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Phloretin

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Phloretin
Names
IUPAC name
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Other names
Dihydronaringenin
Phloretol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.444 Edit this at Wikidata
UNII
  • InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2 ☒N
    Key: VGEREEWJJVICBM-UHFFFAOYSA-N ☒N
  • InChI=1/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
    Key: VGEREEWJJVICBM-UHFFFAOYAB
  • C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O
Properties
C15H14O5
Molar mass 274.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Phloretin is a dihydrochalcone, a type of natural phenols. It can be found in apple tree leaves[1] and the Manchurian apricot.[2]

Pharmacology

Phloretin inhibits the active transport of glucose into cells by SGLT1 and SGLT2, though the inhibition is weaker than by its glycoside phlorizin.[3] Orally consumed phlorizin is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.[4][5] An important effect of this is the inhibition of glucose absorption by the small intestine[5] and the inhibition of renal glucose reabsorption.[4] Phloretin also inhibits a variety of urea transporters.[6][7] It induces urea loss and diuresis when coupled with high protein diets.

Phloretin has been found to inhibit GLUT2.

Metabolism

Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol.

Glycosides

See also

References

  1. ^ Picinelli A.; Dapena E.; Mangas J. J. (1995). "Polyphenolic pattern in apple tree leaves in relation to scab resistance. A preliminary study". Journal of Agricultural and Food Chemistry. 43 (8): 2273–2278. doi:10.1021/jf00056a057.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ "Manchurian Apricot (Prunus armeniaca var. mandshurica)" (PDF). North Dakota State University. Retrieved January 30, 2014.
  3. ^ Chan, Stephen S.; William D. Lotspeich (1962-12-01). "Comparative effects of phlorizin and phloretin on glucose transport in the cat kidney". American Journal of Physiology. Legacy Content. 203 (6): 975–979. ISSN 0002-9513. Retrieved 2012-10-21.
  4. ^ a b Idris, I.; Donnelly, R. (2009). "Sodium-glucose co-transporter-2 inhibitors: An emerging new class of oral antidiabetic drug". Diabetes, Obesity and Metabolism. 11 (2): 79–88. doi:10.1111/j.1463-1326.2008.00982.x.
  5. ^ a b Crespy, V.; Aprikian, O.; Morand, C.; Besson, C.; Manach, C.; Demigné, C.; Rémésy, C. (2001). "Bioavailability of phloretin and phloridzin in rats". The Journal of Nutrition. 131 (12): 3227–3230. PMID 11739871.
  6. ^ Fenton, Robert A.; Chung-Lin Chou; Gavin S. Stewart; Craig P. Smith; Mark A. Knepper (2004-05-11). "Urinary concentrating defect in mice with selective deletion of phloretin-sensitive urea transporters in the renal collecting duct". Proceedings of the National Academy of Sciences of the United States of America. 101 (19): 7469–7474. doi:10.1073/pnas.0401704101. ISSN 0027-8424. Retrieved 2012-10-21.
  7. ^ Shayakul, Chairat; Hiroyasu Tsukaguchi; Urs V. Berger; Matthias A. Hediger (2001-03-01). "Molecular characterization of a novel urea transporter from kidney inner medullary collecting ducts". American Journal of Physiology. Renal Physiology. 280 (3): –487-F494. ISSN 1931-857X. Retrieved 2012-10-21.


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