Beauvericin

• CAT Number: R013931
• CAS Number: 26048-05-5
• PubChem Substance ID: 3007984
• Molecular Formula: C45H57N3O9
• Molecular Weight: 783
• Purity: 97%
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• InChI: InChI=1S/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+/m0/s1
• InChIKey: GYSCAQFHASJXRS-FFCOJMSVSA-N
• SMILES: CC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C

Beauvericin(cas 26048-05-5) 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.

Reference

The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina. Hamill Z. R. L. et al. Tet. Letters 1969, 4255. 

Inhibition of acyl-CoA:cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. Tomoda H. et al. J. Antibiot. 1992, 45, 1626. 

Beauvericin Production by Fusarium Species. Logrieco A. et al. Appl. Environ. Microbiol. 1998, 64, 3084.