From Wikipedia, the free encyclopedia
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
ChemSpider
KEGG
UNII
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
N Key: PMBVHCCVEPYDSN-BADCMNFISA-N
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
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
C 24 H 31 Cl 2 N 5 O 7
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).
Chemical compound
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 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.
[7]
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).
[6]
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 .
^
a
b 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 .
^
a
b 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 .
S2CID
22896792 .
^ 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 .