Fumonisin B2
Names
Preferred IUPAC name
(2R,2′R)-{[(5R,6R,7S,9S,16R,18S,19S)-19-Amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
Other names
FB2
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.114.556 Edit this at Wikidata
KEGG
  • InChI=1S/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)/t20-,21+,22-,23+,24+,25+,26-,27-,32+/m0/s1 checkY
    Key: UXDPXZQHTDAXOZ-STOIETHLSA-N checkY
  • InChI=1/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)/t20-,21+,22-,23+,24+,25+,26-,27-,32+/m0/s1
    Key: UXDPXZQHTDAXOZ-STOIETHLBE
  • O=C(O)C[C@@H](C(=O)O)CC(=O)O[C@@H](C[C@@H](C)CCCCCC[C@@H](O)C[C@H](O)[C@@H](N)C)[C@H](OC(=O)C[C@H](C(=O)O)CC(=O)O)[C@H](C)CCCC
Properties
C34H59NO14
Molar mass 705.83 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Fumonisin B2 is a fumonisin mycotoxin produced by the fungi Fusarium verticillioides (formerly Fusarium moniliforme) and Aspergillus niger.[1]

It is a structural analog of fumonisin B3, while it is lacking one hydroxy group compared to fumonisin B1.[2]

Fumonisin B2 is more cytotoxic than fumonisin B1. Fumonisin B2 inhibits sphingosine acyltransferase.

Fumonisin B2 and other fumonisins frequently contaminate maize and other crops, while recently it has been shown using LC–MS/MS that FB2 can contaminate coffee beans as well.[3]

References

  1. ^ Jens C Frisvad; Jørn Smedsgaard; Robert A Samson; Thomas O Larsen; Ulf Thrane (2007). "Fumonisin B2 production by Aspergillus niger". Journal of Agricultural and Food Chemistry. 55 (23): 9727–32. doi:10.1021/jf0718906. PMID 17929891.
  2. ^ PubChem. "Fumonisin B2". pubchem.ncbi.nlm.nih.gov. PubChem.
  3. ^ P Noonim; W Mahakarnchanakul; K F Nielsen; Jens C Frisvad; Robert A Samson; Ulf Thrane (2009). "Fumonisin B2 production by Aspergillus niger in Thai coffee beans" (PDF). Food Addit Contam Part a Chem Anal Control Expo Risk Assess. 26 (1): 94–100. doi:10.1080/02652030802366090. PMID 19680876. S2CID 21427787.
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