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Saving copy of the {{chembox}} taken from revid 457236395 of page Fumonisin_B2 for the Chem/Drugbox validation project (updated: 'KEGG', 'CASNo').
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Fumonisin_B2|oldid=457236395}} 457236395] of page [[Fumonisin_B2]] with values updated to verified values.}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400096616
| verifiedrevid = 461114500
|ImageFile=Fumonisin B2.png
| ImageFile=Fumonisin B2.png
|ImageSize=200px
| ImageSize=200px
|IUPACName=(2''R'',2<nowiki>'</nowiki>''R'')-2,2'-{[(5''R'',6''S'',7''S'',9''S'',16''R'',18''S'',19''S'')-19-amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}disuccinic acid
| PIN=(2''R'',2′''R'')-<nowiki/>{[(5''R'',6''R'',7''S'',9''S'',16''R'',18''S'',19''S'')-19-Amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
|OtherNames=
| OtherNames=FB2
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2015284
| ChemSpiderID = 2015284
| 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
| 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
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UXDPXZQHTDAXOZ-STOIETHLSA-N
| StdInChIKey = UXDPXZQHTDAXOZ-STOIETHLSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 116355-84-1 -->
| CASNo=116355-84-1
| PubChem=2733489
| PubChem=2733489
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: C19242 -->
| KEGG = C19242
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 38225
| ChEBI = 38225
| 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
| 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
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=34|H=59|N=1|O=14
| C=34 | H=59 | N=1 | O=14
| MolarMass=705.83 g/mol
| MolarMass=705.83 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}

'''Fumonisin B2''' is a [[fumonisin]] [[mycotoxin]] produced by the fungi ''[[Fusarium]] verticillioides'' (formerly ''Fusarium moniliforme'') and ''[[Aspergillus]] niger''.<ref>{{cite journal |author1=Jens C Frisvad |author2=Jørn Smedsgaard |author3=Robert A Samson |author4=Thomas O Larsen |author5=Ulf Thrane |title=Fumonisin B2 production by Aspergillus niger |journal=Journal of Agricultural and Food Chemistry |volume=55 |issue=23 |pages=9727–32 |doi=10.1021/jf0718906 |year=2007|pmid=17929891 |bibcode=2007JAFC...55.9727F }}</ref>

It is a [[structural analog]] of [[fumonisin B3]], while it is lacking one hydroxy group compared to [[fumonisin B1]].<ref>{{Cite web |last=PubChem |title=Fumonisin B2 |url=https://pubchem.ncbi.nlm.nih.gov/compound/2733489 |website=pubchem.ncbi.nlm.nih.gov |publisher=[[PubChem]] |language=en}}</ref>

Fumonisin B2 is more [[Cytotoxicity|cytotoxic]] than fumonisin B1. Fumonisin B2 inhibits [[Sphingosine N-acyltransferase|sphingosine acyltransferase]].

Fumonisin B2 and other fumonisins frequently contaminate [[maize]] and other crops, while recently it has been shown using [[Liquid chromatography-mass spectrometry|LC–MS/MS]] that FB2 can contaminate coffee beans as well.<ref>{{cite journal |author1=P Noonim |author2=W Mahakarnchanakul |author3=K F Nielsen |author4=Jens C Frisvad |author5=Robert A Samson |author6=Ulf Thrane |title=Fumonisin B2 production by Aspergillus niger in Thai coffee beans |journal=Food Addit Contam Part a Chem Anal Control Expo Risk Assess |volume=26 |issue=1 |pages=94–100 |doi=10.1080/02652030802366090 |year=2009|pmid=19680876 |s2cid=21427787 |url=https://hal.archives-ouvertes.fr/hal-00577319/file/PEER_stage2_10.1080%252F02652030802366090.pdf }}</ref>

== References ==
{{reflist}}

{{Toxins}}

[[Category:Mycotoxins]]
[[Category:Enzyme inhibitors]]

{{biochem-stub}}
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