{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 433986377 | ImageFile = Cyclochlorotine.png | ImageSize = 200px | ImageAlt = Skeletal formula of cyclochlorotine | ImageFile1 = Cyclochlorotine 3D ball.png | ImageAlt1 = Ball-and-stick model of the cyclochlorotine molecule | IUPACName = 1,2-Dichloro-15-ethyl-5,12-bis-hydroxymethyl-9-phenyl-dodecahydro-3a,6,10,13,16-pentaaza-cyclopentac yclohexadecene-4,7,11,14,17-pentaone | OtherNames = Cyclo[(''R'')-3-phenyl-β-alanyl-<small>L</small>-seryl-(2α,3α,4α)-3,4-dichloro-<small>L</small>-prolyl-<small>L</small>-2-aminobutanoyl-<small>L</small>-seryl]; Yellowed rice toxin |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 12663-46-6 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = B9GK4M718Q | PubChem = 25565 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C19379 | SMILES = O=C([C@H](CO)NC1=O)N[C@@H](C2=CC=CC=C2)CC(N[C@H](C(N3[C@H](C(N[C@H]1CC)=O)[C@H](Cl)[C@H](Cl)C3)=O)CO)=O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 28426727 | InChI = 1/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1 | InChIKey = PMBVHCCVEPYDSN-BADCMNFIBI | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = PMBVHCCVEPYDSN-BADCMNFISA-N }} |Section2={{Chembox Properties | C=24 | H=31 | Cl=2 | N=5 | O=7 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Cyclochlorotine'''<ref>{{cite journal | title = Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro | journal = Nat. Toxins | year = 1994 | pmid = 7704452 | last1 = Zhou | first1 = ZH | last2 = Komiyama | first2 = M | last3 = Terao | first3 = K | last4 = Shimada | first4 = Y | volume = 2 | issue = 6 | pages = 378–85 |doi=10.1002/nt.2620020607}}</ref> (CC), also known as '''islanditoxin''',<ref name=":0">{{Cite journal|last=Kushiro|first=Masayo|date=2015|title=Historical review of researches on yellow rice and mycotoxigenic fungi adherent to rice in Japan|doi=10.2520/myco.65.19|journal=JSM Mycotoxins|volume=65|pages=12–23|doi-access=free}}</ref> is a mycotoxin produced by the fungus ''Penicillium islandicum''<ref>{{cite journal | title = Toxicology of ''Penicillium islandicum'' | journal = Nature | volume = 191 | issue = 4791 | pages = 864–865 | year = 1961 | bibcode = 1961Natur.191..864. | doi = 10.1038/191864b0| s2cid = 38045877 | doi-access = free }}</ref> that causes liver damage and has carcinogenic properties.<ref>[http://medical-dictionary.thefreedictionary.com/Penicillium+islandicum ''Penicillium islandicum'' causes hepatic necrosis and has carcinogenic properties]</ref> Japanese researchers confirmed that it was one of three strains of ''Penicillin'' fungi responsible for yellowed rice.<ref name=":0" /> It is listed as an IARC Group 3 carcinogen.
Chemically, it is a dichlorinated cyclic peptide.<ref>{{cite journal | title = Structural and conformational analysis of hydroxycyclochlorotine and cyclochlorotine, chlorinated cyclic peptides from ''Penicillium islandicum'' |author1=Kohei Mizutani |author2=Yusuke Hirasawa |author3=Yoshiko Sugita-Konishi |author4=Naoki Mochizuki |author5=Hiroshi Morita | journal = J. Nat. Prod. | year = 2008 | volume = 71 | issue = 7 | pages = 1297–1300 | doi = 10.1021/np800150m | pmid = 18558744}}</ref> Structurally, the only thing that differentiates cyclochlorotine from the plant-derived astins of ''Aster tataricus'', is replacement of a serine with a second 2-aminobutyrate.<ref name="pmid26954535">{{Cite journal|last1=Schafhauser|first1=Thomas|last2=Kirchner|first2=Norbert|last3=Kulik|first3=Andreas|last4=Huijbers|first4=Mieke M. E.|last5=Flor|first5=Liane|last6=Caradec|first6=Thibault|last7=Fewer|first7=David P.|last8=Gross|first8=Harald|last9=Jacques|first9=Philippe|date=2016-11-01|title=The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in ''Talaromyces islandicus'' (''Penicillium islandicum'')|journal=Environmental Microbiology|language=en|volume=18|issue=11|pages=3728–3741|doi=10.1111/1462-2920.13294|pmid=26954535|bibcode=2016EnvMi..18.3728S |s2cid=22896792 |issn=1462-2920|url=https://backend.orbit.dtu.dk/ws/files/123723880/2016_Schafhauser_Cyclochlorotine_EnvMicrobiol_accepted.pdf}}</ref>
Cyclochlorotine is one of the toxins usually found in foods in grains such as rice, wheat, soybeans, peanuts, beans, bread, flour, etc. Such foods serve as medium for the growth of molds such as ''Penicillium islandicum'' which in turn release toxins such as cyclochlorotine.<ref>{{Cite journal|last1=Gosh|first1=Anil|last2=Manmade|first2=Awinash|last3=Townsend|first3=James|last4=Bousquet|first4=Ann|last5=Howes|first5=John|last6=Demain|first6=Arnold|date=June 1978|title=Production of Cyclochlorotine and a New Metabolite, Simatoxin, by ''Penicillium islandicum'' Sopp|journal=American Society for Microbiology|volume=35|issue=6|pages=1074–1078|doi=10.1128/AEM.35.6.1074-1078.1978|pmid=677874|pmc=242987|bibcode=1978ApEnM..35.1074G }}</ref> Research shows that that biosynthesis of cyclochlorotine is a multi-step mechanism and makes use of a vital component in the last step known as NRPS (CctN).<ref name="pmid26954535"/>
== References == {{reflist}}
Category:IARC Group 3 carcinogens Category:Cyclic peptides Category:Mycotoxins Category:Chlorine-containing natural products