![Flavanone num](https://upload.wikimedia.org/wikipedia/commons/e/e9/Flavanone_num.svg)
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. ...
s.
List of flavanones
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Blumeatin
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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
*
Isosakuranetin
*
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.
Pinocembrin can be converted biosynthetically to pinobanksin by hydroxylation
In chemistry, hydroxylation can refer to:
...
*
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 sakuranet ...
*
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
Sterubin (7-methoxy-3',4',5-trihydroxyflavanone) is a bitter-masking flavanone extracted from Yerba Santa (''Eriodictyon californicum'') a plant growing in America.
Sterubin is one of the four flavanones identified by Symrise in this plant whic ...
*
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 fam ...
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+, wherea ...
is an enzyme that uses (2''S'')-
flavan-4-ol 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