Fumonisin B1
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01854 |
| CAS | 116355-83-0 |
| Molecular Weight | 721.83 |
| Molecular Formula | C34H59NO15 |
| Purity | ≥98% |
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Description
Fumonisin B1 is produced by the strain of Gibberella fujikuroi and Fumarium moniliforme. It is a liver toxin, which can activate the cancer promoter and cause liver cancer. It has been reported that it is related to the occurrence of human esophageal cancer in South Africa and other places. It can also cause pig pulmonary edema, and is also the pathogenic substance of equine leukoencephalitis. Fumonisin B1 inhibits sphingosine acyltransferase.
Specification
| Synonyms | Macrofusine; Macrofusine; NSC 629151; (R)-3-Carboxy-pentanedioic acid mono-{(1S,3S,5R,10R,12S,13S)-13-amino-1-[(1R,2R)-1-((R)-3,4-dicarboxy-butyryloxy)-2-methyl-hexyl]-5,10,12-trihydroxy-3-methyl-tetradecyl} ester |
| Storage | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| IUPAC Name | (2R)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid |
| Canonical SMILES | CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)N)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O |
| InChI | 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 |
| Source | Fumonisin B1 is the most prevalent member of a family of toxins, known as fumonisins, produced by several species of Fusarium molds, such as Fusarium moniliforme, which occur mainly in maize, wheat and other cereals. |
Properties
| Appearance | White to Pale Yellow Solid |
| Boiling Point | 713.81°C at 760 mmHg |
| Melting Point | >60°C |
| Density | 1.2207 g/cm3 |
| Solubility | Soluble in Methanol (Slightly), Water (Slightly, Heated) |
Toxicity
| Carcinogenicity | 2B, possibly carcinogenic to humans. |
| Mechanism Of Toxicity | Fumonisins are similar in structure to the long-chain base backbones of sphingolipids, allowing it to inhibit of the biosynthesis of sphingosine and more complex sphingolipids by inhibiting the enzyme ceramide synthase. This causes the accumulation of sphinganine, sphingosine, and possibly also sphingosine 1-phosphate in cells and tissues, leading to apoptosis. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. |
Reference Reading
1. Fumonisin B1-Induced Changes in Cotton Fiber Elongation Revealed by Sphingolipidomics and Proteomics
Yujie Liu, Ming Luo, Li Wang, Chen Liu Biomolecules . 2020 Aug 31;10(9):1258. doi: 10.3390/biom10091258.
Sphingolipids are essential biomolecules and membrane components, but their regulatory role in cotton fiber development is poorly understood. Here, we found that fumonisin B1 (FB1)-a sphingolipid synthesis inhibitor-could block fiber elongation severely. Using liquid chromatography tandem mass spectrometry (LC-MS/MS), we detected 95 sphingolipids that were altered by FB1 treatment; of these, 29 (mainly simple sphingolipids) were significantly increased, while 33 (mostly complex sphingolipids) were significantly decreased. A quantitative analysis of the global proteome, using an integrated quantitative approach with tandem mass tag (TMT) labeling and LC-MS/MS, indicated the upregulation of 633 and the downregulation of 672 proteins after FB1 treatment. Most differentially expressed proteins (DEPs) were involved in processes related to phenylpropanoid and flavonoid biosynthesis. In addition, up to 20 peroxidases (POD) were found to be upregulated, and POD activity was also increased by the inhibitor. To our knowledge, this is the first report on the effects of FB1 treatment on cotton fiber and ovule sphingolipidomics and proteomics. Our findings provide target metabolites and biological pathways for cotton fiber improvement.
2. Developmental Toxicity of Mycotoxin Fumonisin B₁ in Animal Embryogenesis: An Overview
Jyh-Cherng Ju, Chompunut Lumsangkul, Yang-Kwang Fan, Neng-Wen Lo, Hsin-I Chiang Toxins (Basel) . 2019 Feb 13;11(2):114. doi: 10.3390/toxins11020114.
A teratogenic agent or teratogen can disturb the development of an embryo or a fetus.FumonisinB₁ (FB₁), produced byFusarium verticillioidesandF. proliferatum, is among the most commonly seen mycotoxins and contaminants from stale maize and other farm products. It may cause physical or functional defects in embryos or fetuses, if the pregnant animal is exposed to mycotoxin FB₁. Due to its high similarity in chemical structure with lipid sphinganine (Sa) and sphingosine (So), the primary component of sphingolipids, FB₁ plays a role in competitively inhibiting Sa and So, which are key enzymes in de novo ceramide synthase in the sphingolipid biosynthetic pathway. Therefore, it causes growth retardation and developmental abnormalities to the embryos of hamsters, rats, mice, and chickens. Moreover, maternal FB₁ toxicity can be passed onto the embryo or fetus, leading to mortality. FB₁ also disrupts folate metabolism via the high-affinity folate transporter that can then result in folate insufficiency. The deficiencies are closely linked to incidences of neural tube defects (NTDs) in mice or humans. The purpose of this review is to understand the toxicity and mechanisms of mycotoxin FB₁ on the development of embryos or fetuses.
3. Fumonisin B1 induces poly (ADP-ribose) (PAR) polymer-mediated cell death (parthanatos) in neuroblastoma
Monika Bhardwaj, Rekha Jakhar, Souren Paul, Sun Chul Kang, Anil Kumar Chauhan Food Chem Toxicol . 2021 Aug;154:112326. doi: 10.1016/j.fct.2021.112326.
Fumonisin B1 (FB1) is a well-known mycotoxin produced by Fusarium spp. and has a wide range of dose-dependent toxic effects, including nephrotoxicity, hepatotoxicity, and neurotoxicity. This research illustrated that FB1 exerts its toxicity in the neuroblastoma cell line through a distinct cell-death pathway called parthanatos. FB1 can cause excessive DNA strand breaks, leading to poly (ADP-ribose) polymerase-1 (PARP-1) overactivation and cell death. In this study, we used 50 μM FB1-treated SH-SY5Y neuroblastoma cells to elucidate the signaling pathway of FB1-induced parthanatos. We observed that FB1-induced cell death is caspase-independent and accompanied by rapid activation of PARP-1, c-Jun N-terminal kinase activation, reactive oxygen species (ROS) generation, and intracellular calcium increase. FB1 treatment also increased endoplasmic reticulum stress due to the rapid increase of calcium ions and ROS levels. In addition, FB1 induced massive DNA damage and chromatin decondensation. We also observed that apoptosis-inducing factor nuclear translocation and PAR accumulation were associated with the necroptosis signal.
Spectrum
LC-MS/MS Spectrum - 40V, Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
