Phloretin
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Phloretin
Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot. Metabolism In rats, ingested phlorizin is converted into phloretin by hydrolytic enzymes in the small intestine. Phloretin hydrolase hydrolyses phloretin into phloretic acid and phloroglucinol. Pharmacological research In an animal model, phloretin inhibited active transport of glucose into cells by SGLT1 and SGLT2, though the inhibition is weaker than by its glycoside phlorizin. An important effect of this is the inhibition of glucose absorption by the small intestine and the inhibition of renal glucose reabsorption. Phloretin also inhibits a variety of urea transporters. It induces urea loss and diuresis when coupled with high protein diets. Phloretin has been found to inhibit weight gain and improve metabolic homeostasis in mice fed with high-fat diet. Phloretin inhibits aquaporin 9 (AQP9) on mouse hepatocyte A hepatocyte is a cell of the ...
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Phloroglucinol
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are unre ...
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Phlorizin
Phlorizin is a glucoside of phloretin, a dihydrochalcone. A white solid, samples often appear yellow owing to impurities. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes to give rufin. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose. Occurrence Phlorizin is found primarily in unripe ''Malus'' (apple) root bark of apple, and trace amounts have been found in strawberry. In ''Malus'', it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such as pear (''Pyrus communis''), cherry, and other fruit trees in the ''Rosaceae'' do not contain phloridzin. Phloridzin is a phytochemical that belongs to the class of polyphenols. In natural sources, it may occur with other polyphenols such as quercetin, catechin, epicatechin, procyanidins, and rutin. Pharma ...
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Phloretin Hydrolase
In enzymology, a phloretin hydrolase () is an enzyme that catalyzes the chemical reaction :phloretin + H2O \rightleftharpoons phloretate + phloroglucinol Thus, the two substrates of this enzyme are phloretin and H2O, whereas its two products are phloretate and phloroglucinol. This enzyme belongs to the family of hydrolases, specifically those acting on carbon–carbon bonds in ketonic substances. 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 2',4,4',6'-tetrahydroxydehydrochalcone 1,3,5-trihydroxybenzenehydrolase. This enzyme is also called lactase-phlorizin hydrolase. References * EC 3.7.1 Enzymes of unknown structure Dihydrochalcones metabolism {{hydrolase-stub ...
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Phlorizin
Phlorizin is a glucoside of phloretin, a dihydrochalcone. A white solid, samples often appear yellow owing to impurities. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes to give rufin. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose. Occurrence Phlorizin is found primarily in unripe ''Malus'' (apple) root bark of apple, and trace amounts have been found in strawberry. In ''Malus'', it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such as pear (''Pyrus communis''), cherry, and other fruit trees in the ''Rosaceae'' do not contain phloridzin. Phloridzin is a phytochemical that belongs to the class of polyphenols. In natural sources, it may occur with other polyphenols such as quercetin, catechin, epicatechin, procyanidins, and rutin. Pharma ...
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Phloretic Acid
Phloretic acid is an organic compound with the formula HOC6H4(CH2)2CO2H. It is a white solid. The compound contains both phenol and carboxylic acid functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid tyrosine except for the absence of the amino functional group on the alpha carbon. Production and occurrence Phloretic acid is produced by reduction of the unsaturated side chain of p-coumaric acid. Together with phloroglucinol, it is produced by the action of the enzyme phloretin hydrolase on phloretin. It is found in olives. It is found in the rumen of sheep fed with dried grass. It is also an urinary metabolite of tyrosine in rats. Polyesters have been prepared from phloretic acid. It is one of the products of 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 commo ...
