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344850-M

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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).

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Synonym(s):
Fumonisin B1, Fusarium moniliforme, FB₁
Empirical Formula (Hill Notation):
C34H59NO15
CAS Number:
Molecular Weight:
721.83
MDL number:

Quality Level

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

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

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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