Fumonisin B2

Fumonisin B2
Names
	IUPAC name (2R,2'R)-2,2'-{[(5R,6S,7S,9S,16R,18S,19S)-19-amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}disuccinic acid
	Other names FB2
Identifiers
CAS Number	116355-84-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:38225 ;
ChemSpider	2015284 ;
ECHA InfoCard	100.114.556
KEGG	C19242 ;
PubChem CID	2733489;
CompTox Dashboard (EPA)	DTXSID80891857 ;
	InChI 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 Key: UXDPXZQHTDAXOZ-STOIETHLSA-N ; 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;
	SMILES 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
Chemical formula	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).
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	Infobox references

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

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.
PubChem. "Fumonisin B2". pubchem.ncbi.nlm.nih.gov. PubChem.
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". Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 26 (1): 94–100. doi:10.1080/02652030802366090. PMID 19680876.

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[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". Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 26 (1): 94–100. doi:10.1080/02652030802366090. PMID 19680876.