Zearalenone

Zearalenone is a white crystalline solid, with molecular formula C₁₈H₂₂O₅ and 318.364 g/mol molecular weight. It is a resorcyclic acid lactone. It exhibits blue-green fluorescence when excited by long wavelength ultraviolet (UV) light (360 nm) and a more intense green fluorescence when excited with short wavelength UV light (260 nm). In methanol, UV absorption maxima occur at 236 (e = 29,700), 274 (e = 13,909) and 316 nm (e = 6,020). Maximum fluorescence in ethanol occurs with irradiation at 314 nm and with emission at 450 nm. Solubility in water is about 0.002 g/100 mL. It is slightly soluble in hexane and progressively more so in benzene, acetonitrile, methylene chloride, methanol, ethanol, and acetone. It is also soluble in aqueous alkali.{{cn|date=October 2023}}

The naturally occurring isomer trans-zearalenone (trans-ZEN) is transformed by ultraviolet irradiation to cis-zearalenone (cis-ZEN).{{cite journal | vauthors = Brezina U, Kersten S, Valenta H, Sperfeld P, Riedel J, Dänicke S | title = UV-induced cis-trans isomerization of zearalenone in contaminated maize | journal = Mycotoxin Research | volume = 29 | issue = 4 | pages = 221–227 | date = November 2013 | pmid = 24018604 | doi = 10.1007/s12550-013-0178-7 | s2cid = 17466231 }}

Zearalenone is metabolically transformed to α-zearalenol (α-Zel) or (α-Zol), β-zearalenol (β-Zel) or (β-Zol), α-zearalanol (α-Zal), β-zearalanol (β-Zal), and zearalanone (ZAN) in animals. {{cite journal | vauthors = Yang D, Jiang X, Sun J, Li X, Li X, Jiao R, Peng Z, Li Y, Bai W | display-authors = 6 | title = Toxic effects of zearalenone on gametogenesis and embryonic development: A molecular point of review | journal = Food and Chemical Toxicology | volume = 119 | pages = 24–30 | date = September 2018 | pmid = 29864477 | doi = 10.1016/j.fct.2018.06.003 | s2cid = 46927149 }} The relative composition of these metabolic products varies by species. In pigs, cows and ducks, α-Zel is the dominant form detected.{{cite journal | vauthors = Peillod C, Laborde M, Travel A, Mika A, Bailly JD, Cleva D, Boissieu C, Le Guennec J, Albaric O, Labrut S, Froment P, Tardieu D, Guerre P | display-authors = 6 | title = Toxic Effects of Fumonisins, Deoxynivalenol and Zearalenone Alone and in Combination in Ducks Fed the Maximum EUTolerated Level | journal = Toxins | volume = 13 | issue = 2 | pages = 152 | date = February 2021 | pmid = 33669302 | pmc = 7920068 | doi = 10.3390/toxins13020152 | doi-access = free }}{{cite journal | vauthors = Gruber-Dorninger C, Faas J, Doupovec B, Aleschko M, Stoiber C, Höbartner-Gußl A, Schöndorfer K, Killinger M, Zebeli Q, Schatzmayr D | display-authors = 6 | title = Metabolism of Zearalenone in the Rumen of Dairy Cows with and without Application of a Zearalenone-Degrading Enzyme | journal = Toxins | volume = 13 | issue = 2 | pages = 84 | date = January 2021 | pmid = 33499402 | pmc = 7911295 | doi = 10.3390/toxins13020084 | doi-access = free }} In humans, both α-Zel and β-Zel are seen in urine samples, with the beta form being prevalent.{{cite journal | vauthors = Al-Jaal B, Latiff A, Salama S, Hussain HM, Al-Thani NA, Al-Naimi N, Al-Qasmi N, Horvatovich P, Jaganjac M | display-authors = 6 | title = Analysis of Multiple Mycotoxins in the Qatari Population and Their Relation to Markers of Oxidative Stress | journal = Toxins | volume = 13 | issue = 4 | pages = 267 | date = April 2021 | pmid = 33917988 | pmc = 8068385 | doi = 10.3390/toxins13040267 | doi-access = free }} In chickens, β-Zel is the dominant form and in plant cells, the metabolic product zeralenonne-14-O-β-glucoside has been detected. Additionally, in the organs of animals these metabolic products are further modified to yield zearalenone-14-glucuronide (ZEN-14GlcA), α-zearalenol-glucuronide (α-Zel-14G) and β-zearalenol-glucuronide (β-Zel-14G).{{cite journal | vauthors = Yan Z, Wang L, Wang J, Tan Y, Yu D, Chang X, Fan Y, Zhao D, Wang C, De Boevre M, De Saeger S, Sun C, Wu A | display-authors = 6 | title = A QuEChERS-Based Liquid Chromatography-Tandem Mass Spectrometry Method for the Simultaneous Determination of Nine Zearalenone-Like Mycotoxins in Pigs | journal = Toxins | volume = 10 | issue = 3 | pages = 129 | date = March 2018 | pmid = 29558416 | pmc = 5869417 | doi = 10.3390/toxins10030129 | doi-access = free }}

Zearalenone can permeate through the human skin.{{cite journal | vauthors = Boonen J, Malysheva SV, Taevernier L, Diana Di Mavungu J, De Saeger S, De Spiegeleer B | title = Human skin penetration of selected model mycotoxins | journal = Toxicology | volume = 301 | issue = 1–3 | pages = 21–32 | date = November 2012 | pmid = 22749975 | doi = 10.1016/j.tox.2012.06.012 | bibcode = 2012Toxgy.301...21B }} However, no significant hormonal effects are expected after dermal contact in normal agricultural or residential environments.

