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Fumonisin
The fumonisins are a group of mycotoxins derived from ''Fusarium'' and their Liseola section. They have strong structural similarity to sphinganine, the backbone precursor of sphingolipids. More specifically, it can refer to: * Fumonisin B1 * Fumonisin B2 * Fumonisin B3 * Fumonisin B4 As the fumonisins appear to be non-genotoxic the possibility that they belong to another class of non-genotoxic carcinogens, the peroxisome proliferators, was investigated Genetic engineering is reported as a promising means of detoxifying mycotoxins. This approach may provide innovative solutions to the problem of fumonisin in corn. At least 15 different fumonisins have so far been reported and other minor metabolites have been identified, although most of them have not been shown to occur naturally. In 2015, a unique class of non-aminated fumonisins was reported on grapes infected with ''Aspergillus welwitschiae'', although their toxicities have not yet been established. Other ''Fusariu ...
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Fumonisin B1
Fumonisin B1 is the most prevalent member of a family of toxins, known as fumonisins, produced by multiple species of ''Fusarium'' Mold (fungus), molds, such as ''Fusarium verticillioides'', which occur mainly in maize (corn), wheat and other cereals. Fumonisin B1 contamination of maize has been reported worldwide at mg/kg levels. Human exposure occurs at levels of micrograms to milligrams per day and is greatest in regions where maize products are the dietary staple. Fumonisin B1 is hepatotoxic and nephrotoxic in all animal species tested. The earliest histological change to appear in either the liver or kidney of fumonisin-treated animals is increased apoptosis followed by regenerative cell proliferation. While the acute toxicity of fumonisin is low, it is the known cause of two diseases which occur in domestic animals with rapid onset: equine leukoencephalomalacia and porcine pulmonary oedema syndrome. Both of these diseases involve disturbed sphingolipid metabolism and cardiova ...
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Fumonisin B4
Fumonisin B4 (or FB4) is a fumonisin mycotoxin produced mainly by the fungi ''Fusarium proliferatum'', ''Fusarium verticillioides'' (formerly ''Fusarium moniliforme''). Recently FB4 has been detected in fungi ''Aspergillus niger'' and in several ''Tolypocladium'' species. FB4 is similar to fumonisin B2 and fumonisin B3 but it is lacking a hydroxy group located gamma- to the amino substituent while lacking two hydroxy groups compared to fumonisin B1. Fumonisin B4 was first described in 1991. Isomers Several isomers of Fumonisin B4 have been detected. A larger group is the partially hydrolysed form, denoted as PHFB4, which has been detected using HPLC- ITMS. Another significant isomer is the 3-''epi''-FB4, which has been identified using NMR, it has also been shown that this isomer occur 10-40% of the regular FB4 sample in nature. Toxicity Fumonisin B4 belongs to the class of FB analogues, which is the most significant group from toxicity perspective. Currently Fumonisin B4's t ...
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Fumonisin B3
The fumonisins are a group of mycotoxins derived from ''Fusarium'' and their Liseola section. They have strong structural similarity to sphinganine, the backbone precursor of sphingolipids. More specifically, it can refer to: * Fumonisin B1 * Fumonisin B2 * Fumonisin B3 * Fumonisin B4 As the fumonisins appear to be non-genotoxic the possibility that they belong to another class of non-genotoxic carcinogens, the peroxisome proliferators, was investigated Genetic engineering is reported as a promising means of detoxifying mycotoxins. This approach may provide innovative solutions to the problem of fumonisin in corn. At least 15 different fumonisins have so far been reported and other minor metabolites have been identified, although most of them have not been shown to occur naturally. In 2015, a unique class of non-aminated fumonisins was reported on grapes infected with ''Aspergillus welwitschiae'', although their toxicities have not yet been established. Other ''Fusarium'' ...
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Fumonisin B2
Fumonisin B2 is a fumonisin mycotoxin produced by the fungi ''Fusarium verticillioides'' (formerly ''Fusarium moniliforme'') and ''Aspergillus niger''. It is a structural analog of fumonisin B3, while it is lacking one hydroxy group compared to fumonisin B1. Fumonisin B2 is more cytotoxic than fumonisin B1. Fumonisin B2 inhibits sphingosine acyltransferase. Fumonisin B2 and other fumonisins frequently contaminate maize Maize (; ''Zea mays''), also known as corn in North American English, is a tall stout grass that produces cereal grain. It was domesticated by indigenous peoples in southern Mexico about 9,000 years ago from wild teosinte. Native American ... and other crops, while recently it has been shown using LC–MS/MS that FB2 can contaminate coffee beans as well. References Mycotoxins Enzyme inhibitors {{biochem-stub ...
