Hesperidin is a

flavanone The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides. List of flavanones * Blumeatin * Butin * Eriodictyol * Hesperetin * Hesperidin * Homoeriodictyol * Iso ...

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. ...

found in

citrus ''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Lemon, lemons, grapefruits, pomelos, and lim ...

fruits. Its

aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone ...

form is called

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 ...

. Its name is derived from the word "

hesperidium A hesperidium (plural hesperidia) is a modified berry with a tough, leathery rind. Etymology Carl Linnaeus gave the name Hesperideæ to an order containing the genus ''Citrus'', in allusion to the golden apples of the Hesperides. Development ...

", for fruit produced by citrus trees. Hesperidin was first isolated in 1828 by French chemist M. Lebreton from the white inner layer of

peels (

mesocarp Fruit anatomy is the plant anatomy of the internal structure of fruit. Fruits are the mature ovary or ovaries of one or more flowers. They are found in three main anatomical categories: aggregate fruits, multiple fruits, and simple fruits. Agg ...

, albedo). Hesperidin is believed to play a role in

plant Plants are predominantly photosynthetic eukaryotes of the kingdom Plantae. Historically, the plant kingdom encompassed all living things that were not animals, and included algae and fungi; however, all current definitions of Plantae exclud ...

defense.

Sources

''Rutaceae''

* 700–2,500 ppm in fruit of ''

Citrus aurantium Bitter orange, Seville orange, bigarade orange, or marmalade orange is the citrus tree ''Citrus'' × ''aurantium'' and its fruit. It is native to Southeast Asia and has been spread by humans to many parts of the world. It is probably a cross bet ...

'' (

bitter orange Bitter orange, Seville orange, bigarade orange, or marmalade orange is the citrus tree ''Citrus'' × ''aurantium'' and its fruit. It is native to Southeast Asia and has been spread by humans to many parts of the world. It is probably a cross bet ...

petitgrain Petitgrain () is an essential oil that is extracted from the leaves and green twigs of the bitter orange tree (''Citrus aurantium'' ssp. ''amara'') via steam distillation. It is also known as petitgrain bigarade. Etymology Petitgrain (Fr.: � ...

) * in

orange juice Orange juice is a liquid extract of the orange (fruit), orange tree fruit, produced by squeezing or reaming oranges. It comes in several different varieties, including blood orange, navel oranges, valencia orange, clementine, and tangerine. A ...

(''Citrus sinensis'') * in ''

Zanthoxylum gilletii ''Zanthoxylum gilletii'', the East African satinwood, is a tree species in the genus ''Zanthoxylum'' found in Africa. The fruits are used to produce the spice uzazi. Chemistry The alkaloid nitidine can be isolated from the plant. The amide alk ...

'' * in

lemon The lemon (''Citrus limon'') is a species of small evergreen trees in the flowering plant family Rutaceae, native to Asia, primarily Northeast India (Assam), Northern Myanmar or China. The tree's ellipsoidal yellow fruit is used for culin ...

* in

lime Lime commonly refers to: * Lime (fruit), a green citrus fruit * Lime (material), inorganic materials containing calcium, usually calcium oxide or calcium hydroxide * Lime (color), a color between yellow and green Lime may also refer to: Botany ...

* in leaves of ''

Agathosma serratifolia ''Agathosma serratifolia'', known as longleaf buchu or long buchu, is an erect, South African shrub, belonging to the citrus family Rutaceae. It is one of about 135 species mainly occurring in the south-western Cape Province. There, it is found o ...

''Lamiaceae''

Peppermint Peppermint (''Mentha'' × ''piperita'') is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world.Euro+Med Plantbas ...

contains hesperidin. Orange juice UHPLC UV chromatogram

Content in foods

Approximate hesperidin content per 100 ml * 481 mg peppermint, dried * 44 mg

blood orange The blood orange is a variety of orange ( ''Citrus'' × ''sinensis'') (also referred to as raspberry orange) with crimson, almost blood-colored flesh. The distinctive dark flesh color is due to the presence of anthocyanins, a family of polyp ...

