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E9661

Enniatin A

From Gnomonia errabunda, ≥95% (HPLC), Ionophore

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
MDL number:
MFCD19442801
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Quality level:
200
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Product Name

Enniatin A, from Gnomonia errabunda, ≥95% (HPLC)

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

SMILES string

N1([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C1=O)C(C)C)[C@H](CC)C)C)C(C)C)[C@H](CC)C)C)C(C)C)[C@H](CC)C)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).
Enniatins are cyclohexadepsipeptide mycotoxins that have phytotoxic, antibiotic, and insecticidal activities and function as ionophors.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000479047
0000479047
0000332127
0000290420
0000290420

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Multi-mycotoxin contamination of couscous semolina commercialized in Morocco
Zinedine A, et al.
Food Chemistry, 214, 440-446 (2017)
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)
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)
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Global Trade Item Number

SKUGTIN
E9661-1MG04061826690857