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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

product name

Beauvericin, ≥97% (HPLC)

Saggio

≥97% (HPLC)

Forma fisica

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)

Certificati d'analisi (COA)

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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.
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
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
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
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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