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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][5]

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
  • 489-32-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:78420 N
ChEMBL
  • ChEMBL553204 Y
ChemSpider
  • 4477421 Y
ECHA InfoCard 100.107.649
  • 5318997
UNII
  • VNM47R2QSQ Y
  • DTXSID00964133
  • 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 Y
    Key: TZJALUIVHRYQQB-XLRXWWTNSA-N Y
  • 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 YN ?)

References edit

  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.
  5. ^ Fang, Jian; Zhang, Yongjun (2017-10-12). "Icariin, an Anti-atherosclerotic Drug from Chinese Medicinal Herb Horny Goat Weed". Frontiers in Pharmacology. 8: 734. doi:10.3389/fphar.2017.00734. ISSN 1663-9812. PMC 5644024. PMID 29075193.

icariin, confused, with, icaridin, chemical, compound, classified, prenylated, flavonol, glycoside, type, flavonoid, prenyl, derivative, kaempferol, diglucoside, compound, been, isolated, from, several, species, plant, belonging, genus, epimedium, which, commo. Not to be confused with Icaridin 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 5 Icariin NamesIUPAC name 7 b D Glucopyranosyloxy 5 hydroxy 4 methoxy 8 3 methylbut 2 en 1 yl 3 a L rhamnopyranosyloxy flavoneSystematic 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 oneIdentifiersCAS Number 489 32 7 Y3D model JSmol Interactive imageChEBI CHEBI 78420 NChEMBL ChEMBL553204 YChemSpider 4477421 YECHA InfoCard 100 107 649PubChem CID 5318997UNII VNM47R2QSQ YCompTox Dashboard EPA DTXSID00964133InChI 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 YKey TZJALUIVHRYQQB XLRXWWTNSA N YInChI 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 s1Key TZJALUIVHRYQQB XLRXWWTNBASMILES 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 cc5PropertiesChemical formula C 33H 40O 15Molar mass 676 668 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesReferences edit 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 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 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 Horny Goat Weed Drugs com August 5 2019 Retrieved November 7 2019 Fang Jian Zhang Yongjun 2017 10 12 Icariin an Anti atherosclerotic Drug from Chinese Medicinal Herb Horny Goat Weed Frontiers in Pharmacology 8 734 doi 10 3389 fphar 2017 00734 ISSN 1663 9812 PMC 5644024 PMID 29075193 Retrieved from https en wikipedia org w index php title Icariin amp oldid 1212364078, wikipedia, wiki, book, books, library,

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