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Dihydrokaempferol
Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of ''Pinus sibirica''. Metabolism The enzyme dihydrokaempferol 4-reductase uses ''cis''-3,4-leucopelargonidin and NADP+ to produce (+)-aromadendrin, NADPH, and H+. Glycosides (2''R'',3''R'')-''trans''-Aromadendrin-7-''O''-''beta''-D-glucopyranoside-6′′-(4′′′-hydroxy-2′′′-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of '' Afzelia bella'' (Fabaceae). Phellamurin is the 8-prenyl 7- glucoside derivative of aromadendrin. Chemistry (+)- Leucopelargonidin, (2''R'',3''S'',4''R'')-3,4,5,7,4'-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic soluti ...
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Dihydrokaempferol 4-reductase
In enzymology, a dihydrokaempferol 4-reductase () is an enzyme that catalyzes the chemical reaction :cis-3,4- leucopelargonidin + NADP+ \rightleftharpoons (+)- dihydrokaempferol + NADPH + H+ Thus, the two substrates of this enzyme are cis-3,4-leucopelargonidin and NADP+, whereas its 3 products are (+)-dihydrokaempferol, NADPH, and H+. This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-OH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase. Other names in common use include dihydroflavanol 4-reductase (DFR), dihydromyricetin reductase, NADPH-dihydromyricetin reductase, and dihydroquercetin reductase. This enzyme participates in flavonoid biosynthesis. Function Anthocyanidins, common plant pigments, are further reduced by the enzyme dihydroflavonol 4-reductase (DFR) to the corresponding colorless leucoanthocyanidins. DFR uses dihydromyriceti ...
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Phellamurin
Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavanonol, flavan-on-ol Aromadendrin, and may be seen as the 7-O-glucoside of noricaritin. Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible. It can be found in ''Commiphora africana'' and in ''Phellodendron amurense''. Related compounds 6"′-O-acetyl phellamurin is found in the leaves of ''Phellodendron japonicum''. References External links

* Flavanonol glucosides Prenylflavonoids {{Aromatic-stub ...
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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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Flavonoid
Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and a heterocyclic ring (C, the ring containing the embedded oxygen). This carbon structure can be abbreviated C6-C3-C6. According to the IUPAC nomenclature, they can be classified into: *flavonoids or bioflavonoids *isoflavonoids, derived from 3-phenyl chromen-4-one (3-phenyl-1,4-benzopyrone) structure *neoflavonoids, derived from 4-phenylcoumarine (4-phenyl-1,2-benzopyrone) structure The three flavonoid classes above are all ketone-containing compounds and as such, anthoxanthins ( flavones and flavonols). This class was the first to be termed bioflavonoids. The terms flavonoid and bioflavonoid have also been more loosely used to describe non ...
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Pinus Sibirica
''Pinus sibirica'', or Siberian pine, in the family Pinaceae is a species of pine tree that occurs in Siberia from 58°E in the Ural Mountains east to 126°E in the Stanovoy Range in southern Sakha Republic, and from Igarka at 68°N in the lower Yenisei valley, south to 45°N in central Mongolia. Description ''Pinus sibirica'' is a member of the white pine group, ''Pinus'' subgenus ''Strobus'', and like all members of that group, the leaves ('needles') are in fascicles (bundles) of five, with a deciduous sheath. They are 5–10 cm long. Siberian pine cones are 5–9 cm long. The 9–12 mm long seeds have only a vestigial wing and are dispersed by spotted nutcrackers. Siberian pine is treated as a variety or subspecies of the very similar Swiss pine (''Pinus cembra'') by some botanists. It differs in having slightly larger cones, and needles with three resin canals instead of two in Swiss pine. Like other European and Asian white pines, Siberian pine is very resis ...
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Leucopelargonidin
Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in ''Albizia lebbeck'' (East Indian walnut), in the fruit of ''Anacardium occidentale'' (Cashew), in the fruit of ''Areca catechu'' (Areca nut), in the fruit of '' Hydnocarpus wightiana'' (Hindi Chaulmoogra), in the rhizome of '' Rumex hymenosepalus'' (Arizona dock), in '' Zea mays'' (Corn) and in ''Ziziphus jujuba'' (Chinese date). (+)-Leucopelargonidin can be synthesized from (+)-aromadendrin by sodium borohydride reduction. Metabolism Dihydrokaempferol 4-reductase In enzymology, a dihydrokaempferol 4-reductase () is an enzyme that catalyzes the chemical reaction :cis-3,4- leucopelargonidin + NADP+ \rightleftharpoons (+)- dihydrokaempferol + NADPH + H+ Thus, the two substrates of this enzyme are cis-3 ... uses ''cis''-3,4-leucopelargonidin and NADP+ to produce (+)-aromadendrin, NADPH, and H+. Leucoanthocyanidin reductase transforms ''cis''-3,4-leucopelargonidin into afze ...
