Cyclochlorotine

Cyclochlorotine
Names
	IUPAC name 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
	Other names Cyclo[(R)-3-phenyl-β-alanyl-L-seryl-(2α,3α,4α)-3,4-dichloro-L-prolyl-L-2-aminobutanoyl-L-seryl]; Yellowed rice toxin
Identifiers
CAS Number	12663-46-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	28426727 ;
KEGG	C19379 ;
PubChem CID	25565;
UNII	B9GK4M718Q ;
CompTox Dashboard (EPA)	DTXSID1020356 ;
	InChI InChI=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 Key: PMBVHCCVEPYDSN-BADCMNFISA-N ; 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 Key: PMBVHCCVEPYDSN-BADCMNFIBI;
	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;
Properties
Chemical formula	C24H31Cl2N5O7
Molar mass	572.44 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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	Infobox references

Cyclochlorotine[1] (CC), also known as islanditoxin[2] is a mycotoxin produced by the fungus Penicillium islandicum[3] that causes liver damage and has carcinogenic properties.[4] Japanese researchers confirmed that it was one of three strains of Penicillin fungi responsible for yellowed rice.[2] It is listed as an IARC Group 3 carcinogen.

Chemically, it is a dichlorinated cyclic peptide.[5] 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.[6]

Cyclochlorotine are one of the toxins usually found in foods in the grains group like rice , wheat, soybeans, peanuts , beans, bread and flour etc. Such foods serve as medium for the growth of molds like Penicillium islandicum which in turn releases toxins like cyclochlorotine etc.[7] Research shows the detailed biosynthesis of Cyclochlorotine which is a multi step mechanism and makes use of a vital component in the last step known as NRPS ( CctN) which helps produce the desired Cyclochlorotine. [8]

References

Zhou, ZH; Komiyama, M; Terao, K; Shimada, Y (1994). "Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro". Nat. Toxins. 2 (6): 378–85. doi:10.1002/nt.2620020607. PMID 7704452.
Kushiro, Masayo (2015). "Historical review of researches on yellow rice and mycotoxigenic fungi adherent to rice in Japan". JSM Mycotoxins. 65: 12–23. doi:10.2520/myco.65.19.
"Toxicology of Penicillium islandicum". Nature. 191 (4791): 864–865. 1961. Bibcode:1961Natur.191..864.. doi:10.1038/191864b0. S2CID 38045877.
Penicillium islandicum causes hepatic necrosis and has carcinogenic properties
Kohei Mizutani; Yusuke Hirasawa; Yoshiko Sugita-Konishi; Naoki Mochizuki; Hiroshi Morita (2008). "Structural and conformational analysis of hydroxycyclochlorotine and cyclochlorotine, chlorinated cyclic peptides from Penicillium islandicum". J. Nat. Prod. 71 (7): 1297–1300. doi:10.1021/np800150m. PMID 18558744.
Schafhauser, Thomas; Kirchner, Norbert; Kulik, Andreas; Huijbers, Mieke M. E.; Flor, Liane; Caradec, Thibault; Fewer, David P.; Gross, Harald; Jacques, Philippe (2016-11-01). "The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Talaromyces islandicus ('Penicillium islandicum')" (PDF). Environmental Microbiology. 18 (11): 3728–3741. doi:10.1111/1462-2920.13294. ISSN 1462-2920. PMID 26954535.
Gosh, Anil; Manmade, Awinash; Townsend, James; Bousquet, Ann; Howes, John; Demain, Arnold (June 1978). "Production of Cyclochlorotine and a New Metabolite, Simatoxin, by Penicillium islandicum Sopp". American Society for Microbiology. 35 (6): 1074–1078. doi:10.1128/AEM.35.6.1074-1078.1978. PMC 242987. PMID 677874.
Schafhauser, Thomas; Kirchner, Norbert; Kulik, Andreas; Huijbers, Mieke; Flor, Liane; Caradec, Thibault; Fewer, David; Gross, Harald; Jacques, Philippe; Jahn, Linda; Jokela, Jouni (March 2016). "The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Taralomyces islandicus ( ' Penicillium islandicum')" (PDF). Environmental Microbiology. 18 (11): 3728–3741. doi:10.1111/1462-2920.13294. PMID 26954535.

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[1] Zhou, ZH; Komiyama, M; Terao, K; Shimada, Y (1994). "Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro". Nat. Toxins. 2 (6): 378–85. doi:10.1002/nt.2620020607. PMID 7704452.

[:0-2] Kushiro, Masayo (2015). "Historical review of researches on yellow rice and mycotoxigenic fungi adherent to rice in Japan". JSM Mycotoxins. 65: 12–23. doi:10.2520/myco.65.19.

[3] "Toxicology of Penicillium islandicum". Nature. 191 (4791): 864–865. 1961. Bibcode:1961Natur.191..864.. doi:10.1038/191864b0. S2CID 38045877.

[4] Penicillium islandicum causes hepatic necrosis and has carcinogenic properties

[5] Kohei Mizutani; Yusuke Hirasawa; Yoshiko Sugita-Konishi; Naoki Mochizuki; Hiroshi Morita (2008). "Structural and conformational analysis of hydroxycyclochlorotine and cyclochlorotine, chlorinated cyclic peptides from Penicillium islandicum". J. Nat. Prod. 71 (7): 1297–1300. doi:10.1021/np800150m. PMID 18558744.

[6] Schafhauser, Thomas; Kirchner, Norbert; Kulik, Andreas; Huijbers, Mieke M. E.; Flor, Liane; Caradec, Thibault; Fewer, David P.; Gross, Harald; Jacques, Philippe (2016-11-01). "The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Talaromyces islandicus ('Penicillium islandicum')" (PDF). Environmental Microbiology. 18 (11): 3728–3741. doi:10.1111/1462-2920.13294. ISSN 1462-2920. PMID 26954535.

[7] Gosh, Anil; Manmade, Awinash; Townsend, James; Bousquet, Ann; Howes, John; Demain, Arnold (June 1978). "Production of Cyclochlorotine and a New Metabolite, Simatoxin, by Penicillium islandicum Sopp". American Society for Microbiology. 35 (6): 1074–1078. doi:10.1128/AEM.35.6.1074-1078.1978. PMC 242987. PMID 677874.

[8] Schafhauser, Thomas; Kirchner, Norbert; Kulik, Andreas; Huijbers, Mieke; Flor, Liane; Caradec, Thibault; Fewer, David; Gross, Harald; Jacques, Philippe; Jahn, Linda; Jokela, Jouni (March 2016). "The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Taralomyces islandicus ( ' Penicillium islandicum')" (PDF). Environmental Microbiology. 18 (11): 3728–3741. doi:10.1111/1462-2920.13294. PMID 26954535.