Revision as of 14:18, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477352029 of page Astilbin for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 18:56, 31 January 2024 edit Donotforgetmycode (talk | contribs)19 editsm →Natural occurrences: Corrected capitalization of "In food" |
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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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| verifiedrevid = 460313836 |
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| verifiedrevid = 477368956 |
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| Name = Astilbin |
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| ImageFile = Astilbin.svg |
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| Name = Astilbin |
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| ImageFile = Astilbin.svg |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| IUPACName = (2''R'',3''R'')-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-oxy-2,3-dihydrochromen-4-one |
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| IUPACName = (2''R'',3''R'')-3′,4′,5,7-Tetrahydroxy-3-(α-<small>L</small>-rhamnopyranosyloxy)flavan-4-one |
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| SystematicName = (2''R'',3''R'')-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{oxy}-2,3-dihydro-4''H''-1-benzopyran-4-one |
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| OtherNames = Isoastilbin<br>Neoastilbin<br>Neoisoastilbin<br>] 3-O-]<br>Taxifolin 3-rhamnoside<br>(2''R''-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one<ref name="anwabio">http://anwabio.com/asti.htm</ref> |
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| OtherNames = Isoastilbin<br>Neoastilbin<br>Neoisoastilbin<br>] 3-O-]<br>Taxifolin 3-rhamnoside<br>(2''R''-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one<ref name="anwabio">http://anwabio.com/asti.htm{{dead link|date=October 2016 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> |
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| Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 54141-72-9 --> |
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| CASNo = 54141-72-9 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = KA92CW3M68 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 486017 |
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| ChEMBL = 486017 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38200 |
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| ChEBI = 38200 |
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| PubChem = 119258 |
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| PubChem = 119258 |
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| KEGG = C17449 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 106533 |
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| ChemSpiderID = 106533 |
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| SMILES = O=C3c4c(O)cc(O)cc4O(c1ccc(O)c(O)c1)3O2O((O)(O)2O)C |
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| SMILES = O=C3c4c(O)cc(O)cc4O(c1ccc(O)c(O)c1)3O2O((O)(O)2O)C |
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| InChI = 1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 |
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| InChI = 1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 |
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| InChIKey = ZROGCCBNZBKLEL-MPRHSVQHBV |
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| InChIKey = ZROGCCBNZBKLEL-MPRHSVQHBV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 |
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| StdInChI = 1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZROGCCBNZBKLEL-MPRHSVQHSA-N |
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| StdInChIKey = ZROGCCBNZBKLEL-MPRHSVQHSA-N |
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}} |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>11</sub> |
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| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>11</sub> |
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| MolarMass = 450.39 g/mol |
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| MolarMass = 450.39 g/mol |
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| Appearance = brown powder<ref name="anwabio"/> |
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| ExactMass = 450.116212 u |
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| Density= |
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| Appearance = brown powder<ref name="anwabio"/> |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Astilbin''' is a ], a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.<ref name="PubChem"></ref> |
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== Natural occurrences == |
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Astilbin can be found in ] (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in '']''<ref name="Batista"></ref> (Fava d'anta, Fabaceae), in the leaves of '']'' (Hypericaceae),<ref name="Moulari">, </ref> in the rhizome of '']'',<ref name="Yoshiyuki"></ref> in the root of '']''<ref name="Ohmori"></ref>(Saxifragaceae), in the rhizome of '']''<ref name="Jianming">{{Cite web |url=http://www.clinchem.org/cgi/content/abstract/clinchem.2006.077297v1 |title=Identification of a New Metabolite of Astilbin, 3'-O-Methylastilbin, and Its Immunosuppressive Activity against Contact Dermatitis, Jianming Guo, Feng Qian, Jianxin Li, Qiang Xu, Ting Chen, 2006 |access-date=2009-08-30 |archive-url=https://web.archive.org/web/20110607122209/http://www.clinchem.org/cgi/content/abstract/clinchem.2006.077297v1 |archive-date=2011-06-07 |url-status=dead }}</ref> (Chinaroot, Smilacaceae) and in the bark of '']''.<ref></ref> |
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; In food |
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It can be isolated from ] processed from '']'' (huang-qui).<ref name="PubChem"/> It is also present in certain wines.<ref>Levels of Stilbene Oligomers and Astilbin in French Varietal Wines and in Grapes during Noble Rot Development, Nicolas Landrault, Fabienne Larronde, Jean-Claude Delaunay, Chantal Castagnino, Joseph Vercauteren, Jean-Michel Merillon, Francis Gasc, Gérard Cros and Pierre-Louis Teissedre, J. Agric. Food Chem., 2002, 50 (7), pages 2046–2052, {{doi|10.1021/jf010794g}}</ref> |
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== Uses == |
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Astilbin can act as an insecticide against '']'' and '']''.<ref name="Batista"/> It shows ''in vitro'' antibacterial activity<ref name="Moulari"/> and activity on burn wound healing.<ref name="Yoshiyuki"/> Astilbin is used in ].<ref name="Ohmori"/> |
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<!--==Metabolism== |
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The enzyme [[ --> |
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== Related compounds == |
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] shows an immunosuppressive activity against ].<ref name="Jianming"/> |
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<!-- ===Glycosides=== --> |
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== References == |
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{{reflist}} |
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{{Flavanonol}} |
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] |
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] |