Xerocomic Acid
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Xerocomic Acid
Xerocomic acid is a red-orange pigment found in fungi of the order ''Boletales'' (and is named after the genus '' Xerocomus''). It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from ''Serpula lacrymans''. It is soluble in methanol. An oxidase acting on xerocomic acid is responsible for the "bluing" reaction seen in mushrooms. Condensation of two units of xerocomic acid form the pigments sclerocitrin, badione A, and also norbadione A, which are found in the mushroom ''Scleroderma citrinum ''Scleroderma citrinum'', commonly known as the common earthball, pigskin poison puffball, or common earth ball, is the most common species of earthball in the UK and occurs widely in woods, heathland and in short grass from autumn to winter. '' ...'' Pers. Variants include isoxerocomic acid and ''O''-methylxerocomic acid. References {{Reflist, refs= {{cite book, last1=Gill, first1=M., last2=Steglich, first2= W., yea ...
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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 la ...
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Xerocomus
''Xerocomus'' is a genus of poroid fungi related to ''Boletus''. Many mycologists did not originally recognize the distinction between the two genera and placed ''Xerocomus'' taxa in genus ''Boletus''. However, several molecular phylogenetic studies have demonstrated that ''Xerocomus'' is a heterogeneous genus of polyphyletic origin, which has resulted in further division of ''Xerocomus'' into '' Xerocomellus'' and '' Hemileccinum''. The members of the genus ''Xerocomellus'' are more closely related to ''Boletus'' than true ''Xerocomus'' is, which is relatively distantly related to ''Boletus'' and more closely related to ''Phylloporus''. Other former ''Xerocomus'' species have since been moved to ''Aureoboletus'', '' Imleria'', '' Hortiboletus'' and '' Rheubarbariboletus''. Ladurner and Simonini published a monograph on ''Xerocomus'' in 2003, but this predated the taxonomical revisions based on phylogenetic inferences. In 2008, Hills included 18 species found in Britain, not inc ...
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Variegatic Acid
Variegatic acid (3,3',4,4'-tetrahydroxypulvinic acid) is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form (due to the production of a second lactone ring) is variegatorubin, similar to xerocomorubin. It was first isolated from '' Suillus variegatus''. It has strong antioxidant properties, and a nonspecific inhibitory effect on cytochrome P450 enzymes. A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction. It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg. However, at similar concen ...
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Atromentic Acid
Atromentic acid is a red-organge pigment found in fungi within the Boletales group. It is the precursor to variegatic acid and xerocomic acid, and is preceded by atromentin. As an example, it is isolated from ''Serpula lacrymans ''Serpula lacrymans'' is one of the fungi that cause damage to timber referred to as dry rot. It is a basidiomycete in the order Boletales. The ''Serpula lacrymans'' has the ability to rapidly colonise sites through unique and highly specialise ...''. It is soluble in methanol. Variants include homoatromentic acid. This pigment has been studied and elucidated by Wolfgang Steglich and colleagues over decades. When atromentin is oxidised with hydrogen peroxide a yellow product is produced. A sodium hydroxide solution is also yellow, but when this is neutralized with acid the red atromentic acid crystallises. Concentrated potassium hydroxide breaks up the compound to p-hydroxyphenylacetic acid and oxalic acid. References {{Reflist, refs= Gill, M., a ...
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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 atro ...
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Serpula Lacrymans
''Serpula lacrymans'' is one of the fungi that cause damage to timber referred to as dry rot. It is a basidiomycete in the order Boletales. The ''Serpula lacrymans'' has the ability to rapidly colonise sites through unique and highly specialised mycelium which also leads to greater degradation rates of wood cellulose. Taxonomy The species was first described under the name ''Boletus lacrymans'' by Franz Xavier von Wulfen in 1781. It was transferred to the genus ''Serpula'' by Petter Karsten in 1884. The specific epithet is derived from the Latin words ''serpula'' for "creeping" (as in a serpent) and ''lacrymans'', meaning "making tears". Environment ''Serpula lacrymans'' has a preference for temperatures of but can survive any temperature from . It is not clear how much light is needed to promote ''Serpula lacrymans'' growth. In terms of aeration ''Serpula lacrymans'' often grows near ventilation shafts which shows a preference for concentrated oxygen. A moisture content of ...
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Methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide. Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals. Occurrence Small amounts of methanol are present in normal, healthy ...
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Norbadione A
Norbadione A is a pigment found in the bay bolete mushroom (''Boletus badius''). A polyphenol, norbadione A is related to a family of mushroom pigments known as pulvinic acids. The molecule has also been reported as a potassium salt from the mushrooms '' Pisolithus tinctorius'' (horse dung fungus) and ''Chalciporus piperatus''. Properties Norbadione A has seven acid-base functional groups, among which are two enolic and two carboxylic acid moieties. These functional groups confer water-solubility to the molecule. It selectively complexes cesium cations (Cs+), with an efficiency comparable to that of some calixarenes or crown ethers. It has been investigated for its ability to provide a protective effect against the damaging effects of ionizing radiation, an effect attributed to its ability to protect DNA-related targets from irradiation. Tests with cell cultures and mice show that although it has some protective effect, it is toxic to cells in higher doses. A diverse arr ...
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Scleroderma Citrinum
''Scleroderma citrinum'', commonly known as the common earthball, pigskin poison puffball, or common earth ball, is the most common species of earthball in the UK and occurs widely in woods, heathland and in short grass from autumn to winter. ''Scleroderma citrinum'' has two synonyms, ''Scleroderma aurantium'' (Vaill.) and ''Scleroderma vulgare'' Horn. Earthballs are superficially similar to, and considered look-alikes of, the edible puffball (particularly '' Apioperdon pyriforme''), but whereas the puffball has a single opening on top through which the spores are dispersed, the earthball just breaks up to release the spores. Moreover, ''Scleroderma citrinum'' has much firmer flesh and a dark gleba (interior) much earlier in development than puffballs. ''Scleroderma citrinum'' has no stem but is attached to the soil by mycelial cords. The peridium, or outer wall, is thick and firm, usually ochre yellow externally with irregular warts. The earthball may be parasitized by '' Pseu ...
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Isoxerocomic Acid
Isoxerocomic acid is a red-orange pigment found in ''Boletales''. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from ''Serpula lacrymans''. It is soluble in methanol. It is the isomer of xerocomic acid Xerocomic acid is a red-orange pigment found in fungi of the order ''Boletales'' (and is named after the genus '' Xerocomus''). It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolate ... and precursor to xerocomorubin. References {{Reflist, refs= Gill, M., and Steglich, W. (1987) Pigments of fungi (Macromycetes). Prog Chem Org Nat Prod 51: 1–317. Catechols Furanones 3-Hydroxypropenals ...
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