Syringetin

Syringetin
Names
IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-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
Properties
C17H14O8
Molar mass 346.29 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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Infobox references

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.[5]

Metabolism

Syringetin is formed from laricitrin by the action of the enzyme laricitrin 5'-O-methyltransferase[1][6] (myricetin O-methyltransferase).[7]

Glycosides

  • syringetin-3-O-galactoside[1][8]
  • Syringetin-3-O-glucoside[9][10]
  • Syringetin 3-rhamnoside (CAS number 93126-00-2)
  • Syringetin-3-O-rutinoside[9] found in Larix sibirica[11]
  • Syringetin 3-O-(6″-acetyl)-β-glucopyranoside found in Picea abies (Norway spruce)[12]

References

  1. 1 2 3 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. doi:10.1021/jf061538c. PMID 17002441.
  2. ↑ Flavonol glycosides from Lysimachia congestiflora. Jian Guo, , Dong-Lei Yu, Lizhen Xu, Min Zhu and Shi-Lin Yang, Phytochemistry, Volume 48, Issue 8, August 1998, Pages 1445-1447
  3. ↑ LäTti, Anja K.; Jaakola, Laura; Riihinen, Kaisu R.; Kainulainen, Pirjo S. (2010). "Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland". Journal of Agricultural and Food Chemistry. 58 (1): 427–433. doi:10.1021/jf903033m. PMID 20000402.
  4. ↑ Syringetin, a flavonoid derivative in grape and wine, induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway. Ya-Ling Hsu, Hsin-Lin Liang, Chih-Hsing Hung and Po-Lin Kuo, Molecular Nutrition & Food Research, Volume 53 Issue 11, Pages 1452-1461
  5. ↑ Syringetin, a flavonoid derivative in grape and wine, induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway. Hsu Ya-Ling, Liang Hsin-Lin, Hung Chih-Hsing and Kuo Po-Lin, Molecular nutrition & food research, 2009, vol. 53, no11, pp. 1452-1461
  6. ↑ laricitrin 5'-O-methyltransferase on amigo.geneontology.org
  7. ↑ Syringetin biosynthetis pathway on metacyc.org
  8. ↑ Syringetin-3-O-galactoside on www.massbank.jp
  9. 1 2 Syringetin-3-O-glucoside on www.massbank.jp
  10. ↑ Characterisation of Phenolic Constituents from Juvenile and Mature Needles of Norway Spruce by Means of High Performance Liquid Chromatography-Mass Spectrometry. Rune Slimestad and Kurt Hostettmann, Phytochemical Analysis, Volume 7 Issue 1, pp 42-48
  11. ↑ New flavonol glycosides from the needles of Larix sibirica. N. A. Tyukavkina, S. A. Medvedeva and S. Z. Ivanova, Chemistry of Natural Compounds, Volume 10, Number 2 / march 1974
  12. ↑ Syringetin 3-O-(6″-acetyl)-β-glucopyranoside and other flavonols from needles of norway spruce, Picea abies. Rune Slimestad, Øyvind M. Andersen, George W. Francis, Andrew Marston and Kurt Hostettmann, Phytochemistry, Volume 40, Issue 5, November 1995, Pages 1537-1542


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