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Beauvericin

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]

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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.

References

^ ^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
^ 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
^ 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.