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. [1] The 7-O-glycoside of hesperetin, hesperidin, is a naturally occurring flavanone-glycoside, the main flavonoid in grapefruits, lemons, and sweet oranges. [1] [2]

Contents

Glycosides

Various glycosides of hesperetin are known, including hesperidin (hesperetin-7-O-rutinoside), a water-insoluble flavonoid glycoside with low water solubility, [3] Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. Neohesperidin is the 7-O-neohesperidoside of hesperetin.

Metabolism

Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. [1] Upon digestion in the gastrointestinal tract, hesperetin as for all flavonoids is rapidly metabolized in intestinal and liver cells, releasing smaller metabolites into the blood and urine for excretion. [1] The biological effects of such metabolites in vivo are unknown.

Laboratory research

In vitro , hesperetin may affect the slow inactivation phase of inward sodium current channels, and therefore could be used as a template to develop drugs against cardiac arrhythmias. [4] Hesperetin also inhibits TRPM3 channels in vitro. [5]

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">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">CYP3A4</span> Enzyme that metabolizes substances by oxidation

Cytochrome P450 3A4 is an important enzyme in the body, mainly found in the liver and in the intestine, which in humans is encoded by CYP3A4 gene. It oxidizes small foreign organic molecules (xenobiotics), such as toxins or drugs, so that they can be removed from the body. It is highly homologous to CYP3A5, another important CYP3A enzyme.

<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 flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.

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

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside 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 (debittering) 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 is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">CYP1A1</span> Protein-coding gene in the species Homo sapiens

Cytochrome P450, family 1, subfamily A, polypeptide 1 is a protein that in humans is encoded by the CYP1A1 gene. The protein is a member of the cytochrome P450 superfamily of enzymes.

<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.

<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.

<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.

The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.

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.

<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 in preclinical research.

<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.

<span class="mw-page-title-main">4'-Hydroxyflavanone</span> Chemical compound

4'-Hydroxyflavanone is a naturally occurring monohydroxybenzoic acid and a member of the 4'-hydroxyflavanones family. It is white to pale orange in color and generally soluble in organic solvents such as chloroform and ethanol, but insoluble with water. 4'-Hydroxyflavanone is a naturally occurring product with cosmetic and potential clinical applications that is found in plants such as carnations.

References

  1. 1 2 3 4 "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 10 May 2024.
  2. "Hesperetin". PubChem, US National Library of Medicine. 4 May 2024.
  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. 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.
  5. 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.