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Merck

B7510

Sigma-Aldrich

Beauvericin

≥97% (HPLC), suitable for HPLC

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C45H57N3O9
Número de CAS:
Peso molecular:
783.95
Número MDL:
Código UNSPSC:
12352209
ID de la sustancia en PubChem:
NACRES:
NA.26

Nombre del producto

Beauvericin, ≥97% (HPLC)

Ensayo

≥97% (HPLC)

Formulario

powder or crystals

técnicas

HPLC: suitable

color

white to off-white

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

GYSCAQFHASJXRS-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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.

Acciones bioquímicas o 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.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Los clientes también vieron

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
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.
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
Tanvi Shekhar-Guturja et al.
Antimicrobial agents and chemotherapy, 60(12), 7468-7480 (2016-11-01)
Invasive fungal infections are a leading cause of human mortality. Effective treatment is hindered by the rapid emergence of resistance to the limited number of antifungal drugs, demanding new strategies to treat life-threatening fungal infections. Here, we explore a powerful
Manuel S López-Berges et al.
Molecular microbiology, 87(1), 49-65 (2012-10-31)
Fungal pathogens provoke devastating losses in agricultural production, contaminate food with mycotoxins and give rise to life-threatening infections in humans. The soil-borne ascomycete Fusarium oxysporum attacks over 100 different crops and can cause systemic fusariosis in immunocompromised individuals. Here we

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