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Oudemansin A
Oudemansin A is a natural product first isolated from the basidiomycete fungus ''Oudemansiella mucida''. Its chemical structure was determined by X-ray crystallography in 1979 and absolute stereochemistry by total synthesis. Two closely related derivatives, oudemansin B and X have also been isolated from other basidiomycetes. They are all biologically active against many filamentous fungi and yeasts but with insufficient potency and stability to become useful commercial products. However, their discovery, together with the strobilurins led to agricultural fungicides including azoxystrobin with the same mechanism of action. Isolation and Characterization Oudemansin A (initially known simply as oudemansin) with R1 = R2 = H was first described in 1979, after being isolated from mycelial fermentations of the basidiomycota, basidiomycete fungus ''Oudemansiella mucida''. Its structure, including the relative configuration of the methoxy and adjacent methyl groups, was established by bo ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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Oudemansiella Mucida
''Oudemansiella mucida'', commonly known as porcelain fungus, is a basidiomycete fungus of the family Physalacriaceae and native to Europe. ''O. mucida'' is a white, slimy wood-rot fungus and is strongly tied to rotting beech, where it grows in clusters. It is in season late summer to late autumn, and tiny fungi can then sometimes be seen parachuting from high branches, when they are dislodged by the wind on breezy days. Taxonomy Porcelain fungus has also been referred to as Beech Tuft, Poached Egg fungus or simply Porcelain Mushroom. Strongly tied to beech and being a delicate, white and slimy mushroom, it is reminiscent of porcelain or egg white; hence its English common names. In 1794 Heinrich Adolf Schrader described the fungus and gave it the scientific name ''Agaricus mucidus''. Its present accepted name dates from 1909, when Austrian mycologist ´Franz Xaver Rudolf von Höhnel transferred it to the genus ''Oudemansiella''. The genus Oudemansiella was established in 1881 ...
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Absolute Stereochemistry
Absolute configuration refers to the spatial arrangement of atoms within a chiral molecular entity (or group) and its resultant stereochemical description. Absolute configuration is typically relevant in organic molecules, where carbon is bonded to four different substituents. This type of construction creates two possible enantiomers. Absolute configuration uses a set of rules to describe the relative positions of each bond around the chiral center atom. The most common labeling method uses the descriptors ''R'' or ''S'' is based on the Cahn–Ingold–Prelog priority rules. R and S refer to Rectus and Sinister, which are Latin for right and left, respectively. Chiral molecules can differ in their chemical properties, but are identical in their physical properties, which can make distinguishing enantiomers challenging. Absolute configurations for a chiral molecule (in pure form) are most often obtained by X-ray crystallography, although with some important limitations. All enant ...
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Biologically Active
In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or pharmacophore but can be modified by the other constituents. Among the various properties of chemical compounds, pharmacological/biological activity plays a crucial role since it suggests uses of the compounds in the medical applications. However, chemical compounds may show some adverse and toxic effects which may prevent their use in medical practice. Activity is generally dosage-dependent. Further, it is common to have effects ranging from beneficial to adverse for one substance when going from low to high doses. Activity depends critically on fulfillment of the ADME criteria. To be an effective drug, a compound not only must be active against a target, but also possess the appropriate ADME (Absorption, Distribution, Metabolism, and Exc ...
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Strobilurins
Strobilurins are a group of natural products and their synthetic analogs. A number of strobilurins are used in agriculture as fungicides. They are part of the larger group of QIs (Quinone outside Inhibitors), which act to inhibit the respiratory chain at the level of Complex III. The first parent natural products, strobilurins A and B, were extracted from the fungus ''Strobilurus tenacellus''. Commercial strobilurin fungicides were developed through optimization of photostability and activity. Strobilurins represented a major development in fungus-based fungicides. First released in 1996, there are now ten major strobilurin fungicides on the market, which account for 23-25 % of the global fungicide sales. Examples of commercialized strobilurin derivatives are azoxystrobin, kresoxim-methyl, picoxystrobin, fluoxastrobin, oryzastrobin, dimoxystrobin, pyraclostrobin and trifloxystrobin. Strobilurins are mostly contact fungicides with a long half time as they are absorbed into the ...
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Azoxystrobin
Azoxystrobin is the ISO common name for an organic compound that is used as a fungicide. It is a broad spectrum systemic active ingredient widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status. History In 1977, academic research groups in Germany published details of two new antifungal antibiotics they had isolated from the basidiomycete fungus ''Strobilurus tenacellus''. They named these strobilurin A and B but did not provide detailed structures, only data based on their high-resolution mass spectra, which showed that the simpler of the two had molecular formula C16H18O3. In the following year, further details including structures were published and a related fungicide, oudemansin A from the fungus ''Oudemansiella mucida'', whose identity had b ...
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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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Mycena Polygramma
''Mycena polygramma'', commonly known as the grooved bonnet, is a species of mushroom in the family Mycenaceae. The inedible fruit bodies are small, pale gray-brown mushrooms with broadly conical caps, pinkish gills. They are found in small troops on stumps and branches of deciduous and occasionally coniferous trees. The mushroom is found in Asia, Europe, and North America, where it is typically found on twigs or buried wood, carrying out its role in the forest ecosystem by decomposing organic matter, recycling nutrients, and forming humus in the soil. ''M. polygramma'' contains two uncommon hydroxy fatty acids and is also a bioluminescent fungus whose intensity of light emission follows a diurnal pattern. Taxonomy First called ''Agaricus polygrammus'' by French mycologist Jean Bulliard in 1789, the species was later sanctioned under that name by Elias Magnus Fries in his ''Systema Mycologicum''. It was soon after transferred into the genus ''Mycena'' in 1821 by Samu ...
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Oudemansiella Radicata
''Hymenopellis radicata'', commonly known as the deep root mushroom or the rooting shank, is a widespread agaric readily identified by its deeply rooted stalk ( stipe). Description The cap is medium to large, flat, grayish or yellowish brown and streaked, with a central hump and has a size of between 5 and 12.5 cm. The surface of the cap is sticky or slimy when moist, with the underside displaying wide white gills, or lamellae Lamella (plural lamellae) means a small plate or flake in Latin, and in English may refer to: Biology * Lamella (mycology), a papery rib beneath a mushroom cap * Lamella (botany) * Lamella (surface anatomy), a plate-like structure in an animal * .... The brittle stalk tapers at both ends and is nearly white above to brown below the soil. The stem grows into a long deeply rooting tap root until it touches a piece of wood. This may grow up to 20 cm in length in some specimens. Similar species Similar to ''Oudemansiella longipes''. Refe ...
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Cahn–Ingold–Prelog Priority Rules
In organic chemistry, the Cahn–Ingold–Prelog (CIP) sequence rules (also the CIP priority convention; named for R.S. Cahn, C.K. Ingold, and Vladimir Prelog) are a standard process to completely and unequivocally name a stereoisomer of a molecule. The purpose of the CIP system is to assign an ''R'' or ''S'' descriptor to each stereocenter and an ''E'' or ''Z'' descriptor to each double bond so that the configuration of the entire molecule can be specified uniquely by including the descriptors in its systematic name. A molecule may contain any number of stereocenters and any number of double bonds, and each usually gives rise to two possible isomers. A molecule with an integer describing the number of stereocenters will usually have stereoisomers, and diastereomers each having an associated pair of enantiomers. The CIP sequence rules contribute to the precise naming of every stereoisomer of every organic molecule with all atoms of ligancy of fewer than 4 (but includi ...
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