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Nicotinamide Adenine Dinucleotide Phosphate
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a Cofactor (biochemistry), cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NADPH as a reducing agent ('hydrogen source'). It is used by all forms of cellular life. NADPH is the redox, reduced form of NADP. NADP differs from NAD+, NAD by the presence of an additional phosphate group on the 2' position of the ribose ring that carries the adenine Moiety (chemistry), moiety. This extra phosphate is added by NAD+ kinase, NAD+ kinase and removed by NADP+ phosphatase. Biosynthesis NADP In general, NADP+ is synthesized before NADPH is. Such a reaction usually starts with NAD+, NAD+ from either the de-novo or the salvage pathway, with NAD+ kinase, NAD+ kinase adding the extra phosphate group. ADP-ribosyl cyclase allows for synthesis from nicotinamide in the salvage pathway, and NADP+ phosphatase ...
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Glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was originally given to plant products of this nature, in which the other part of the molecule was, in the greater number of cases, an aromatic aldehydic or phenolic compound (exceptions are Jinigrin and Jalapin or Scammonin). It has now been extended to include synthetic ethers, such as those obtained by acting on alcoholic glucose solutions with hydrochloric acid, and also the polysaccharoses, e.g. cane sugar, which appear to be ethers also. Although glucose is the most common sugar present in glucosides, many are known which yield rhamnose or iso-dulcite; these may be termed pentosides. Much attention has been given to the non-sugar parts (aglyca) of the molecules; the constitutions of many have been determined, and the compounds synthesi ...
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Afzelia Bella
''Afzelia'' is a genus of plants in family Fabaceae. The thirteen species all are trees, native to tropical Africa or Asia. The genus name of ''Afzelia'' is in honour of Adam Afzelius (1750–1837), a Swedish botanist and an apostle of Carl Linnaeus. Uses ''Afzelia'' species are used primarily for wood, though some species also have medicinal uses. The timber is most commonly traded under the collective name "doussie", as well as under name "afzelia". One of the common names is also "pod mahogany", adding to the confusion surrounding the name mahogany. The seeds are red and black and are used as beads. The wood is often used as the surface material for outdoor velodromes. The highly figured wood of the Asian species, ''Afzelia xylocarpa'', is sold as Afzelia xylay. The seeds and bark of this species are used as medicine. The dense and wavy wood of an ''Afzelia africana'' is used in ship-building Shipbuilding is the construction of ships and other floating vessels. ...
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Prenyl
Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to lipid anchors like the GPI anchor, though direct evidence of this has not been observed. Prenyl groups (also called isoprenyl groups, having one hydrogen atom more than isoprene) have been shown to be important for protein–protein binding through specialized prenyl-binding domains. Protein prenylation Protein prenylation involves the transfer of either a farnesyl or a geranylgeranyl moiety to C-terminal cysteine(s) of the target protein. There are three enzymes that carry out prenylation in the cell, farnesyl transferase, Caax protease and geranylgeranyl transferase I. Farnesylation is a type of prenylation, a post-translational modification of proteins by which an isoprenyl group is added to a cysteine residue. It is an important ...
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Leucopelargonidin
Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in ''Albizia lebbeck'' (East Indian walnut), in the fruit of ''Anacardium occidentale'' (Cashew), in the fruit of ''Areca catechu'' (Areca nut), in the fruit of '' Hydnocarpus wightiana'' (Hindi Chaulmoogra), in the rhizome of '' Rumex hymenosepalus'' (Arizona dock), in '' Zea mays'' (Corn) and in ''Ziziphus jujuba'' (Chinese date). (+)-Leucopelargonidin can be synthesized from (+)-aromadendrin by sodium borohydride reduction. Metabolism Dihydrokaempferol 4-reductase In enzymology, a dihydrokaempferol 4-reductase () is an enzyme that catalyzes the chemical reaction :cis-3,4- leucopelargonidin + NADP+ \rightleftharpoons (+)- dihydrokaempferol + NADPH + H+ Thus, the two substrates of this enzyme are cis-3 ... uses ''cis''-3,4-leucopelargonidin and NADP+ to produce (+)-aromadendrin, NADPH, and H+. Leucoanthocyanidin reductase transforms ''cis''-3,4-leucopelargonidin into afze ...
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Sodium Borohydride
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds application in papermaking and dye industries. It is also used as a reagent in organic synthesis. The compound was discovered in the 1940s by H. I. Schlesinger, who led a team seeking volatile uranium compounds.Hermann I Schlesinger and Herbert C Brown (1945)Preparation of alkali metal compounds. US Patent 2461661. Granted on 1949-02-15; expired on 1966-02-15. Results of this wartime research were declassified and published in 1953. Properties The compound is soluble in alcohols, certain ethers, and water, although it slowly hydrolyzes. Sodium borohydride is an odorless white to gray-white microcrystalline powder that often forms lumps. It can be purified by recrystallization from warm (50 °C) diglyme. Sodium borohydride is soluble ...
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