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Nivalenol is a Fusarium type B trichothecene mycotoxin. Nivalenol is cytotoxic to leukocytes, inhibiting cell proliferation, increasing IL-8 secretion, and decreasing MCP-1 secretion in an NF-κB-dependent manner. In macrophages and Jurkat T cells, nivalenol increases cytochrome c release and degradation of Bcl-2, stimulating caspase 3-mediated apoptosis. Additionally, nivalenol induces the breakdown of polyribosomes and inhibits polypeptide chain initiation in eukaryotes.
| Cas No. | 23282-20-4 |
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| Purity | ≥99%, TLC |
| Formula | C15H20O7 |
| Formula Wt. | 312.32 |
| Chemical Name | (1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one |
| IUPAC Name | (1S,2R,3S,7R,9R,10R,11S,12S)-3,10,11-trihydroxy-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-one |
| Melting Point | 127-130°C |
| Solubility | DMSO, Methanol, dichloromethane. Slightly soluble in water. |
| Appearance | White to off white powder |
| Store Temp | -20°C |
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| Ship Temp | Ambient |
| MSDS | |
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| Info Sheet |
Alassane-Kpembi I, Kolf-Clauw M, Gauthier T, et al. New insights into mycotoxin mixtures: the toxicity of low doses of Type B trichothecenes on intestinal epithelial cells is synergistic. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):191-8. PMID: 23735874.
Wu W, Flannery BM, Sugita-Konishi Y, et al. Comparison of murine anorectic responses to the 8-ketotrichothecenes 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, fusarenon X and nivalenol. Food Chem Toxicol. 2012 Jun;50(6):2056-61. PMID: 22465835.
Nagashima H, Kushiro M, Nakagawa H. Nuclear factor-κB inhibitors alleviate nivalenol-induced cytotoxicity in HL60 cells. Environ Toxicol Pharmacol. 2011 Jan;31(1):258-61. PMID: 21787693.
Marzocco S, Russo R, Bianco G, et al. Pro-apoptotic effects of nivalenol and deoxynivalenol trichothecenes in J774A.1 murine macrophages. Toxicol Lett. 2009 Aug 25;189(1):21-6. PMID: 19410639.
Nasri T, Bosch RR, Voorde St, et al. Differential induction of apoptosis by type A and B trichothecenes in Jurkat T-lymphocytes. Toxicol In Vitro. 2006 Sep;20(6):832-40. PMID: 16472964.
Cundliffe E, Cannon M, Davies J. Mechanism of inhibition of eukaryotic protein synthesis by trichothecene fungal toxins. Proc Natl Acad Sci U S A. 1974 Jan;71(1):30-4. PMID: 4521056.