Record Information |
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Version | 1.0 |
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Created at | 2021-06-22 17:29:29 UTC |
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Updated at | 2021-06-22 17:29:29 UTC |
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NP-MRD ID | NP0043925 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Myricetin 3-beta-O-galactoside |
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Description | Myricetin 3-galactoside, also known as gmelinoside I, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Myricetin 3-galactoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Myricetin 3-beta-O-galactoside is found in Betula pendula, Betula pubescens, Catha edulis, Dioscorea bulbifera, Epilobium hirsutum, Fagopyrum megacarpum, Guiera senegalensis, Hypericum richeri, Juglans mandshurica, Kunzea ambigua, Limonium aureum, Limonium sinense, Morella rubra, Nothofagus antarctica, Nymphaea odorata, Rhoiptelea chiliantha, Saxifraga cernua, Vitis vinifera, Vitis vinifera and Warburgia ugandensis. It was first documented in 2009 (PMID: 19061313). Based on a literature review a significant number of articles have been published on Myricetin 3-galactoside (PMID: 33396768) (PMID: 33858274) (PMID: 29234420) (PMID: 28872626) (PMID: 28716425) (PMID: 27690414). |
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Structure | OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C21H20O13/c22-5-12-15(28)17(30)18(31)21(33-12)34-20-16(29)13-8(24)3-7(23)4-11(13)32-19(20)6-1-9(25)14(27)10(26)2-6/h1-4,12,15,17-18,21-28,30-31H,5H2/t12-,15+,17+,18-,21+/m1/s1 |
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Synonyms | Value | Source |
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Myricetin-3-O-beta-D-galactoside | ChEBI | Myricetin-3-O-b-D-galactoside | Generator | Myricetin-3-O-β-D-galactoside | Generator | Myricetin 3-O-beta-D-galactopyranoside | HMDB | Myricetin 3-O-galactoside | HMDB | Myricetin 3-O-b-D-galactopyranoside | HMDB | Myricetin 3-O-β-D-galactopyranoside | HMDB | 3,3',4',5,5',7-Hexahydroxyflavone 3-β-D-galactopyranoside | HMDB | 3,3',4',5,5',7-Hexahydroxyflavone 3-beta-D-galactopyranoside | HMDB | Myricetin 3-O-galactopyranoside | HMDB | Myricetin 3-O-β-D-galactoside | HMDB | Myricetin 3-O-β-galactopyranoside | HMDB | Myricetin 3-β-D-galactoside | HMDB | Myricetin 3-O-beta-D-galactoside | HMDB | Myricetin 3-O-beta-galactopyranoside | HMDB | Myricetin 3-beta-D-galactoside | HMDB | Gmelinoside I | HMDB | Myricetin 3-galactoside | PhytoBank |
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Chemical Formula | C21H20O13 |
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Average Mass | 480.3757 Da |
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Monoisotopic Mass | 480.09039 Da |
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IUPAC Name | 5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | 5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C21H20O13/c22-5-12-15(28)17(30)18(31)21(33-12)34-20-16(29)13-8(24)3-7(23)4-11(13)32-19(20)6-1-9(25)14(27)10(26)2-6/h1-4,12,15,17-18,21-28,30-31H,5H2/t12-,15+,17+,18-,21+/m1/s1 |
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InChI Key | FOHXFLPXBUAOJM-MGMURXEASA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Flavonoid-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Benzenetriol
- Pyrogallol derivative
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Oxane
- Monocyclic benzene moiety
- Pyran
- Monosaccharide
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Castillo-Munoz N, Gomez-Alonso S, Garcia-Romero E, Gomez MV, Velders AH, Hermosin-Gutierrez I: Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes. J Agric Food Chem. 2009 Jan 14;57(1):209-19. doi: 10.1021/jf802863g. [PubMed:19061313 ]
- Aksornchu P, Chamnansilpa N, Adisakwattana S, Thilavech T, Choosak C, Marnpae M, Makynen K, Dahlan W, Ngamukote S: Inhibitory Effect of Antidesma bunius Fruit Extract on Carbohydrate Digestive Enzymes Activity and Protein Glycation In Vitro. Antioxidants (Basel). 2020 Dec 30;10(1). pii: antiox10010032. doi: 10.3390/antiox10010032. [PubMed:33396768 ]
- Ibrahim II, Moussa AA, Chen Z, Zhang J, Cao WG, Yu C: Bioactive phenolic components and antioxidant activities of water-based extracts and flavonoid-rich fractions from Salvadora persica L. leaves. Nat Prod Res. 2021 Apr 15:1-5. doi: 10.1080/14786419.2021.1908281. [PubMed:33858274 ]
- Bae MJ, Karadeniz F, Oh JH, Yu GH, Jang MS, Nam KH, Seo Y, Kong CS: MMP-Inhibitory Effects of Flavonoid Glycosides from Edible Medicinal Halophyte Limonium tetragonum. Evid Based Complement Alternat Med. 2017;2017:6750274. doi: 10.1155/2017/6750274. Epub 2017 Sep 20. [PubMed:29234420 ]
- Lee SG, Karadeniz F, Seo Y, Kong CS: Anti-Melanogenic Effects of Flavonoid Glycosides from Limonium tetragonum (Thunb.) Bullock via Inhibition of Tyrosinase and Tyrosinase-Related Proteins. Molecules. 2017 Sep 5;22(9). pii: molecules22091480. doi: 10.3390/molecules22091480. [PubMed:28872626 ]
- Wang Y, Johnson-Cicalese J, Singh AP, Vorsa N: Characterization and quantification of flavonoids and organic acids over fruit development in American cranberry (Vaccinium macrocarpon) cultivars using HPLC and APCI-MS/MS. Plant Sci. 2017 Sep;262:91-102. doi: 10.1016/j.plantsci.2017.06.004. Epub 2017 Jun 8. [PubMed:28716425 ]
- Wang Y, Singh AP, Nelson HN, Kaiser AJ, Reker NC, Hooks TL, Wilson T, Vorsa N: Urinary Clearance of Cranberry Flavonol Glycosides in Humans. J Agric Food Chem. 2016 Oct 26;64(42):7931-7939. doi: 10.1021/acs.jafc.6b03611. Epub 2016 Oct 18. [PubMed:27690414 ]
- Wang Z, Sha Y, Yu X, Liang Y: [Determination of flavonol glycosides in tea samples by ultra-high performance liquid chromatography-photodiode array detection-tandem mass spectrometry]. Se Pu. 2015 Sep;33(9):974-80. doi: 10.3724/sp.j.1123.2015.04028. [PubMed:26753286 ]
- Roitto M, Rautio P, Markkola A, Julkunen-Tiitto R, Varama M, Saravesi K, Tuomi J: Induced accumulation of phenolics and sawfly performance in Scots pine in response to previous defoliation. Tree Physiol. 2009 Feb;29(2):207-16. doi: 10.1093/treephys/tpn017. Epub 2008 Dec 5. [PubMed:19203946 ]
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