Fumonisin B 1

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Structural formula
Fumonisin B1.svg
Fumonisin B 1
General
Surname Fumonisin B 1
other names
  • Bis (1,2,3-propane tricarboxylic acid) - (5 R , 6 R , 7 S , 9 S , 11 R , 16 R , 18 S , 19 S ) -19-amino-11,16,18-trihydroxy-5 , 9-dimethyl-eicosane-6,7-diyl diester
  • Macrofusin
Molecular formula C 34 H 59 NO 15
Brief description

light brown solid

External identifiers / databases
CAS number 116355-83-0
EC number 621-436-3
ECHA InfoCard 100.150.289
PubChem 62314
ChemSpider 56109
Wikidata Q420762
properties
Molar mass 721.83 g mol −1
Physical state

firmly

safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 351
P: 281
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fumonisin B 1 is a mycotoxin produced by various Fusarium species, including Fusarium verticillioides . It belongs to the group of fumonisins .

properties

Fusarium on a corn cob

Fumonisin B 1 occurs mainly in maize, wheat and other cereals and is an important food poison in agriculture . Fumonisin B 1 is hepatotoxic and nephrotoxic . Chronic poisoning leads to equine leukoencephalomalacia (ELEM) in horses and porcine pulmonary edema syndrome in pigs. Both of these diseases are characterized by disorders of the sphingolipid metabolism and cardiovascular dysfunction.

Inhibition of ceramide synthase by FB 1

Fumonisin B 1 is biosynthesized via a polyketide pathway. It consists of two parts, one of which (amino alcohol) is adsorbed on the binding site for sphinganine or sphingosine and one (tricarballylic acid) is attached to the binding site for acyl-CoA in the ceramide synthase . As a result, the ceramide synthase is competitively inhibited . A synthetic derivative ( N -palmitoyl-AP1) with a palmitoyl group instead of the tricarballyic acid group inhibits ceramide synthase even more.

Individual evidence

  1. ↑ a b c data sheet fumonisin B 1 from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  2. ↑ European Commission: Opinion of the Scientific Committee on Food on Fusarium-toxins Part 3: Fumonisin B 1 (FB 1 ) (PDF; 185 kB).
  3. ↑ AH Merrill, MC Sullards, E. Wang, KA Voss, RT Riley: Sphingolipid metabolism: roles in signal transduction and disruption by fumonisins. In: Environmental health perspectives. Volume 109 Suppl 2, May 2001, pp. 283-289, PMID 11359697 , PMC 1240677 (free full text).