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- phlorhizin
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/06/11 06:20:35」(JST)
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Phlorizin
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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
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Other names
Isosalipurposide
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Identifiers |
CAS Number
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60-81-1 Y |
ChEBI |
CHEBI:8113 N |
ChEMBL |
ChEMBL245067 N |
ChemSpider |
16498836 N |
IUPHAR/BPS
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4757 |
Jmol 3D model |
Interactive image |
PubChem |
6072 |
UNII |
CU9S17279X Y |
InChI
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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 N
Key: IOUVKUPGCMBWBT-QNDFHXLGSA-N N
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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
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SMILES
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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
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Properties |
Chemical formula
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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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N verify (what is YN ?) |
Infobox references |
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Phlorizin is a 2'-glucoside of phloretin. It belongs to the group of dihydrochalcones, a type of flavonoids.
Contents
- 1 Occurrence
- 2 Properties
- 3 Pharmacology
- 4 References
Occurrence
Phlorizin, or phloridzin is a naturally occurring flavonoid produced in some plants. It is found primarily in Malus (apple) species although trace amounts exist in other species. In Malus it is most abundant in vegetative tissues (leaves, bark, etc...) and seeds. Closely related species, such as pear (Pyrus communis), cherry and other fruit trees in the Rosaceae do not contain phloridzin.[1] Trace amounts have been reported in strawberry [2] and it is responsible for the petal color in Dianthus caryophyllus.[3] 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.[4]
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.[5][6] 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.[7][8] Orally consumed phlorizin is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.[9][10] Apart from conventional antidiabetic activity, phlorizin is also studied for its antioxidant activity.[11]
References
- ^ Gosch, C.; Halbwirth, H.; Stich, K. (2010). "Phloridzin: biosynthesis, distribution and physiological relevance in plants". Phytochemistry 71 (8): 838–843. doi:10.1016/j.phytochem.2010.03.003.
- ^ Hilt, P.; Schieber, A.; Yildirim, C.; Arnold, G.; Klaiber, I.; Conrad, J.; Carle, R. (2003). "Detection of phloridzin in strawberries (Fragaria x ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy". Journal of Agricultural and Food Chemistry 51 (10): 2896–2899. doi:10.1021/jf021115k.
- ^ 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): 79–88. 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
Dihydrochalcones and their glycosides
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Dihydrochalcones: |
- 3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone
- 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol)
- 2′-hydroxy-3′,4′,5′,6′-tetramethoxychalcone (kanakugiol)
- methyl linderone
- 2′,3′,4′,5′,6′-pentamethoxychalcone (pedicellin)
- Phloretin
- Pinocembrin chalcone
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Dihydrochalcone glycosides: |
- Aspalathin
- Naringin dihydrochalcone
- Neohesperidin dihydrochalcone
- Nothofagin
- Phlorizin
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UpToDate Contents
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English Journal
- Inhibition of SGLT1 abrogates preconditioning-induced cardioprotection against ischemia-reperfusion injury.
- Kanwal A1, Nizami HL, Mallapudi S2, Putcha UK2, Mohan GK3, Banerjee SK4.
- Biochemical and biophysical research communications.Biochem Biophys Res Commun.2016 Apr 1;472(2):392-8. doi: 10.1016/j.bbrc.2016.02.016. Epub 2016 Feb 23.
- BACKGROUND: Recently, we reported Na+/glucose co-transporter (SGLT1) expression in mouse and human heart. We speculated that SGLT1 might play an important role in ischemic preconditioning-induced cardioprotection. Therefore, the present study was designed to find the role of SGLT1 in ischemic precon
- PMID 26920054
- Bile Diversion in Roux-en-Y Gastric Bypass Modulates Sodium-Dependent Glucose Intestinal Uptake.
- Baud G1, Daoudi M2, Hubert T1, Raverdy V1, Pigeyre M1, Hervieux E1, Devienne M1, Ghunaim M1, Bonner C1, Quenon A1, Pigny P3, Klein A4, Kerr-Conte J1, Gmyr V1, Caiazzo R1, Pattou F5.
- Cell metabolism.Cell Metab.2016 Mar 8;23(3):547-53. doi: 10.1016/j.cmet.2016.01.018. Epub 2016 Feb 25.
- Gastro-intestinal exclusion by Roux-en-Y gastric bypass (RYGB) improves glucose metabolism, independent of weight loss. Although changes in intestinal bile trafficking have been shown to play a role, the underlying mechanisms are unclear. We performed RYGB in minipigs and showed that the intestinal
- PMID 26924216
- Experimental diabetes induced by alloxan and streptozotocin: The current state of the art.
- Radenković M1, Stojanović M2, Prostran M3.
- Journal of pharmacological and toxicological methods.J Pharmacol Toxicol Methods.2016 Mar-Apr;78:13-31. doi: 10.1016/j.vascn.2015.11.004. Epub 2015 Nov 17.
- Diabetes mellitus is a chronic metabolic disorder with a high prevalence worldwide. Animal models of diabetes represent an important tool in diabetes investigation that helps us to avoid unnecessary and ethically challenging studies in human subjects, as well as to obtain a comprehensive scientific
- PMID 26596652
Japanese Journal
- Phlorizin Prevents Electrically-Induced Ventricular Tachyarrhythmia during Ischemia in Langendorff-Perfused Guinea-Pig Hearts
- Hirose Masamichi,Shibazaki Toshihide,Nakada Tsutomu [他]
- Biological & pharmaceutical bulletin 37(7), 1168–1176, 2014-07
- NAID 40020103594
- Enzymatically Modified Isoquercitrin, .ALPHA.-Oligoglucosyl Quercetin 3-O-Glucoside, Is Absorbed More Easily than Other Quercetin Glycosides or Aglycone after Oral Administration in Rats
- Makino Toshiaki,Shimizu Ryosuke,Kanemaru Misaki [他],Suzuki Yukio,Moriwaki Masamitsu,Mizukami Hajime
- Biological and Pharmaceutical Bulletin 32(12), 2034-2040, 2009
- Quercetin, a flavonol contained in various vegetables and herbal medicines, has various biological activities including anti-cancer, anti-allergic and anti-oxidative activities. However, low oral bioa …
- NAID 130000116991
- コンビナトリアルケミストリーを活用した天然物とその類縁体の高速合成法の開発
- 土井 隆行,田中 浩士,高橋 孝志
- 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 65(8), 795-804, 2007-08-01
- … Solid-phase syntheses of combinatorial libraries based on natural products, such as, (i) vitamin D<SUB>3</SUB>, (ii) macrosphelide A, (iii) aurilide, (iv) aeruginosin 298-A, (v) trisaccharides, (vi) clavulone, (vii) 15-deoxyPGJ<SUB>2</SUB>, (viii) phlorizin, (ix) naltrindole, and (x) norbinaltorphimine are described. …
- NAID 10019753608
Related Links
- 1. Diabetes Metab Res Rev. 2005 Jan-Feb;21(1):31-8. Phlorizin: a review. Ehrenkranz JR(1), Lewis NG, Kahn CR, Roth J. Author information: (1)Department of Medicine, University of Colorado Health Sciences Center ...
- Phlorizin definition, a bitter, crystalline glucoside, C 2 1 H 2 4 O 1 0 , obtained from the root bark of the apple, pear, cherry, etc.: formerly used as a tonic and in the treatment of malaria; now used chiefly in biochemical research ...
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