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Urea Transporter
A urea transporter is a membrane transport protein, transporting urea. Humans and other mammals have two types of urea transport proteins, UT-A and UT-B. The UT-A proteins are important for renal urea handling and are produced by alternative splicing of the SLC14A2 gene. Urea transport in the kidney is regulated by vasopressin. The structure of a urea transport family protein from '' Desulfovibrio vulgaris'' was determined by x-ray crystallography. The structure has a pathway through the membrane that is similar to that of ion channel proteins, accounting for the ability of urea transport proteins to move up to one million urea molecules per second across the membrane. Urea transporters can be inhibited by the action of urea analogues like thiourea and glycosides like phloretin. Their inhibition results in increased diuresis due to urea induced osmosis in the collecting ducts of the kidney. Types In mammals, there are two urea transporter genes: UT-A ('' SLC14A2'') and UT- ...
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Dihydrochalcone
Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs. Natural dihydrochalcones left, Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent. * Aspalathin, a C-linked dihydrochalcone glucoside found in rooibos, a common herbal tea * Naringin dihydrochalcone, an artificial sweetener derived from naringin * Neohesperidin dihydrochalcone, an artificial sweetener derived from citrus * Nothofagin, a C-linked phloretin glucoside found in rooibos * Phloretin Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot. Metabolism In rats, ingested phlorizin is converted into phloretin ...
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Dihydrochalcones
Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs. Natural dihydrochalcones left, Neohesperidin dihydrochalcone is a commercial artificial sweetener that features the dihydrochalcone substituent. * Aspalathin, a C-linked dihydrochalcone glucoside found in rooibos, a common herbal tea * Naringin dihydrochalcone, an artificial sweetener derived from naringin * Neohesperidin dihydrochalcone, an artificial sweetener derived from citrus * Nothofagin, a C-linked phloretin glucoside found in rooibos * Phloretin * Isosalipurpurin Dihydrochalcones (3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone (methyl linderone) and 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol ...
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Phloretin-glucosidase
In enzymology, a glycosylceramidase () is an enzyme that catalyzes the chemical reaction :glycosyl-N-acylsphingosine + H2O \rightleftharpoons N-acylsphingosine + a sugar Thus, the two substrates of this enzyme are glycosyl-N-acylsphingosine and H2O, whereas its two products are N-acylsphingosine and sugar. This enzyme belongs to the family of hydrolases, specifically those glycosidases that hydrolyse O- and S-glycosyl compounds. 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 glycosyl-N-acylsphingosine glycohydrolase. Other names in common use include phlorizin hydrolase, phloretin-glucosidase, glycosyl ceramide glycosylhydrolase, cerebrosidase, phloridzin beta-glucosidase, lactase-phlorizin hydrolase, and phloridzin glucosidase. ...
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Naringin Dihydrochalcone
Naringin dihydrochalcone, sometimes abbreviated to naringin DC, is an artificial sweetener derived from naringin, a bitter compound found in citrus. Naringin dihydrochalcone is a phloretin glycoside discovered at the same time as neohesperidin dihydrochalcone during the 1960s as part of a United States Department of Agriculture research program to find methods for minimizing the taste of bitter flavorants in citrus juices. When naringin is treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes a dihydrochalcone Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor si ... that is roughly 300–1800 times sweeter than sugar at threshold concentrations. References External links * {{Dihydrochalcone Sugar substitutes Dihydrochalcone gl ...
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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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Prunus Mandshurica
''Prunus mandshurica'', also called Manchurian apricot and scout apricot, is a tree in the genus ''Prunus''. It was first described by Karl Maximovich in 1883 as a variety of the Siberian apricot (Tibetan apricot) '' Prunus armeniaca''. It is resistant to cold and is native to northeast China, Korea, and Manchuria. It is highly susceptible to plum pox potyvirus. Description ''Prunus mandshurica'' is a deciduous, broad-leaved tree, which grows to a height of about . The inner bark is red and the outer bark is black. The leaves are oval, with an elongated tip (acuminate or caudate), some hairs, and serrated edges. The tree grows best in loam soils. Its petioles are . The sepals and petals are oval, while the length of the stamens is similar to that of the stigma, which is cup-shaped. Flowers appear in spring and are white or pale pink. Fruits appear in late summer and are yellow with some red. In the autumn, the leaves turn golden orange. Uses Seed oil from ''P. mandshuri ...
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