Dihydrochalcone Glycosides
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Dihydrochalcone Glycosides
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 (dihydrokanakugio ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Chalcone
Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. Chemical properties Chalcones have two absorption maxima at 280 nm and 340 nm. Synthesis Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone. : This reaction, which can be carried out without any solvent, is so reliable that it is used in as an example of green chemistry in undergraduate education. Biosynthesis Chalcones and chalconoids are synthesized in plants as secondary metabolites. The enzyme chalcone synthase, a type III polyketide synthase, is responsible for the biosynthesis of these compounds. The enzyme is found in all "higher" (vascular) and several "lower" ( non-vascular) plants. Potential pharmacology Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation. Some 2′-amino ...
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Neohesperidin Dihydrochalcone
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus. It is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin. Industrially, it is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC. Discovery NHDC was discovered 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. Neohesperidin is one such bitter compound. When treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes NHDC. Profile NHDC in pure form is found as a white substance not unlike powdered sugar. It has an intense sweet taste because it stimulates the sweet receptor TAS1R2+TAS1R3 in humans, although this is species-dependent, as the equivalent receptor in ...
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Aspalathin
Aspalathin is a C-linked dihydrochalcone glucoside found in rooibos tea, a herbal tea prepared from the South African rooibos plant, ''Aspalathus linearis'' ( Fabaceae). It was first isolated in 1965 by chromatography In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system ( .... It has demonstrated antidiabetic activity. References External links * Dihydrochalcone glycosides Phenol glucosides {{Aromatic-stub ...
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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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Neohesperidin Dihydrochalcone
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus. It is particularly effective in masking the bitter tastes of other compounds found in citrus, including limonin and naringin. Industrially, it is produced by extracting neohesperidin from the bitter orange, and then hydrogenating this to make NHDC. Discovery NHDC was discovered 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. Neohesperidin is one such bitter compound. When treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes NHDC. Profile NHDC in pure form is found as a white substance not unlike powdered sugar. It has an intense sweet taste because it stimulates the sweet receptor TAS1R2+TAS1R3 in humans, although this is species-dependent, as the equivalent receptor in ...
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Nothofagin
Nothofagin is a dihydrochalcone. It is a ''C''-linked phloretin glucoside found in rooibos Rooibos ( ; , meaning "red bush"), or ''Aspalathus linearis'', is a broom-like member of the plant family Fabaceae that grows in South Africa's fynbos biome. The leaves are used to make a herbal tea that is called rooibos (especially in S ... (''Aspalathus linearis'') and New Zealand red beech (''Nothofagus fusca''). It is a phenolic antioxidant. References External links * Dihydrochalcone glycosides Glucosides Polyphenols {{Aromatic-stub ...
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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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Dihydrokanakugiol
Dihydrokanakugiol is 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 ... isolated from '' Lindera lucida''.A dihydrochalcone from Lindera lucida. Yuan-Wah Leong, Leslie J. Harrison, Graham J. Bennett, Azizol A. Kadir and Joseph D. Connolly, Phytochemistry, Volume 47, Issue 5, March 1998, Pp. 891-894, References {{Dihydrochalcone Dihydrochalcones ...
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Lindera Lucida
''Lindera lucida'' is a species of flowering plant in the family Lauraceae. It is found in Malaysia. Dihydrochalcones (3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone, methyl linderone, 5-hydroxy-6,7,8-trimethoxyflavone ( alnetin) and 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) can be found in twigs of ''L. lucida''. References lucida Lucida (pronunciation: ) is an extended family of related typefaces designed by Charles Bigelow and Kris Holmes and released from 1984 onwards. The family is intended to be extremely legible when printed at small size or displayed on a low-resol ... Plants described in 1900 Taxa named by Jacob Gijsbert Boerlage Taxa named by Carl Ludwig Blume {{Laurales-stub ...
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