Fumonisin B1

Cayman Chemical Item Number 62580

(CAS 116355-83-0)

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Description

Fumonisin B1 is a mycotoxin produced from F. moniliforme, a prevalent fungus of corn and other grains. Outbreaks of food poisoning in livestock and humans following the consumption of Fusarium infested corn are caused by fumonisins.1 It functions as an inhibitor of ceramide synthase (sphingosine N-acyltransferase).2 Fumonisin B1 attenuates the response of P388D1 cells to PAF and LPS by inhibiting ceramide formation.3 It also blocks the apoptotic response of HaCaT cells to the antiproliferative drug hexadecylphosphocholine, again through inhibition of ceramide production.4 Incubation of Swiss 3T3 cells with fumonisin B1 results in both an altered cell morphology due to disruption of axonal growth and a decrease in cell proliferation.5

1. Gelderblom, W.C.A., Jaskiewicz, K., Marasas, W.F.O., et al. Fumonisins - novel mycotoxins with cancer-promoting activity produced by Fusarium moniliforme. Appl Environ Microbiol 54 1806-1811 (1988).

2. Wang, E., Norred, W.P., Bacon, C.W., et al. Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme. J Biol Chem 266 14486-14490 (1991).

3. Balsinde, J., Balboa, M.A., and Dennis, E.A. Inflammatory activation of arachidonic acid signaling in murine P388D1 macrophages via sphingomyelin synthesis. J Biol Chem 272 20373-20377 (1997).

4. Wieder, T., Orfanos, C.E., and Geilen, C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J Biol Chem 273 11025-11031 (1998).

5. Meivar-Levy, I., Sbanay, H., Bershadsky, A.D., et al. The role of sphingolipids in the maintenance of fibroblast morphology. The inhibition of protrusional activity, cell spreading, and cytokinesis induced by fumonisin B1 can be reversed by ganglioside GM3. J Biol Chem 272 1558-1564 (1997).

Formal Name 1,​2,​3-​propanetricarboxylic acid,​ 1,​-​1'-​[1-​(12-​amino-​4,​9,​11-​trihydroxy-​2-​methyltridecyl)-​2-​(1-​methylpentyl)-​1,​2-​ethanediyl] ester
CAS Number 116355-83-0
Molecular Formula C34H59NO15
Formula Weight 721.8
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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C[C@H]​(N)​[C@@H]​(O)​C[C@H]​(O)​CCCC[C@@H]​(O)​C[C@H]​(C)​CC(OC(C[C@H]​(C(O)​=O)​CC(O)​=O)​=O)​C(OC(C[C@@H]​(C(O)​=O)​CC(O)​=O)​=O)​[C@@H]​(C)​CCCC
InCHI Code
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​1S/C34H59NO15/c1-5-6-9-20(3)​32(50-31(44)​17-23(34(47)​48)​15-29(41)​42)​27(49-30(43)​16-22(33(45)​46)​14-28(39)​40)​13-19(2)​12-24(36)​10-7-8-11-25(37)​18-26(38)​21(4)​35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)​(H,41,42)​(H,45,46)​(H,47,48)​/t19-,20+,21-,22?,2
InCHI Key
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UVBUBMSSQKOIBE-BQLGDNNVSA-N

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Fumonisin B1 is available in the following screening library:

Size Price Quantity Subtotal
1 mg $48.00 $0.00
5 mg $216.00 $0.00
10 mg $384.00 $0.00
25 mg $768.00 $0.00
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Cart Total $0.00

Pricing updated 2015-07-31. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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