Phloretin: Difference between revisions

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| pmid = 11739871
| pmid = 11739871
}}</ref> An important effect of this is the inhibition of glucose absorption by the small intestine<ref name=Crespy2001/> and the inhibition of [[renal glucose reabsorption]].<ref name=Idris2009/> Phloretin also inhibits a variety of [[urea transporter]]s.<ref>{{Cite journal| doi = 10.1073/pnas.0401704101| issn = 0027-8424| volume = 101| issue = 19| pages = 7469–7474| last = Fenton| first = Robert A. |author2=Chung-Lin Chou |author3=Gavin S. Stewart |author4=Craig P. Smith |author5=Mark A. Knepper| title = Urinary concentrating defect in mice with selective deletion of phloretin-sensitive urea transporters in the renal collecting duct| journal = Proceedings of the National Academy of Sciences of the United States of America| accessdate = 2012-10-21| date = 2004-05-11| url = http://www.pnas.org/content/101/19/7469 | pmid=15123796 | pmc=409942}}</ref><ref>{{Cite journal| issn = 1931-857X| volume = 280| issue = 3| pages = –487-F494| last = Shayakul| first = Chairat|author2=Hiroyasu Tsukaguchi |author3=Urs V. Berger |author4=Matthias A. Hediger | title = Molecular characterization of a novel urea transporter from kidney inner medullary collecting ducts| journal = American Journal of Physiology. Renal Physiology| accessdate = 2012-10-21| date = 2001-03-01| url = http://ajprenal.physiology.org/content/280/3/F487}}</ref> It induces urea loss and [[Osmotic diuresis|diuresis]] when coupled with high protein diets.
}}</ref> An important effect of this is the inhibition of glucose absorption by the small intestine<ref name=Crespy2001/> and the inhibition of [[renal glucose reabsorption]].<ref name=Idris2009/> Phloretin also inhibits a variety of [[urea transporter]]s.<ref>{{Cite journal| doi = 10.1073/pnas.0401704101| issn = 0027-8424| volume = 101| issue = 19| pages = 7469–7474| last = Fenton| first = Robert A. |author2=Chung-Lin Chou |author3=Gavin S. Stewart |author4=Craig P. Smith |author5=Mark A. Knepper| title = Urinary concentrating defect in mice with selective deletion of phloretin-sensitive urea transporters in the renal collecting duct| journal = Proceedings of the National Academy of Sciences of the United States of America| accessdate = 2012-10-21| date = 2004-05-11| url = http://www.pnas.org/content/101/19/7469 | pmid=15123796 | pmc=409942}}</ref><ref>{{Cite journal| issn = 1931-857X| volume = 280| issue = 3| pages = –487-F494| last = Shayakul| first = Chairat|author2=Hiroyasu Tsukaguchi |author3=Urs V. Berger |author4=Matthias A. Hediger | title = Molecular characterization of a novel urea transporter from kidney inner medullary collecting ducts| journal = American Journal of Physiology. Renal Physiology| accessdate = 2012-10-21| date = 2001-03-01| url = http://ajprenal.physiology.org/content/280/3/F487}}</ref> It induces urea loss and [[Osmotic diuresis|diuresis]] when coupled with high protein diets.

Phloretin has been found to inhibit weight gain and improve metabolic homeostasis in mice fed with high-fat diet. <ref>{{Cite journal|last=Alsanea|first=Sary|last2=Gao|first2=Mingming|last3=Liu|first3=Dexi|date=May 2017|title=Phloretin Prevents High-Fat Diet-Induced Obesity and Improves Metabolic Homeostasis|url=https://www.ncbi.nlm.nih.gov/pubmed/28197827|journal=The AAPS journal|volume=19|issue=3|pages=797–805|doi=10.1208/s12248-017-0053-0|issn=1550-7416|pmid=28197827}}</ref>


Phloretin has been found to inhibit [[GLUT2]]{{citation needed|date=October 2016}} and [[aquaporin 9]] (AQP9) on mouse [[hepatocyte]]s.<ref>{{Cite journal|last=Fenton|first=Robert A.|last2=Chou|first2=Chung-Lin|last3=Stewart|first3=Gavin S.|last4=Smith|first4=Craig P.|last5=Knepper|first5=Mark A.|date=2004-05-11|title=Urinary concentrating defect in mice with selective deletion of phloretin-sensitive urea transporters in the renal collecting duct|url=http://www.pnas.org/content/101/19/7469|journal=Proceedings of the National Academy of Sciences of the United States of America|language=en|volume=101|issue=19|pages=7469–7474|doi=10.1073/pnas.0401704101|issn=0027-8424|pmid=15123796|pmc=409942}}</ref>
Phloretin has been found to inhibit [[GLUT2]]{{citation needed|date=October 2016}} and [[aquaporin 9]] (AQP9) on mouse [[hepatocyte]]s.<ref>{{Cite journal|last=Fenton|first=Robert A.|last2=Chou|first2=Chung-Lin|last3=Stewart|first3=Gavin S.|last4=Smith|first4=Craig P.|last5=Knepper|first5=Mark A.|date=2004-05-11|title=Urinary concentrating defect in mice with selective deletion of phloretin-sensitive urea transporters in the renal collecting duct|url=http://www.pnas.org/content/101/19/7469|journal=Proceedings of the National Academy of Sciences of the United States of America|language=en|volume=101|issue=19|pages=7469–7474|doi=10.1073/pnas.0401704101|issn=0027-8424|pmid=15123796|pmc=409942}}</ref>

Revision as of 16:13, 22 November 2017

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 weight gain and improve metabolic homeostasis in mice fed with high-fat diet. [8]

Phloretin has been found to inhibit GLUT2[citation needed] and aquaporin 9 (AQP9) on mouse hepatocytes.[9]

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.
  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. PMC 409942. PMID 15123796. 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.
  8. ^ Alsanea, Sary; Gao, Mingming; Liu, Dexi (May 2017). "Phloretin Prevents High-Fat Diet-Induced Obesity and Improves Metabolic Homeostasis". The AAPS journal. 19 (3): 797–805. doi:10.1208/s12248-017-0053-0. ISSN 1550-7416. PMID 28197827.
  9. ^ Fenton, Robert A.; Chou, Chung-Lin; Stewart, Gavin S.; Smith, Craig P.; Knepper, Mark A. (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. PMC 409942. PMID 15123796.


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