Enniatin A
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| Category | Antibiotics |
| Catalog number | BBF-01785 |
| CAS | 2503-13-1 |
| Molecular Weight | 681.90 |
| Molecular Formula | C36H63N3O9 |
| Purity | >99% by HPLC |
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Description
It is produced by the strain of Fusarium orthoceras var. enniatinum. It has insecticidal and antifungal activity.
Specification
| Synonyms | 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); N-Methylcyclo(L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-); Lateritin I |
| Storage | -20 °C |
| IUPAC Name | (3S,6R,9S,12R,15S,18R)-3,9,15-tris[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
| Canonical SMILES | CCC(C)C1C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N1C)C(C)C)C(C)CC)C)C(C)C)C(C)CC)C)C(C)C |
| InChI | 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 |
| Source | Enniatins are mycotoxins that appear in nature as a mixture of cyclohexadepsipeptides produced by bacteria, fungi, and plants. They may be found in contaminated cereal crops. |
Properties
| Appearance | White to Off-White Crystalline Solid |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 847.4±65.0 °C (Predicted) |
| Melting Point | 121-124 °C |
| Density | 1.022±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform, Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Enniatins are toxic due to their ability to act as ionophores, changing ion transport across membranes and disrupting the ionic selectivity of cell walls. In the membrane, enniatins form a dimeric structure and are able to transport monovalent ions (especially K+, Mg2+,Ca2+ and Na+) across the membranes. This effect is particularly harmful in mitochondrial membranes, resulting in the uncoupling of oxidative phosphorylation. They are also know to inhibit several enzymes, including acyl coenzyme A:cholesterol acyltransferase and cyclic nucleotide phosphodiesterase. Enniatins are cytotoxic and can cause DNA fragmentation, induce apoptosis, and disrupt the ERK signalling pathway. They can also inhibit the activity of membrane-located ATP-binding cassette (ABC) transporters, multidrug pumps which affect the bioavailability of xenobiotics and pharmaceuticals. |
Reference Reading
1. Investigating the in vitro catabolic fate of Enniatin B in a human gastrointestinal and colonic model
Laura Righetti, Silvia Generotti, Michele Suman, Daniele Cavanna, Noelia Pallarés, Chiara Dall'Asta, Emilia Ferrer Food Chem Toxicol . 2020 Mar;137:111166. doi: 10.1016/j.fct.2020.111166.
Enniatin B is an emerging mycotoxin known to present biological activity because of its ionophoric characteristics. This compound has demonstrated strong in vitro cytotoxicity against different cancer cells, also at low molecular concentrations. Its natural occurrence in food commodities and feed is highly reported world-wide, but few information is available about its stability in the human gastro-intestinal tract. The present work evaluates the catabolic fate of enniatin B upon in vitro simulated digestion and colonic fermentation. LC-MS target and untargeted analysis have been performed to quantify the extent of enniatin B degradation and the formation of catabolic products. The results obtained showed significant degradation of enniatin B (degradation rate 79 ± 5%) along the gastrointestinal tract and further degradation of residual enniatin B was observed during colonic fermentation after 24 h of incubation. Moreover, 5 catabolic metabolites of enniatin B were putatively identified after gastrointestinal digestion resulting from the oxidation and opening of the depsipeptide ring. As a final step, the pharmacokinetic properties of enniatin B degradation products were tested in silico revealing that some of them may be adsorbed at the gastrointestinal level more than the parent compound. Additionally, the smaller degradation products showed moderate blood-brain-barrier crossing.
2. Assessment of cytotoxic and genotoxic effects of enniatin-A in vitro
Sevcan Mamur, Deniz Yuzbasioglu, Fatma Unal, Esra Erikel, Serkan Yılmaz Food Addit Contam Part A Chem Anal Control Expo Risk Assess . 2018 Aug;35(8):1633-1644. doi: 10.1080/19440049.2018.1486513.
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 (MTT) assay in human cervix carcinoma (HeLa) cell line, and genotoxic effects of EN-A using chromosome aberrations (CAs), sister chromatid exchanges (SCEs), micronuclei (MN) and comet assays in human lymphocytes. The cells were treated with 0.07, 0.14, 0.29, 0.57, 1.15, 2.29, 4.59 and 9.17 μM concentrations of EN-A. It exhibited cytotoxic effects in HeLa cell lines especially when the concentrations were increased. The half-inhibitory value (IC50) was determined as 1.15 μM concentration for 24 h and 0.57 μM concentration for 48 h. However, EN-A failed to affect the frequency of CAs, SCEs and MN in human lymphocytes. Only a slight increase was observed in the frequency of SCEs at 0.57 μM concentration over 48 h. The replication (RI) and nuclear division (NDI) indices were not affected. On the contrary, EN-A decreased the mitotic index (MI) significantly at all concentrations compared to the negative control and solvent control (except at 0.29 μM for 24 h, and except at 0.14, 0.29 and 0.57 μM for 48 h). Treatments over 2.29 μM showed toxic effects in human lymphocytes. EN-A significantly increased comet tail intensity (except at 0.07 and 0.57 μM) in isolated human lymphocytes. The results of this study demonstrate that EN-A has an obvious cytotoxic effect especially when the EN-A concentration was increased. In addition, EN-A could exhibit a mild genotoxic effect.
3. Enniatin B and ochratoxin A in the blood serum of workers from the waste management setting
Ana Almeida, Hans-Ulrich Humpf, Susana Viegas, Benedikt Cramer, Carla Viegas, Bernd Osteresch Mycotoxin Res . 2018 May;34(2):85-90. doi: 10.1007/s12550-017-0302-1.
The waste management occupational environment is recognized by the simultaneous presence of several substances and biologic agents. Therefore, workers are exposed simultaneously to multiple contaminants. Occupational exposure to aflatoxin B1in one Portuguese waste sorting plant was already reported. However, besides this mycotoxin, data regarding fungal contamination showed that exposure to other mycotoxins could be expected. A study was developed to analyze if exposure to other mycotoxins besides aflatoxin B1was occurring in the workers from the waste sorting plant previously assessed and to discuss how these findings need to be considered in the risk assessment process. In addition to aflatoxin B1detected previously by ELISA, two additional mycotoxins and one mycotoxin degradation product were detected and quantified by a multi-mycotoxin HPLC-MS/MS approach: Enniatin B and ochratoxin A as well as 2'R-ochratoxin A. Besides the confirmation of co-exposure to several mycotoxins, results probably indicate different exposure routes for the mycotoxins reported.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C36H63N3O9
Molecular Weight (Monoisotopic Mass): 681.4564 Da
Molecular Weight (Avergae Mass): 681.9001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C36H63N3O9
Molecular Weight (Monoisotopic Mass): 681.4564 Da
Molecular Weight (Avergae Mass): 681.9001 Da
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
