 Molecular structure of fumonisin B4 | |
| Names | |
|---|---|
| Preferred IUPAC name (2R,2′R)-{[(5R,6R,7S,9S,18S,19S)-19-Amino-18-hydroxy-5,9-dimethylicosane-6,7-diyl]bis(oxy)}bis(4-oxobutane-1,2-dicarboxylic acid) | |
| Other names FB4 | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| |
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| Properties | |
| C34H59NO13 | |
| Molar mass | 689.83 g/mol |
| Appearance | White to off-white powder |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Fumonisin B4 (or FB4) is afumonisinmycotoxin produced mainly by the fungiFusarium proliferatum,Fusarium verticillioides (formerlyFusarium moniliforme). Recently FB4 has been detected in fungiAspergillus niger and in severalTolypocladium species.[1]
FB4 is similar tofumonisin B2 andfumonisin B3 but it is lacking a hydroxy group located gamma- to the amino substituent while lacking two hydroxy groups compared tofumonisin B1.[2]
Fumonisin B4 was first described in 1991.[3]
Severalisomers of Fumonisin B4 have been detected. A larger group is the partially hydrolysed form, denoted as PHFB4, which has been detected usingHPLC-ITMS.[4] Another significant isomer is the 3-epi-FB4, which has been identified usingNMR, it has also been shown that this isomer occur 10-40% of the regular FB4 sample in nature.[5]
Fumonisin B4 belongs to the class of FB analogues, which is the most significant group from toxicity perspective.[6]Currently Fumonisin B4'stoxicity compared toFumonisin B1 or B2 is unknown as further research is actively ongoing, however in nature its concentration is significantly lower. Fumonisin B4 inhibitssphingosine acyltransferase.
Fumonisin B4 and other fumonisins frequently contaminatemaize and other crops.[7]
