F1147

Fumonisin B₁ from Fusarium moniliforme

≥98% (HPLC)

• Synonyme(s) : Macrofusine
• 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

Propriétés

• 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

Description

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 PrP^Sc 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.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H301,H351,H361d,H373
• Conseils de prudence: P202 - P260 - P264 - P280 - P301 + P310 - P405
• 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