| Identification | Back Directory | [Name]
BEAUVERICIN | [CAS]
26048-05-5 | [Synonyms]
nivea
bovein
bassiana
beauverin
Beauveria
BEAUVERICIN
BEAUVERFICIN
Beauveria sp.
Beauvericin 97%
Beauveria Vuillemin
Beauveria brongiartii
BEAUVERICIN USP/EP/BP
Beauveria Vuillemin sp
Beauveria bassiana AS 3.4271
beauverin bassiaua vuillemin
Beauvericin, froM Beauveria bassiana
Beauveria bassiana (Balsamo) Vuillemin
Cyclo(-D-a-hydroxyisovaleryl-N-Me-Phe)3
Beauveria bassiana (Bals.-Criv.) Vuill.
Beauvericin, 99%, from Beauveria bassiana
CYCLO(-D-ALPHA-HYDROXYISOVALERYL-N-ME-PHE)3
cyclo(d-α-hydroxyisovaleryl-l-n-methyl-phe)3
CYCLO-[D-ALPHA-HYDROXYISOVALERYL-L-N-METHYLPHENYLALANYL]3
N-Methylcyclo(L-Phe-D-Hmb-N-methyl-L-Phe-D-Hmb-N-methyl-L-Phe-D-Hmb-)
Cyclo[(2R)-2-hydroxy-3-Methylbutanoyl-N-Methyl-L-phenylalanyl-(2R)-2-hydroxy-3-Methylbutanoyl-N-Methyl-L-phenylalanyl-(2R)-2-hydroxy-3-Methylbutanoyl-N-Methyl-L-phenylalanyl] | [EINECS(EC#)]
618-347-7 | [Molecular Formula]
C45H57N3O9 | [MDL Number]
MFCD00056846 | [MOL File]
26048-05-5.mol | [Molecular Weight]
783.95 |
| Chemical Properties | Back Directory | [Melting point ]
93-94℃ | [Boiling point ]
975.6±65.0 °C(Predicted) | [density ]
1.126±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in DMSO (30 mg/ml) | [form ]
neat | [pka]
-1.02±0.70(Predicted) | [color ]
White | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChIKey]
GYSCAQFHASJXRS-ABKJGVMTSA-N |
| Hazard Information | Back Directory | [Description]
Beauvericin (CAS 26048-05-5) induces apoptosis in A549 cancer cells.1 Disrupts mitochondrial volume regulation.2 Antifungal activity acting via inhibition of both multidrug efflux and TORC1 kinase.3 Crosses the blood-brain barrier in mice.4 Inhibits HIV-1 integrase.5 | [Chemical Properties]
White powder | [Uses]
Beauvericin is a cyclic depsipeptide isolated from several fungal genera, notably Beauveria and Fusarium, first reported in 1969. Beauvericin exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities. At the molecular level, beauvericin exhibits ionophore properties, and inhibits acyl-CoA:cholesterol acyltransferase activity. Beauvericin induces apoptosis by elevating intracellular calcium levels. | [Uses]
Beauvericin is a cyclic depsipeptide isolated from several fungal genera, notably Beauveria and Fusarium, first reported in 1969. Beauvericin exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities. At the molecular level, beauvericin exhibits ionophoric properties, and inhibits acyl-CoA:cholesterol acyltransferase activity. Beauvericin induces apoptosis by elevating intracellular calcium levels. | [Uses]
Toxic depsipeptide with antibiotic and insecticidal effects. | [Definition]
ChEBI: A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues. | [Biological Activity]
Depsipeptide belonging to the enniatin family. Active against gram-positive bacteria and mycobacteria. Also active against insects and brine shrimp. The ion-complexing capability allows it to transport alkaline earth metal and alkali metal ions across cell membranes. Has been shown to potentiate the antifungal activity of miconazole. | [References]
1) Lu et al. (2016), Beauvericin-induced cell apoptosis through the mitogen-activated protein kinase pathway in human nonsmall cell lung cancer A549 cells.; J. Toxicol. Sci., 41 429
2) Tonshin et al. (2010), The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis.; Toxicology, 276 49
3) Shekhar-Guturja et al. (2016), Dual action antifungal small molecule modulates multidrug efflux and TOR signaling; Nat. Chem. Biol., 12 867
4) Taevernier et al. (2016), Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins; Toxicol. Lett., 258 175
5) Shin et al. (2009), Beauvericin and enniatins H,I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase; J. Antibiot. (Tokyo), 62 687 |
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