Isoquercetin

Isoquercetin

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
CAS Number	482-35-9  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:68352
ChEMBL	ChEMBL250450
ChemSpider	4444361
DrugBank	DB12665
ECHA InfoCard	100.123.856
EC Number	640-533-1
KEGG	C05623  Y
PubChem CID	5280804
UNII	6HN2PC637T  Y
CompTox Dashboard (EPA)	DTXSID3041110
InChI 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 InChI=1/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-QSOFNFLRBX
SMILES 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
Chemical formula	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). Y  verify  (what is  YN ?) Infobox references

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]

Spectral data

The lambda-max for isoquercetin is 254.8 and 352.6 nm.

Potential clinical uses

Isoquercetin 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

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. 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
6. NCT02195232
7. NCT02446795
8. 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.
9. 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.

See also

• Quercitrin