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F1147

Fumonisin B₁

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

Key Documents

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Product Name

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

form

powder

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

biological source

Fusarium sp. (Fusarium moniliforme)

assay

≥98% (HPLC)

solubility

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

storage temp.

2-8°C

Quality Level

300

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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.

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
0000490224
0000490224
0000484224
0000484224
0000463729

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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)
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
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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