Icariin

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,[1] and Herba epimedii.[2] Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.[3] However, clinical trial data are lacking to support these claims.[4]

Not to be confused with Icaridin.
Icariin
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-5-hydroxy-4′-methoxy-8-(3-methylbut-2-en-1-yl)-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name
5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.107.649
UNII
  • InChI=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 checkY
    Key: TZJALUIVHRYQQB-XLRXWWTNSA-N checkY
  • 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
    Key: TZJALUIVHRYQQB-XLRXWWTNBA
  • 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
Properties
C33H40O15
Molar mass 676.668 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. Liu JJ, Li SP, Wang YT (2006). "Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design". J Chromatogr A. 1103 (2): 344–349. doi:10.1016/j.chroma.2005.11.036. PMID 16337210.
  2. Cai WJ, Huang JH, Zhang SQ, Wu B, Kapahi P, Zhang XM, Shen ZY (2011). Blagosklonny MV (ed.). "Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans". PLOS ONE. 6 (12): e28835. Bibcode:2011PLoSO...628835C. doi:10.1371/journal.pone.0028835. PMC 3244416. PMID 22216122.
  3. Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP (2007). "Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats". J Ethnopharmacol. 114 (3): 412–416. doi:10.1016/j.jep.2007.08.021. PMID 17890032.
  4. "Horny Goat Weed". Drugs.com. August 5, 2019. Retrieved November 7, 2019.
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