Beauvericin ACAS# 165467-50-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 165467-50-5 | SDF | Download SDF |
| PubChem ID | 12082078 | Appearance | Powder |
| Formula | C46H59N3O9 | M.Wt | 798.0 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6-[(2S)-butan-2-yl]-4,10,16-trimethyl-12,18-di(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone | ||
| SMILES | CCC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C | ||
| Standard InChIKey | JQUGYVKOYKGIRB-PGVJVUNISA-N | ||
| Standard InChI | InChI=1S/C46H59N3O9/c1-10-31(6)40-43(52)49(9)36(27-33-22-16-12-17-23-33)45(54)57-38(29(2)3)41(50)47(7)35(26-32-20-14-11-15-21-32)44(53)56-39(30(4)5)42(51)48(8)37(46(55)58-40)28-34-24-18-13-19-25-34/h11-25,29-31,35-40H,10,26-28H2,1-9H3/t31-,35-,36-,37-,38+,39+,40+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Beauvericin A Dilution Calculator
Beauvericin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.2531 mL | 6.2657 mL | 12.5313 mL | 25.0627 mL | 31.3283 mL |
| 5 mM | 0.2506 mL | 1.2531 mL | 2.5063 mL | 5.0125 mL | 6.2657 mL |
| 10 mM | 0.1253 mL | 0.6266 mL | 1.2531 mL | 2.5063 mL | 3.1328 mL |
| 50 mM | 0.0251 mL | 0.1253 mL | 0.2506 mL | 0.5013 mL | 0.6266 mL |
| 100 mM | 0.0125 mL | 0.0627 mL | 0.1253 mL | 0.2506 mL | 0.3133 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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In vitro effects of two environmental toxicants, beauvericin and glyphosate in Roundup, on cell numbers and steroidogenesis of bovine ovarian cells.[Pubmed:38558370]
Vet Res Commun. 2024 Apr 1.
Beauvericin is an emerging Fusariotoxin naturally occurring in cereal grains throughout the world whereas glyphosate (N-phosphonomethyl-glycine) is a non-selective systemic herbicide used worldwide. The purpose of this study is to evaluate a newly developed ovarian cell culture system (that includes both granulosa and theca cells) as an in vitro model for toxicological studies. Specifically, the effects of Beauvericin And glyphosate in formulation with Roundup on ovarian cell numbers and steroid production were evaluated. Ovaries collected from cattle without luteal structures were sliced into 30-70 pieces each, and granulosa and theca cells were collected. Harvested cells were cultured for 48 h in 10% fetal bovine serum-containing medium followed by 48 h in serum-free medium containing testosterone (500 ng/mL; as an estrogen precursor) with the following eight treatments: (1) controls, (2) FSH (30 ng/mL) alone, (3) FSH plus insulin-like growth factor-1 (IGF1; 30 ng/mL), (4) FSH plus IGF1 plus beauvericin (3 microM), (5) FSH plus IGF1 plus glyphosate in Roundup (10 microg/mL), (6) FSH plus IGF1 plus fibroblast growth factor 9 (FGF9, 30 ng/mL), (7) a negative control without added testosterone, and (8) IGF1 plus LH (30 ng/mL) with basal medium without added testosterone. In the presence of FSH, IGF1 significantly increased cell numbers, estradiol and progesterone production by severalfold. Glyphosate in Roundup formulation significantly inhibited IGF1-induced cell numbers and estradiol and progesterone production by 89-94%. Beauvericin inhibited IGF1-induced cell numbers and estradiol and progesterone by 50-97% production. LH plus IGF1 significantly increased androstenedione secretion compared with controls without added testosterone indicating the presence of theca cells. In conclusion, the present study demonstrates that toxicological effects of Beauvericin And glyphosate in Roundup formulation are observed in a newly developed ovarian cell model system and further confirms that both glyphosate and beauvericin may have the potential to impair reproductive function in cattle.
Beauvericin and enniatin B mycotoxins alter aquatic ecosystems: Effects on green algae.[Pubmed:38503354]
Environ Toxicol Pharmacol. 2024 Apr;107:104415.
Myxotoxins can contaminate algal-based products and arrive to the food chain to consumers producing chronic toxicity effects. Here, we studied phytotoxicity of mycotoxins, beauvericin (BEA) and ennaitin B (ENN B) in four phytoplankton strains: Acutodesmus sp., Chlamydomonas reinhardtii, Haematococcus pluvialis, and Monoraphidium griffithii, which are all green algae. It was tested the capacity of clearing the media of BEA and ENN B at different concentrations by comparing nominal and measured quantifications. Results revealed that Acutodesmus sp. and C. reinhardtii tended to flow up and down growth rate without reaching values below 50% or 60%, respectively. On the other hand, for H. pluvialis and M. griffith, IC(50) values were reached. Regarding the clearance of media, in individual treatment a decrease of the quantified mycotoxin between nominal and measured values was observed; while in binary treatment, differences among both values were higher and more noted for BEA than for ENN B.
First Total Syntheses of Beauvericin A and allo-Beauvericin A.[Pubmed:38496974]
ACS Omega. 2024 Feb 26;9(10):12228-12236.
The first total syntheses of Beauvericin A and allo-Beauvericin A were achieved. N-Methyl-l-phenylalanine, (2R)-hydroxylvaleric acid, and (2R,3S)- or (2R,3R)-2-hydroxy-2-methylpentanoic acid were linked and cyclized to form the target natural products. The structure of synthetic Beauvericin A was confirmed by X-ray crystallographic analysis. NMR data of the synthetic beauvericins were identical with those of the reported natural products. These results secure the structures of natural products, as originally proposed in the isolation studies.
Toxicity of the emerging mycotoxins beauvericin and enniatins: A mini-review.[Pubmed:38013058]
Toxicon. 2024 Feb 23;239:107534.
Beauvericin And enniatins, emerging mycotoxins produced mainly by Fusarium species, are natural contaminants of cereals and cereal products. These mycotoxins are cyclic hexadepsipeptides with ionophore properties and their toxicity mechanism is related to their ability to transport cations across the cell membrane. Beauvericin And enniatins are cytotoxic, as they decrease cell viability, promote cell cycle arrest, and increase apoptosis and the generation of reactive oxygen species in several cell lines. They also cause changes at the transcriptomic level and have immunomodulatory effects in vitro and in vivo. Toxicokinetic results are scarce, and, despite its proven toxic effects in vitro, no regulation or risk assessment has yet been performed due to a lack of in vivo data. This mini-review aims to report the information available in the literature on studies of in vitro and in vivo toxic effects with Beauvericin And enniatins, which are mycotoxins of increasing interest to animal and human health.
