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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 406730897 |
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| Name = Syringetin |
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| Name = Syringetin |
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| ImageFile = Syringetin.PNG |
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| ImageFile = Syringetin.svg |
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| ImageSize = 200px |
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| ImageName = Chemical structure of syringetin |
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| ImageName = Chemical structure of syringetin |
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| IUPACName = 3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one |
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| IUPACName = 3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavone |
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| SystematicName = 3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4''H''-1-benzopyran-4-one |
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| OtherNames = 3',5'-O-Dimethylmyricetin<br>3',5'-Dimethoxy-3,5,7,4'-tetrahydroxyflavone<br>3,5,7,4'-tetrahydroxy-3',5'dimethoxyflavone |
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| OtherNames = 3′,5′-''O''-Dimethylmyricetin<br>3′,5′-Dimethoxy-3,5,7,4′-tetrahydroxyflavone<br>3,5,7,4′-Tetrahydroxy-3′,5′-dimethoxyflavone |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 4423-37-4 |
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| CASNo = 4423-37-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = |
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| UNII = J68JG79B9W |
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| CASOther = |
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| CASNoOther = |
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| PubChem = 5281953 |
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| PubChem = 5281953 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 18215 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 489142 |
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| SMILES = COc1cc(cc(OC)c1O)C=3Oc2cc(O)cc(O)c2C(=O)C=3O |
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| SMILES = COc1cc(cc(OC)c1O)C=3Oc2cc(O)cc(O)c2C(=O)C=3O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| InChI = |
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| ChemSpiderID = 4445230 |
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| MeSHName = |
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| InChI = 1/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3 |
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| InChIKey = UZMAPBJVXOGOFT-UHFFFAOYAJ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UZMAPBJVXOGOFT-UHFFFAOYSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=17 | H=14 | O=8 |
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| Formula = C<sub>17</sub>H<sub>14</sub>O<sub>8</sub> |
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| MolarMass = 346.28 g/mol |
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| ExactMass = 346.068867 u |
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| Appearance = |
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| MeltingPt = <!-- °C --> |
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| BoilingPt = <!-- °C --> |
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'''Syringetin''' is a ], a type of flavonoid. It is found in ] (absent in white grape)<ref name=Mattivi>, in '']''<ref>billberries)<ref>. It is one of the ]<ref>. |
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'''Syringetin''' is an ], a type of flavonoid. It is found in ] (absent in white grape),<ref name=Mattivi>{{cite journal |last1=Mattivi |first1=Fulvio |last2=Guzzon |first2=Raffaele |last3=Vrhovsek |first3=Urska |last4=Stefanini |first4=Marco |last5=Velasco |first5=Riccardo |date=2006 |title=Metabolite profiling of grape: Flavonols and anthocyanins |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=20 |pages=7692–7702 |doi=10.1021/jf061538c |pmid=17002441 |bibcode=2006JAFC...54.7692M |s2cid=21407928}}</ref> in '']''<ref>{{cite journal |last1=Guo |first1=Jian |last2=Yu |first2=Dong-Lei |last3=Xu |first3=Lizhen |last4=Zhu |first4=Min |last5=Yang |first5=Shi-Lin |date=1998 |title=Flavonol glycosides from ''Lysimachia congestiflora'' |journal=Phytochemistry |volume=48 |issue=8 |pages=1445–1447 |doi=10.1016/s0031-9422(97)01025-x |bibcode=1998PChem..48.1445G |s2cid=85252109}}</ref> and in '']'' (bog bilberries).<ref>{{cite journal |last1=Lätti |first1=Anja K. |last2=Jaakola |first2=Laura |last3=Riihinen |first3=Kaisu R. |last4=Kainulainen |first4=Pirjo S. |date=2010 |title=Anthocyanin and flavonol variation in bog bilberries (''Vaccinium uliginosum'' L.) in Finland |journal=Journal of Agricultural and Food Chemistry |volume=58 |issue=1 |pages=427–433 |doi=10.1021/jf903033m |pmid=20000402 |bibcode=2010JAFC...58..427L |s2cid=28304488}}</ref> It is one of the ].<ref name="Hsu2009">{{cite journal |last1=Hsu |first1=Ya-Ling |last2=Liang |first2=Hsin-Lin |last3=Hung |first3=Chih-Hsing |last4=Kuo |first4=Po-Lin |date=2009 |title=Syringetin, a flavonoid derivative in grape and wine, induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway |journal=Molecular Nutrition & Food Research |volume=53 |issue=11 |pages=1452–1461 |doi=10.1002/mnfr.200800483 |pmid=19784998 |s2cid=42240173}}</ref> |
