Syringetin
From Self-sufficiency
| Syringetin | |
|---|---|
| Chemical structure of syringetin | |
| 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 | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 4423-37-4 |
| PubChem | 5281953 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C17H14O8 |
| Molar mass | 346.28 g/mol |
| Exact mass | 346.068867 u |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Syringetin is a 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[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
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- ↑ Jump up to: 1.0 1.1 Metabolite Profiling of Grape: Flavonols and Anthocyanins. Fulvio Mattivi, Raffaele Guzzon, Urska Vrhovsek, Marco Stefanini and Riccardo Velasco, J. Agric. Food Chem., 2006, 54 (20), pp 7692–7702
- Jump up ↑ 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
- Jump up ↑ Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosum L.) in Finland. Anja K. Lätti, Laura Jaakola, Kaisu R. Riihinen and Pirjo S. Kainulainen, J. Agric. Food Chem., 2010, 58 (1), pp 427–433
- Jump up ↑ 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
- Jump up ↑ 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
- Jump up ↑ laricitrin 5'-O-methyltransferase on amigo.geneontology.org
- Jump up ↑ Syringetin biosynthetis pathway on metacyc.org
- Jump up ↑ Syringetin-3-O-galactoside on www.massbank.jp
- ↑ Jump up to: 9.0 9.1 Syringetin-3-O-glucoside on www.massbank.jp
- Jump up ↑ 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
- Jump up ↑ 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
- Jump up ↑ 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
