{{chembox | verifiedrevid = 444328279 | Name = Isoquercetin | ImageFile = Isoquercitin.svg | ImageSize = 250px | ImageName = Isoquercitrin structure | IUPACName = 3-(β-<small>D</small>-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone | SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4''H''-1-benzopyran-4-one | OtherNames= Isoquercitroside<br>Isoquercitrin<br>Isoquercetin<br>Trifoliin<br>Isotrifolin<br>Trifoliin A<br>Isohyperoside<br>Isotrifoliin<br>Quercetin-3-glucoside<br>Quercetin-3-''O''-glucoside<br>Quercetin 3-''O''-β-<small>D</small>-glucopyranoside |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 482-35-9 | ChEBI = 68352 | ChEMBL = 250450 | ChemSpiderID = 4444361 | DrugBank = DB12665 | EC_number = 640-533-1 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C05623 | PubChem = 5280804 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6HN2PC637T | 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 | 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 | InChIKey = OVSQVDMCBVZWGM-QSOFNFLRBX | StdInChI = 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 | StdInChIKey = OVSQVDMCBVZWGM-QSOFNFLRSA-N }} |Section2={{Chembox Properties | C=21 | H=20 | O=12 | Density = | MeltingPt = }} }} '''Isoquercetin''' (also known as '''isoquercitrin''' or '''isotrifoliin'''<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/5280804#section=Top |title=Isoquercetin |publisher=PubChem |access-date=2018-09-11}}</ref>) 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)<ref>{{Cite journal |vauthors=Singh UP, Singh DP, Singh M, etal |title=Characterization of phenolic compounds in some Indian mango cultivars |journal=International Journal of Food Sciences and Nutrition |volume=55 |issue=2 |pages=163–9 |year=2004 |pmid=14985189 |doi=10.1080/09637480410001666441}}</ref> and ''Rheum nobile'' (the Noble rhubarb). It is also present in the leaves of ''Annona squamosa'', ''Camellia sinensis'' (tea),<ref name="pmid18997283">{{cite journal| author=Panda S, Kar A| title=Antidiabetic and antioxidative effects of ''Annona squamosa'' leaves are possibly mediated through quercetin-3-O-glucoside | journal=BioFactors | year= 2007 | volume= 31 | issue= 3–4 | pages= 201–210 | pmid=18997283 |doi=10.1002/biof.5520310307}}</ref><ref>{{Cite journal | doi = 10.1021/jf020926l | title = Simultaneous determination of all polyphenols in vegetables, fruits, and teas | year = 2003 | last1 = Sakakibara | first1 = H | last2 = Honda | first2 = Y | last3 = Nakagawa | first3 = S | last4 = Ashida | first4 = H | last5 = Kanazawa | first5 = K | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 3 | pages = 571–81 | pmid = 12537425| bibcode = 2003JAFC...51..571S }}</ref> and ''Vestia foetida''.<ref>{{cite journal | last1 = Brevis | first1 = C. | last2 = Quezada | first2 = M. | last3 = Bustamante | first3 = P. | last4 = Carrasco | first4 = L. | last5 = Ruiz | first5 = A. | last6 = Donoso | first6 = S. | title = Huevil ( ''Vestia foetida'' ) poisoning of cattle in Chile | journal = Veterinary Record | date = 2005 | volume = 156 | issue = 14 | pages = 452–453 | doi = 10.1136/vr.156.14.452 | pmid = 15828729 }}</ref>
== 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<ref>[https://www.cancer.gov/about-cancer/treatment/clinical-trials/search/view?cdrid=763277 NCT02195232]</ref> and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.<ref>[https://clinicaltrials.gov/ct2/show/study/NCT02446795#contacts NCT02446795]</ref>
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.<ref>{{cite journal| title = Use of Isoquercetin in the Treatment of Prurigo Nodularis |url=http://jddonline.com/articles/dermatology/S1545961617P1156X/1 |date=November 2017 | volume=16 | issue=11 | pages=1156–1158 |journal=Journal of Drugs in Dermatology |first1=Christine M. |last1=Pennesi |first2=John |last2=Neely |first3=Ames G. |last3=Marks Jr. |first4=S. |last4=Alison Basak|pmid=29141065 }}</ref>
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.<ref>{{Cite journal | journal = Nature | year = 2014| volume = 513| issue = 7519 | pages = 481–483 | title = Chemistry: Chemical con artists foil drug discovery |author1=J Baell |author2=M A Walters | doi = 10.1038/513481a |name-list-style=amp | pmid= 25254460 | doi-access = free | bibcode = 2014Natur.513..481B}}</ref>
== See also == * Quercitrin
== References == {{Reflist}}
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Category:Quercetin glycosides Category:Flavonoid glucosides