Hesperetin is the 4'-methoxy derivative of

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 ...

, 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 ...

. Hesperetin's 7-O-glycoside,

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. ...

, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin (and

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 ...

, the parent

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 ...

) are not found to a significant extent in ''Citrus'' spp.

Glycosides

A variety of

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 of hesperetin are known, including: *

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. ...

(hesperetin-7-''O''-rutinoside) is a water-insoluble flavonoid glycoside whose solubility is below 5 μg/ml in water. Hesperidin is 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 and upon ingestion it releases 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 ...

, hesperetin. *

Neohesperidin Neohesperidin is a flavanone glycoside found in citrus fruits. It is the 7-O- neohesperidose derivative of hesperetin, which in turn is the 4'-methoxy derivative of eriodictyol. Neohesperidin dihydrochalcone Neohesperidin dihydrochalcone, sometim ...

is the 7-''O''-

neohesperidoside Neohesperidose is the disaccharide which is present in some flavonoids. It can be found in species of ''Typha.'' ''Delphinidin-3-neohesperidoside and cyanidin-3- neohesperidoside from receptacles of Podocarpus species, Oyvind M. Andersen, Phytoche ...

of hesperetin. * Hesperetin-7-''O''-α-L-Rhamnopyranoside (CAS 66513-83-5) is found in the roots of clammy cherry (''Cordia obliqua'' a.k.a. ''Cordia obliqua'' var. ''wallichii'').

Metabolism

Hesperidin 6-''O''-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses

and H₂O to produce hesperetin 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 ...

. It is found in the

hyphomycetes Hyphomycetes are a form classification of fungi, part of what has often been referred to as fungi imperfecti, Deuteromycota, or anamorphic fungi. Hyphomycetes lack closed fruit bodies, and are often referred to as moulds (or molds). Most hyph ...

species ''Stilbella fimetaria''.

Effects

Hesperetin was found to be affecting the slow inactivation phase of inward sodium current channels (INa) and therefore could be used as a template to develop drugs against lethal cardiac arrhythmias in LQT3. Hesperetin also inhibits

TRPM3 Transient receptor potential cation channel subfamily M member 3 is a protein that in humans is encoded by the ''TRPM3'' gene. Function The product of this gene belongs to the family of transient receptor potential (TRP) channels. TRP channels ...

channels.

References

{{Flavanone Aromatase inhibitors O-methylated flavanones Flavonoids found in Rutaceae 3-Hydroxypropenals