Fumonisin B4

Fumonisin B4

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
  • 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=1S/C34H59NO13/c1-5-6-14-22(3)32(48-31(42)20-25(34(45)46)18-29(39)40)27(47-30(41)19-24(33(43)44)17-28(37)38)16-21(2)13-11-9-7-8-10-12-15-26(36)23(4)35/h21-27,32,36H,5-20,35H2,1-4H3,(H,37,38)(H,39,40)(H,43,44)(H,45,46)/t21-,22+,23-,24+,25+,26-,27-,32+/m0/s1
    Key: WYYKRDVIBOEORL-JLCKPESSSA-N
  • CCCCC(C)C(C(CC(C)CCCCCCCCC(C(C)N)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O
Properties
C34H59NO13
Molar mass 689.83 g/mol
Appearance White to off-white powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N (what is checkY☒N ?)

Fumonisin B4 (or FB4) is a fumonisin mycotoxin produced mainly by the fungi Fusarium proliferatum, Fusarium verticillioides (formerly Fusarium moniliforme). Recently FB4 has been detected in fungi Aspergillus niger and in several Tolypocladium species.[1]

FB4 is similar to fumonisin B2 and fumonisin B3 but it is lacking a hydroxy group located gamma- to the amino substituent while lacking two hydroxy groups compared to fumonisin B1.[2]

Fumonisin B4 was first described in 1991.[3]

  1. ^ Jesper Mølgaard Mogensen; Kirsten Amalie Møller; Pernille Freiesleben; Roman Labuda; Elisabeth Varga; Michael Sulyok; Alena Kuba ́tova; Ulf Thrane; Birgitte Andersen; Kristian Fog Nielsen (2010). "Production of fumonisins B2 and B4 in Tolypocladium species". Journal of Industrial Microbiology & Biotechnology. 38 (9): 1329–35. doi:10.1007/s10295-010-0916-1. PMID 21132348. S2CID 36017788.
  2. ^ PubChem. "Fumonisin B4". pubchem.ncbi.nlm.nih.gov. PubChem. Retrieved 2020-10-06.
  3. ^ Maria E. Cawood; Wentzel C. A. Gelderblom; Robert Vleggaar; Yosef Behrend; Pieter G. Thiel; Walter F. O. Marasas (1991). "Isolation of the Fumonisin Mycotoxins: A Quantitative Approach". Journal of Agricultural and Food Chemistry. 39 (11): 1958–1962. Bibcode:1991JAFC...39.1958C. doi:10.1021/jf00011a014.