Beauvericin

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Beauvericin
IUPAC name (3S,6R,9S,12R,15S,18R)-6,12,18-triisopropyl-
4,10,16-trimethyl-3,9,15-tris(phenylmethyl)-
1,7,13-trioxa-4,10,16-triazacyclooctadecane-
2,5,8,11,14,17-hexone
Identifiers
CAS number [26048-05-5]
PubChem 3007984
KEGG C11590
ChEBI 3000
Properties
Molecular formula C45H57N3O9
Molar mass 783.940 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Beauvericin is a toxic depsipeptide with antibiotic and insecticidal effects belonging to the enniatin family. It was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species;[1] it may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi.[1][2][3] Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals.[1]

Chemically, beauvericin is a cyclic hexadepsipeptide with alternating methyl-phenylalanyl and hydroxy-iso-valeryl residues. Its ion-complexing capability allows beauvericin to transport alkaline earth metal and alkali metal ions across cell membranes.

[edit] References

  1. ^ a b c Logrieco A, Moretti A, Castella G, et al. (1998). "Beauvericin production by Fusarium species". Appl Environ Microbiol 64 (8): 3084–8. PMID 9687479.  Full text at PMC: 106821
  2. ^ Logrieco A, Rizzo A, Ferracane R, Ritieni A (2002). "Occurrence of beauvericin and enniatins in wheat affected by Fusarium avenaceum head blight". Appl Environ Microbiol 68 (1): 82–5. PMID 11772612.  Full text at PMC: 126553
  3. ^ Jestoi M, Rokka M, Yli-Mattila T, Parikka P, Rizzo A, Peltonen K (2004). "Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples". Food additives and contaminants 21 (8): 794–802. doi:10.1080/02652030410001713906. PMID 15370831. 
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