| Revision as of 12:48, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,283 edits Saving copy of the {{chembox}} taken from revid 449572090 of page Phlorizin for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 07:07, 25 August 2024 edit Sufangxi (talk | contribs)11 editsm Not mentioned in the ref.Tag: Visual edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 409318549 |
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| verifiedrevid = 464204632 |
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| ImageFile = Phlorhizin.svg |
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| ImageFile = Phlorhizin.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = 1-oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one |
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| IUPACName = 1--3-(4-hydroxyphenyl)propan-1-one |
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| SystematicName = 1-(2,4-Dihydroxy-6-<nowiki/>{oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one |
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| OtherNames = Isosalipurposide |
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| OtherNames = Isosalipurposide |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| IUPHAR_ligand = 4757 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CU9S17279X |
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| UNII = CU9S17279X |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 245067 --> |
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| ChEMBL = 245067 |
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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 |
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| InChIKey1 = IOUVKUPGCMBWBT-GHRYLNIYSA-N |
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| InChI1 = 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 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 60-81-1 |
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| CASNo = 60-81-1 |
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| PubChem = 6072 |
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| PubChem = 6072 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5847 |
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| ChEBI = 8113 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 16498836 |
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| StdInChIKey = IOUVKUPGCMBWBT-GHRYLNIYSA-N |
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| SMILES = O=C(c2c(O1O((O)(O)1O)CO)cc(O)cc2O)CCc3ccc(O)cc3 |
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| SMILES = c1cc(ccc1CCC(=O)c2c(cc(cc2O3((((O3)CO)O)O)O)O)O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI=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 |
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| StdInChIKey = IOUVKUPGCMBWBT-QNDFHXLGSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=21|H=24|O=10 |
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| C=21 | H=24 | O=10 |
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| Appearance = White solid |
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| ExactMass = 436.136947 u |
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| Density = |
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| Appearance = White to yellow crystalline solid |
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| MeltingPtC = 106 to 109 |
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| Density = |
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| BoilingPtC = 200 |
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| MeltingPt = 106–109 °C |
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| BoilingPt_notes = decomposition |
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| BoilingPt = |
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| Solubility = |
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| Solubility = water, low MW alcohols |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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'''Phlorizin''' is a ] of ], a ]. A white solid, samples often appear yellowing to impurities. It is of sweet taste and contains four molecules of ]. It is poorly soluble in ] and cold water, but soluble in ] and hot water. Upon prolonged exposure to aqueous solutions phlorizin ] to phloretin and glucose. |
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<ref>{{cite journal |doi=10.1002/dmrr.532|title=Phlorizin: A review|year=2005|last1=Ehrenkranz|first1=Joel R. L.|last2=Lewis|first2=Norman G.|last3=Ronald Kahn|first3=C.|last4=Roth|first4=Jesse|journal=Diabetes/Metabolism Research and Reviews|volume=21|issue=1|pages=31–38|pmid=15624123|s2cid=37909306}}</ref> |
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==Occurrence== |
