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F1147 Sigma-Aldrich

Fumonisin B1 from Fusarium moniliforme

≥98% (HPLC)

Synonym: Macrofusine

  • CAS Number 116355-83-0

  • Empirical Formula (Hill Notation) C34H59NO15

  • Molecular Weight 721.83

  •  MDL number MFCD27977580

  •  PubChem Substance ID 24894752

  •  NACRES NA.32

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme,
Quality Level   300
biological source   Fusarium sp. (Fusarium moniliforme)
assay   ≥98% (HPLC)
form   powder
solubility   methanol: 9.80-10.20 mg/mL, clear, colorless to light yellow
storage temp.   2-8°C
SMILES string   CCCC[C@@H](C)[C@@H](OC(=O)C[C@@H](CC(O)=O)C(O)=O)[C@H](C[C@@H](C)C[C@H](O)CCCC[C@@H](O)C[C@H](O)[C@H](C)N)OC(=O)C[C@@H](CC(O)=O)C(O)=O
InChI   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+,23+,24+,25+,26-,27-,32+/m0/s1
InChI key   UVBUBMSSQKOIBE-DSLOAKGESA-N

Description

General description

Fumonisin B1 is a mycotoxin found in many Fusarium fungi, such as Fusarium moniliforme, Fusarium proliferatum, and Fusarium verticillioides. This toxin can also be found in feedstocks and food stocks, such as corn / maize, that have been infected with Fusarium.

Fumonisin B1 (FB1) shares structure similarities with sphingosine. Thus fumonisin B1 can inhibit ceramide synthase (sphingosine N-acetyltransferase), which can lead to disruption of ceramide biosynthesis and complex sphingolipid biosynthesis.

Application

Fumonisin B1 from Fusarium moniliforme has been used:
• as a standard in the analysis of mycotoxins in caecal content obtained from adult pigs
• in the study of the effect of fumonisin B1 on the metabolism of prion protein (PrP) isoforms and the synthesis of scrapie prion protein PrPSc and
• in the study of the toxic effects of fumonisin B1 on explants obtained from pig jejunum.

Biochem/physiol Actions

Fumonisin B1 acts as a hepatocarcinogen and causes hepatotoxicity in rats. In horses, it causes leukoencephalitis, and in pigs, it causes pulmonary edema syndrome. In China and southern parts of Africa, it is linked with high incidence of esophageal cancer in humans. It acts as an inhibitor of sphingosine N-acyltransferase enzyme (ceramide synthase), related to structural similarities between fumonisin B1 and sphingoid bases like sphingosine.

Fungal metabolite believed to cause leukoencephalomalacia in horses.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TZ8350000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

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Peer-Reviewed Papers
15

References

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