Terphenylquinone
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Terphenylquinone
Terphenylquinones are fungal dyes from the group of phenyl-substituted ''p''-benzoquinones having the following general structure. General chemical structure of terphenylquinones Also derivatives with a central ''o''-benzoquinone structure are known. Biosynthesis The biosynthesis of terphenylquinones is carried out by dimerization of substituted oxophenylpropanoic acids (phenylpyruvic acids). Occurrence Terphenylquinones are typical constituents of the Boletales. Examples :{, class="wikitable sortable" !Name, , Structure, , CAS-Nr., , Origin , - , Polyporic acid, , , , 548-59-4, , Polypore of the order Aphyllophorales, lichen ''Yarrumia coronata'' , - , Atromentin, , , , 519-67-5, , ''Paxillus atrotomentosus'' (Basidiomycota) , - , Aurantiacin, , , , 548-32-3, , ''Hydnellum aurantiacum'' (Basidiomycota) , - , Phlebiarubron, , , , 7204-23-1, , Cultures of ''Phlebia strigosozonata'' and ''Punctularia atropurpurascens'' (Basidiomycota) , - , Spiromentin B, , , , 121254-5 ...
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Thelephoric Acid
Thelephoric acid is a terphenylquinone pigment that is found in several fungi, such as '' Omphalotus subilludens'' and ''Polyozellus multiplex''. Thelephoric acid has been shown to inhibit prolyl endopeptidase, an enzyme that has a role in processing proteins (specifically, amyloid precursor protein) in Alzheimer's disease. Chemicals that inhibit prolyl endopeptidase have attracted research interest due to their potential therapeutic effects. It is derived from atromentin Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by laboratory synthesis. Chemically, it is a polyphenol and a benzoquinone. Occurrences Atromentin has ..., and its precursor can be from cyclovariegatin. Fragmentation patterns have suggested that polymers of thelephoric acid exists. References {{Reflist, refs= {{Cite journal , vauthors=Hwang JS, Song KS, Kim WG, Lee TH, Koshino H, Yoo ID , title=Polyozellin, a new ...
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Polyporic Acid
Polyporic acid is a para-terphenyl benzoquinone compound first identified by German chemist Stahlschmidt from a mycelial culture of the fungus species ''Hapalopilus nidulans'' in 1877. This chemical, present at 20–40% of the fresh weight of the fruit bodies, inhibits the enzyme dihydroorotate dehydrogenase. It is found in other mushrooms, but in much lower amounts. In animal studies, consumption of polyporic acid caused reduced locomotor activity, depressed visual placing response, hepatorenal failure, metabolic acidosis, hypokalaemia, and hypocalcaemia. Because these effects are similar to those observed in individuals poisoned by ''H. nidulans'', polyporic acid is thought to be the primary toxin in ''H. nidulans''. Polyporic acid has some antifungal and antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely use ...
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Phenyl Group
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with C6H5− and is represented by the symbol Ph or, archaically, Φ. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane (Ph3 ...
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Atromentin V2
Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by organic synthesis, laboratory synthesis. Chemically, it is a polyphenol and a benzoquinone. Occurrences Atromentin has been found in cultures of ''Clitocybe subilludens'' and in extracts of ''Hydnellum peckii''. The first enzymes in its biosynthesis have been characterized in ''Tapinella panuoides''. One of those is called atromentin synthetase. Biological activities A number of potential biological activities of atromentin have been studied ''in vitro''. Atromentin possesses ''in vitro'' antibacterial activity, inhibiting the enzyme enoyl-acyl carrier protein reductase (essential for the Fatty acid metabolism#Synthesis, biosynthesis of fatty acids) in the bacteria ''Streptococcus pneumoniae''. Atromentin has been shown to be a smooth muscle stimulant. It also induces apoptosis in isolated human leukemia U937 cells. It is also an a ...