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Phlorizin is found primarily in unripe ''Malus'' (])<ref>{{cite journal |last1=Makarova |first1=Elina |last2=Górnaś |first2=Paweł |last3=Konrade |first3=Ilze |last4=Tirzite |first4=Dace |last5=Cirule |first5=Helena |last6=Gulbe |first6=Anita |last7=Pugajeva |first7=Iveta |last8=Seglina |first8=Dalija |last9=Dambrova |first9=Maija |display-authors=7 |date=2015 |title=Acute anti-hyperglycaemic effects of an unripe apple preparation containing phlorizin in healthy volunteers: A preliminary study |journal=Journal of the Science of Food and Agriculture |volume=95 |issue=3 |pages=560–568 |doi=10.1002/jsfa.6779 |pmid=24917557}}</ref> root bark of ],<ref>{{cite journal |last=Bays |first=Harold |date=2013 |title=Sodium glucose co-transporter type 2 (SGLT2) inhibitors: Targeting the kidney to improve glycemic control in diabetes mellitus |journal=Diabetes Therapy |volume=4 |issue=2 |pages=195–220 |doi=10.1007/s13300-013-0042-y |doi-access=free |pmc=3889318 |pmid=24142577}}</ref> and trace amounts have been found in strawberry.<ref>{{cite journal |last1=Hilt |first1=Petra |last2=Schieber |first2=Andreas |last3=Yildirim |first3=Caner |last4=Arnold |first4=Gabi |last5=Klaiber |first5=Iris |last6=Conrad |first6=Jürgen |last7=Beifuss |first7=Uwe |last8=Carle |first8=Reinhold |display-authors=7 |date=2003 |title=Detection of phloridzin in strawberries (<em>Fragaria x ananassa</em> Duch.) by HPLC–PDA–MS/MS and NMR spectroscopy |journal=Journal of Agricultural and Food Chemistry |volume=51 |issue=10 |pages=2896–2899 |doi=10.1021/jf021115k |pmid=12720368}}</ref> In ''Malus'', it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such as ] (''Pyrus communis''), ], and other ] trees in the '']'' do not contain phlorizin.<ref>{{cite journal |last1=Gosch |first1=Christian |last2=Halbwirth |first2=Heidi |last3=Stich |first3=Karl |date=2010 |title=Phloridzin: Biosynthesis, distribution and physiological relevance in plants |journal=Phytochemistry |volume=71 |issue=8–9 |pages=838–843 |doi=10.1016/j.phytochem.2010.03.003 |pmid=20356611}}</ref> Phlorizin is a phytochemical that belongs to the class of ]s. In natural sources, it may occur with other polyphenols such as ], ], ], ]s, and ]. |
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==Pharmacology== |
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Phlorizin is an inhibitor of ] and ] because it competes with ] for binding to the carrier; this action reduces ] ], lowering the amount of glucose in the blood.<ref name=Example2006>{{cite journal |last1=Rossetti |first1=Luciano |last2=Smith |first2=Douglas |last3=Shulman |first3=Gerald I. |last4=Papachristou |first4=Dimitrios |last5=DeFronzo |first5=Ralph A. |date=1987 |title=Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats |journal=The Journal of Clinical Investigation |volume=79 |issue=5 |pages=1510–1515 |doi=10.1172/JCI112981 |doi-access=free |pmc=424427 |pmid=3571496}}</ref><ref>{{cite journal |last1=Tatoń |first1=Jan |last2=Piątkiewicz |first2=Paweł |last3=Czech |first3=Anna |date=2010 |title=Molecular physiology of cellular glucose transport – A potential area for clinical studies in diabetes mellitus |journal=Endokrynologia Polska |url=https://journals.viamedica.pl/endokrynologia_polska/article/view/25386 |volume=61 |issue=3 |pages=303–310 |pmid=20602306}}</ref> Phlorizin was studied as a potential pharmaceutical treatment for ], but has since been superseded by more selective and more promising synthetic ], such as ], ] and ].<ref>{{cite journal |last1=Chao |first1=Edward C. |last2=Henry |first2=Robert R. |date=2010 |title=SGLT2 inhibition – A novel strategy for diabetes treatment |journal=Nature Reviews Drug Discovery |volume=9 |issue=7 |pages=551–559 |doi=10.1038/nrd3180 |pmid=20508640}}</ref> Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.<ref name=Idris2009>{{cite journal |last1=Idris |first1=Iskandar |last2=Donnelly |first2=Richard |date=2009 |title=Sodium–glucose co-transporter-2 inhibitors: An emerging new class of oral antidiabetic drug |journal=Diabetes, Obesity and Metabolism |volume=11 |issue=2 |pages=79–88 |doi=10.1111/j.1463-1326.2008.00982.x |doi-access= |pmid=19125776}}</ref><ref name=Crespy2001>{{cite journal |last1=Crespy |first1=Vanessa |last2=Aprikian |first2=Olivier |last3=Morand |first3=Christine |last4=Besson |first4=Catherine |last5=Manach |first5=Claudine |last6=Demigné |first6=Christian |last7=Rémésy |first7=Christian |date=2001 |title=Bioavailability of phloretin and phloridzin in rats |journal=The Journal of Nutrition |volume=131 |issue=12 |pages=3227–3230 |doi=10.1093/jn/131.12.3227 |doi-access=free |pmid=11739871}}</ref> |
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==References== |
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{{Reflist}} |
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{{Dihydrochalcones}} |
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{{Purine receptor modulators}} |
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{{Sodium-glucose transporter modulators}} |
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] |
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] |