AdipoGen Life Sciences

Enniatin B1

CHF 210.00
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AG-CN2-0480-M0011 mgCHF 210.00
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Product Details
Synonyms 2-(N-Methyl-L-isoleucine)enniatin B
Product Type Chemical
Properties
Formula

C34H59N3O9

MW 653.9
Merck Index 14: 3585
CAS 19914-20-6
Source/Host Chemicals Isolated from fungus Fusarium sp.
Purity Chemicals ≥96% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in DMSO, ethanol, methanol or DMF. Almost insoluble in water.
InChi Key UQCSETXJXJTMKO-UMURLBKASA-N
Smiles [H][C@@]1([C@@H](C)CC)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • 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, decreasing the activation of the cell proliferation kinase, ERK (p44/p42).
  • Moderate inhibitor of ACAT (acylcoenzyme A:cholesterolacyl transferase).
  • Inhibitor of the pleiotropic drug resistance protein 5 (Pdr5p) in yeast.
  • Shown to have a variety of other biological activities such as antifungal, anthelmintic, insecticidal, immunomodulatory and phytotoxic activity.
Product References
  1. Structure of the K+ complex with enniatin B, a macrocyclic antibiotic with K+ transport properties: M. Dobler, et al.; J. Mol. Biol. 42, 603 (1969)
  2. A comparison of beauvericin, enniatin and valinomycin as calcium transporting agents in liposomes and chromatophores: R.C. Prince, et al.; BBRC 59, 697 (1974)
  3. Inhibition of acyl-CoA: Cholesterol acyltransferase activity by cyclodepsipeptide antibiotics: H. Tomoda, et al.; J. Antibiot. (Tokyo) 45, 1626 (1992)
  4. Investigation of the electrophysiological properties of enniatins: M. Kamyar, et al.; Arch. Biochem. Biophys. 429, 215 (2004)
  5. Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae: K. Hiraga, et al.; BBRC 328, 1119 (2005)
  6. Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum: L. Ivanova, et al.; Toxicon 47, 868 (2006)
  7. Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells: R. Dornetshuber, et al.; Chem. Res. Toxicol. 20, 465 (2007)
  8. Emerging Fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin - a review: M. Jestoi; Crit. Rev. Food Sci. Nutr. 48, 21 (2008)
  9. 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)
  10. 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: W. Waetjen, et al.; Mol. Nutr. Food Res. 53, 431 (2009)
  11. Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana): D.C. Tan, et al.; Toxicon 57, 817 (2011)
  12. 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)
  13. 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)
  14. Pilot toxicokinetic study and absolute oral bioavailability of the Fusarium mycotoxin enniatin B1 in pigs: M. Devreese, et al.; Food Chem. Toxicol. 63, 161 (2014)
  15. Enniatin A1, enniatin B1 and beauvericin on HepG2: Evaluation of toxic effects: A. Juan-Garcia, et al.; Food Chem. Toxicol. 84, 188 (2015)
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