Isoquercetin, 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
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| 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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| ChemSpider | |
| ECHA InfoCard | 100.123.856 |
| 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
editThe lambda-max for isoquercetin is 254.8 and 352.6 nm.
Potential clinical uses
editIsoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients[6] and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.[7]
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.[8]
However it belongs to the PAINS (Pan-assay interference compounds) categories of chemicals.[9]
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. doi:10.1021/jf020926l. PMID 12537425.
- ^ C. Brevis, M. Quezada, P. Bustamante, L. Carrasco, A. Ruiz, S. Donoso, Huevil (Vestia foetida) poisoning of cattle in Chile The Veterinary record 156(14):452-3 May 2005
- ^ 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.
- ^ J Baell & M A Walters (2014). "Chemistry: Chemical con artists foil drug discovery". Nature. 513 (7519): 481–483. doi:10.1038/513481a. PMID 25254460.