Hesperetin
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| Names | |
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| IUPAC name
(2S)-3′,5,7-Trihydroxy-4′-methoxyflavan-4-one
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| Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
| Identifiers | |
3D model (JSmol)
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| DrugBank | |
| ECHA InfoCard | 100.007.538 |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
[edit]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
[edit]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
[edit]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
[edit]- ^ a b c d "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 10 May 2024.
- ^ "Hesperetin". PubChem, US National Library of Medicine. 4 May 2024.
- ^ 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.
- ^ 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.
- ^ 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.
External links
[edit]
Media related to Hesperetin at Wikimedia Commons