Zearalenone structure is similar to estrogens and α-zearalenol binds with an even greater affinity estrogen receptors, while β-zearalenol's affinity is lower than both the parent compound's and α-Zel's binding affinity. This identifies ZEN and its metabolites as xenoestrogens. The human and livestock exposure to ZEN through the diet poses health concern due to the onset of several sexual disorders and alterations in the development of sexual apparatus.{{cite journal | vauthors = Massart F, Saggese G | title = Oestrogenic mycotoxin exposures and precocious pubertal development | journal = International Journal of Andrology | volume = 33 | issue = 2 | pages = 369–376 | date = April 2010 | pmid = 20002219 | doi = 10.1111/j.1365-2605.2009.01009.x | doi-access = free }}{{cite journal | vauthors = Schoevers EJ, Santos RR, Colenbrander B, Fink-Gremmels J, Roelen BA | title = Transgenerational toxicity of Zearalenone in pigs | journal = Reproductive Toxicology | volume = 34 | issue = 1 | pages = 110–119 | date = August 2012 | pmid = 22484360 | doi = 10.1016/j.reprotox.2012.03.004 | bibcode = 2012RepTx..34..110S }} There are reliable case reports of early puberty in girls chronically exposed to ZEN in various regions of the world.{{cite journal | vauthors = Hueza IM, Raspantini PC, Raspantini LE, Latorre AO, Górniak SL | title = Zearalenone, an estrogenic mycotoxin, is an immunotoxic compound | journal = Toxins | volume = 6 | issue = 3 | pages = 1080–1095 | date = March 2014 | pmid = 24632555 | pmc = 3968378 | doi = 10.3390/toxins6031080 | doi-access = free }} In mice, ZEN consumption was linked to a decline of potent sperm and egg cells, an increase to double-stranded breaks in DNA and activation of DNA repair mechanisms, followed by embryonic development challenges that reduced the viability of offspring.

In common with other mycotoxins, sampling food commodities for zearalenone must be carried out to obtain samples representative of the consignment under test. Commonly used extraction solvents are aqueous mixtures of methanol, acetonitrile, or ethyl acetate followed by a range of different clean-up procedures that depend in part on the food and on the detection method in use. Thin-layer chromatography (TLC) methods and high-performance liquid chromatography (HPLC) are commonly used. The TLC method for zearalenone is: normal phase silica gel plates, the eluent: 90% dichloromethane, 10% v/v acetone; or reverse phase C18 silica plates; the eluent: 90% v/v methanol, 10% water. Zearalenone gives unmistakable blue luminiscence under UV. HPLC alone is not sufficient, as it may often yield false positive results. Today, HPLC-MS/MS analysis is used to quantify and confirm the presence of zearalenone.

Typically, the representative sample is commuted and homogenized then few grams are used for extraction with acetonitrile/water mixture. The procedure is the widely used QuEChERS method that quickly and effectively extracts small molecules, like mycotoxins and pesticides, from complex food matrices and animal tissues. The determination step relies on liquid chromatography - mass-spectrometry (LC-MS/MS). Another approach for the analysis of ZEA, without the requirement of expensive instrumentation, is developing specific peptide mimetic with the bioluminescent Gaussia luciferase fused as one protein that can bind specifically to ZEA.{{cite journal | vauthors = Peltomaa R, Fikacek S, Benito-Peña E, Barderas R, Head T, Deo S, Daunert S, Moreno-Bondi MC | display-authors = 6 | title = Bioluminescent detection of zearalenone using recombinant peptidomimetic Gaussia luciferase fusion protein | journal = Mikrochimica Acta | volume = 187 | issue = 10 | pages = 547 | date = September 2020 | pmid = 32886242 | doi = 10.1007/s00604-020-04538-7 | pmc = 7938698 }}

• α-Zearalenol
• β-Zearalenol
• Taleranol
• Trichothecene
• Zeranol
• Zearalanone

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• {{ cite web | url = http://www.inchem.org/documents/jecfa/jecmono/v44jec14.htm | vauthors = Eriksen GS, Pennington J, Schlatter J | work = WHO International Programme on Chemical Safety - Safety Evaluation of Certain Food Additives and Contaminants | title = Zearalenone | publisher = Inchem | id = WHO Food Additives Series | volume = 44 | year = 2000 }}

{{Toxins}}

{{Xenoestrogens}}

{{Estrogen receptor modulators}}

Category:Aromatase inhibitors

Category:Ecotoxicology

Category:Female reproductive toxins

Category:GPER modulators

Category:Heterocyclic compounds with 2 rings

Category:Mycoestrogens

Category:Mycotoxins

Category:Oxygen heterocycles

Category:Resorcinols

Category:Lactones

Category:Ketones