Phloretin

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Phloretin
Phloretin.png
Identifiers
CAS number 60-82-2 YesY
PubChem 4788
ChemSpider 4624 N
UNII S5J5OE47MK YesY
ChEBI CHEBI:17276 N
Jmol-3D images Image 1
Properties
Molecular formula C15H14O5
Molar mass 274.26 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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

Pharmacology[edit]

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[edit]

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

Glycosides[edit]

See also[edit]

References[edit]

  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. 
  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. doi:10.1111/j.1463-1326.2008.00982.x.  edit
  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.  edit
  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.