Mycotoxins

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.

harmful effects from ingestion of toxic substances present in a mushroom

thumb|Amanita muscaria

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time d

Muscimol, also known as agarin, pantherine, or pyroibotenic acid, is a GABAA receptor agonist with sedative and hallucinogenic effects and the principal psychoactive constituent of Amanita mushrooms such as Amanita muscaria (fly agaric) and Amanita pantherina (panther cap). It is a 3-hydroxyisoxazole alkaloid and is closely related structurally to the neurotransmitter γ-aminobutyric acid (GABA). The compound is widely used as a ligand and agonist of the GABAA receptor in scientific research. Muscimol is typically taken orally, but may also be smoked. Peak effects occur after 1 to 3hours orally

Monomethylhydrazine (MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula . It is used as a rocket propellant in bipropellant rocket engines because it is hypergolic with various oxidizers such as nitrogen tetroxide () and nitric acid (). As a propellant, it is described in specification MIL-PRF-27404.

Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, Penicillium patulum. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened. It is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, the amount of patulin in apple products is generally viewed as a measure of the quali

Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum (Gibberella zeae) and F. culmorum, both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or fusarium ear blight in corn. The incidence of fusarium head blight is strongly associated with moisture at the time of flowering (anthesis),

Ochratoxins are a group of mycotoxins produced by some Aspergillus species (mainly A. ochraceus and A. carbonarius, but also by 33% of A. niger industrial strains) and some Penicillium species, especially P. verrucosum. Ochratoxin A is the most prevalent and relevant fungal toxin of this group, while ochratoxins B and C are of lesser importance.

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

Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminates long-stored food and it can cause a variety of toxic effects, including kidney, liver and cell damage. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products.

chemical compound

chemical compound

Muscazone is a toxic chemical compound. It is an amino acid found in European fly agaric mushrooms.

Gyromitrin is a toxin and carcinogen present in several members of the fungal genus Gyromitra, like G. esculenta. Its formula is . It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine . Monomethylhydrazine acts on the central nervous system and interferes with the normal use and function of vitamin B6. Poisoning results in nausea, stomach cramps, and diarrhea, while severe poisoning can result in convulsions, jaundice, or even coma or death. Exposure to monomethylhydrazine has been shown to be carcinogenic in small mammals.

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of th

Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genus Coprinopsis, specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome". It inhibits the enzyme aldehyde dehydrogenase, which is involved in the metabolism of alcohol. This inhibition leads to a buildup of acetaldehyde, causing an alcohol flush reaction. Because of this, the mushroom is commonly referred to as '''Tippler's Bane.'''

chemical compound

Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.

chemical compound

Zeranol (, , ) (brand names Frideron, Ralabol, Ralgro, Ralone, Zerano; developmental code names MK-188, P-1496), or zearanol, also known as α-zearalanol or simply zearalanol, is a synthetic nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in fungi in the Fusarium genus and is used mainly as an anabolic agent in veterinary medicine.

chemical compound

Beauvericin is a depsipeptide with antibiotic and insecticidal effects belonging to the enniatin family. It was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species; it may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals.

Alternariol (commonly abbreviated as AOH) is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals and fruits. Alternariol exhibits antifungal and phytotoxic activity. It is reported to inhibit cholinesterase enzymes. It is also a mycoestrogen.

thumb|right|400px|The chemical structure of fumonisin B1. Fumonisin refers to any one of a class of related chemical structures, the fumonisins, that constitute a group of fungal mycotoxins originally identified with genus Fusarium, a mycotoxin known for its contamination of infested corn seed (as well as other plants and foodstuffs), the infecting species, in particular, being within ''Fusarium's'' Liseola section. As shown in the example in the figure (of fumonisin B1), members of the family are composed of a central "chai[n] of about 20 carbons", and bear an "acidic ester, acetylamino and s

Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus. It is an α-aminoacid and a derivative of phenylhydrazine.

chemical compound found in a biological pathway

Aristolochene is a bicyclic sesquiterpene produced by certain fungi, most notably the cheese mold Penicillium roqueforti. It is biosynthesized from farnesyl pyrophosphate by the enzyme aristolochene synthase and serves as the parent hydrocarbon for a variety of fungal toxins.

chemical compound

chemical compound

chemical compound

Nivalenol (NIV) is a mycotoxin of the trichothecene group. In nature it is mainly found in fungi of the Fusarium species. The Fusarium species belongs to the most prevalent mycotoxin producing fungi in the temperate regions of the northern hemisphere, therefore making them a considerable risk for the food crop production industry.

Monocerin is a dihydroisocoumarin and a polyketide metabolite that originates from various fungal species. It has been shown to display antifungal, plant pathogenic, and insecticidal characteristics. Monocerin has been isolated from Dreschlera monoceras, D. ravenelii, Exserohilum turcicum, and Fusarium larvarum.

chemical compound

Asperlicin is a mycotoxin, derived from the fungus Aspergillus alliaceus. It acts as a selective antagonist for the cholecystokinin receptor CCKA, and has been used as a lead compound for the development of a number of novel CCKA antagonists with potential clinical applications. He et al. 1998 present a synthesis from aryl iodide and vinyl iodide.

Slaframine is an bicyclic alkaloid mycotoxin that causes salivation (slobbers) in most animals. It is usually produced by the fungus Rhizoctonia leguminicola which is a common fungal pathogen of red clover (Trifolium pratense) that causes black patch disease in the plant. Slaframine has the molecular formula C10H18N2O2. Wet and humid weather are the favorable environmental condition for the growth of the fungus and production of slaframine. Legume hays contaminated with slaframine cause slobber syndrome and various animals are sensitive to its effects.

Cytochalasins are fungal metabolites that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result of the inhibition of actin polymerization, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and even cause cells to undergo apoptosis. Cytochalasins have the ability to permeate cell membranes, prevent cellular translocation and cause cells to enucleate. Cytochalasins can also have an effect on other aspects of biological processes unrelated to actin polymerization. For example, cytochalasin A and

chemical compound

chemical compound

chemical compound

Moniliformin is the organic compound with the formula (M+ = K+ or Na+). Both the sodium and potassium salts are generally hydrated, e.g. . In terms of its structure, it is the alkali metal salt of the conjugate base of 3-hydroxy-1,2-cyclobutenedione (the enolate of 1,2,3-cyclobutanetrione), a planar molecule related to squaric acid. It is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.

chemical compound

Taleranol (INN, USAN) (developmental code name P-1560), or teranol, also known as β-zearalanol, is a synthetic, nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in Fusarium spp which was never marketed. It is the β epimer of zeranol (α-zearalanol) and is a major metabolite of zeranol but with less biological activity.

MT81 is a mycotoxin with antibiotic activity.

Luteoskyrin is a carcinogenic mycotoxin with the molecular formula which is produced by the mold Penicillium islandicum. Luteoskyrin has strong cytotoxic effects. Luteoskyrin can cause the yellow rice disease.

class of chemical compounds

Aeruginascin, also known as '4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT'), is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens, Pholiotina cyanopus, and Psilocybe cubensis. It was discovered by Jochen Gartz.

Zearalanone (ZAN) is a mycoestrogen that is a derivative of zearalenone (ZEN). Zearalanone can be extracted from foodstuffs along with aflatoxins in the same time by a specific immunoaffinity column.