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Atromentin Synthetase
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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Agaricomycetes
The Agaricomycetes are a class of fungi in the division Basidiomycota. The taxon is roughly identical to that defined for the Homobasidiomycetes (alternatively called holobasidiomycetes) by Hibbett & Thorn, with the inclusion of Auriculariales and Sebacinales. It includes not only mushroom-forming fungi, but also most species placed in the deprecated taxa Gasteromycetes and Homobasidiomycetes. Within the subdivision Agaricomycotina, which already excludes the smut and rust fungi, the Agaricomycetes can be further defined by the exclusion of the classes Tremellomycetes and Dacrymycetes, which are generally considered to be jelly fungi. However, a few former "jelly fungi", such as ''Auricularia'', are classified in the Agaricomycetes. According to a 2008 estimate, Agaricomycetes include 17 orders, 100 families, 1147 genera, and about 21000 species. Modern molecular phylogenetic analyses have been since used to help define several new orders in the Agaricomycetes: Amylocorticiales ...
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Apoptosis
Apoptosis (from grc, ἀπόπτωσις, apóptōsis, 'falling off') is a form of programmed cell death that occurs in multicellular organisms. Biochemical events lead to characteristic cell changes (morphology) and death. These changes include blebbing, cell shrinkage, nuclear fragmentation, chromatin condensation, DNA fragmentation, and mRNA decay. The average adult human loses between 50 and 70 billion cells each day due to apoptosis. For an average human child between eight and fourteen years old, approximately twenty to thirty billion cells die per day. In contrast to necrosis, which is a form of traumatic cell death that results from acute cellular injury, apoptosis is a highly regulated and controlled process that confers advantages during an organism's life cycle. For example, the separation of fingers and toes in a developing human embryo occurs because cells between the digits undergo apoptosis. Unlike necrosis, apoptosis produces cell fragments called apoptotic ...
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Xerocomorubin
Xerocomorubin is a pigment from the fungus order Boletales. It is the oxidized form of isoxerocomic acid. Air oxidation is responsible its formation, and it oxidizes faster to a similar pulvinic acid type pigment oxidized variant, variegatorubin. The long wavelength has an absorption at 497 nm, 106 nm higher than its precursor isoxerocomic acid. Synthesis experiments have shown tetra-acetylation by acetic anhydride and sulfuric acid. Although xerocomorubin and variegatorubin give off the same deep red color and could simultaneously occur in a mushroom, extracts from the deep red colored mushroom '' Boletus rubellus'' Krombh. identified only variegatorubin by thin layer chromatography Thin-layer chromatography (TLC) is a chromatography technique used to separate non-volatile mixtures. Thin-layer chromatography is performed on a sheet of an inert substrate such as glass, plastic, or aluminium foil, which is coated with a t ... (TLC), leading to the question the n ...
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Variegatorubin
Variegatorubin is a pulvinic acid derivative. It is a red pigment that is present in many members of the Boletales, an order of the division Basidiomycota. It is generated from the oxidation of variegatic acid. Bolete species that contain variegatorubin include '' Neoboletus luridiformis'', ''Chalciporus piperatus'', '' Rhizopogon roseolus'', '' Exsudoporus frostii'', '' Suillellus luridus'', ''Rubroboletus rhodoxanthus'', and '' R. satanas''. Variegatorubin was discovered by Wolfgang Steglich Wolfgang Steglich (born 12 August 1933) is a German chemist . Life Wolfgang Steglich was born in Kamenz and studied chemistry at the Technical University of Berlin and later at the Technical University of Munich where he received his PhD in 19 ... and colleagues, and described as a new compound in 1970. References {{Reflist, refs= {{cite book , author1=Gill, M. , author2=Steglich, W. , title=Pigments of Fungi (Macromycetes) , series=Progress in the Chemistry of Organic Natural P ...
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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''. 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 Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early inve .... References {{Reflist, refs= Gill, M., and St ...
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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 and precursor to xerocomorubin Xerocomorubin is a pigment from the fungus order Boletales. It is the oxidized form of isoxerocomic acid. Air oxidation is responsible its formation, and it oxidizes faster to a similar pulvinic acid type pigment oxidized variant, variegatorubin .... 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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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'' Pers. Variants include 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 i ... and ''O''-methylxerocomic acid. References {{Reflist, refs= {{cite book, last1=Gill, first1=M., last2=Steglich, first2= W., year=19 ...
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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 concentrat ...
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4-hydroxyphenylpyruvic Acid
4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyrosine to 4-HPPA is in turn catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. It is an intermediary compound in the biosynthesis of scytonemin. See also * 4-Hydroxyphenylpyruvate dioxygenase 4-Hydroxyphenylpyruvate dioxygenase (HPPD), also known as α-ketoisocaproate dioxygenase (KIC dioxygenase), is an Fe(II)-containing non-heme oxygenase that catalyzes the second reaction in the catabolism of tyrosine - the conversion of 4-hydro ... References Natural phenols Phenols Alpha-keto acids Propionic acids Hydroxy acids {{biochem-stub ...
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