1-galloyl-beta-D-glucose
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1-galloyl-beta-D-glucose
Glucogallin is chemical compound formed from gallic acid and β-D-glucose. It can be found in oaks species like the North American white oak (''Quercus alba''), European red oak (''Quercus robur'') and Amla fruit (''Phyllanthus emblica''). It is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and glucogallin. This enzyme can be found in oak leaf preparations. This the first step in the biosynthesis of gallotannins. The molecule is then used by enzymes in the gallotannins synthetics pathway like beta-glucogallin O-galloyltransferase or beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase. β-Glucogallin is aldose reductase inhibitor Aldose reductase inhibitors are a class of drugs being studied as a way to prevent eye and nerve damage in people with diabetes. Mechanism Their target, aldose reductase, is an enzyme ...
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Gallate 1-beta-glucosyltransferase
In enzymology, a gallate 1-beta-glucosyltransferase () is an enzyme that catalyzes the chemical reaction :UDP-glucose + gallate \rightleftharpoons UDP + 1-galloyl-beta-D-glucose Thus, the two substrates of this enzyme are UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose. This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ... of this enzyme class is UDP-glucose:gallate beta-D-glucosyltransferase. Other names in common use include UDP-glucose-vanillate 1-glucosyltransferase, UDPglucose:vanillate 1-O-glucosyltransferase, and UDPglucose:gallate glucosyltransferase. References * * EC 2.4.1 Enzymes of unknown structure P ...
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Gallotannin
A gallotannin is any of a class of molecules belonging to the hydrolysable tannins. Gallotannins are polymers formed when gallic acid, a polyphenol monomer, esterifies and binds with the hydroxyl group of a polyol carbohydrate such as glucose. Metabolism Gallate 1-beta-glucosyltransferase uses UDP-glucose and gallic acid, gallate to produce uridine diphosphate, UDP and 1-galloyl-beta-D-glucose. Beta-glucogallin O-galloyltransferase uses 1-O-galloyl-beta-D-glucose to produce D-glucose and 1-O,6-O-digalloyl-beta-D-glucose. Beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase uses 1-O-galloyl-beta-D-glucose and 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose to produce D-glucose and 1,2,3,4,6-pentagalloyl-glucose, 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose (1,2,3,4,6-penta-O-galloyl-β-D-glucose, the common precursor of gallotannins and the related ellagitannins). Tannase is a key enzyme in the degradation of gallotannins that uses digallic acid and H2O to produce gallic acid. See ...
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Gallic Acid
Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates". Isolation and derivatives Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. When heated with concentrated sulfuric acid, gallic acid converts to rufigallol. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, respectively. Biosynthesis Gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound aromatizes. Reactions Oxidation and oxidative coupling Alkaline solutions of gallic a ...
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Glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Gluco ...
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Quercus Alba
An oak is a tree or shrub in the genus ''Quercus'' (; Latin "oak tree") of the beech family, Fagaceae. There are approximately 500 extant species of oaks. The common name "oak" also appears in the names of species in related genera, notably '' Lithocarpus'' (stone oaks), as well as in those of unrelated species such as ''Grevillea robusta'' (silky oaks) and the Casuarinaceae (she-oaks). The genus ''Quercus'' is native to the Northern Hemisphere, and includes deciduous and evergreen species extending from cool temperate to tropical latitudes in the Americas, Asia, Europe, and North Africa. North America has the largest number of oak species, with approximately 160 species in Mexico of which 109 are endemic and about 90 in the United States. The second greatest area of oak diversity is China, with approximately 100 species. Description Oaks have spirally arranged leaves, with lobate margins in many species; some have serrated leaves or entire leaves with smooth margins. ...
