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F1147

Fumonisin B₁

Name: Fumonisin B&#8321;
Brand: SIGMA

From Fusarium sp. (Fusarium moniliforme), ≥98% (HPLC), ceramide synthase (sphingosine N-acetyltransferase) inhibitor, powder

Synonym(s):

Macrofusine

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₅₉NO₁₅

CAS Number:

116355-83-0

Molecular Weight:

721.83

UNSPSC Code:

12352200

PubChem Substance ID:

24894752

NACRES:

NA.32

MDL number:

MFCD27977580

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Product Name

Fumonisin B₁ from Fusarium moniliforme, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H351,H361d,H373

pcodes

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

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

ppe

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

Regulatory Information

高风险级别生物产品--毒素类产品

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Deoxynivanelol and fumonisin, alone or in combination, induce changes on intestinal junction complexes and in E-cadherin expression.

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

In vitro microbial metabolism of fumonisin B1.

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

Inhibition of Protein Serine/Threonine Phosphatases by Fumonisin B1, a Mycotoxin.

Fukuda H

Biochemical and Biophysical Research Communications, 220, 160-165 (1996)

Visualisation and quantification of fumonisins bound by lactic acid bacteria isolates from traditional African maize-based fermented cereals, ogi and mahewu.

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

The kinetics of urinary fumonisin B1 excretion in humans consuming maize-based diets.

Ronald T Riley et al.

Molecular nutrition & food research, 56(9), 1445-1455 (2012-07-21)

Fumonisins (FB) are mycotoxins found in maize. The purpose of this study was to (i) determine the relationship between FB(1) , FB(2) , and FB(3) intake and urinary excretion in humans, (ii) validate a method to isolate urinary FB on

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Global Trade Item Number

SKU	GTIN
F1147-10MG	04061833611708
F1147-5MG	04061833611722
F1147-1MG	04061833611715

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