ENNIATIN B
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| Category | Antibiotics |
| Catalog number | BBF-01786 |
| CAS | 917-13-5 |
| Molecular Weight | 639.82 |
| Molecular Formula | C33H57N3O9 |
| Purity | >99% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-01786 | 1 mg | $469 | In stock |
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Add to cartDescription
It is produced by the strain of Fusarium orthoceras var. enniatinum. It has insecticidal and antifungal activity.
Specification
| Synonyms | 3-N-Methylvaline Enniatin; Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl]; Cyclo(3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl-3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl-3-methyl-D-2-hydroxybutanoyl-N-methyl-L-valyl) |
| Storage | -20 °C |
| IUPAC Name | (3S,6R,9S,12R,15S,18R)-4,10,16-trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
| Canonical SMILES | CC(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)C)C)C(C)C)C(C)C)C)C(C)C |
| InChI | InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25+,26+,27+/m0/s1 |
| InChI Key | MIZMDSVSLSIMSC-VYLWARHZSA-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 powder |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 827.0±65.0 °C (Predicted) |
| Melting Point | 173-175 °C |
| Density | 1.036±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.Mouse tissue distribution and persistence of the food-born fusariotoxins Enniatin B and Beauvericin.
Rodríguez-Carrasco Y1, Heilos D2, Richter L3, Süssmuth RD3, Heffeter P4, Sulyok M5, Kenner L6, Berger W7, Dornetshuber-Fleiss R8. Toxicol Lett. 2016 Apr 15;247:35-44. doi: 10.1016/j.toxlet.2016.02.008. Epub 2016 Feb 15.
The fusariotoxins Enniatin B (Enn B) and Beauvericin (Bea) have recently aroused interest as food contaminants and as potential anticancer drugs. However, limited data are available about their toxic profile. Aim of this study was to investigate their pharmacological behavior in vivo and their persistence in mice. Therefore, liquid chromatography tandem mass spectrometry (LC-MS/MS) was used to analyze the distribution of Enn B and Bea in selected tissue samples and biological fluids originating from mice treated intraperitoneally with these cyclohexadepsipeptides. Overall, no toxicological signs during life time or pathological changes were observed. Moreover, both fusariotoxins were found in all tissues and serum but not in urine. Highest amounts were measured in liver and fat demonstrating the moleculeś tendency to bioaccumulate in lipophilic tissues. While for Bea no metabolites could be detected, for Enn B three phase I metabolites (dioxygenated-Enn B, mono- and di-demethylated-Enn B) were found in liver and colon, with dioxygenated-Enn B being most prominent.
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: C33H57N3O9
Molecular Weight (Monoisotopic Mass): 639.4095 Da
Molecular Weight (Avergae Mass): 639.8204 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C33H57N3O9
Molecular Weight (Monoisotopic Mass): 639.4095 Da
Molecular Weight (Avergae Mass): 639.8204 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
