The flavanones, a type of
flavonoids, are various
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
, colorless
ketones derived from
flavone that often occur in plants as
glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycoside ...
s.
List of flavanones
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Blumeatin
Blumeatin is a flavanone found in ''Blumea balsamifera'', and has been reported to be present in ''Artemisia annua''.
Structure
Blumeatin has the skeleton structure of a flavanone with three hydroxy groups at 5, 3' and 5' carbon positions and a ...
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Butin
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Eriodictyol
Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa (''Eriodictyon californicum''), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying pro ...
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Hesperetin
Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin (and naringenin, the parent flav ...
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Hesperidin
Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.
Hesperidin was first isolated in 1828 by French chemist M. ...
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Homoeriodictyol
Homoeriodictyol is a bitter-masking flavanone extracted from Yerba Santa (''Eriodictyon californicum'') a plant growing in America.
Homoeriodictyol (3`-methoxy-4`,5,7-trihydroxyflavanone) is one of the 4 flavanones identified by Symrise in this ...
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Isosakuranetin
Isosakuranetin, an O-methylated flavonoid, is the 4'-methoxy derivative of naringenin, a flavanone. Didymin, a disaccharide of isosakuranetin, occur e.g. in sweet orange, blood orange and mandarin. Isosakuranetin is a potent inhibitor of TRPM3 ch ...
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Naringenin
Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.
Structure
Naringenin has the skeleton structure of a flavanone with three hydro ...
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Naringin
Naringin is a flavanone-7-''O''- glycoside between the flavanone naringenin and the disaccharide neohesperidose.
The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit' ...
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Pinocembrin
Pinocembrin is a flavanone, a type of flavonoid. It is an antioxidant found in damiana, honey, fingerroot, and propolis
Propolis or bee glue is a resinous mixture that honey bees produce by mixing saliva and beeswax with exudate gathere ...
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Poncirin
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Sakuranetin
Sakuranetin is a flavan-on, the 7-methoxy derivative of naringenin, found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of '' Pyricularia oryzae''.
Glycosides
Sakuranin is the 5-O- glucoside of sakura ...
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Sakuranin
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Sterubin
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Pinostrobin
Metabolism
The enzyme
chalcone isomerase
In enzymology, a chalcone isomerase () is an enzyme that catalyzes the chemical reaction
:a chalcone \rightleftharpoons a flavanone
Hence, this enzyme has one substrate, a chalcone, and one product, a flavanone.
This enzyme belongs to the ...
uses a
chalcone-like compound to produce a flavanone.
Flavanone 4-reductase
In enzymology, a flavanone 4-reductase () is an enzyme that catalyzes the chemical reaction
:(2S)-flavan-4-ol + NADP+ \rightleftharpoons (2S)-flavanone + NADPH + H+
Thus, the two substrates of this enzyme are (2S)-flavan-4-ol and NADP+, wher ...
is an enzyme that uses (2''S'')-
flavan-4-ol
The flavan-4-ols (3-deoxyflavonoids) are flavone-derived alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments. They can be found in the sorghum. Glycosides (abacopteri ...
and NADP
+ to produce (2''S'')-flavanone, NADPH, and H
+.
Synthesis
Numerous methods exist for the enantioselective chemical and biochemical synthesis of flavanones and related compounds.
References
External links
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{{Flavanone