Isoquercetin

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Isoquercetin
Isoquercitrin structure
Isoquercitrin structure
Names
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)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.123.856
EC Number
  • 640-533-1
KEGG
UNII
  • InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
    Key: OVSQVDMCBVZWGM-QSOFNFLRSA-N
  • C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
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).

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

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]

isoquercetin + UDP-L-rhamnose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of rutin .
rutin

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]

See also

References

  1. "Isoquercetin". PubChem. Retrieved 2018-09-11.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. NCT02195232
  9. NCT02446795
  10. 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.
  11. 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.