3794
T3D3740
Beauvericin
Beauvericin is a mycotoxin with antibiotic and insecticidal effects. It was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species. It may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals. (L1962)
26048-05-5
105014
C45H57N3O9
352274.08500000765
Clear solution.
>10 mg/mL
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Beauvericin is cytotoxic and increases ion permeability in cell membranes by forming complexes with essential cations (Ca2+, Na+, K+) and by forming cation-selective channels in lipid membranes. This may affect ionic homeostasis, increasing the intracellular calcium concentration, and lead to apoptosis. Beauvericin is also genotoxic and causes DNA damage, either by directly forming DNA adducts, through increased intracellular calcium levels influencing endonuclease activity, or through oxidative stress. Beauvericin induces lipid peroxidation and production of reactive oxygen species, producing cytotoxic effects and immunosuppressive activity. In addition, beauvericin is a potent inhibitor of the acyl-CoA:cholesterol acyltransferase (ACAT), which plays an important role in cholesterol ester accumulation in atherogenesis and in cholesterol absorption from the intestine. In isolated terminal ilea and heart muscles of guinea pig, beauvericin decreases the contractility, shortening the action potential duration and depolarizing the membrane resting potential. Beauvericin is also known to inhibit certain cytochrome P-450 enzymes. (A3015, A3016, A3017, A3018, A3077)
Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.
Not listed by IARC.
Beauvericin is a mycotoxin with antibiotic and insecticidal effects. It was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species. It may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. (L1962)
Beauvericin is cytotoxic and immunosuppressive. It is also genotoxic and may thus be carcinogenic. (A3015)
2010-05-06T21:03:09Z
2014-12-24T20:26:28Z
http://en.wikipedia.org/wiki/Beauvericin
C11590
3000
Beauvericin
true
CC(C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC2=CC=CC=C2)N(C)C1=O)C(C)C)C(C)C
C45H57N3O9
InChI=1/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/s2
InChIKey=GYSCAQFHASJXRS-JTPGOKIJNA-N
783.9488
783.409480437
Exogenous
Liquid
CHEMBL1977672
2277520
Beauvericin.jpg
image/jpeg
58278
2014-10-03T23:25:42Z
BSEQ0008533