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E9661

Sigma-Aldrich

Enniatin A

from Gnomonia errabunda, ≥95% (HPLC)

Synonym(s):

Cyclo[(2R)- 2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl- N-methyl-L- isoleucyl]

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About This Item

Empirical Formula (Hill Notation):
C36H63N3O9
CAS Number:
2503-13-1
Molecular Weight:
681.90
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Gnomonia errabunda

Quality Level

200

Assay

≥95% (HPLC)

solubility

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

storage temp.

−20°C

InChI

1S/C36H63N3O9/c1-16-22(10)25-34(43)46-29(20(6)7)32(41)38(14)27(24(12)18-3)36(45)48-30(21(8)9)33(42)39(15)26(23(11)17-2)35(44)47-28(19(4)5)31(40)37(25)13/h19-30H,16-18H2,1-15H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+/m0/s1

InChI key

TWHBYJSVDCWICV-BHZTXFQCSA-N

Application

Enniatin A may be used as a mycotoxin reference standard in ultra-performance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS) and liquid chromatography with tandem mass spectrometry (LC-MS-MS)

Biochem/physiol Actions

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).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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No transfer of the non-regulated mycotoxins, beauvericin and enniatins, from feeds to farmed fish reared on plant-based diets
Nacher-Mestre J, et al.
Food Chemistry, 126773-126773 (2020)
Sevcan Mamur et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 35(8), 1633-1644 (2018-06-12)
Enniatin A (EN-A) is a Fusarium mycotoxin which is a common contaminant in grains and especially in maize and it causes serious loss of product. The aim of this study was to investigate the cytotoxic effects using 3-(4,5-dimethylthiazolyl-2)-2,5 diphenyltetrazolium bromide
Multi-mycotoxin contamination of couscous semolina commercialized in Morocco
Zinedine A, et al.
Food Chemistry, 214, 440-446 (2017)
Development and validation of ultra-high-performance liquid chromatography-tandem mass spectrometry methods for the simultaneous determination of beauvericin, enniatins (A, A1, B, B1) and cereulide in maize, wheat, pasta and rice
Decleer M, et al.
Journal of Chromatography A, 1472, 35-43 (2016)
Terje Svingen et al.
Environmental toxicology, 32(5), 1658-1664 (2016-09-16)
Mycotoxins are fungi-born metabolites that can contaminate foods through mould-infected crops. They are a significant food/feed-safety issue across the globe and represent a substantial financial burden for the world economy. Moreover, with a changing climate and fungal biota, there is

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