Zearalenone
Chemical compound / From Wikipedia, the free encyclopedia
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Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species.[1] Specifically, the Gibberella zeae, the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as Fusarium graminearum.[2] Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti,[3] Fusarium verticillioides,[4] and Fusarium incarnatum. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine.[4] Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the presence of other toxins.[5]
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Preferred IUPAC name
(3S,11E)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione | |
Other names
Mycotoxin F2 | |
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ChEBI | |
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ECHA InfoCard | 100.038.043 |
KEGG |
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CompTox Dashboard (EPA) |
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Properties | |
C18H22O5 | |
Molar mass | 318.369 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum.[6][7][8] Its production increases when the climate is warm with air humidity at or above twenty percent. [4] The environmental pH plays also a role in the toxin's production. When temperatures fall to 15oC, alkaline soils still support ZEN production. At the preferred Fusarium temperature, which ranges between 25oC and 30oC, neutral pH results in the greatest toxin production. [9]
In addition to its actions on the classical estrogen receptors, zearalenone has been found to act as an agonist of the GPER (GPR30).[8]