poultry diets is mycotoxin contamination. Aflatoxin, fumonisin, ochratoxin, trichothecene (deoxynivalenol, T-2 and HT-2) and zearalenone (ZEN) are mycotoxins that have been frequently reported in animal feed. ZEN, which has raised additional concern due to its estrogenic response in animals, is mainly produced byFusariumgraminearum(F.graminearum),F.culmorum,F.cerealis,F.equiseti,F.crookwellenseandF.semitectums, and often co-occurs with deoxynivalenol in grains. The commonly elaborated derivatives of ZEN are -zearalenol, -zearalenol, zearalanone, -zearalanol, and -zearalanol. Other modified and masked forms of ZEN (including the extractable conjugated and non-extractable bound derivatives of ZEN) have also been quantified. In this review, common dose of ZEN in animal feed was summarized. The absorption rate, distribution ("carry-over"), major metabolites, toxicity and estrogenicity of ZEN related to poultry, swine and ruminants are discussed.
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
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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