Syringetin

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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 mass 346.291 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Syringetin is an

phenolic compounds present in wine.[4]

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

Metabolism

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

Glycosides

References

  1. ^
    S2CID 21407928
    .
  2. S2CID 85252109
    .
  3. S2CID 28304488
    .
  4. ^
    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. ^
    S2CID 95953333
    .
  10. S2CID 4819832
    .
  11. S2CID 84506810
    .


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