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Quercus Robur
''Quercus robur'', commonly known as common oak, pedunculate oak, European oak or English oak, is a species of flowering plant in the beech and oak family, Fagaceae. It is a large tree, native plant, native to most of Europe west of the Caucasus. It is widely cultivated in temperate regions elsewhere and has escaped into the wild in scattered parts of China and North America. Description ''Quercus robur'' is a large deciduous tree, with circumference of grand oaks from to an exceptional . The Majesty Oak with a circumference of is the thickest tree in Great Britain. The Brureika (Bridal Oak) in Norway with a circumference of (2018) and the Kaive Oak in Latvia with a circumference of are among the thickest trees in Northern Europe. The largest historical oak was known as the Imperial Oak from Bosnia and Herzegovina. This specimen was recorded at 17.5 m in circumference at breast height and estimated at over 150 m³ in total volume. It collapsed in 1998. The species has l ...
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Phyllanthus Emblica
''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla, from the Sanskrit आमलकी (āmalakī), is a deciduous tree of the family Phyllanthaceae. Its native range is tropical and southern Asia. Plant morphology and harvesting The tree is small to medium in size, reaching in height. The branchlets are not glabrous or finely pubescent, long, usually deciduous; the leaves are simple, subsessile and closely set along branchlets, light green, resembling pinnate leaves. The flowers are greenish-yellow. The fruit is nearly spherical, light greenish-yellow, quite smooth and hard on appearance, with six vertical stripes or furrows. The fruit is up to in diameter, and, while the fruit of wild plants weigh approximately , cultivated fruits average to Ripening in autumn, the berries are harvested by hand after climbing to upper branches bearing the fruits. The taste of Indian emblic is sour, bitter and astringent, ...
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Esterification
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology The ...
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UDP-glucose
Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism. Functions UDP-glucose is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases. UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid. UDP-glucose can also be used as a precursor of sucrose, lipopolysaccharides and glycosphingolipids. Components UDP-glucose consists of the pyrophosphate group, ribose, glucose, and uracil. See also * DNA * Nucleoside * Nucleotide * Oligonucleotide * RNA * TDP-glucose * Uracil * Uridine diphosphate Uridine diphosphate, abbreviated UDP, is a nucleotide diphosphate. It is an ester of pyrophosphoric acid with the nucleoside uridine. UDP consists of the pyro ...
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Uridine Diphosphate
Uridine diphosphate, abbreviated UDP, is a nucleotide diphosphate. It is an ester of pyrophosphoric acid with the nucleoside uridine. UDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase uracil. UDP is an important factor in glycogenesis. Before glucose can be stored as glycogen in the liver and muscles, the enzyme UDP-glucose pyrophosphorylase forms a UDP-glucose unit by combining glucose 1-phosphate with uridine triphosphate, cleaving a pyrophosphate ion in the process. Then, the enzyme glycogen synthase combines UDP-glucose units to form a glycogen chain. The UDP molecule is cleaved from the glucose ring during this process and can be reused by UDP-glucose pyrophosphorylase. See also * DNA * Nucleoside * Nucleotide * Oligonucleotide * RNA * UGGT UGGT, or UDP-glucose:glycoprotein glucosyltransferase, is a soluble enzyme resident in the lumen of the endoplasmic reticulum (ER). The main function of UGGT is to recognize misfolded glycoprotein ...
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Beta-glucogallin O-galloyltransferase
In enzymology, a beta-glucogallin O-galloyltransferase () is an enzyme that catalyzes the chemical reaction :2 1-O-galloyl-beta-D-glucose \rightleftharpoons D-glucose + 1-O,6-O-digalloyl-beta-D-glucose Hence, this enzyme has one substrate, 1-O-galloyl-beta-D-glucose, and two products, D-glucose and 1-O,6-O-digalloyl-beta-D-glucose. This enzyme belongs to the family of transferases, specifically those acyltransferases transferring groups other than aminoacyl groups. The systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ... of this enzyme class is 1-O-galloyl-beta-D-glucose:1-O-galloyl-beta-D-glucose O-galloyltransferase. References * * EC 2.3.1 Enzymes of unknown structure {{2.3-enzyme-stub ...
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