, pure juice * 26 mg

orange Orange most often refers to: *Orange (fruit), the fruit of the tree species '' Citrus'' × ''sinensis'' ** Orange blossom, its fragrant flower *Orange (colour), from the color of an orange, occurs between red and yellow in the visible spectrum * ...

, pure juice * 18 mg

, pure juice * 14 mg

, pure juice * 1 mg

grapefruit The grapefruit (''Citrus'' × ''paradisi'') is a subtropical citrus tree known for its relatively large, sour to semi-sweet, somewhat bitter fruit. The interior flesh is segmented and varies in color from pale yellow to dark pink. Grapefruit is ...

, pure juice

Metabolism

Hesperidin 6-''O''-α--rhamnosyl-β--glucosidase, an enzyme that uses hesperidin and water to produce

and

rutinose Rutinose is the disaccharide also known as 6-''O''-α-L- rhamnosyl-D-glucose (C12H22O10) that is present in some flavonoid glycosides. It is prepared from rutin by hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of wat ...

, is found in the ''

Ascomycetes Ascomycota is a phylum of the kingdom Fungi that, together with the Basidiomycota, forms the subkingdom Dikarya. Its members are commonly known as the sac fungi or ascomycetes. It is the largest phylum of Fungi, with over 64,000 species. The defi ...

'' species.

Research

As a

found in the rinds of

fruits (such as oranges or lemons), hesperidin is under preliminary research for its possible biological properties

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...

. One review did not find evidence that hesperidin affected

blood lipid Blood lipids (or blood fats) are lipids in the blood, either free or bound to other molecules. They are mostly transported in a protein capsule, and the density of the lipids and type of protein determines the fate of the particle and its influence ...

levels or

hypertension Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...

. Another review found that hesperidin may improve endothelial function in humans, but the overall results were inconclusive.

Biosynthesis

The biosynthesis of hesperidin stems from the

phenylpropanoid pathway The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

, in which the natural amino acid -

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

undergoes a deamination by

phenylalanine ammonia lyase The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and ''trans''-cinnamic acid.: :L-phenylalanine = ''trans''-cinnamate + NH3 Phenylalanine ammonia lyase (PAL) is the first and committed ...

to afford (''E'')-cinnamate. The resulting monocarboxylate undergoes an

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...

cinnamate 4-hydroxylase In enzymology, a trans-cinnamate 4-monooxygenase () is an enzyme that catalyzes the chemical reaction :trans-cinnamate + NADPH + H+ + O2 \rightleftharpoons 4-hydroxycinnamate + NADP+ + H2O The 4 substrates of this enzyme are trans-cinnamate, ...

to afford (''E'')-4-coumarate, which is transformed into (''E'')-4-coumaroyl-CoA by 4-coumarate-CoA ligase. (''E'')-4-coumaroyl-CoA is then subjected to the

type III polyketide synthase Type may refer to: Science and technology Computing * Typing, producing text via a keyboard, typewriter, etc. * Data type, collection of values used for computations. * File type * TYPE (DOS command), a command to display contents of a file. * Ty ...

naringenin chalcone synthase, undergoing successive

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

s and ultimately a ring-closing

Claisen condensation The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone. It is named after Ra ...

to afford

naringenin chalcone Naringenin chalcone is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin ...

. The corresponding

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 ...

undergoes an

isomerization In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomeriz ...

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 ...

to afford (2''S'')-naringenin, which is oxidized to (2''S'')-eriodictyol by flavonoid 3′-hydroxylase. After ''O''-methylation by caffeoyl-CoA ''O''-methyltransferase, the hesperitin product undergoes a

glycosylation Glycosylation is the reaction in which a carbohydrate (or ' glycan'), i.e. a glycosyl donor, is attached to a hydroxyl or other functional group of another molecule (a glycosyl acceptor) in order to form a glycoconjugate. In biology (but not al ...

by flavanone 7-''O''-glucosyltransferase to afford hesperitin-7-''O''-β--glucoside. Finally, a rhamnosyl moiety is introduced to the monoglycosylated product by 1,2-rhamnosyltransferase, forming hesperidin.

References

External links

* {{Glycosides Flavanone glycosides Flavonoid antioxidants Bitter compounds Flavonoids found in Rutaceae