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Basidiomycota
Basidiomycota () is one of two large divisions that, together with the Ascomycota, constitute the subkingdom Dikarya (often referred to as the "higher fungi") within the kingdom Fungi. Members are known as basidiomycetes. More specifically, Basidiomycota includes these groups: mushrooms, puffballs, stinkhorns, bracket fungi, other polypores, jelly fungi, boletes, chanterelles, earth stars, smuts, bunts, rusts, mirror yeasts, and ''Cryptococcus'', the human pathogenic yeast. Basidiomycota are filamentous fungi composed of hyphae (except for basidiomycota-yeast) and reproduce sexually via the formation of specialized club-shaped end cells called basidia that normally bear external meiospores (usually four). These specialized spores are called basidiospores. However, some Basidiomycota are obligate asexual reproducers. Basidiomycota that reproduce asexually (discussed below) can typically be recognized as members of this division by gross similarity to others, by the form ...
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Aphyllophorales
The Aphyllophorales is an obsolete order of fungi in the Basidiomycota. The order is entirely artificial, bringing together a miscellany of species now grouped among the clavarioid fungi, corticioid fungi, cyphelloid fungi, hydnoid fungi, and poroid fungi.Kirk PM ''et al.'' (2008). ''Dictionary of the Fungi'' (10th Ed.). Wallingford: CABI. History The order Aphyllophorales was first proposed in 1922 by Carleton Rea.Rea C. (1922). ''British Basidiomycetaceae. A handbook of the larger British fungi''. Cambridge: Cambridge University Press. ''A-phyllo-phora'' means 'not bearing gills', distinguishing the Aphyllophorales from the gilled agarics (mushrooms and toadstools) that Rea placed in the Agaricales. The Gasteromycetales and Heterobasidiomycetes were also excluded. As originally conceived, the Aphyllophorales contained the families Clavariaceae, Cyphellaceae, Fistulinaceae, Hydnaceae, Meruliaceae, Polyporaceae, Polystictaceae, and Thelephoraceae. Most of these families ar ...
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Atromentin
Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by laboratory synthesis. Chemically, it is a polyphenol and a benzoquinone. Occurrences Atromentin has been found in cultures of ''Clitocybe subilludens'' and in extracts of ''Hydnellum peckii''. The first enzymes in its biosynthesis have been characterized in ''Tapinella panuoides''. One of those is called atromentin synthetase. Biological activities A number of potential biological activities of atromentin have been studied ''in vitro''. Atromentin possesses ''in vitro'' antibacterial activity, inhibiting the enzyme enoyl-acyl carrier protein reductase (essential for the biosynthesis of fatty acids) in the bacteria ''Streptococcus pneumoniae''. Atromentin has been shown to be a smooth muscle stimulant. It also induces apoptosis in isolated human leukemia U937 cells. It is also an anticoagulant. Genetic and enzymatic basis of atrom ...
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P-Benzoquinone
1,4-Benzoquinone, commonly known as ''para''-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound. Preparation 1,4-Benzoquinone is prepared industrially by oxidation of hydroquinone, which can be obtained by several routes. One route involves oxidation of diisopropylbenzene and the Hock rearrangement. The net reaction can be represented as follows: :C6H4(CHMe2)2 + 3 O ...
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Boletales
The Boletales are an order of Agaricomycetes containing over 1300 species with a diverse array of fruiting body types. The boletes are the best known members of this group, and until recently, the Boletales were thought to only contain boletes. The Boletales are now known to contain distinct groups of agarics, puffballs, and other fruiting-body types. Taxonomy The order Boletales originally was created to describe boletes, but based on micromorphological and molecular phylogenetic characteristics, a large number of nonbolete species have recently been reclassified to belong to this group, as well. The order also includes some gilled mushrooms, in the families Gomphidiaceae, Serpulaceae, Tapinellaceae, Hygrophoropsidaceae, and Paxillaceae, which often have the same flesh texture as the boletes, spore-bearing tissue which is also easily separable from the cap, and similar microscopic characteristics of spores and cystidia. Taxonomic studies using secondary metabolites and later ...
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