Hesperetin

Hesperetin
Hesperetin
Hesperetin
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 Edit this at Wikidata
EC Number
  • 208-290-2
KEGG
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 checkY
    Key: AIONOLUJZLIMTK-AWEZNQCLSA-N checkY
  • 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 solvents Sol. EtOH, alkalis
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Glycosides

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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

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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

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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]

References

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  1. ^ a b c d "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.
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