FUMONISIN B1

FUMONISIN B1 Basic information
Product Name:FUMONISIN B1
Synonyms:MACROFUSINE;FUMONISIN B1;FUMONISIN B1, FUSARIUM MONILIFORME;FB1;1,2,3-PROPANETRICARBOXYLIC ACID 1,1′-[1-(12-AMINO-4,9,11-TRIHYDROXY-2-METHYLTRIDECYL)-2-(1-METHYLPENTYL)-1,2-ETHANEDIYL] ESTER;1,2,3-PROPANETRICARBOXYLIC ACID 1,1′-[12-AMINO-4,9,11-TRIHYDROXY-2-METHYLTRIDECYL)-2-(1-METHYLPENTYL)-1,2-ETHANEDIYL]ESTER;1,2,3-propanetricarboxylicacid,1,1’-(1-(12-amino-4,9,11-trihydroxy-2-methyltr;idecyl)-2-(1-methylpentyl)-1,2-ethanediyl)ester
CAS:116355-83-0
MF:C34H59NO15
MW:721.83
EINECS:621-436-3
Product Categories:antibiotic;Miscellaneous Natural Products;Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:116355-83-0.mol
FUMONISIN B1 Structure
FUMONISIN B1 Chemical Properties
Melting point >60oC
Boiling point 713.81°C (rough estimate)
density 1.2207 (rough estimate)
refractive index 1.6630 (estimate)
Fp 6 °C
storage temp. 2-8°C
solubility Soluble in Water (up to 25 mg/ml).
form Powder
pka3?+-.0.23(Predicted)
color White to tan
Stability:Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
CAS DataBase Reference116355-83-0
IARC2B (Vol. 56) 1993, 2B (Vol. 82) 2002
Safety Information
Hazard Codes Xn,T,F
Risk Statements 40-36-20/21/22-11
Safety Statements 36/37-16-26-45
RIDADR 3172
WGK Germany 3
RTECS TZ8350000
HazardClass 6.1(b)
PackingGroup III
HS Code 29221990
Hazardous Substances Data116355-83-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROSEnglish
SigmaAldrichEnglish
FUMONISIN B1 Usage And Synthesis
DescriptionFumonisin B1 (116355-83-0) inhibits ceramide synthesis (sphinganine N-acyltransferase), IC50 = 100 nM. Inhibits de novo sphingolipid biosynthesis (IC50 = 0.7 μM) thereby blocking glycosphingolipid production.
Chemical Propertieswhite to tan powder
UsesFumonisin B1 is a major analogue of a family of potent mycotoxins produced by various Fusarium species, associated with animal toxicity worldwide. In vitro, fumonisin B1 inhibits sphingosine N-acyl-transferase (ceramide synthase) and blocks the growth of axons.
UsesA serine/threonine phosphatase inhibitor.
UsesA mycotoxin produced by mold associated with corn. Fungal metabolite believed to cause leukoencephalomalacia in horses.
DefinitionChEBI: Fumonisin B1 is a diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol. It has a role as a metabolite and a carcinogenic agent. It is a fumonisin, a primary amino compound, a diester and a triol. It is functionally related to a (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol. It is a conjugate acid of a fumonisin B1(3-).
General DescriptionFumonisin 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.
Biological ActivityMycotoxin produced by Fusarium moniliforme . Potently inhibits sphingosine N-acyltransferase (ceramide synthase), causing an accumulation of sphingoid bases (IC 50 ~ 75 nM). Also inhibits protein phosphatases; IC 50 values are 80, 300, 400, 500 and 3000 μ M for PP5, PP2C α , PP2A, PP1 γ 2 and PP2B respectively.
Biochem/physiol ActionsFumonisin 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.
References1) Merrill et al. (1993), Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ; J. Biol. Chem., 268 27299
FUMONISIN B1 Preparation Products And Raw materials

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