Purpurogallin: Difference between revisions

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 {{chembox
+| Verifiedfields = changed
-| verifiedrevid = 415112548
+| Watchedfields = changed
+| verifiedrevid = 423643879
 | Name = Purpurogallin
 | ImageFile = Purpurogallin.svg
-| ImageSize = 250px
+| ImageSize = 200px
 | ImageName = Chemical structure of purpurogallin
 | ImageAlt = Chemical structure of purpurogallin
-| IUPACName = <nowiki>2,3,4,5-tetrahydroxybenzo[7]annulen-6-one</nowiki>
+| PIN = 1,7,8,9-Tetrahydroxy-2''H''-benzo[7]annulen-2-one
 | OtherNames = Purpurogalline<br>2,3,4,6-Tetrahydroxybenzocyclohepten-5-one<br>PPG
-|Section1= {{Chembox Identifiers
+|Section1={{Chembox Identifiers
+| CASNo_Ref = {{cascite|correct|??}}
 | CASNo = 569-77-7
+| UNII_Ref = {{fdacite|correct|FDA}}
-| CASNo_Ref =
-| CASOther =
+| UNII = L3Z7U4N28P
+| CASNoOther =
 | PubChem = 5281571
 | SMILES = C1=CC(=O)C(=C2C(=C1)C=C(C(=C2O)O)O)O
+|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)
+|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = WDGFFVCWBZVLCE-UHFFFAOYSA-N
+|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID = 4444893
 | InChI =
-| MeSHName =
+|  MeSHName = C026133
+|  ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 8647
+|  KEGG_Ref = {{keggcite|changed|kegg}}
+| KEGG = C09964
 }}
-|Section2= {{Chembox Properties
+|Section2={{Chembox Properties
+| C=11|H=8|O=5
-| Formula = C<sub>11</sub>H<sub>8</sub>O<sub>5</sub>
+| Appearance = Red crystalline solid
-| MolarMass = 220.17 g/mol
-| ExactMass = 220.037173 u
-| Appearance =
 | Density =
-| MeltingPt = <!-- °C -->
+| MeltingPt =
-| BoilingPt = <!-- °C -->
+| BoilingPt =
 | Solubility =
 }}
 }}
-'''Purpurogallin''' is a red, crystalline compound, and the aglycon of several glycosides from [[nutgall]]s and [[oak bark]]s.<ref>Molecular structure and antioxidant specificity of purpurogallin in three types of human cardiovascular cells. Tai-Wing Wu, Ling-Hua Zeng, Jun Wu, Kwok-Pui Fung, Richard D. Weisel, Andrew Hempel and Norman Camerman, Biochemical Pharmacology, Volume 52, Issue 7, 11 October 1996, Pages 1073-1080, {{doi|:10.1016/0006-2952(96)00447-9}}</ref> It can inhibit [[hydroxyestradiol]] methylation by [[catechol-O-methyltransferase]].<ref>Benzo[[tropolone]] inhibitors of estradiol methylation: kinetics and in silico modeling studies. Joshua D. Lambert, Dapeng Chena, Ching Y. Wang, Ni Ai, Shengmin Sang, Chi-Tang Ho, William J. Welsh and Chung S. Yang, Bioorganic & Medicinal Chemistry, Volume 13, Issue 7, 1 April 2005, Pages 2501-2507, {{doi|10.1016/j.bmc.2005.01.037}}</ref>
+'''Purpurogallin''' is an [[aglycone]] natural product. It is an orange-red solid that is soluble in polar organic solvents but not in water.  Its [[glycoside]] (ether-linked to sugar), called dryophantin, is found in [[nutgall]]s and [[oak bark]]s.  Purpurogallin can be prepared by oxidation of [[pyrogallol]] with [[sodium periodate]].<ref>{{cite journal |doi=10.1021/acs.jchemed.1c00699|title=Synthesis and Analytical Characterization of Purpurogallin: A Pharmacologically Active Constituent of Oak Galls |year=2022 |last1=Kelly-Hunt |first1=Alexandra E. |last2=Mehan |first2=Aman |last3=Brooks |first3=Sarah |last4=Leanca |first4=Miron A. |last5=McKay |first5=Jack E. D. |last6=Mahamed |first6=Nashad |last7=Lambert |first7=Daniel |last8=Dempster |first8=Nicola M. |last9=Allen |first9=Robert J. |last10=Evans |first10=Andrew R. |last11=Sarker |first11=Satyajit D. |last12=Nahar |first12=Lutfun |last13=Sharples |first13=George P. |last14=Drew |first14=Michael G. B. |last15=Fielding |first15=Alistair J. |last16=Ismail |first16=Fyaz M. D. |journal=Journal of Chemical Education |volume=99 |issue=2 |pages=983–993 |bibcode=2022JChEd..99..983K |s2cid=245366264 |url=https://researchonline.ljmu.ac.uk/id/eprint/16051/3/Synthesis%20and%20analytical%20characterization%20of%20purpurogallin%20-%20a%20pharmacologically%20active%20constituent%20of%20oak%20galls.pdf }}</ref>
+==Medicinal aspects==
+Purpurogallin is bioactive<ref>{{cite journal | doi = 10.1016/0006-2952(96)00447-9| pmid = 8831727| title = Molecular structure and antioxidant specificity of purpurogallin in three types of human cardiovascular cells| journal = Biochemical Pharmacology| volume = 52| issue = 7| pages = 1073–80| year = 1996| last1 = Wu| first1 = Tai-Wing| last2 = Zeng| first2 = Ling-Hua| last3 = Wu| first3 = Jun| last4 = Fung| first4 = Kwok-Pui| last5 = Weisel| first5 = Richard D| last6 = Hempel| first6 = Andrew| last7 = Camerman| first7 = Norman}}</ref> It can inhibit [[2-Hydroxyestradiol|2-hydroxy]] and [[4-Hydroxyestradiol|4-hydroxyestradiol]] methylation by [[catechol-O-methyltransferase]].<ref>{{cite journal | doi = 10.1016/j.bmc.2005.01.037| title = Benzotropolone inhibitors of estradiol methylation: Kinetics and in silico modeling studies| journal = Bioorganic & Medicinal Chemistry| volume = 13| issue = 7| pages = 2501–7| year = 2005| last1 = Lambert| first1 = Joshua D| last2 = Chen| first2 = Dapeng| last3 = Wang| first3 = Ching Y| last4 = Ai| first4 = Ni| last5 = Sang| first5 = Shengmin| last6 = Ho| first6 = Chi-Tang| last7 = Welsh| first7 = William J| last8 = Yang| first8 = Chung S| pmid = 15755652}}</ref> It potently and specifically inhibits [[TLR1]]/[[TLR2]] activation pathway.<ref>{{cite journal | doi = 10.1002/anie.201204910| pmid = 22969053| title = Discovery of Small-Molecule Inhibitors of the TLR1/TLR2 Complex| journal = Angewandte Chemie International Edition| volume = 51| issue = 49| pages = 12246–9| year = 2012| last1 = Cheng| first1 = Kui| last2 = Wang| first2 = Xiaohui| last3 = Zhang| first3 = Shuting| last4 = Yin| first4 = Hang| pmc=3510333}}</ref>
 ==References==
 {{reflist}}
-[[Category:Natural phenols]]
+[[Category:Polyphenols]]
+[[Category:Tropolones]]
+[[Category:Tetrols]]
+[[Category:Azulenes]]
+[[Category:Pyrogallols]]
-{{Natural-phenol-stub}}
+{{phenol-stub}}