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Fumonisin B2

From Wikipedia, the free encyclopedia
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 InfoCard100.114.556Edit 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 mass705.83 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Fumonisin B2 is afumonisinmycotoxin produced by the fungiFusarium verticillioides (formerlyFusarium moniliforme) andAspergillus niger.[1]

It is astructural analog offumonisin B3, while it is lacking one hydroxy group compared tofumonisin B1.[2]

Fumonisin B2 is morecytotoxic than fumonisin B1. Fumonisin B2 inhibitssphingosine acyltransferase.

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

References

[edit]
  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.Bibcode:2007JAFC...55.9727F.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.
Bacterial
toxins
Exotoxin
Gram
positive
Bacilli
Clostridium:
Other:
Cocci
Staphylococcus
Actinomycetota
Gram
negative
Mechanisms
Endotoxin
Virulence
factor
Mycotoxins
Plant toxins
Invertebrate
toxins
Scorpion:
Spider:
Mollusca:
Vertebrate
toxins
Fish:
Amphibian:
Reptile/
Snake venom:
  • note: some toxins are produced by lower species and pass through intermediate species
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