The flavanones, a type 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 commonly consumed in the diets of humans. Chemically, flavonoids ...

s, 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

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

s derived from

flavone Flavone is an organic compound with the formula . A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but susbstituted derivatives, t ...

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 glycosides. ...

List of flavanones

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 ...

* Butin *

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 proper ...

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 flavan ...

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. ...

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 ...

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 ...

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 hyd ...

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's bit ...

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 ...

Poncirin Poncirin is the 7-O-neohesperidoside of isosakuranetin. Poncirin can be extracted from trifoliate orange The trifoliate orange, ''Citrus trifoliata'' or ''Poncirus trifoliata'', is a member of the family Rutaceae. Whether the trifoliate oranges ...

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 ...

Sakuranin Sakuranin is a flavanone, a type of flavonoid. It is the ''O''- glucoside of sakuranetin. It can be found in ''Prunus ''Prunus'' is a genus of trees and shrubs, which includes (among many others) the fruits plums, Cherry, cherries, peaches, Pea ...

* Sterubin * 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 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 a ...

-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

* {{Flavanone