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B7510

Sigma-Aldrich

Beauvericin

≥97% (HPLC), suitable for HPLC

Sinônimo(s):

cyclo(D-α-Hydroxyisovaleryl-L-N-methyl-Phe)3

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About This Item

Fórmula empírica (Notação de Hill):
C45H57N3O9
Número CAS:
26048-05-5
Peso molecular:
783.95
Número MDL:
MFCD00056846
Código UNSPSC:
12352209
ID de substância PubChem:
24891996
NACRES:
NA.26

product name

Beauvericin, ≥97% (HPLC)

Ensaio

≥97% (HPLC)

forma

powder or crystals

técnica(s)

HPLC: suitable

cor

white to off-white

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CC(C)C1OC(=O)C(Cc2ccccc2)N(C)C(=O)C(OC(=O)C(Cc3ccccc3)N(C)C(=O)C(OC(=O)C(Cc4ccccc4)N(C)C1=O)C(C)C)C(C)C

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

chave InChI

GYSCAQFHASJXRS-UHFFFAOYSA-N

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Descrição geral

Beauvericin is a cyclohexadepsipeptide from the fungus Beauveria bassiana that belongs to the enniatin antibiotic family. It comprises three D-hydroxyisovaleryl and N-methylphenylalanyl residues each.

Aplicação

Beauvericin has been used as an antimicrobial bioactive compound to test its effect on engineered Saccharomyces cerevisiae strains. It has also been used as a mycotoxin standard in the reverse-phase (RP) high-pressure liquid chromatography (HPLC) to quantify mycotoxins produced by Fusarium oxysporum isolates.

Ações bioquímicas/fisiológicas

Beauvericin (BEA) is a commercial entomopathogenic mycoinsecticide with antiviral, antibacterial, insecticidal, and cytotoxic properties. It elicits apoptotic and nematicidal activities as well. Beauvericin blocks multidrug efflux and Tor complex 1 (TORC1) kinase. It possesses ionophoric functionality and favors channel formation in patches of ventricular myocytes and synthetic membranes. It is shown to inhibit L-type voltage-dependent Ca2+ current in the neuroblastoma cells.
Beauvericin (BEA), a cyclohexadepsipeptide produced by the fungus Beauveria bassiana (Bals.), has antiviral, antibacterial, nematicidal, insecticidal, cytotoxic, and apoptotic activity.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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Francesca Caloni et al.
Environmental toxicology and pharmacology, 75, 103349-103349 (2020-02-07)
Beauvericin (BEA) is a natural bioactive compound, with a dual nature. On the one hand, the peculiar characteristics of its molecule confer to BEA interesting properties, such as antibacterial, antiviral, antifungal, antiparasitic, insecticidal and anticarcinogenic activities. On the other hand
Hyuk-Hwan Song et al.
International journal of food microbiology, 122(3), 296-301 (2008-02-19)
Beauvericins and enniatins are cyclohexadepsipeptide mycotoxins that exhibit phytotoxicity and insecticidal activities. In the present study, the production of beauvericin and newly found enniatins (H, I, and MK1688) was characterized in 28 Fusarium strains isolated from potato samples in Korea.
K Kouri et al.
Biochimica et biophysica acta, 1609(2), 203-210 (2003-01-25)
The antibiotic Beauvericin (BEA) was previously shown to express ionophoric properties under simple experimental systems. Its channel-forming activity was examined in inside-out patches of ventricular myocytes and synthetic membranes with the patch clamp and fluorescence imaging techniques. Current transitions to
Sheng-Nan Wu et al.
Chemical research in toxicology, 15(6), 854-860 (2002-06-18)
The effects of beauverficin, a cyclodepsipeptide compound, on ion currents in a mouse neuroblastoma and rat glioma hybrid cell line, NG108-15, were investigated with the aid of the whole-cell voltage-clamp technique. Beauvericin (0.3-100 microM) reversibly produced an inhibition of L-type
A S Ficheux et al.
Toxicon : official journal of the International Society on Toxinology, 71, 1-10 (2013-05-21)
The aim of this study was to assess the in vitro effects of emerging mycotoxins beauvericin, enniatin B and moniliformin on human dendritic cells and macrophages. Beauvericin and enniatin B were cytotoxic on these cells. IC50 were equal to 1.0 μM, 2.9 μM
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