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B7510

Sigma-Aldrich

Beauvericin

≥97% (HPLC), suitable for HPLC

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C45H57N3O9
Numero CAS:
26048-05-5
Peso molecolare:
783.95
Numero MDL:
MFCD00056846
Codice UNSPSC:
12352209
ID PubChem:
24891996
NACRES:
NA.26

Nome del prodotto

Beauvericin, ≥97% (HPLC)

Livello qualitativo

200

Saggio

≥97% (HPLC)

Stato

powder or crystals

tecniche

HPLC: suitable

Colore

white to off-white

Temperatura di conservazione

2-8°C

Stringa SMILE

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
GYSCAQFHASJXRS-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Azioni biochim/fisiol

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.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG5735
BCCD6333
BCCB6084
BCCB2429
BCBW3858

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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
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
Anton A Tonshin et al.
Toxicology, 276(1), 49-57 (2010-07-14)
The mechanisms of cell toxicity of mycotoxins of the enniatin family produced by Fusarium sp. enniatin B, a mixture of enniatin homologues (3% A, 20% A(1), 19% B, 54% B1) and beauvericin, were investigated. In isolated rat liver mitochondria, exposure
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
Sofie Monbaliu et al.
Journal of agricultural and food chemistry, 58(19), 10475-10479 (2010-09-10)
In this work the presence and migration behavior of mycotoxins formed in sweet pepper, inoculated by Fusarium species involved in internal fruit rot, were investigated. Two different commercial sweet pepper cultivars were inoculated with two different Fusarium proliferatum isolates that
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