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Phlorizin

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Phlorizin
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IUPAC name
1-[2,4-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one
Other names
Isosalipurposide
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60-81-1 7pxY
ChEBI CHEBI:8113 7pxN
ChEMBL ChEMBL245067 7pxN
ChemSpider 16498836 7pxN
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C21H24O10
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance White to yellow crystalline solid
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phlorizin is a 2'-glucoside of phloretin. It belongs to the group of dihydrochalcones, a type of flavonoids.

Occurrence

Phlorizin is naturally occurring in some plants. It could be found in the bark of pear (Pyrus communis), apple, cherry and other fruit trees (Rosaceae) and is responsible for the petal color in Dianthus caryophyllus.[1] Phloridzin, a phytocemical belongs to a class of polyphenols. It may be present with other polyphenols such as quercetin, catechin, epicatechin, procynidins, rutin etc. These polyhydroxy compounds have been proved to be potent antioxidants.[2]

Properties

Phlorizin is a white to yellow crystalline solid with a melting point of 106–109 °C. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose.

Pharmacology

Phlorizin is a competitive inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this reduces renal glucose transport, lowering the amount of glucose in the blood.[3][4] Phlorizin was studied as a potential pharmaceutical treatment for type II diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as canagliflozin and dapagliflozin.[5][6] Orally consumed phlorizin is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.[7][8] Apart from conventional antidiabetic activity, phlorizin is also studied for its antioxidant activity.[9]

References

  1. ^ Isosalipurposide on PubChem
  2. ^ http://www.chemkind.com/chemicals-p_3685039_phloridzin.htm
  3. ^ Rossetti L, Smith D, Shulman GI, Papachristou D, DeFronzo RA (May 1987). "Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats". J Clin Invest. 79 (5): 1510–5. PMC 424427. PMID 3571496. doi:10.1172/JCI112981. 
  4. ^ Tatoń, J; Piatkiewicz, P; Czech, A. (May–Jun 2010). "Molecular physiology of cellular glucose transport - a potential area for clinical studies in diabetes mellitus". Endokrynol Pol 61 (3): 303–10. PMID 20602306. 
  5. ^ Chao, Edward C.; Henry, Robert R. (2010). "SGLT2 inhibition — a novel strategy for diabetes treatment". Nature Reviews Drug Discovery 9 (7): 551–9. PMID 20508640. doi:10.1038/nrd3180. 
  6. ^ SGLT2 Inhibitors - UEndocrine.com
  7. ^ 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
  8. ^ 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
  9. ^ http://www.chamberlins.com/ns/DisplayMonograph.asp?StoreID=2CB86C7B36BE4CFD914079104818C49B&DocID=bottomline-phlorizin