Syringetin Explained

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape),[1] in Lysimachia congestiflora[2] and in Vaccinium uliginosum (bog billberries).[3] It is one of the 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

Notes and 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 . 10.1021/jf061538c . 17002441 . 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 . 10.1016/s0031-9422(97)01025-x . 1998PChem..48.1445G . 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 . 10.1021/jf903033m . 20000402 . 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 . 10.1002/mnfr.200800483 . 19784998 . 42240173.
  5. Web site: Laricitrin 5′-O-methyltransferase activity . . 2009-02-28 . AmiGO 2 . Gene Ontology Consortium . 2021-04-04.
  6. Web site: MetaCyc pathway: Syringetin biosynthesis . Foerster . Hartmut . 2006-11-03 . MetaCyc . SRI International . 2021-04-04.
  7. Web site: Syringetin-3-O-galactoside; LC-ESI-QTOF; MS2; CE:Ramp 5-60 V; [M+H]+ ]. Matsuda . F. . Suzuki . M. . Sawada . Y. . 2016-01-19 . MassBank . 2021-04-04.
  8. Web site: Syringetin-3-O-glucoside; LC-ESI-QTOF; MS . Tohge . T. . 2016-01-19 . MassBank . 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 . 10.1002/(SICI)1099-1565(199601)7:1<42::AID-PCA282>3.0.CO;2-K . 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 . 10.1007/BF00563605 . 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 . 10.1016/0031-9422(95)00383-I . 84506810.

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