Enniatin A CAS 2503-13-1

CAS Number

2503-13-1

Grade

Highly Purified

Molecular Formula

C₃₆H₆₃N₃O₉

Molecular Weight

681.9

EU Commodity Code

38220090

Shipping Temp

Blue Ice

Storage Temp

-20°C

Lateritin I; 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-isoleucyl]; N-(D-2-Hydroxy-3-methylbutyryl)-N-methyl-Isoleucine Trimol. Cyclic Ester; 1,7,13-Trioxa-4,10,16-triazacyclooctadecane Cyclic Peptide Deriv.;|Cyclo(D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl)

Enniatins are a family of depsipeptides produced several Fusarium species. The enniatins have been shown to act as ionophores. More recently their effects on acyl-CoA cholesterol transferase, transporters and the selectivity of their antitumor action have received more focus. Enniatin A is one of four major analogs of the enniatin complex and has previously not been available for investigation.

• Cyclohexadepsipeptide mycotoxin. One of four major analogs in the enniatin complex. Commonly found food contaminant in cereals and their products. • Ionophore antibiotic. Incorporation into the cell membrane forms dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. • Anticancer compound. Triggers apoptosis in several cancer cell lines. Leads to loss of mitochondrial membrane potential and cell cycle arrest. • Moderate inhibitor of ACAT (acylcoenzyme A:cholesterolacyl transferase). • Shown to have a variety of other biological activities such as antifungal, anthelmintic, insecticidal, immunomodulatory and phytotoxic activity.

Source

Fusarium sp. MST-FP1765

Synonyms

Lateritin I; 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-isoleucyl]; N-(D-2-Hydroxy-3-methylbutyryl)-N-methyl-Isoleucine Trimol. Cyclic Ester; 1,7,13-Trioxa-4,10,16-triazacyclooctadecane Cyclic Peptide Deriv.; Cyclo(D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-α-hydroxyisovaleryl-N-methyl-L-isoleucyl)

CAS No

2503-13-1

Molecular Formula

C₃₆H₆₃N₃O₉

Molecular Weight

681.9

Appearance

White to off-white solid

Purity

≥98% by HPLC

Source

Enniati

Solubility

Soluble in ethanol, methanol, DMF or DMSO.

Storage and Stability

Lyophilized powder may be stored at 4°C. Stable for 12 months at -20°C. Reconstitute with ethanol, methanol, DMF or DMSO. Aliquot to avoid repeated freezing and thawing. Store at -20°C. Protect from light. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Further dilutions can be made in assay buffer.

References

1. Sy-Cordero, A.A., Pearce, C.J., and Oberlies, N.H. Revisiting the enniatins: A review of their isolation, biosynthesis, structure determination and biological activities. J. Antibiot. (Tokyo) 65(11), 541-549 (2012).|2. Kamyar, M.R., Rawnduzi, P., Studenik, C.R., et al. Investigation of the electrophysiological properties of enniatins. Arch. Biochem. Biophys. 429(2), 215-223 (2004).|3. Tomoda, H., Huang, X.H., Cao, J., et al. Inhibition of acyl-CoA: Cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J.Antibiot.(Tokyo) 45(10), 1626-1632 (1992).|4. Kirjavainen, P. et al.: Indoor Air., 26, 448 (2016)|5. Taevernier, L. et al.: Toxicol. Lett., 258, 175 (2016)||Additional References:| 1 A comparison of beauvericin, enniatin and valinomycin as calcium transporting agents in liposomes and chromatophores: R.C. Prince, et al.; BBRC 59, 697 (1974)| 2 Inhibition of acyl-CoA: Cholesterol acyltransferase activity by cyclodepsipeptide antibiotics: H. Tomoda, et al.; J. Antibiot. (Tokyo) 45, 1626 (1992)| 3 Investigation of the electrophysiological properties of enniatins: M. Kamyar, et al.; Arch. Biochem. Biophys. 429, 215 (2004)| 4 Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum: L. Ivanova, et al.; Toxicon 47, 868 (2006)| 5 Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells: R. Dornetshuber, et al.; Chem. Res. Toxicol. 20, 465 (2007)| 6 Emerging Fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin - a review: M. Jestoi; Crit. Rev. Food Sci. Nutr. 48, 21 (2008)| 7 Oxidative stress and DNA interactions are not involved in Enniatin- and Beauvericin-mediated apoptosis induction: R. Dornetshuber, et al.; Mol. Nutr. Food Res. 53, 1112 (2009)| 8 Stimulation of erythrocyte phospholipid scrambling by enniatin A: K. Jilani, et al.; Mol. Nutr. Food Res. 55, 294 (2011)| 9 Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana): D.C. Tan, et al.; Toxicon 57, 817 (2011)| 10 Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities: A.A. Sy-Cordero, et al.; J. Antibiot. 65, 541 (2012)| 11 Quantitative determination of the Fusarium mycotoxins beauvericin, enniatin A, A1, B and B1 in pig plasma using high performance liquid chromatography-tandem mass spectrometry: M. Devreese, et al.; Talanta 106, 212 (2013)| 12 A preliminary study in Wistar rats with enniatin A contaminated feed: L. Manyes, et al.; Toxicol. Mech. Methods 24, 179 (2014)| 13 Evaluation of immunologic effect of Enniatin A and quantitative determination in feces, urine and serum on treated Wistar rats: C. Juan, et al.; Toxicon 87, 45 (2014)

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E3222-26 Enniatin A (Lateritin I) CAS: 2503-13-1

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