Aristolochene
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Aristolochene
Aristolochene is a bicyclic sesquiterpene produced by certain fungi including the cheese mold '' Penicillium roqueforti''. It is biosynthesized from farnesyl pyrophosphate by aristolochene synthase and is the parent hydrocarbon of a large variety of fungal toxins.Terpene Biosynthesis
, Chem 549, College of Pharmacy, University of Arizona The substance was first isolated from '' Penicillium roqueforti'', a fungus used to make blue cheeses like , ,
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Aristolochene Synthase
The enzyme aristolochene synthase (EC 4.2.3.9) catalyzes the chemical reaction : This enzyme belongs to the family of lyases, specifically those carbon-oxygen lyases acting on phosphates. The systematic name of this enzyme class is (2''E'',6''E'')-farnesyl-diphosphate diphosphate-lyase (cyclizing, aristolochene-forming). Other names in common use include sesquiterpene cyclase, ''trans'',''trans''-farnesyl diphosphate aristolochene-lyase, ''trans'',''trans''-farnesyl-diphosphate diphosphate-lyase (cyclizing and aristolochene-forming). This enzyme participates in terpenoid biosynthesis. This protein may use the morpheein model of allosteric regulation. Structural studies As of late 2007, two structures A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ... have been solved for this ...
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Bicyclic Molecule
In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all of the ring atoms are carbons), or heterocyclic (the rings' atoms consist of at least two elements), like DABCO. Moreover, the two rings can both be aliphatic (''e.g.'' decalin and norbornane), or can be aromatic (''e.g.'' naphthalene), or a combination of aliphatic and aromatic (''e.g.'' tetralin). Three modes of ring junction are possible for a bicyclic compound: * In spirocyclic compounds, the two rings share only one single atom, the spiro atom, which is usually a quaternary carbon. An example of a spirocyclic compound is the photochromic switch spiropyran. * In fused/condensed bicyclic compounds, two rings share two adjacent atoms. In other words, the rings share one covalent bond, ''i.e.'' the so-called bridgehead atoms are direc ...
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Danish Blue
Danablu, often marketed under the trademark Danish Blue Cheese within North America, is a strong, blue-veined cheese. This semi-soft creamery cheese is typically drum- or block-shaped and has a yellowish, slightly moist, edible rind. Made from full fat cow's milk and homogenized cream, it has a fat content of 25–30% (50–60% in dry matter) and is aged for eight to twelve weeks. Before ageing, copper wires or rods are used to pierce the formed curds to distribute the mould ('' Penicillium roqueforti'') evenly through the cheese. The holes can still be seen when the finished wheel is cut open. Danablu was invented early in the 20th century by a Danish cheese maker named Marius Boel with the intention of emulating a Roquefort-style cheese. Danablu has a milder flavor characterised by a sharp, salty taste, and is often served crumbled on salads or as a dessert cheese with fruit. In Denmark, it is often served on bread or savory biscuits. Danablu, Danbo and Esrom are the only ...
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Patulin
Patulin is an organic compound classified as a polyketide. 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.http://www.sigmaaldrich.com/catalog/product/sigma/p1639?lang=en®ion=US 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 quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. Its presence is highly regulated. Biosynthesis, synthesis, and reactivity The immediate precursor is 6-methylsalicylic acid. Isoepoxydon dehydrogenase (IDH) is an important enzyme in the multi-step biosynthesis of patulin. Its gene is present in other fu ...
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Aflatoxin
Aflatoxins are various poisonous carcinogens and mutagens that are produced by certain molds, particularly ''Aspergillus'' species. The fungi grow in soil, decaying vegetation and various staple foodstuffs and commodities such as hay, sweetcorn, wheat, millet, sorghum, cassava, rice, chili peppers, cottonseed, peanuts, tree nuts, sesame seeds, sunflower seeds, and various spices. In short, the relevant fungi grow on almost any crop or food. When such contaminated food is processed or consumed, the aflatoxins enter the general food supply. They have been found in both pet and human foods, as well as in feedstocks for agricultural animals. Animals fed contaminated food can pass aflatoxin transformation products into eggs, milk products, and meat. For example, contaminated poultry feed is the suspected source of aflatoxin-contaminated chicken meat and eggs in Pakistan. Children are particularly affected by aflatoxin exposure, which is associated with stunted growth, delayed de ...
