Fustin
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Fustin
Fustin, sometimes called "dihydrofisetin", is a flavanonol, a type of flavonoid. It can be found in young fustic (''Cotinus coggygria'') and in the lacquer tree (''Toxicodendron vernicifluum''). Fustin shows protective effects on 6-hydroxydopamine-induced neuronal cell death. Unlike fisetin, fustin has no double bond in the C-ring. This makes fustin a flavan, with two stereocenters and four stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...s. References {{flavanonol Flavanonols Catechols ...
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Flavanonol
The flavanonols (with two "o"s a.k.a. 3-hydroxyflavanone or 2,3-dihydroflavonol) are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one (IUPAC name) backbone. Some examples include: * Taxifolin (or Dihydroquercetin) * Aromadedrin (or Dihydrokaempferol) * Engeletin (or Dihydrokaempferol-3-rhamnoside) Metabolism * Flavanone 3-dioxygenase * Flavonol synthase * Dihydroflavonol 4-reductase Glycosides Glycosides ( chrysandroside A and chrysandroside B) can be found in the roots of ''Gordonia chrysandra''. Xeractinol, a dihydroflavonol C-glucoside, can be isolated from the leaves of ''Paepalanthus argenteus var. argenteus''. Dihydro-flavonol glycosides ( astilbin, neoastilbin, isoastilbin, neoisoastilbin, (2''R'', 3''R'')-taxifolin-3'-''O''-β-D-pyranoglucoside) have been identified in the rhizome of ''Smilax glabra ''Smilax glabra'', sarsaparilla, is a plant species in the genus ''Smilax''. It is native to flora of China, China, the Himalayas, and In ...
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Young Fustic
''Cotinus coggygria'', syn. ''Rhus cotinus'', the European smoketree, Eurasian smoketree, smoke tree, smoke bush, Venetian sumach, or dyer's sumach, is a Eurasian species of flowering plant in the family Anacardiaceae. Description It is a multiple-branching deciduous shrub growing to tall with an open, spreading, irregular habit, only rarely forming a small tree. The leaves are long rounded ovals, green with a waxy glaucous sheen. The autumn colour can be strikingly varied, from peach and yellow to scarlet. The flowers are numerous, produced in large inflorescences long; each flower in diameter, with five pale yellow petals. Most of the flowers in each inflorescence abort, elongating into yellowish-pink to pinkish-purple feathery plumes (when viewed en masse these have a wispy 'smoke-like' appearance, hence the common name "smoke tree") which surround the small () drupaceous fruit that develop. Fossil record Macrofossils of ''C. coggygria'' from the early Pliocene epoch have ...
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Toxicodendron Vernicifluum
''Toxicodendron vernicifluum'' (formerly ''Rhus verniciflua''), also known by the common name Chinese lacquer tree, is an Asian tree species of genus ''Toxicodendron'' native to China and the Indian subcontinent, and cultivated in regions of China, Japan and Korea. Other common names include ''Japanese lacquer tree'', ''Japanese sumac'', and ''varnish tree''. The trees are cultivated and tapped for their toxic sap, which is used as a highly durable lacquer to make Chinese, Japanese, and Korean lacquerware. The trees grow up to 20 metres tall with large leaves, each containing from 7 to 19 leaflets (most often 11–13). The sap contains the allergenic compound urushiol, which gets its name from this species' Japanese name urushi (); "urushi" is also used in English as a collective term for all kinds of Asian lacquerware made from the sap of this and related Asian tree species, as opposed to European "lacquer" or Japanning made from other materials. Urushiol is also the oil foun ...
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Fisetin
Fisetin (7,3′,4′- flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891. The biological activity of fisetin has been studied in many laboratory assays; like other polyphenols it has many activities. Biological sources Fisetin can be found in a wide variety of plants. It is found in Eudicotyledons, such as trees and shrubs in the family Fabaceae, such as the acacias ''Acacia greggii'' and ''Acacia berlandieri'', the parrot tree ('' Butea frondosa''), the honey locust (''Gleditsia triacanthos''), members of the family Anacardiaceae such as the ''Quebracho colorado'' and species of the genus '' Rhus'', which contains the sumacs. Along with myricetin, fisetin provides the color of the tra ...
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Flavan
The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2''H''-chromene skeleton. They may be found in plants. These compounds include the flavan-3-ols, flavan-4-ols and flavan-3,4-diols (leucoanthocyanidin). A ''C''-glycosidic flavan can be isolated from cocoa liquor. ''Casuarina glauca'' is an actinorhizal plant producing root nitrogen-fixing nodules infested by ''Frankia ''Frankia'' is a genus of nitrogen-fixing bacteria that live in symbiosis with actinorhizal plants, similar to the ''Rhizobium'' bacteria found in the root nodules of legumes in the family Fabaceae. ''Frankia'' also initiate the forming of root ...''. There is a regular pattern of cell layers containing flavans. References {{Aromatic-stub ...
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Stereocenter
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups creates a new stereoisomer. Stereocenters are also referred to as stereogenic centers. A stereocenter is geometrically defined as a point (location) in a molecule; a stereocenter is usually but not always a specific atom, often carbon. Stereocenters can exist on chiral or achiral molecules; stereocenters can contain single bonds or double bonds. The number of hypothetical stereoisomers can be predicted by using 2''n'', with ''n'' being the number of tetrahedral stereocenters; however, exceptions such as meso compounds can reduce the prediction to below the expected 2''n''. Chirality centers are a type of stereocenter with four different substituent groups; chirality centers are a specific subset of stereocenters because they can only ha ...
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Stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer. Enantiomers Enantiomers, also known as optical isomers, are two stereoisomers that are related to each other by a reflection: they are mirror images of each other that are non-superposable. Human hands are a macroscopic analog of this. Every stereogenic center in one has the opposite configuration in the other. Two compounds that are enantiomers of each other have the same physical properties, except for the direction in which they rotate polarized light and how they interact with different optical isom ...
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Flavanonols
The flavanonols (with two "o"s a.k.a. 3-hydroxyflavanone or 2,3-dihydroflavonol) are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one (IUPAC name) backbone. Some examples include: * Taxifolin (or Dihydroquercetin) * Aromadedrin (or Dihydrokaempferol) * Engeletin (or Dihydrokaempferol-3-rhamnoside) Metabolism * Flavanone 3-dioxygenase * Flavonol synthase * Dihydroflavonol 4-reductase Glycosides Glycosides ( chrysandroside A and chrysandroside B) can be found in the roots of '' Gordonia chrysandra''. Xeractinol, a dihydroflavonol C-glucoside, can be isolated from the leaves of ''Paepalanthus argenteus var. argenteus''. Dihydro-flavonol glycosides ( astilbin, neoastilbin, isoastilbin, neoisoastilbin, (2''R'', 3''R'')-taxifolin Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. Stereocenters Taxifolin has two stereocenters on t ...
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