344850-M

Fumonisin B₁, Fusarium moniliforme

A cell-permeable mycotoxin that inhibits sphingolipid biosynthesis in rat kidney and in liver microsomes by inhibition of sphingosine N-acyltransferase (ceramide synthase; IC₅₀ = 100 nM).

• Synonym(s): Fumonisin B₁, Fusarium moniliforme, FB₁
• Empirical Formula (Hill Notation): C₃₄H₅₉NO₁₅
• CAS Number: 116355-83-0
• Molecular Weight: 721.83
• MDL number: MFCD27977580
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• Assay: ≥95% (TLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white to beige
• solubility: methanol: 5 mg/mL
• storage temp.: 2-8°C
• 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-/m1/s1
• InChI key: UVBUBMSSQKOIBE-ZWKVXHQASA-N

Description

General description

A cell-permeable mycotoxin that inhibits sphingolipid biosynthesis in rat kidney and in liver microsomes by inhibition of sphingosine N-acyltransferase (ceramide synthase; IC₅₀ = 100 nM). Preferentially inhibits sphingomyelin biosynthesis in neuronal cells. Exhibits carcinogenic properties.

Fumonisin B₁ is a neurotoxin and a phytotoxin. A cell-permeable mycotoxin that inhibits sphingolipid biosynthesis in rat kidney and in liver microsomes by inhibition of sphingosine N-acyltransferase (ceramide synthase) (IC₅₀ = 100 nM). Cellular effects also appear to be induced by micromolar levels of FB₁. Because it inhibits ceramide synthase activity, it elevates cellular levels of sphingoid bases, including sphinganine, resulting in overall inhibition of sphingolipid biosynthesis. Preferentially inhibits sphingomyelin biosynthesis in neuronal cells. Has carcinogenic properties.

Biochem/physiol Actions

Primary Target
ceramide synthase

Target IC₅₀: 100 nM against sphingosine N-acyltransferase (ceramide synthase)

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Wu, W.I., et al. 1995. J. Biol. Chem.270, 13171.
Riley, R.T., et al. 1994. J. Nutr. 124, 594.
Wolf, G. 1994. Nutr. Rev. 52, 246.
Merrill, A.H. Jr., et al. 1993. Adv. Lipid Res.26, 215.
Merrill, Jr., A.H., et al. 1993. J. Biol. Chem.268, 27299.
Voss, K.A., et al. 1993. Nat. Toxins1, 222.
Wang, E., et al. 1991. J. Biol. Chem.266, 14486.
Harrison, L.R., et al. 1990. J. Vet. Diag. Invest. 2, 217.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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
• 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