F1147

Fumonisin B₁ from Fusarium moniliforme

≥98% (HPLC)

• Synonym(s): Macrofusine
• Empirical Formula (Hill Notation): C₃₄H₅₉NO₁₅
• CAS Number: 116355-83-0
• Molecular Weight: 721.83
• MDL number: MFCD27977580
• UNSPSC Code: 12352200
• PubChem Substance ID: 24894752
• NACRES: NA.32

Properties

• biological source: Fusarium sp. (Fusarium moniliforme)
• Quality Level: 300
• Assay: ≥98% (HPLC)
• form: powder
• solubility: methanol: 9.80-10.20 mg/mL, clear, colorless to light yellow
• storage temp.: 2-8°C
• SMILES string: 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
• InChI key: UVBUBMSSQKOIBE-DSLOAKGESA-N

Description

General description

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.

Biochem/physiol Actions

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.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H351,H361d,H373
• Precautionary Statements: P202 - P260 - P264 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Carc. 2 - Repr. 2 - STOT RE 2
• Target Organs: Kidney,Liver
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves