Enniatin B1
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| Category | Antibiotics |
| Catalog number | BBF-04590 |
| CAS | 19914-20-6 |
| Molecular Weight | 653.85 |
| Molecular Formula | C34H59N3O9 |
| Purity | >99% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04590 | 1 mg | $519 | In stock |
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Add to cartDescription
A family of depsipeptide ionophores, produced by several fusarium species. It has antibiotic properties. It is a cytotoxic and insecticidal agent.
Specification
| Synonyms | 2-(N-Methyl-L-isoleucine)enniatin B; Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-valyl]; cyclo[N-methyl-L-isoleucyl-N-oxa-D-valyl-N-methyl-L-valyl-N-oxa-D-valyl-N-methyl-L-valyl-N-oxa-D-valyl] |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6R,9S,12R,15S,18R)-3-[(2S)-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 |
| 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)C)C)C(C)C)C(C)C)C)C(C)C |
| InChI | 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/t22-,23-,24-,25-,26+,27+,28+/m0/s1 |
| InChI Key | UQCSETXJXJTMKO-UMURLBKASA-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 |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 833.8±65.0°C (Predicted) |
| Melting Point | 178.5°C |
| Density | 1.031±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in 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.A new enniatin antibiotic from the endophyte Fusarium tricinctum Corda.
Zaher AM1, Makboul MA2, Moharram AM3, Tekwani BL4, Calderón AI5. J Antibiot (Tokyo). 2015 Mar;68(3):197-200. doi: 10.1038/ja.2014.129. Epub 2014 Oct 15.
Enniatins (ENs), a group of antibiotics commonly produced by various strains of Fusarium, are six-membered cyclic depsipeptides formed by the union of three molecules of D-α-hydroxyisovaleric acid and three N-methyl-L-amino acids. The endophyte Fusarium tricinctum Corda was isolated from the fruits of Hordeum sativum Jess. and cultivated on a rice medium. The fungal metabolites were extracted with methanol and were identified, employing liquid chromatography-mass spectrometry as ENs A, A1, B, B1, B2 and Q. EN Q is a new analog of EN A and the occurrence of EN B2 is reported for the first time from this endophyte, in addition to four well-known ENs (A, A1, B and B1). The methanol extract of F. tricinctum showed mild antibacterial and antileishmanial activities. Additionally the tested extract displayed inhibition of the activity of thioredoxin reductase enzyme of Plasmodium falciparum.
2.Enniatin A1, enniatin B1 and beauvericin on HepG2: Evaluation of toxic effects.
Juan-García A1, Ruiz MJ2, Font G2, Manyes L2. Food Chem Toxicol. 2015 Oct;84:188-96. doi: 10.1016/j.fct.2015.08.030. Epub 2015 Sep 3.
Hepatotoxicity of three Fusarium mycotoxins, beauvericin (BEA) and two enniatins (ENNs) ENN A1 and ENN B1, in hepatocarcinoma cells (HepG2) were evaluated and compared. Concentrations used were 1.5 and 3 μM at 24, 48 and 72 h for each mycotoxin. Flow cytometry was used to examine enniatins effects on cell proliferation, to characterize the cell cycle phase where the cells blocked and to study the mitochondria role in ENNs-induced apoptosis. ENN B1 treated cells showed a time dependent G1 blockade at both concentrations used. ENN A1 and BEA decreased the apoptotic-necrotic percentage of cells comparing to control and disrupted the MMP as observed by TMRM and ToPro-3 fluorochromes signal. It is proposed a decreasing mycotoxin order by number of effects as follows: BEA > ENN B1 > ENN A1, with 47, 20 and 16%, respectively out of all situations compared.
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: C34H59N3O9
Molecular Weight (Monoisotopic Mass): 653.4251 Da
Molecular Weight (Avergae Mass): 653.847 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C34H59N3O9
Molecular Weight (Monoisotopic Mass): 653.4251 Da
Molecular Weight (Avergae Mass): 653.847 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 ╳