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Roquefortine C
Roquefortine C is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from the genus ''Penicillium''. It was first isolated from a strain of ''Penicillium roqueforti'', a species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses, Roquefort, Danish Blue, Stilton cheese, Stilton and Gorgonzola. Roquefortine C is a cyclodipeptide mycotoxin derived from the diketopiperazine cyclo(Trp-dehydro-His) and is a relatively common fungal metabolite produced by a number of ''Penicillium'' species. It is also considered one of the most important fungal contaminants of carbonated beverages, beer, wine, meats, cheese and bread. At high doses roquefortine C is classified as a toxic compound. Although it is a potent neurotoxin at high doses, at low concentrations of 0.05 to 1.47 mg/kg that occur in domestic cheeses, it was found to be "safe for the consumer". ...
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Mycotoxicosis
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 producti ...
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Gorgonzola
Gorgonzola (; ) is a veined blue cheese, originally from Italy, made from unskimmed cow's milk. It can be buttery or firm, crumbly and quite salty, with a "bite" from its blue veining. History Historically, gorgonzola has been produced for centuries in Gorgonzola, Milan, acquiring its greenish-blue marbling in the 11th century. However, the town's claim of geographical origin is disputed by other localities. Production Today, gorgonzola is produced worldwide, with high concentrations of production located in the northern Italian regions of Piedmont and Lombardy, as well as production in the United States. Whole cow's milk is used, to which starter bacteria are added with spores of the mould ''Penicillium glaucum''. The whey is then removed during curdling, and the result is aged at low temperatures. During the ageing process, metal rods are quickly inserted and removed, creating air channels that allow the mould spores to grow into hyphae and cause the cheese's charact ...
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Stilton Cheese
Stilton is an English cheese, produced in two varieties: Blue, which has '' Penicillium roqueforti'' added to generate a characteristic smell and taste, and White, which does not. Both have been granted the status of a protected designation of origin (PDO) by the European Commission, requiring that only such cheese produced in the three counties of Derbyshire, Leicestershire and Nottinghamshire may be called Stilton. The cheese takes its name from the village of Stilton, now in Cambridgeshire, where it has long been sold. History Frances Pawlett (or Paulet), a cheese maker of Wymondham, Leicestershire, has traditionally been credited with setting up the modern Stilton cheese shape and style in the 1720s, but others have also been named. Early 19th-century research published by William Marshall provides logic and oral history to indicate a continuum between the locally produced cheese of Stilton, and the later development of a high turnover commercial industry importing cheese pr ...
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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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Roquefort
Roquefort is a sheep milk cheese from Southern France, and is one of the world's best known blue cheeses. Though similar cheeses are produced elsewhere, EU law dictates that only those cheeses aged in the natural Combalou caves of Roquefort-sur-Soulzon may bear the name Roquefort, as it is a recognised geographical indication, or has a protected designation of origin. The cheese is white, tangy, crumbly and slightly moist, with distinctive veins of blue mold. It has a characteristic fragrance and flavor with a notable taste of butyric acid; the blue veins provide a sharp tang. It has no rind; the exterior is edible and slightly salty. A typical wheel of Roquefort weighs between , and is about thick. Each kilogram of finished cheese requires about 4.5 liters of milk to produce. In France, Roquefort is often called the "King of Cheeses" or the "Cheese of Kings", although those names are also used for other cheeses. History Legend has it that the cheese was discovered when a y ...
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Sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. Sesquiterpenes are found naturally in plants and insects, as semiochemicals, e.g. defensive agents or pheromones. Biosynthesis and examples The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate (FPP), which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Cyclic sesquiterpenes are more common than cyclic monoterpenes because of the increased chain length and additional double bond in the sesquiterpene precursors. In addition to common six-membered ring systems such as the ones found in zingiberene and bisacurone, cyclization of one end of the chain to the other end can l ...
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