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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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Flavanonol Num
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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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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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 the C-ring, as opposed to quercetin which has none. For example, (+)-taxifolin has (2R,3R)-configuration, making it 1 out of 4 stereoisomers that comprise 2 pairs of enantiomers. Natural occurrences Taxifolin is found in non-glutinous rice boiled with adzuki bean (adzuki-meshi). It can be found in conifers like the Siberian larch, ''Larix sibirica'', in Russia, in ''Pinus roxburghii'', in ''Cedrus deodara'' and in the Chinese yew, '' Taxus chinensis var. mairei''. It is also found in the silymarin extract from the milk thistle seeds. Taxifolin is present in vinegars aged in cherry wood. Taxifolin, and flavonoids in general, can be found in many beverages and products. Specifically, taxifolin is found in plant-based foods like fruit, vegetables, wine, tea, and coco ...
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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 the C-ring, as opposed to quercetin which has none. For example, (+)-taxifolin has (2R,3R)-configuration, making it 1 out of 4 stereoisomers that comprise 2 pairs of enantiomers. Natural occurrences Taxifolin is found in non-glutinous rice boiled with adzuki bean (adzuki-meshi). It can be found in conifers like the Siberian larch, ''Larix sibirica'', in Russia, in ''Pinus roxburghii'', in ''Cedrus deodara'' and in the Chinese yew, '' Taxus chinensis var. mairei''. It is also found in the silymarin extract from the milk thistle seeds. Taxifolin is present in vinegars aged in cherry wood. Taxifolin, and flavonoids in general, can be found in many beverages and products. Specifically, taxifolin is found in plant-based foods like fruit, vegetables, wine, tea, and coco ...
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Astilbin
Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer. Natural occurrences Astilbin can be found in St John's wort (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in '' Dimorphandra mollis'' (Fava d'anta, Fabaceae), in the leaves of ''Harungana madagascariensis'' (Hypericaceae),
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Aromadedrin
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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Neoisoastilbin
Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer. Natural occurrences Astilbin can be found in St John's wort (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in ''Dimorphandra mollis'' (Fava d'anta, Fabaceae), in the leaves of ''Harungana madagascariensis'' (Hypericaceae),
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Isoastilbin
Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer. Natural occurrences Astilbin can be found in St John's wort (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in '' Dimorphandra mollis'' (Fava d'anta, Fabaceae), in the leaves of ''Harungana madagascariensis'' (Hypericaceae),
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Neoastilbin
Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer. Natural occurrences Astilbin can be found in St John's wort (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in '' Dimorphandra mollis'' (Fava d'anta, Fabaceae), in the leaves of ''Harungana madagascariensis'' (Hypericaceae),
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Xeractinol
Xeractinol is a flavanonol, a type of flavonoid. It is a glucoside that can be found in the leaves of ''Paepalanthus argenteus ''Paepalanthus bromelioides'' is a species in the flowering plant family Eriocaulaceae. This family is placed in the Poales, close to the Bromeliaceae, whose Morphology (biology), morphology this genus shares. ''Paepalanthus bromelioides'' i ...'' (Eriocaulaceae). References External links * Flavanonol glucosides C-glycoside natural phenols {{Aromatic-stub ...
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Engeletin
Engeletin is a flavanonol rhamnoside, a phenolic compound found in wine and isolated from the bark of ''Hymenaea martiana''. See also * Phenolic compounds in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ... References Flavonoid rhamnosides {{aromatic-stub ...
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Dihydroflavonol 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 dihydromyricetin ( am ...
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