Back زآرالنون AZB Zearalenona Catalan Zearalenon German Zearalenona Spanish Zearelanona Basque زآرالنون Persian Tsearalenoni Finnish Zéaralénone French Zearalenone Italian ゼアラレノン Japanese

Zearalenone

Zearalenone
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.038.043 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: MBMQEIFVQACCCH-QBODLPLBSA-N checkY
  • InChI=1/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
    Key: MBMQEIFVQACCCH-QBODLPLBBS
  • C[C@H]1CCCC(=O)CCC/C=C/c2cc(cc(c2C(=O)O1)O)O
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 (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]

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]

  1. ^ "Zearalenone". Fermentek. January 2002.
  2. ^ Liu J, Applegate T (June 2020). "Zearalenone (ZEN) in Livestock and Poultry: Dose, Toxicokinetics, Toxicity and Estrogenicity". Toxins. 12 (6): 377. doi:10.3390/toxins12060377. PMC 7354539. PMID 32517357.
  3. ^ Bulgaru CV, Marin DE, Pistol GC, Taranu I (March 2021). "Zearalenone and the Immune Response". Toxins. 13 (4): 248. doi:10.3390/toxins13040248. PMC 8066068. PMID 33807171.
  4. ^ a b c Ropejko K, Twarużek M (January 2021). "Zearalenone and Its Metabolites-General Overview, Occurrence, and Toxicity". Toxins. 13 (1): 35. doi:10.3390/toxins13010035. PMC 7825134. PMID 33418872.
  5. ^ Peillod C, Laborde M, Travel A, Mika A, Bailly JD, Cleva D, et al. (February 2021). "Toxic Effects of Fumonisins, Deoxynivalenol and Zearalenone Alone and in Combination in Ducks Fed the Maximum EUTolerated Level". Toxins. 13 (2): 152. doi:10.3390/toxins13020152. PMC 7920068. PMID 33669302.
  6. ^ Kuiper-Goodman T, Scott PM, Watanabe H (September 1987). "Risk assessment of the mycotoxin zearalenone". Regulatory Toxicology and Pharmacology. 7 (3): 253–306. doi:10.1016/0273-2300(87)90037-7. PMID 2961013.
  7. ^ Tanaka T, Hasegawa A, Yamamoto S, Lee US, Sugiura Y, Ueno Y (1988). "Worldwide Contamination of Cereals by the Fusarium Mycotoxins Nivalenol, Deoxynivalenol, and Zearalenone. 1. Survey of 19 Countries". Journal of Agricultural and Food Chemistry. 36 (5). American Chemical Society: 979–983. Bibcode:1988JAFC...36..979T. doi:10.1021/jf00083a019.
  8. ^ a b Prossnitz ER, Barton M (May 2014). "Estrogen biology: new insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. PMC 4040308. PMID 24530924.
  9. ^ Mahato DK, Devi S, Pandhi S, Sharma B, Maurya KK, Mishra S, et al. (January 2021). "Occurrence, Impact on Agriculture, Human Health, and Management Strategies of Zearalenone in Food and Feed: A Review". Toxins. 13 (2): 92. doi:10.3390/toxins13020092. PMC 7912641. PMID 33530606.
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