Isoquercetin
Chemical compound
From Wikipedia, the free encyclopedia
Isoquercetin (also known as isoquercitrin or isotrifoliin[1]) is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango)[2] and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa, Camellia sinensis (tea),[3][4] and Vestia foetida.[5]
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| Names | |
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| IUPAC name
3-(β-D-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone | |
| Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | |
| Other names
Isoquercitroside Isoquercitrin Isoquercetin Trifoliin Isotrifolin Trifoliin A Isohyperoside Isotrifoliin Quercetin-3-glucoside Quercetin-3-O-glucoside Quercetin 3-O-β-D-glucopyranoside | |
| Identifiers | |
3D model (JSmol) |
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| DrugBank | |
| ECHA InfoCard | 100.123.856 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C21H20O12 | |
| Molar mass | 464.379 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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Spectral data
The lambda-max for isoquercetin is 254.8 and 352.6 nm.
Biosynthesis and metabolism
Isoquercetin if formed from quercetin by action of the enzyme flavonol 3-O-glucosyltransferase in plants such as the tulip.[6]
The enzyme flavonol-3-O-glucoside L-rhamnosyltransferase in tulips converts isoquercetin to rutin by adding an L-rhamnose sugar unit from UDP-L-rhamnose, with uridine diphosphate (UDP) as byproduct.[7]
Potential clinical uses
Isoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients[8] and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.[9]
There is a single case report of its use in the successful treatment of prurigo nodularis, a difficult to treat pruritic eruption of the skin.[10]
Isoquercetin belongs to the class of chemical compounds known as pan-assay interference compounds (PAINS), which frequently give false positive results in assays for pharmacological activities.[11]