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Mycotoxin
A mycotoxin (from the Greek μύκης , "fungus" and τοξικός , "poisonous") is a toxic secondary metabolite produced by fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually reserved for the toxic chemical products produced by fungi that readily colonize crops. Examples of mycotoxins causing human and animal illness include aflatoxin, citrinin, fumonisins, ochratoxin A, patulin, trichothecenes, zearalenone, and ergot alkaloids such as ergotamine. One mold species may produce many different mycotoxins, and several species may produce the same mycotoxin. Production Most fungi are aerobic (use oxygen) and are found almost everywhere in extremely small quantities due to the diminutive size of their spores. They consume organic matter wherever humidity and temperature are sufficient. Where conditions are right, fungi proliferate into colonies and mycotoxin levels become high. The reason for the production of m ...
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Fusarium
''Fusarium'' (; ) is a large genus of filamentous fungi, part of a group often referred to as hyphomycetes, widely distributed in soil and associated with plants. Most species are harmless saprobes, and are relatively abundant members of the soil microbial community. Some species produce mycotoxins in cereal crops that can affect human and animal health if they enter the food chain. The main toxins produced by these ''Fusarium'' species are fumonisins and trichothecenes. Despite most species apparently being harmless (some existing on the skin as commensal members of the skin flora), some ''Fusarium'' species and subspecific groups are among the most important fungal pathogens of plants and animals. The name of ''Fusarium'' comes from Latin ''fusus'', meaning a spindle. Taxonomy The taxonomy of the genus is complex. A number of different schemes have been used, and up to 1,000 species have been identified at times, with approaches varying between wide and narrow concep ...
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Sphingolipids
Sphingolipids are a class of lipids containing a backbone of sphingoid bases, which are a set of aliphatic amino alcohols that includes sphingosine. They were discovered in brain extracts in the 1870s and were named after the mythological sphinx because of their enigmatic nature. These compounds play important roles in signal transduction and cell recognition. Sphingolipidoses, or disorders of sphingolipid metabolism, have particular impact on neural tissue. A sphingolipid with a terminal hydroxyl group is a ceramide. Other common groups bonded to the terminal oxygen atom include phosphocholine, yielding a sphingomyelin, and various sugar monomers or dimers, yielding cerebrosides and globosides, respectively. Cerebrosides and globosides are collectively known as glycosphingolipids. Structure The long-chain bases, sometimes simply known as sphingoid bases, are the first non-transient products of '' de novo'' sphingolipid synthesis in both yeast and mammals. These compoun ...
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Sphinganine
Safingol is a lyso-sphingolipid protein kinase inhibitor. It has the molecular formula C18H39NO2 and is a colorless solid. Medicinally, safingol has demonstrated promising anticancer potential as a modulator of multi-drug resistance and as an inducer of necrosis. The administration of safingol alone has not been shown to exert a significant effect on tumor cell growth. However, preclinical and clinical studies have shown that combining safingol with conventional chemotherapy agents such as fenretinide, vinblastine, irinotecan and mitomycin C can dramatically potentiate their antitumor effects. In phase I clinical trials, it was found to be safe to co-administer with cisplatin, but caused reversible dose-dependent hepatotoxicity. Mechanism The underlying mechanism by which safingol induces cell death is poorly understood. It is believed to exert a variety of inhibitory effects, resulting in a series of cascades that result in accidental necrotic cell death brought about by r ...
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Trichothecene
Trichothecenes constitute a large group of chemically related mycotoxins. They are produced by Fungus, fungi of the genera ''Fusarium'', ''Myrothecium'', ''Trichoderma'', ''Podostroma'', ''Trichothecium'', ''Cephalosporium'', ', ''Stachybotrys'' (most in Hypocreales) and possibly others. Chemically, trichothecenes are a class of sesquiterpenes. All trichothecenes share the Cyclic compound, cyclic sesquiterpene structure but differ in the type of functional group attached to the carbon backbone. They are produced on many different grains such as wheat, Oat, oats, or maize by various ''Fusarium'' species including ''Gibberella zeae, F. graminearum'', ''Fusarium sporotrichioides, F. sporotrichioides'', ''F. poae,'' and ''Fusarium equiseti, F. equiseti''. Some moulds that produce trichothecene mycotoxins, such as ''Stachybotrys chartarum'', can grow in damp indoor environments. It has been found that macrocyclic trichothecenes produced by ''Stachybotrys chartarum, S. chartarum'' can ...
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Zearalenone
Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some ''Fusarium'' and '' Gibberella'' species. Specifically, the '' Gibberella zeae'', the fungal species where zearalenone was initially detected, in its asexual/ anamorph stage is known as ''Fusarium graminearum.'' Several ''Fusarium'' species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by '' Fusarium graminearum'', '' Fusarium culmorum'', '' Fusarium cerealis'', '' Fusarium equiseti'', '' Fusarium verticillioides'', and '' Fusarium incarnatum''. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination ...
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