Isoquercetin
(Redirected from Isoquercitrin)
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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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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.123.856 |
| EC Number |
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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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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]
Spectral data
[edit]The lambda-max for isoquercetin is 254.8 and 352.6 nm.
Biosynthesis and metabolism
[edit]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
[edit]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]
See also
[edit]References
[edit]- ↑ "Isoquercetin". PubChem. Retrieved 2018-09-11.
- ↑ Singh UP, Singh DP, Singh M, et al. (2004). "Characterization of phenolic compounds in some Indian mango cultivars". International Journal of Food Sciences and Nutrition. 55 (2): 163–9. doi:10.1080/09637480410001666441. PMID 14985189.
- ↑ Panda S, Kar A (2007). "Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside". BioFactors. 31 (3–4): 201–210. doi:10.1002/biof.5520310307. PMID 18997283.
- ↑ Sakakibara, H; Honda, Y; Nakagawa, S; Ashida, H; Kanazawa, K (2003). "Simultaneous determination of all polyphenols in vegetables, fruits, and teas". Journal of Agricultural and Food Chemistry. 51 (3): 571–81. Bibcode:2003JAFC...51..571S. doi:10.1021/jf020926l. PMID 12537425.
- ↑ Brevis, C.; Quezada, M.; Bustamante, P.; Carrasco, L.; Ruiz, A.; Donoso, S. (2005). "Huevil ( Vestia foetida ) poisoning of cattle in Chile". Veterinary Record. 156 (14): 452–453. doi:10.1136/vr.156.14.452. PMID 15828729.
- ↑ Kleinehollenhorst, G.; Behrens, H.; Pegels, G.; Srunk, N.; Wiermann, R. (1982). "Formation of Flavonol 3-O-Diglycosides and Flavonol 3-O-Triglycosides by Enzyme Extracts from Anthers of Tulipa cv. Apeldoorn / Characterization and Activity of Three Different O -Glycosyltransferases during Anther Development". Zeitschrift für Naturforschung C. 37 (7–8): 587–599. doi:10.1515/znc-1982-7-808.
- ↑ Wiermann R (1982). "Formation of flavonol 3-O-diglycosides and flavonol 3-O-triglycosides by enzyme extracts from anthers of Tulipa cv apeldoorn - characterization and activity of 3 different O-glycosyltransferases during anther development". Z. Naturforsch. C. 37: 587–599. doi:10.1515/znc-1982-7-808.
- ↑ NCT02195232
- ↑ NCT02446795
- ↑ Pennesi, Christine M.; Neely, John; Marks Jr., Ames G.; Alison Basak, S. (November 2017). "Use of Isoquercetin in the Treatment of Prurigo Nodularis". Journal of Drugs in Dermatology. 16 (11): 1156–1158. PMID 29141065.
- ↑ J Baell & M A Walters (2014). "Chemistry: Chemical con artists foil drug discovery". Nature. 513 (7519): 481–483. Bibcode:2014Natur.513..481B. doi:10.1038/513481a. PMID 25254460.
