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E5286

Sigma-Aldrich

Enniatin B1

from Gnomonia errabunda, ≥95% (HPLC)

Synonyme(s) :

2-(N-Methyl-L-isoleucine) Enniatin B, 3-Butan-2-yl-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

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About This Item

Formule empirique (notation de Hill):
C34H59N3O9
Numéro CAS:
19914-20-6
Poids moléculaire :
653.85
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Source biologique

Gnomonia errabunda

Niveau de qualité

200

Pureté

≥95% (HPLC)

Solubilité

DMSO: 10 mg/mL
ethanol: 10 mg/mL
methanol: 10 mg/mL

Température de stockage

−20°C

InChI

1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3

Clé InChI

UQCSETXJXJTMKO-UHFFFAOYSA-N

Application

Enniatin B1 has been used as a mycotoxin in the cell viability assay of primary porcine brain capillary endothelial cells (PBCEC) and human brain microvascular capillary cells (HBMEC). It has also been used as an analytical standard in mass spectrometry measurements.

Actions biochimiques/physiologiques

Enniatins are a group of cyclohexadepsipeptide mycotoxins produced by Gnomonia errabuda and several Fusaria species, with phytotoxic, antibiotic, and insecticidal activities. Enniatins function as ionophors by their incorporation into the cellular membrane to form dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. It has been demonstrated that enniatins have a cytotoxic effect on human cancer cells. Furthermore, incubation of H4IIE hepatoma cells with enniatins strongly diminished phosphorylation of the ERK (p44/p42). Enniatins B and B1 inhibit the multi-drug resistance transporter Pdr5p from Saccharomyces cerevisiae, indicating their beneficial potential in cases of drug resistant patients.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311 + H331

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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PloS one, 13(5), e0197406-e0197406 (2018-05-17)
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