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Aflatoxin B1 exo-8,9-epoxide

Aflatoxin B1 exo-8,9-epoxide is a toxic metabolite of aflatoxin B1. It's formed by the action of cytochrome P450 enzymes in the liver.[1]

Aflatoxin B1 exo-8,9-epoxide
Names
Preferred IUPAC name
(6aS,7aS,8aR,8bR)-4-Methoxy-2,3,6a,7a,8a,8b-hexahydrocyclopenta[c]oxireno[2′′,3′′:4′,5′]furo[3′,2′:4,5]furo[2,3-h][1]benzopyran-1,10-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3/t12-,14-,16+,17+/m1/s1
    Key: KHBXRZGALJGBPA-IRWJRLHMSA-N
  • COc1cc2c(c3c1c4c(c(=O)o3)C(=O)CC4)[C@@H]5[C@@H]6[C@@H](O6)O[C@@H]5O2
Properties
C17H12O7
Molar mass 328.276 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In the liver, aflatoxin B1 is metabolized to aflatoxin B1 exo-8,9-epoxide by the cytochrome P450 enzymes. The resulting epoxide can react with guanine in the DNA to cause DNA damage.[2]

See also

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References

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  1. ^ Arinç, Emel; Schenkman, John B.; Hodgson, Ernest (2012). Molecular and Applied Aspects of Oxidative Drug Metabolizing Enzymes. Springer Science & Business Media. p. 200. ISBN 9781461548553.
  2. ^ Turner, Paul Craig (2013). "The Molecular Epidemiology of Chronic Aflatoxin Driven Impaired Child Growth". Scientifica. 2013: 152879. doi:10.1155/2013/152879. PMC 3881689. PMID 24455429.


 

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