Hesperetin

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Hesperetin
Hesperetin.svg
Hesperetin 3D BS.png
Names
IUPAC name
(2S)-3′,5,7-Trihydroxy-4′-methoxyflavan-4-one
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.538 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-290-2
KEGG
PubChem CID
UNII
  • InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Yes check.svgY
    Key: AIONOLUJZLIMTK-AWEZNQCLSA-N Yes check.svgY
  • InChI=1/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
    Key: AIONOLUJZLIMTK-AWEZNQCLBH
  • O=C2c3c(O[C@H](c1ccc(OC)c(O)c1)C2)cc(O)cc3O
Properties
C16H14O6
Molar mass 302.282 g·mol−1
Melting point 226–228 °C (439–442 °F; 499–501 K)
Solubility in other solventsSol. EtOH, alkalis
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] Hesperetin (and naringenin, the parent flavanone of naringin) are not found to a significant extent in Citrus spp. [2]

Contents

Glycosides

A variety of glycosides of hesperetin are known, including:

Metabolism

Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. It is found in the hyphomycetes 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. [6] Hesperetin also inhibits TRPM3 channels. [7]

Related Research Articles

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

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. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<span class="mw-page-title-main">Quercetin</span> Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

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.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Naringin</span> Chemical compound

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 bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans naringin is metabolized to the aglycone naringenin by naringinase present in the gut.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

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.

<span class="mw-page-title-main">Apigenin</span> Chemical compound

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

<span class="mw-page-title-main">Flavanone</span>

The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides.

TRPM is a family of transient receptor potential ion channels (M standing for wikt:melastatin). Functional TRPM channels are believed to form tetramers. The TRPM family consists of eight different channels, TRPM1–TRPM8.

<span class="mw-page-title-main">TRPM5</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily M member 5 (TRPM5), also known as long transient receptor potential channel 5 is a protein that in humans is encoded by the TRPM5 gene.

<span class="mw-page-title-main">TRPM3</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily M member 3 is a protein that in humans is encoded by the TRPM3 gene.

In enzymology, a flavanone 7-O-beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Isosakuranetin</span> Chemical compound

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 channels.

Daflon is an oral micronized purified phlebotonic flavonoid fraction containing 90% diosmin and 10% hesperidin. It is manufactured by Laboratoires Servier and often used to treat or manage disorders of the blood vessels. Flavonoids are a type of phytochemical that have been associated with various effects on human health and are a component of many different pharmaceutical, nutraceutical, and cosmetic preparations. Diosmin is a flavone glycoside that is derived from hesperidin. Hesperidin is a flavone that is extracted from citrus fruits.

Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase (EC 3.2.1.168) is an enzyme with systematic name hesperetin 7-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside) 6-O-alpha-rhamnopyranosyl-beta-glucohydrolase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Neoeriocitrin</span> Chemical compound

Neoeriocitrin is a 7-O-glycoside of the flavanone eriodictyol and the disaccharide neohesperidose . Note that the 'neo' in the name in this case does not refer to the position of the B-ring, but refer to the glycosyl moiety.

<span class="mw-page-title-main">Melitidin</span> Chemical compound

Melitidin is a flavanone glycoside. Melitidin was discovered in bergamot orange juice and exhibits statin-like properties so the juice seems to have hypolipidemic activity.

<span class="mw-page-title-main">Neohesperidin</span> Chemical compound

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 has an intense sweet taste, and is listed as a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association.

<span class="mw-page-title-main">Ononetin</span> Chemical compound

Ononetin is a natural product from the deoxybenzoin group, which is found in the Russian traditional medicine plant Ononis spinosa. It acts as an inhibitor of the transient receptor potential ion channel TRPM3 and has analgesic effects in animal studies, as well as being used for research into the role of TRPM3 in the immune system dysfunction associated with chronic fatigue syndrome.

References

  1. "Hesperetin".
  2. Lewinsohn, E; Britsch, L; Mazur, Y; Gressel, J (1989). "Flavanone Glycoside Biosynthesis in Citrus: Chalcone Synthase, UDP-Glucose:Flavanone-7-O-Glucosyl-Transferase and -Rhamnosyl-Transferase Activities in Cell-Free Extracts". Plant Physiology. 91 (4): 1323–1328. doi:10.1104/pp.91.4.1323. PMC   1062186 . PMID   16667183.
  3. Majumdar S.; Srirangam, R. (2009). "Solubility, stability, physicochemical characteristics and in vitro ocular tissue permeability of hesperidin: a natural bioflavonoid". Pharm. Res. 26 (5): 1217–1225. doi:10.1007/s11095-008-9729-6. PMC   2664388 . PMID   18810327.
  4. http://ccd.chemnetbase.com/AAA00.entry?parentCHNumber=CNB06-R:CNB07-S%5B%5D
  5. http://www.newcropslisting.info/listing/species_pages_C/Cordia_obliqua.htm%5B%5D
  6. Alvarez‐Collazo, Julio; López‐Requena, Alejandro; Galán, Loipa; Talavera, Ariel; Alvarez, Julio L.; Talavera, Karel (27 March 2019). "The citrus flavanone hesperetin preferentially inhibits slow‐inactivating currents of a long QT syndrome type 3 syndrome Na+ channel mutation". British Journal of Pharmacology. 176 (8): 1090–1105. doi:10.1111/bph.14577. PMC   6451064 . PMID   30650182.
  7. Straub, Isabelle; Krügel, Ute; Mohr, Florian; Teichert, Jens; Rizun, Oleksandr; Konrad, Maik; Oberwinkler, Johannes; Schaefer, Michael (November 2013). "Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo". Molecular Pharmacology. 84 (5): 736–750. doi:10.1124/mol.113.086843. ISSN   1521-0111. PMID   24006495.