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F1147

Sigma-Aldrich

Fumonisin B1 from Fusarium moniliforme

≥98% (HPLC)

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Synonym(s):
Macrofusine
Empirical Formula (Hill Notation):
C34H59NO15
CAS Number:
Molecular Weight:
721.83
MDL number:
PubChem Substance ID:
NACRES:
NA.32

biological source

Fusarium sp. (Fusarium moniliforme)

Quality Level

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

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1 of 4

This Item
SML128632936344850-M
vibrant-m

SML1286

Fumonisin B1 Ready Made Solution

vibrant-m

32936

Fumonisin B1

assay

≥98% (HPLC)

assay

-

assay

-

assay

≥95% (TLC)

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

100

form

powder

form

DMSO solution

form

-

form

powder

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

methanol: 9.80-10.20 mg/mL, clear, colorless to light yellow

solubility

-

solubility

-

solubility

methanol: 5 mg/mL

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 PrPSc 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.

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

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Fumonisin B1-13C34 solution ~25 μg/mL in acetonitrile: water, analytical standard

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Karina Basso et al.
Toxins, 5(12), 2341-2352 (2013-11-30)
Fusariotoxins such as fumonisin B1 (FB1) and deoxynivalenol (DON) cause deleterious effects on the intestine of pigs. The aim of this study was to evaluate the effect of these mycotoxins, alone and in combination, on jejunal explants from piglets, using
Pranitha Dawlal et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 36(2), 296-307 (2019-01-25)
Consumption of fumonisin-contaminated foods has a negative influence on the health of humans (carcinogen; oesophageal cancer in Eastern Cape in South Africa). Lactic acid bacteria (LAB) have emerged as a promising natural detoxification agent against mycotoxins. The aim of this
Inhibition of Protein Serine/Threonine Phosphatases by Fumonisin B1, a Mycotoxin.
Fukuda H
Biochemical and Biophysical Research Communications, 220, 160-165 (1996)
Judit Fodor et al.
Food additives and contaminants, 24(4), 416-420 (2007-04-25)
There is a lack of information on the effect of swine caecal microbiota on fumonisin metabolism. In this in vitro study, the biotransformation of fumonisin B(1) (FB(1)) by the gut microbiota of adult, healthy pigs was examined. Suspensions of caecal
Candida P Shirima et al.
Environmental health perspectives, 123(2), 173-178 (2014-10-18)
Aflatoxin and fumonisin are toxic food contaminants. Knowledge about effects of their exposure and coexposure on child growth is inadequate. We investigated the association between child growth and aflatoxin and fumonisin exposure in Tanzania. A total of 166 children were

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