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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 |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 |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> '''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>


It induces human osteoblast differentiation through ]/] 1/2 pathway.<ref name="Hsu2009"/> It induces human osteoblast differentiation through ]/] 1/2 pathway.<ref name="Hsu2009"/>
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===Glycosides=== ===Glycosides===
* ]<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> * ]<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>
* ]<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 |s2cid=95953333}}</ref> * ]<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>
* ] (CAS number 93126-00-2) * ] (CAS number 93126-00-2)
* ]<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 |s2cid=4819832}}</ref> * ]<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>
* ] 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> * ] 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>


Latest revision as of 03:08, 24 December 2024

Syringetin
Chemical structure of syringetin
Names
IUPAC name 3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavone
Systematic IUPAC name 3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one
Other names 3′,5′-O-Dimethylmyricetin
3′,5′-Dimethoxy-3,5,7,4′-tetrahydroxyflavone
3,5,7,4′-Tetrahydroxy-3′,5′-dimethoxyflavone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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,1-2H3Key: UZMAPBJVXOGOFT-UHFFFAOYSA-N
  • 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,1-2H3Key: UZMAPBJVXOGOFT-UHFFFAOYAJ
SMILES
  • COc1cc(cc(OC)c1O)C=3Oc2cc(O)cc(O)c2C(=O)C=3O
Properties
Chemical formula C17H14O8
Molar mass 346.291 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape), in Lysimachia congestiflora and in Vaccinium uliginosum (bog bilberries). It is one of the phenolic compounds present in wine.

It induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway.

Metabolism

Syringetin is formed from laricitrin by the action of the enzyme laricitrin 5′-O-methyltransferase (myricetin O-methyltransferase).

Glycosides

References

  1. ^ Mattivi, Fulvio; Guzzon, Raffaele; Vrhovsek, Urska; Stefanini, Marco; Velasco, Riccardo (2006). "Metabolite profiling of grape: Flavonols and anthocyanins". Journal of Agricultural and Food Chemistry. 54 (20): 7692–7702. Bibcode:2006JAFC...54.7692M. doi:10.1021/jf061538c. PMID 17002441. S2CID 21407928.
  2. Guo, Jian; Yu, Dong-Lei; Xu, Lizhen; Zhu, Min; Yang, Shi-Lin (1998). "Flavonol glycosides from Lysimachia congestiflora". Phytochemistry. 48 (8): 1445–1447. Bibcode:1998PChem..48.1445G. doi:10.1016/s0031-9422(97)01025-x. S2CID 85252109.
  3. Lätti, Anja K.; Jaakola, Laura; Riihinen, Kaisu R.; Kainulainen, Pirjo S. (2010). "Anthocyanin and flavonol variation in bog bilberries (Vaccinium uliginosum L.) in Finland". Journal of Agricultural and Food Chemistry. 58 (1): 427–433. Bibcode:2010JAFC...58..427L. doi:10.1021/jf903033m. PMID 20000402. S2CID 28304488.
  4. ^ Hsu, Ya-Ling; Liang, Hsin-Lin; Hung, Chih-Hsing; Kuo, Po-Lin (2009). "Syringetin, a flavonoid derivative in grape and wine, induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway". Molecular Nutrition & Food Research. 53 (11): 1452–1461. doi:10.1002/mnfr.200800483. PMID 19784998. S2CID 42240173.
  5. "Laricitrin 5′-O-methyltransferase activity". AmiGO 2. Gene Ontology Consortium. 2009-02-28. Retrieved 2021-04-04.
  6. Foerster, Hartmut (2006-11-03). "MetaCyc pathway: Syringetin biosynthesis". MetaCyc. SRI International. Retrieved 2021-04-04.
  7. Matsuda, F.; Suzuki, M.; Sawada, Y. (2016-01-19). "Syringetin-3-O-galactoside; LC-ESI-QTOF; MS2; CE:Ramp 5-60 V; [M+H]+". MassBank. Retrieved 2021-04-04.
  8. Tohge, T. (2016-01-19). "Syringetin-3-O-glucoside; LC-ESI-QTOF; MS". MassBank. Retrieved 2021-04-04.
  9. ^ Slimestad, Rune; Hostettmann, Kurt (1996). "Characterisation of phenolic constituents from juvenile and mature needles of Norway spruce by means of high performance liquid chromatography–mass spectrometry". Phytochemical Analysis. 7 (1): 42–48. Bibcode:1996PChAn...7...42S. doi:10.1002/(SICI)1099-1565(199601)7:1<42::AID-PCA282>3.0.CO;2-K. S2CID 95953333.
  10. Tyukavkina, N. A.; Medvedeva, S. A.; Ivanova, S. Z. (1974). "New flavonol glycosides from the needles of Larix sibirica". Chemistry of Natural Compounds. 10 (2): 170–172. Bibcode:1974CNatC..10..170T. doi:10.1007/BF00563605. S2CID 4819832.
  11. Slimestad, Rune; Andersen, Øyvind M.; Francis, George W.; Marston, Andrew; Hostettmann, Kurt (1995). "Syringetin 3-O-(6′′-acetyl)-β-glucopyranoside and other flavonols from needles of Norway spruce, Picea abies". Phytochemistry. 40 (5): 1537–1542. doi:10.1016/0031-9422(95)00383-I. S2CID 84506810.


Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
Glycosides of myricetin
Conjugates of quercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
Categories: