Miquelianin
Chemical compound
From Wikipedia, the free encyclopedia
Miquelianin (quercetin 3-O-glucuronide) is a flavonol glucuronide, a type of phenolic compound present in wine,[1] in species of St John's wort,[2] like Hypericum hirsutum,[3] in Nelumbo nucifera (Indian lotus)[4] or in green beans.[5]
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| Names | |
|---|---|
| IUPAC name
3′,4′,5,7-Tetrahydroxy-4-oxoflav-2-en-3-yl β-D-glucopyranosiduronic acid | |
| Systematic IUPAC name
(2S,3S,4S,5R,6S)-6-{[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid | |
| Other names
Quercetin 3-O-glucuronide Quercetol glucuronide Quercetin 3-glucuronide Quercetol 3-O-glucuronide quercetin 3-O-β-D-glucuronopyranoside Querciturone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C21H18O13 | |
| Molar mass | 478.362 g·mol−1 |
| Density | 1.961 g/mL |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is also a rat plasma quercetin metabolite.[6] It shows an antioxidant effect in human plasma.[7] In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine.[8]
Formation
The enzyme glucuronosyltransferase converts quercetin to its glucuronide by adding a sugar acid at one of the hydroxy groups, with uridine diphosphate (UDP) as byproduct:[9]
