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Syringetin

From Wikipedia, the free encyclopedia
Syringetin
Chemical structure of 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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,1-2H3 ☒N
    Key: UZMAPBJVXOGOFT-UHFFFAOYSA-N ☒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,1-2H3
    Key: UZMAPBJVXOGOFT-UHFFFAOYAJ
  • COc1cc(cc(OC)c1O)C=3Oc2cc(O)cc(O)c2C(=O)C=3O
Properties
C17H14O8
Molar mass346.291 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Syringetin is anO-methylated flavonol, a type of flavonoid. It is found inred grape (absent in white grape),[1] inLysimachia congestiflora[2] and inVaccinium uliginosum (bog bilberries).[3] It is one of thephenolic compounds present in wine.[4]

It induces human osteoblast differentiation throughbone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway.[4]

Metabolism

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Syringetin is formed fromlaricitrin by the action of the enzyme laricitrin 5′-O-methyltransferase[1][5] (myricetinO-methyltransferase).[6]

Glycosides

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References

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  1. ^abcMattivi, 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 fromLysimachia 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. ^abHsu, 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. Retrieved2021-04-04.
  6. ^Foerster, Hartmut (2006-11-03)."MetaCyc pathway: Syringetin biosynthesis".MetaCyc. SRI International. Retrieved2021-04-04.
  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. Retrieved2021-04-04.
  8. ^Tohge, T. (2016-01-19)."Syringetin-3-O-glucoside; LC-ESI-QTOF; MS".MassBank. Retrieved2021-04-04.
  9. ^abSlimestad, 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 ofLarix 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 ofherbacetin
Glycosides ofkaempferol
Glycosides ofmyricetin
Conjugates ofquercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
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