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Enniatin A1 Sale

(Synonyms: 恩镰孢菌素 A1) 目录号 : GC43610

An ionophore antibiotic

Enniatin A1 Chemical Structure

Cas No.:4530-21-6

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产品描述

Enniatins are cyclohexadepsipeptides commonly isolated from fungi that are known to have antibiotic properties and to induce apoptosis in several cancer lines. Many function as ionophores, forming pores in cellular membranes to allow selective ion transport. Enniatin A1 is one of four major analogs in the enniatin complex . Its ionophoric activity has been described. Additionally, enniatin A1 has been found to induce apoptosis in cancer cells (EC50 = 5 µM in H4IIE rat hepatoma cells), decreasing the activation of the cell proliferation kinase, ERK (p44/p42) and inhibiting TNF-α-induced NF-κB activation.

Chemical Properties

Cas No. 4530-21-6 SDF
别名 恩镰孢菌素 A1
Canonical SMILES C[C@@H](CC)[C@]([H])(N(C)C([C@@H](C(C)C)OC([C@H]([C@H](CC)C)N(C)C1=O)=O)=O)C(O[C@]([H])(C(C)C)C(N(C)[C@@H](C(C)C)C(O[C@@H]1C(C)C)=O)=O)=O
分子式 C35H61N3O9 分子量 667.9
溶解度 DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble 储存条件 Store at -20°C
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1 mM 1.4972 mL 7.4862 mL 14.9723 mL
5 mM 0.2994 mL 1.4972 mL 2.9945 mL
10 mM 0.1497 mL 0.7486 mL 1.4972 mL
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Research Update

Enniatin A1, enniatin B1 and beauvericin on HepG2: Evaluation of toxic effects

Food Chem Toxicol 2015 Oct;84:188-96.PMID:26342765DOI:10.1016/j.fct.2015.08.030.

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.

Enniatin A1, A Natural Compound with Bactericidal Activity against Mycobacterium tuberculosis In Vitro

Molecules 2019 Dec 20;25(1):38.PMID:31861925DOI:10.3390/molecules25010038.

Background: Tuberculosis remains a global disease that poses a serious threat to human health, but there is lack of new and available anti-tuberculosis agents to prevent the emergence of drug-resistant strains. To address this problem natural products are still potential sources for the development of novel drugs. Methods: A whole-cell screening approach was utilized to obtain a natural compound Enniatin A1 from a natural products library. The target compound's antibacterial activity against Mycobacterium tuberculosis (M. tuberculosis) was evaluated by using the resazurin reduction micro-plate assay (REMA) method. The cytotoxicity of the compound against Vero cells was measured to calculate the selectivity index. The intracellular inhibition activity of Enniatin A1 was determined. We performed its time-kill kinetic assay against M. tuberculosis. We first tested its synergistic effect in combination with the first and second-line anti-tuberculosis drugs. Finally, we measured the membrane potential and intracellular ATP levels of M. tuberculosis after exposure to Enniatin A1. Results: We identified enniatinA1 as a potential antibacterial agent against M. tuberculosis, against which it showed strong selectivity. Enniatin A1 exhibited a time-concentration-dependent bactericidal effect against M. tuberculosis, and it displayed synergy with rifamycin, amikacin, and ethambutol. After exposure to enniatinA1, the membrane potential and intracellular ATP levels of M. tuberculosis was significantly decreased. Conclusions: Enniatin A1 exhibits the positive potential anti-tuberculosis agent characteristics.

Fusarium species and enniatin mycotoxins in wheat, durum wheat, triticale and barley harvested in France

Mycotoxin Res 2019 Nov;35(4):369-380.PMID:31093880DOI:10.1007/s12550-019-00363-x.

Contamination with enniatins A, A1, B and B1 was investigated in 1240 samples of small grain cereals (470 wheat, 260 durum wheat, 282 spring barley, 172 triticale and 56 winter barley) from the French harvests of 2012 to 2014. Associations with Fusarium avenaceum, F. tricinctum and F. poae were assessed, with the identification of Fusarium species by real-time PCR and mycotoxin quantification by LC-MS/MS. Enniatins were common in the fields sampled. Enniatin concentrations varied between years but were consistently highest on spring barley (mean values of 199 to 1316 μg/kg) and triticale (mean values from 131 to 1218 μg/kg), and lower on wheat (mean values from 47 to 142 μg/kg) and durum wheat (mean values from 55 to 596 μg/kg). The concentrations of the various enniatins were strongly correlated with each other (Pearson's correlation coefficient of 0.61 to 0.98). Enniatin B was the most frequent (68% of the total enniatin content), followed by enniatin B1 (22%), Enniatin A1 (7%) and enniatin A (3%). Fusarium species were quantified by calculating arithmetic mean total DNA levels. F. tricinctum was the most abundant (0.177 pg/ng total DNA), followed by F. avenaceum (0.141 pg/ng total DNA) and F. poae (0.091 pg/ng total DNA). Total DNA levels for each species, and the predominant species varied between years and crops. Small grain cereal species (p value < 0.001), harvest year (p value = < 0.001) and the presence of F. avenaceum (p value < 0.001), F. tricinctum (p value < 0.001) or F. poae (p value = 0.017) affected enniatin content. F. tricinctum was the leading enniatin producer on durum wheat (29% to 45%) and spring barley (23 to 37%). F. avenaceum produced large amounts of enniatins on durum wheat (13% to 17%) and wheat (1% to 18%) and was the leading producer on triticale (30% to 55%). F. poae made a minor contribution on all crops, never accounting for more than 2% of total enniatin content. Enniatins are, thus, highly prevalent in French small grain cereals and are mostly produced by F. avenaceum and F. tricinctum.

A 28-day repeated oral dose toxicity study of enniatin complex in mice

J Toxicol Sci 2021;46(4):157-165.PMID:33814509DOI: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.

Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation

Mol Nutr Food Res 2009 Apr;53(4):431-40.PMID:19065580DOI:10.1002/mnfr.200700428.

Enniatins are mycotoxins which have important impact on human health, e.g. as contaminants of cereals, but also are discussed as possible anticancer agents. We investigated toxic effects of enniatins A1, B and B1 isolated from Fusarium tricinctum on different cancer cell lines. The enniatins showed moderate activity in HepG2 and C6 cells (EC(50)-values approximately 10-25 microM), but were highly toxic in H4IIE cells (EC(50)-values approximately 1-2.5 microM). In H4IIE cells, all enniatins increased caspase 3/7 activity and nuclear fragmentation as markers for apoptotic cell death. Enniatin A1, enniatin B1, and, to a lesser extent, also enniatin B decreased the activation of extracellular regulated protein kinase (ERK) (p44/p42), a mitogen-activated protein kinase which is associated with cell proliferation. Furthermore, enniatins A1 and B1, but not enniatin B were able to inhibit moderately tumor necrosis factor alpha (TNF-alpha)-induced NF-kappaB activation. Screening of 24 additional protein kinases involved in signal transduction pathways (cell proliferation, survival, angiogenesis and metastasis) showed no inhibitory activity of enniatins. We conclude that enniatins A1 and B1 and, to a lesser extent, enniatin B may possess anticarcinogenic properties by induction of apoptosis and disruption of ERK signalling pathway. Further analysis of these substances is necessary to analyse their usefulness for cancer therapy.