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F1147

Sigma-Aldrich

Fumonisin B1 from Fusarium moniliforme

≥98% (HPLC)

Synonyme(s) :

Macrofusine

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About This Item

Formule empirique (notation de Hill):
C34H59NO15
Numéro CAS:
116355-83-0
Poids moléculaire :
721.83
Numéro MDL:
MFCD27977580
Code UNSPSC :
12352200
ID de substance PubChem :
24894752
Nomenclature NACRES :
NA.32

Source biologique

Fusarium sp. (Fusarium moniliforme)

Niveau de qualité

300

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

methanol: 9.80-10.20 mg/mL, clear, colorless to light yellow

Température de stockage

2-8°C

Chaîne SMILES 

CCCC[C@@H](C)[C@@H](OC(=O)C[C@@H](CC(O)=O)C(O)=O)[C@H](C[C@@H](C)C[C@H](O)CCCC[C@@H](O)C[C@H](O)[C@H](C)N)OC(=O)C[C@@H](CC(O)=O)C(O)=O

InChI

1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)/t19-,20+,21-,22+,23+,24+,25+,26-,27-,32+/m0/s1

Clé InChI

UVBUBMSSQKOIBE-DSLOAKGESA-N

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Description générale

Fumonisin B1 is a mycotoxin found in many Fusarium fungi, such as Fusarium moniliforme, Fusarium proliferatum, and Fusarium verticillioides. This toxin can also be found in feedstocks and food stocks, such as corn / maize, that have been infected with Fusarium.

Fumonisin B1 (FB1) shares structure similarities with sphingosine. Thus fumonisin B1 can inhibit ceramide synthase (sphingosine N-acetyltransferase), which can lead to disruption of ceramide biosynthesis and complex sphingolipid biosynthesis.

Application

Fumonisin B1 from Fusarium moniliforme has been used:
  • as a standard in the analysis of mycotoxins in caecal content obtained from adult pigs
  • in the study of the effect of fumonisin B1 on the metabolism of prion protein (PrP) isoforms and the synthesis of scrapie prion protein PrPSc and
  • in the study of the toxic effects of fumonisin B1 on explants obtained from pig jejunum.

Actions biochimiques/physiologiques

Fumonisin B1 acts as a hepatocarcinogen and causes hepatotoxicity in rats. In horses, it causes leukoencephalitis, and in pigs, it causes pulmonary edema syndrome. In China and southern parts of Africa, it is linked with high incidence of esophageal cancer in humans. It acts as an inhibitor of sphingosine N-acyltransferase enzyme (ceramide synthase), related to structural similarities between fumonisin B1 and sphingoid bases like sphingosine.
Fungal metabolite believed to cause leukoencephalomalacia in horses.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H351,H361d,H373

Classification des risques

Acute Tox. 3 Oral - Carc. 2 - Repr. 2 - STOT RE 2

Organes cibles

Kidney,Liver

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Karina Basso et al.
Toxins, 5(12), 2341-2352 (2013-11-30)
Fusariotoxins such as fumonisin B1 (FB1) and deoxynivalenol (DON) cause deleterious effects on the intestine of pigs. The aim of this study was to evaluate the effect of these mycotoxins, alone and in combination, on jejunal explants from piglets, using
Pranitha Dawlal et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 36(2), 296-307 (2019-01-25)
Consumption of fumonisin-contaminated foods has a negative influence on the health of humans (carcinogen; oesophageal cancer in Eastern Cape in South Africa). Lactic acid bacteria (LAB) have emerged as a promising natural detoxification agent against mycotoxins. The aim of this
Judit Fodor et al.
Food additives and contaminants, 24(4), 416-420 (2007-04-25)
There is a lack of information on the effect of swine caecal microbiota on fumonisin metabolism. In this in vitro study, the biotransformation of fumonisin B(1) (FB(1)) by the gut microbiota of adult, healthy pigs was examined. Suspensions of caecal
Inhibition of Protein Serine/Threonine Phosphatases by Fumonisin B1, a Mycotoxin.
Fukuda H
Biochemical and Biophysical Research Communications, 220, 160-165 (1996)
N Naslavsky et al.
The Journal of biological chemistry, 274(30), 20763-20771 (1999-07-20)
Sphingolipid-rich rafts play an essential role in the posttranslational (Borchelt, D. R., Scott, M., Taraboulos, A., Stahl, N., and Prusiner, S. B. (1990) J. Cell Biol. 110, 743-752)) formation of the scrapie prion protein PrP(Sc) from its normal conformer PrP(C)
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