Icariin

{{distinguish|Icaridin}} {{Chembox | Verifiedfields = changed | verifiedrevid = 461936642  | ImageFile = Icariin.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt =  | IUPACName = 7-(β-<small>D</small>-Glucopyranosyloxy)-5-hydroxy-4′-methoxy-8-(3-methylbut-2-en-1-yl)-3-(α-<small>L</small>-rhamnopyranosyloxy)flavone | SystematicName = 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4''H''-1-benzopyran-4-one | OtherNames =  | Section1 = {{Chembox Identifiers | CASNo = 489-32-7 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = VNM47R2QSQ | SMILES = O=C3C(\O[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)=C(/Oc4c(c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5 | InChI = 1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 | InChIKey = TZJALUIVHRYQQB-XLRXWWTNBA | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = TZJALUIVHRYQQB-XLRXWWTNSA-N | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 553204 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 78420 | PubChem = 5318997 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4477421 }} | Section2 = {{Chembox Properties | C=33 | H=40 | O=15 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Icariin''' is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-''O''-diglucoside. The compound has been isolated from several species of plant belonging to the genus ''Epimedium'' which are commonly known as horny goat weed, Yin Yang Huo,<ref>{{cite journal |vauthors=Liu JJ, Li SP, Wang YT |title=Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design |journal=J Chromatogr A |volume=1103 |issue=2 |pages=344–349 |year=2006 |pmid=16337210 |doi=10.1016/j.chroma.2005.11.036 }}</ref> and ''Herba epimedii''.<ref name="pmid22216122">{{cite journal |vauthors=Cai WJ, Huang JH, Zhang SQ, Wu B, Kapahi P, Zhang XM, Shen ZY| title=Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans | journal=PLOS ONE | volume=6 | issue=12 | year=2011 | article-number=e28835 | pmid=22216122 | pmc = 3244416 | doi-access=free | doi=10.1371/journal.pone.0028835 | veditors=Blagosklonny MV | bibcode=2011PLoSO...628835C }}</ref> Extracts from these plants produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.<ref>{{cite journal |vauthors=Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP |title=Effect of lipid-based suspension of ''Epimedium koreanum Nakai'' extract on sexual behavior in rats |journal=J Ethnopharmacol |volume=114 |issue=3 |pages=412–416 |year=2007 |pmid=17890032 |doi=10.1016/j.jep.2007.08.021 }}</ref> == References == {{reflist|2}}

Category:PDE5 inhibitors Category:Flavonol glucosides Category:Flavonol rhamnosides Category:Prenylflavonoids Category:4-Methoxyphenyl compounds