Cyclochlorotine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Cyclochlorotine
Skeletal formula of cyclochlorotine
Ball-and-stick model of the cyclochlorotine molecule
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
3D model (JSmol)
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
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).
☒N verify (what is checkY☒N ?)
Close

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

Related Articles

Wikiwand AI