Beauvericin

Beauvericin is a cyclohexapeptide Fusarium toxin with insecticidal, antibacterial, anticancer, antiviral and cytotoxic activities. Beauvericin causes cellular genotoxicity by producing DNA breaks, chromosomal aberrations and micronuclei, and inhibits the PI3K/AKT pathway to induce apoptosis, thereby inhibiting the growth of HCC. In addition, Beauvericin affects immune function by inhibiting lymphocyte proliferation and interfering with the differentiation process of human monocytes into macrophages[1][2][3][4][5][6][7][8][9].

Product Specifications

CAS Number

[26048-05-5]

UNSPSC

12352005

Hazard Statement

H302+H312+H332, H315, H319, H335

Target

Akt; Apoptosis; Bacterial; Fungal; Interleukin Related; PI3K; TNF Receptor

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Immunology/Inflammation; PI3K/Akt/mTOR

Applications

COVID-19-immunoregulation

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/beauvericin.html

Purity

99.97

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

CN([C@H](C(O[C@](C(N([C@H](C(O[C@@H]1C(C)C)=O)CC2=CC=CC=C2)C)=O)([H])C(C)C)=O)CC3=CC=CC=C3)C([C@H](OC([C@@H](N(C1=O)C)CC4=CC=CC=C4)=O)C(C)C)=O

Molecular Formula

C45H57N3O9

Molecular Weight

783.95

Precautions

H302+H312+H332, H315, H319, H335

References & Citations

[1]Mallebrera B, et al. In vitro mechanisms of Beauvericin toxicity: A review[J]. Food and Chemical Toxicology, 2018, 111: 537-545.|[2]Wang Q, et al. Beauvericin, a bioactive compound produced by fungi: a short review[J]. Molecules, 2012, 17 (3) : 2367-2377.|[3]Heilos D, et al. The natural fungal metabolite beauvericin exerts anticancer activity in vivo: a pre-clinical pilot study[J]. Toxins, 2017, 9 (9) : 258.|[4]Maranghi F, et al. In vivo toxicity and genotoxicity of beauvericin and enniatins. Combined approach to study in vivo toxicity and genotoxicity of mycotoxins beauvericin (BEA) and enniatin B (ENNB) [J]. EFSA Supporting Publications, 2018, 15 (5) : 1406E.|[5]Wang G, et al. Beauvericin exerts an anti-tumor effect on hepatocellular carcinoma by inducing PI3K/AKT-mediated apoptosis[J]. Archives of Biochemistry and Biophysics, 2023, 745: 109720.|[6]Dombrink-Kurtzman M A. Fumonisin and beauvericin induce apoptosis in turkey peripheral blood lymphocytes[J]. Mycopathologia, 2003, 156: 357-364.|[7]Wu S N, et al. Block of L-type Ca2+ current by beauvericin, a toxic cyclopeptide, in the NG108-15 neuronal cell line[J]. Chemical research in toxicology, 2002, 15 (6) : 854-860.|[8]Ficheux A S, et al. Effects of beauvericin, enniatin b and moniliformin on human dendritic cells and macrophages: An in vitro study[J]. Toxicon, 2013, 71: 1-10.|[9]Mei L, et al. An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats[J]. Journal of enzyme inhibition and medicinal chemistry, 2009, 24 (3) : 753-762.