Beauvericin

Chembox new
ImageFile=Beauvericin.svg
ImageSize=280px
IUPACName=(3"S",6"R",9"S",12"R",15"S",18"R")-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
OtherNames=
Section1= Chembox Identifiers
CASNo=26048-05-5
PubChem=3007984
ChEBI = 3000
KEGG = C11590
SMILES=
Section2= Chembox Properties
Formula=C₄₅H₅₇N₃O₉
MolarMass=783.940 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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;cite journal |author=Logrieco A, Moretti A, Castella G, "et al." |title=Beauvericin production by Fusarium species |journal=Appl Environ Microbiol |volume=64 |issue=8 |pages=3084–8 |year=1998 |pmid=9687479 |doi= PMC|106821] it may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. [cite journal |author=Logrieco A, Rizzo A, Ferracane R, Ritieni A |title=Occurrence of beauvericin and enniatins in wheat affected by "Fusarium avenaceum" head blight |journal=Appl Environ Microbiol |volume=68 |issue=1 |pages=82–5 |year=2002 |pmid=11772612 |doi= PMC|126553] [cite journal |author=Jestoi M, Rokka M, Yli-Mattila T, Parikka P, Rizzo A, Peltonen K |title=Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples |journal=Food additives and contaminants |volume=21 |issue=8 |pages=794–802 |year=2004 |pmid=15370831 |doi=10.1080/02652030410001713906] Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals.

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