Zearalenoneのソースを表示

{{chembox
| verifiedrevid = 470635656
| ImageFile = Zearalenone.svg
| ImageSize =
| ImageFile1 = Zearalenone-from-xtal-3D-bs-17.png
| PIN = (3''S'',11''E'')-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1''H''-2-benzoxacyclotetradecine-1,7(8''H'')-dione
| OtherNames = Mycotoxin F2
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444897
| 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
| InChIKey = MBMQEIFVQACCCH-QBODLPLBBS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MBMQEIFVQACCCH-QBODLPLBSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 17924-92-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5W827M159J
| PubChem = 5281576
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 454173
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09981
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10106
| SMILES = C[C@H]1CCCC(=O)CCC/C=C/c2cc(cc(c2C(=O)O1)O)O
}}
| Section2 = {{Chembox Properties
| C=18|H=22|O=5
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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.<ref name="Fermentek2">{{cite web|title=Zearalenone|date=January 2002 |url=http://www.fermentek.com/zearalenone|publisher=[[Fermentek]]}}</ref> Specifically, the ''[[Gibberella zeae]]'', the fungal species where zearalenone was initially detected, in its asexual/[[anamorph]] stage is known as ''Fusarium graminearum.''<ref>{{cite journal | vauthors = Liu J, Applegate T | title = Zearalenone (ZEN) in Livestock and Poultry: Dose, Toxicokinetics, Toxicity and Estrogenicity | journal = Toxins | volume = 12 | issue = 6 | pages = 377 | date = June 2020 | pmid = 32517357 | pmc = 7354539 | doi = 10.3390/toxins12060377 | doi-access = free }}</ref> 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]]'',<ref name=":3">{{cite journal | vauthors = Bulgaru CV, Marin DE, Pistol GC, Taranu I | title = Zearalenone and the Immune Response | journal = Toxins | volume = 13 | issue = 4 | pages = 248 | date = March 2021 | pmid = 33807171 | doi = 10.3390/toxins13040248 | pmc = 8066068 | doi-access = free }}</ref> ''[[Fusarium verticillioides]]'',<ref name=":0">{{cite journal | vauthors = Ropejko K, Twarużek M | title = Zearalenone and Its Metabolites-General Overview, Occurrence, and Toxicity | journal = Toxins | volume = 13 | issue = 1 | pages = 35 | date = January 2021 | pmid = 33418872 | doi = 10.3390/toxins13010035 | pmc = 7825134 | doi-access = free }}</ref> and ''[[Fusarium incarnatum]]''.  Zearalenone is the primary toxin that binds to [[estrogen receptor]]s, causing [[infertility]], [[abortion]] or other breeding problems, especially in swine.<ref name=":0" /> 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.<ref>{{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 }}</ref>

Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as [[maize]], [[barley]], [[oats]], [[wheat]], [[rice]], and [[sorghum]].<ref>{{cite journal | vauthors = Kuiper-Goodman T, Scott PM, Watanabe H | title = Risk assessment of the mycotoxin zearalenone | journal = Regulatory Toxicology and Pharmacology | volume = 7 | issue = 3 | pages = 253–306 | date = September 1987 | pmid = 2961013 | doi = 10.1016/0273-2300(87)90037-7 }}</ref><ref>{{cite journal| vauthors = Tanaka T, Hasegawa A, Yamamoto S, Lee US, Sugiura Y, Ueno Y |year=1988|title=Worldwide Contamination of Cereals by the ''Fusarium'' Mycotoxins Nivalenol, Deoxynivalenol, and Zearalenone. 1. Survey of 19 Countries|journal=Journal of Agricultural and Food Chemistry|publisher=American Chemical Society|volume=36|issue=5|pages=979–983|doi=10.1021/jf00083a019|bibcode=1988JAFC...36..979T }}</ref><ref name="ProssnitzBarton20142">{{cite journal | vauthors = Prossnitz ER, Barton M | title = Estrogen biology: new insights into GPER function and clinical opportunities | journal = Molecular and Cellular Endocrinology | volume = 389 | issue = 1–2 | pages = 71–83 | date = May 2014 | pmid = 24530924 | pmc = 4040308 | doi = 10.1016/j.mce.2014.02.002 }}</ref> Its production increases when the climate is warm with air humidity at or above twenty percent. <ref name=":0" /> The environmental pH plays also a role in the toxin's production. When temperatures fall to 15<sup>o</sup>C, alkaline soils still support ZEN production.  At the preferred ''Fusarium'' temperature, which ranges between 25<sup>o</sup>C and 30<sup>o</sup>C, neutral pH results in the greatest toxin production. <ref name=":1">{{cite journal | vauthors = Mahato DK, Devi S, Pandhi S, Sharma B, Maurya KK, Mishra S, Dhawan K, Selvakumar R, Kamle M, Mishra AK, Kumar P | display-authors = 6 | title = Occurrence, Impact on Agriculture, Human Health, and Management Strategies of Zearalenone in Food and Feed: A Review | journal = Toxins | volume = 13 | issue = 2 | pages = 92 | date = January 2021 | pmid = 33530606 | doi = 10.3390/toxins13020092 | pmc = 7912641 | doi-access = free }}</ref>

In addition to its actions on the classical [[estrogen receptor]]s, zearalenone has been found to act as an [[agonist]] of the [[GPER]] (GPR30).<ref name="ProssnitzBarton20142"/>