Phloretin

Phloretin

Phloretin
Identifiers
CAS number  YesY
PubChem
ChemSpider  N
UNII  YesY
ChEBI  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   YesY/N?)

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

Contents

  • Pharmacology 1
  • Metabolism 2
  • Glycosides 3
  • See also 4
  • References 5

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.  
  2. ^ )"mandshurica var. Prunus armeniaca (Manchurian Apricot" (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.  
  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.  
  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.  
  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.  
  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.