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It induces human osteoblast differentiation through ]/] 1/2 pathway<ref></ref>. |
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It induces human osteoblast differentiation through ]/] 1/2 pathway.<ref name="Hsu2009"/> |
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==Metabolism== |
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==Metabolism== |
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Syringetin is formed from ] by the action of the enzyme ]<ref name=Mattivi/><ref>. |
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Syringetin is formed from ] by the action of the enzyme laricitrin 5′-''O''-methyltransferase<ref name=Mattivi/><ref>{{cite web |url=http://amigo.geneontology.org/amigo/term/GO:0070448 |title=Laricitrin 5′-O-methyltransferase activity |author=<!--Not stated--> |date=2009-02-28 |website=AmiGO 2 |publisher=Gene Ontology Consortium |access-date=2021-04-04}}</ref> (]).<ref>{{cite web |url=https://metacyc.org/META/NEW-IMAGE?object=PWY-5391 |title=MetaCyc pathway: Syringetin biosynthesis |last=Foerster |first=Hartmut |date=2006-11-03 |website=MetaCyc |publisher=SRI International |access-date=2021-04-04}}</ref> |
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===Glycosides=== |
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===Glycosides=== |
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* ]<ref name=Mattivi/><ref> |
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* ]<ref name=Mattivi/><ref>{{cite web |url=http://www.massbank.jp/RecordDisplay?id=PR100366 |title=Syringetin-3-O-galactoside; LC-ESI-QTOF; MS2; CE:Ramp 5-60 V; + |last1=Matsuda |first1=F. |last2=Suzuki |first2=M. |last3=Sawada |first3=Y. |date=2016-01-19 |website=MassBank |access-date=2021-04-04}}</ref> |
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* ]<ref name=Slimestad></ref><ref> |
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* ]<ref>{{cite web |url=http://www.massbank.jp/RecordDisplay?id=PR020084 |title=Syringetin-3-O-glucoside; LC-ESI-QTOF; MS |last=Tohge |first=T. |date=2016-01-19 |website=MassBank |access-date=2021-04-04}}</ref><ref name="Slimestad1996">{{cite journal |last1=Slimestad |first1=Rune |last2=Hostettmann |first2=Kurt |date=1996 |title=Characterisation of phenolic constituents from juvenile and mature needles of Norway spruce by means of high performance liquid chromatography–mass spectrometry |journal=Phytochemical Analysis |volume=7 |issue=1 |pages=42–48 |doi=10.1002/(SICI)1099-1565(199601)7:1<42::AID-PCA282>3.0.CO;2-K |bibcode=1996PChAn...7...42S |s2cid=95953333}}</ref> |
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* ] (CAS number 93126-00-2) |
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* ] (CAS number 93126-00-2) |
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* ]<ref name=Slimestad/> found in '']''<ref> |
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* ]<ref name="Slimestad1996"/> found in '']''<ref>{{cite journal |last1=Tyukavkina |first1=N. A. |last2=Medvedeva |first2=S. A. |last3=Ivanova |first3=S. Z. |date=1974 |title=New flavonol glycosides from the needles of ''Larix sibirica'' |journal=Chemistry of Natural Compounds |volume=10 |issue=2 |pages=170–172 |doi=10.1007/BF00563605 |bibcode=1974CNatC..10..170T |s2cid=4819832}}</ref> |
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* ] found in '']'' (Norway spruce)<ref> |
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* ] found in '']'' (Norway spruce)<ref>{{cite journal |last1=Slimestad |first1=Rune |last2=Andersen |first2=Øyvind M. |last3=Francis |first3=George W. |last4=Marston |first4=Andrew |last5=Hostettmann |first5=Kurt |date=1995 |title=Syringetin 3-''O''-(6′′-acetyl)-β-glucopyranoside and other flavonols from needles of Norway spruce, ''Picea abies'' |journal=Phytochemistry |volume=40 |issue=5 |pages=1537–1542 |doi=10.1016/0031-9422(95)00383-I |s2cid=84506810}}</ref> |
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==References== |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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