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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 The trichothecene (T-2) mycotoxins are a group of over 40 compounds produced by fungi of the genus ''Fusarium'', a common grain mold. The estrogenic metabolite, 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 ..., is also referred to as F-2 toxin. 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 ...
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Fumonisin B1
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 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 cardiovascular dysfuncti ...
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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 has been first published 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 ...
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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'' subsp. ''mays'', from es, maíz after tnq, mahiz), also known as corn (North American and Australian English), is a cereal grain first domesticated by indigenous peoples in southern Mexico about 10,000 years ago. Th ... 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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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 The trichothecene (T-2) mycotoxins are a group of over 40 compounds produced by fungi of the genus ''Fusarium'', a common grain mold. The estrogenic metabolite, 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, ..., is also referred to as F-2 toxin. 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 myc ...
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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 with the ...
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Mycotoxin
A mycotoxin (from the Greek μύκης , "fungus" and τοξίνη , "toxin") is a toxic secondary metabolite produced by organisms of kingdom 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 diminute 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 product ...
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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 concepts of speci ...
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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.Schwartz, G. K., Haimovitz-Friedman, A., Dhupar, S. K., Ehleiter, D., Maslak, P., Lai, L., ... & Albino, A. P. (1995). Potentiation of apoptosis by treatment with the protein kinase C-specific inhibitor safingol in mitomycin C-treated gastric cancer cells. Journal of the National Cancer Institute, 87(18), 1394-1399. 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. Currently in Phase I clinical trials, it is believed to be safe to co-admini ...
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Sphingolipids
Sphingolipids are a class of lipids containing a backbone of sphingoid bases, 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 an R group consisting of a hydrogen atom only is a ceramide. Other common R groups 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 compounds, specifically known as phytosp ...
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Trichothecene
The trichothecenes are a large family of chemically related mycotoxins. They are produced by various species of ''Fusarium'', ''Myrothecium'', ''Trichoderma''/''Podostroma'', '' Trichothecium'', ''Cephalosporium'', '' Verticimonosporium'', and '' Stachybotrys''. Chemically, trichothecenes are a class of sesquiterpenes. The determining structural features causing the biological activity of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus, and the structure and position of the side-chain. They are produced on many different grains such wheat, oats or maize by various ''Fusarium'' species including ''F. graminearum'', ''F. sporotrichioides'', ''F. poae'' and ''F. equiseti''. Some molds that produce trichothecene mycotoxins, for example '' Stachybotrys chartarum'', can grow in damp indoor environments. It has been found that macrocyclic trichothecenes produced by ''S. chartarum'' can become airborn ...
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