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ProductsBack/Enniatin A [2503-13-1]
Chemical Structure
Chemical Structure
Chemical Structure

Enniatin A [2503-13-1]

Research Use Only
AG-CN2-0477
AdipoGen Life Sciences
CAS Number2503-13-1
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight681.9
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Enniatin A
  • Delivery Days Customer
    10
  • CAS Number
    2503-13-1
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Warning
  • Molecular Formula
    C36H63N3O9
  • Molecular Weight
    681.9
  • Scientific Description
    Chemical. CAS: 2503-13-1. Formula: C36H63N3O9. MW: 681.9. Isolated from fungus Fusarium sp. 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. - 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.
  • SMILES
    [H][C@@]1([C@@H](C)CC)N(C)C(=O)[C@H](OC(=O)[C@]([H])([C@@H](C)CC)N(C)C(=O)[C@H](OC(=O)[C@]([H])([C@@H](C)CC)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • A comparison of beauvericin, enniatin and valinomycin as calcium transporting agents in liposomes and chromatophores: R.C. Prince, et al.; BBRC 59, 697 (1974)
  • Inhibition of acyl-CoA: Cholesterol acyltransferase activity by cyclodepsipeptide antibiotics: H. Tomoda, et al.; J. Antibiot. (Tokyo) 45, 1626 (1992)
  • Investigation of the electrophysiological properties of enniatins: M. Kamyar, et al.; Arch. Biochem. Biophys. 429, 215 (2004)
  • Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum: L. Ivanova, et al.; Toxicon 47, 868 (2006)
  • Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells: R. Dornetshuber, et al.; Chem. Res. Toxicol. 20, 465 (2007)
  • Emerging Fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin - a review: M. Jestoi; Crit. Rev. Food Sci. Nutr. 48, 21 (2008)
  • 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)
  • Stimulation of erythrocyte phospholipid scrambling by enniatin A: K. Jilani, et al.; Mol. Nutr. Food Res. 55, 294 (2011)
  • Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana): D.C. Tan, et al.; Toxicon 57, 817 (2011)
  • 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)