Enniatin A1
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| Category | Antibiotics |
| Catalog number | BBF-04603 |
| CAS | 4530-21-6 |
| Molecular Weight | 667.87 |
| Molecular Formula | C35H61N3O9 |
| Purity | >99% by HPLC |
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Description
A family of depsipeptide ionophores, produced by several fusarium species. It has antibiotic properties. Enniatin A1 is one of four major analogues in the enniatin complex. Enniatin A1 has been found to induce apoptosis in cancer cells, decrease the activation of the cell proliferation kinase, ERK (p44/p42) and inhibit TNF-α-induced NF-κB activation.
Specification
| Synonyms | 2-(N-Methyl-L-valine)enniatin A; Cyclo(D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-valyl); cyclo[N-methyl-L-isoleucyl-N-oxa-D-valyl-N-methyl-L-isoleucyl-N-oxa-D-valyl-N-methyl-L-valyl-N-oxa-D-valyl]; 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-valyl) |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6R,9S,12R,15S,18R)-3,9-bis[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,15,18-tetra(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)CC)C)C(C)C |
| InChI | InChI=1S/C35H61N3O9/c1-16-22(11)25-34(43)46-27(19(5)6)30(39)36(13)24(18(3)4)33(42)45-28(20(7)8)31(40)37(14)26(23(12)17-2)35(44)47-29(21(9)10)32(41)38(25)15/h18-29H,16-17H2,1-15H3/t22-,23-,24-,25-,26-,27+,28+,29+/m0/s1 |
| InChI Key | OWUREPXBPJFMOK-CIRFPNLUSA-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 |
| Boiling Point | 840.5±65.0°C (Predicted) |
| Melting Point | 116-117°C |
| Density | 1.027±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
Ahmed M Zaher, Babu L Tekwani, Makboul A Makboul, Ahmad M Moharram, Angela I Calderón J Antibiot (Tokyo) . 2015 Mar;68(3):197-200. doi: 10.1038/ja.2014.129.
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. Enniatins A1 and B1 alter calcium homeostasis of neuronal cells leading to apoptotic death
Amparo Alfonso, Jesús González-Jartín, Sandra Gegunde, Nadia Pérez-Fuentes, Luis M Botana, Mercedes R Vieytes, Rebeca Alvariño Food Chem Toxicol . 2022 Oct;168:113361. doi: 10.1016/j.fct.2022.113361.
Enniatins (ENNs) A1 and B1 are non-regulated mycotoxins produced by Fusarium spp. that commonly occur in different types of food. These toxins are cytotoxic in several cell lines, but their mechanism of action is unclear. In this study, the cytotoxic effects of ENNs A1 and B1 in SH-SY5Y human neuroblastoma cells were analysed. Moreover, to better understand their mechanism of action, mitochondrial function, reactive oxygen species (ROS) levels and calcium fluxes were monitored. ENNs A1 and B1 reduced cell viability, presenting IC50values of 2.0 and 2.7 μM, respectively. Both toxins induced caspase-dependent apoptosis, but only ENN A1 increased ROS production. Apoptotic cell death seems to be triggered by the increase in cytosolic calcium produced by both ENNs, since the toxins altered Ca2+homeostasis by depleting intracellular reservoirs. Finally, binary combinations of ENN A1, ENN B1, ENN A and ENN B were tested. All mixtures resulted in an antagonistic effect, with the exception of ENN A and ENN B1 combination, which produced an additive effect. The results presented in this study provide the first evidence of ENNs A1 and B1 effects on calcium fluxes, providing new insights into the mechanism of action of these mycotoxins.
3. A 28-day repeated oral dose toxicity study of enniatin complex in mice
Toshiya Okamura, Kazumi Takashima, Satomi Kikuchi, Bunichiro Ogawa, Toshinori Yoshida, Makoto Shibutani, Tomoya Yoshinari, Meilan Jin, Qian Tang, Hiromu Okano, Ryota Ojiro, Yasunori Takahashi J Toxicol Sci . 2021;46(4):157-165. doi: 10.2131/jts.46.157.
Enniatins are so-called "emerging mycotoxins" that commonly occur in milligrams per kilogram levels in grains and their derived products, as well as in fish, dried fruits, nuts, spices, cocoa, and coffee. The present study investigated the 28-day repeated oral dose toxicity of enniatin complex in CD1(ICR) mice. Enniatin B, enniatin B1, and enniatin A1 at a ratio of 4:4:1 were administered to male and female mice at doses of 0 (vehicle controls), 0.8, 4, and 20 mg/kg body weight/day. In life parameters did not change during the study period, with the exception of slight reductions in food consumption in male mice administered 4 and 20 mg/kg and in female mice administered 20 mg/kg. Body and organ weights did not change, and no alterations in hematology, blood biochemistry, or histopathology parameters were observed at the end of the administration period. Thus, we determined that the no-observed-adverse-effect level of enniatin complex was 20 mg/kg/day for both sexes under the present experimental conditions.
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: C35H61N3O9
Molecular Weight (Monoisotopic Mass): 667.4408 Da
Molecular Weight (Avergae Mass): 667.8735 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C35H61N3O9
Molecular Weight (Monoisotopic Mass): 667.4408 Da
Molecular Weight (Avergae Mass): 667.8735 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 ╳
