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phlorizin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/09 13:35:51」(JST)

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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blood.^[3]^[4] Phlorizin was studied as a potential pharmaceutical treatment for type II diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as canagliflozin and dapagliflozin.^[5]^[6] Orally consumed phlorizin is nearly entirely converted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

^ Isosalipurposide on PubChem
^ http://www.chemkind.com/chemicals-p_3685039_phloridzin.htm
^ 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. doi:10.1172/JCI112981. PMC 424427. PMID 3571496.
^ 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.
^ Chao, Edward C.; Henry, Robert R. (2010). "SGLT2 inhibition — a novel strategy for diabetes treatment". Nature Reviews Drug Discovery 9 (7): 551–9. doi:10.1038/nrd3180. PMID 20508640.
^ SGLT2 Inhibitors - UEndocrine.com
^ 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.
^ 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.
^ http://www.chamberlins.com/ns/DisplayMonograph.asp?StoreID=2CB86C7B36BE4CFD914079104818C49B&DocID=bottomline-phlorizin

English Journal

Antioxidant and cytoprotective properties of partridgeberry polyphenols.

Bhullar KS1, Rupasinghe HP2.
Food chemistry.Food Chem.2015 Feb 1;168:595-605. doi: 10.1016/j.foodchem.2014.07.103. Epub 2014 Jul 30.
Partridgeberry (Vaccinium vitis-idaea) is a polyphenol-rich berry of the Ericaceous family, grown in Newfoundland and Labrador province of Canada. The aims of this study were to identify extraction solvents for the maximum recovery of polyphenols, to establish fractionation technique for isolation o
PMID 25172753

Membrane dipole modifiers modulate single-length nystatin channels via reducing elastic stress in the vicinity of the lipid mouth of a pore.

Chulkov EG1, Schagina LV2, Ostroumova OS2.
Biochimica et biophysica acta.Biochim Biophys Acta.2015 Jan;1848(1 Pt A):192-9. doi: 10.1016/j.bbamem.2014.09.004. Epub 2014 Sep 16.
The polyene antifungal antibiotic nystatin confers its biological activity by forming pores in the membranes of target cells. Exposure of only one side of the membrane to nystatin is more relevant than two-side exposure because in vivo antibiotic molecules initially interact with cell membrane from
PMID 25223717

The transport mechanism of the human sodium/myo-inositol transporter 2 (SMIT2/SGLT6), a member of the LeuT structural family.

Sasseville LJ1, Longpré JP1, Wallendorff B1, Lapointe JY2.
American journal of physiology. Cell physiology.Am J Physiol Cell Physiol.2014 Sep 1;307(5):C431-41. doi: 10.1152/ajpcell.00054.2014. Epub 2014 Jun 18.
The sodium/myo-inositol transporter 2 (SMIT2) is a member of the SLC5A gene family, which is believed to share the five-transmembrane segment inverted repeat of the LeuT structural family. The two-electrode voltage-clamp (TEVC) technique was used to measure the steady-state and the pre-steady-state
PMID 24944204

Japanese Journal

Phlorhizin感度の個体差に関する臨床的研究

大海健太郎
医学研究 29(11), ????, 1959-11
NAID 40017475319

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リンク元	「phlorizin」

「phlorizin」

Phlorizin
Names
	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
Identifiers
CAS Registry Number	60-81-1
ChEBI	CHEBI:8113
ChEMBL	ChEMBL245067
ChemSpider	16498836
	InChI InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1 ; Key: IOUVKUPGCMBWBT-QNDFHXLGSA-N ; InChI=1/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1; Key: IOUVKUPGCMBWBT-QNDFHXLGBL ;
IUPHAR/BPS	4757
Jmol-3D images	Image
PubChem	6072
	SMILES c1cc(ccc1CCC(=O)c2c(cc(cc2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O ;
UNII	CU9S17279X
Properties
Chemical formula	C21H24O10
Molar mass	436.41 g·mol−1
Appearance	White to yellow crystalline solid
Melting point	106 to 109 °C (223 to 228 °F; 379 to 382 K)
	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

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フロリジン

関: phlorhizin

[1] Isosalipurposide on PubChem

[2] ttp://www.chemkind.com/chemicals-p_3685039_phloridzin.htm

[Example2006-3] 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. doi:10.1172/JCI112981. PMC 424427. PMID 3571496.

[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. doi:10.1038/nrd3180. PMID 20508640.

[6] SGLT2 Inhibitors - UEndocrine.com

[Idris2009-7] 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.

[Crespy2001-8] 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.

[9] ttp://www.chamberlins.com/ns/DisplayMonograph.asp?StoreID=2CB86C7B36BE4CFD914079104818C49B&DocID=bottomline-phlorizin

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phlorhizin