Icariin

Icariin

Names
IUPAC name 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-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]oxychromen-4-one
Identifiers
CAS Number	489-32-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78420
ChEMBL	ChEMBL553204
ChemSpider	4477421
ECHA InfoCard	100.107.649
PubChem	5318997
InChI 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 Key: TZJALUIVHRYQQB-XLRXWWTNSA-N 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
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
Properties
Chemical formula	C33H40O15
Molar mass	676.67 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Icariin is a chemical compound classified as a 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 plants belonging to the genus Epimedium which are commonly known as Horny Goat Weed or Yin Yang Huo.^[1] Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.^[2]

It is thought that icariin is an active component of Epimedium extracts, as it has been shown to share several mechanisms of action with compounds used in Western medicine to treat impotence. In particular, icariin is a weak PDE5 inhibitor in vitro^[3][4][5] and enhances the production of nitric oxide,^[6] as well as mimicking the effects of testosterone in rats.^[7] It is a weak antioxidant^[8][9] and has antidepressant-like effects in mice.^[10][11][12] It also has neuroprotective effects in rats.^[13][14]

References

1. Liu JJ, Li SP, Wang YT (January 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): 344–9. doi:10.1016/j.chroma.2005.11.036. PMID 16337210.
2. Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP (December 2007). "Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats". J Ethnopharmacol. 114 (3): 412–6. doi:10.1016/j.jep.2007.08.021. PMID 17890032.
3. Jiang Z, Hu B, Wang J, et al. (2006). "Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum". J. Huazhong Univ. Sci. Technol. Med. Sci. 26 (4): 460–2. doi:10.1007/s11596-006-0421-y. PMID 17120748.
4. Ning H, Xin ZC, Lin G, Banie L, Lue TF, Lin CS (December 2006). "Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells". Urology. 68 (6): 1350–4. doi:10.1016/j.urology.2006.09.031. PMID 17169663.
5. Dell'Agli M, Galli GV, Dal Cero E, et al. (September 2008). "Potent inhibition of human phosphodiesterase-5 by icariin derivatives". J. Nat. Prod. 71 (9): 1513–7. doi:10.1021/np800049y. PMID 18778098.
6. Xu HB, Huang ZQ (July 2007). "Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro". Vascul. Pharmacol. 47 (1): 18–24. doi:10.1016/j.vph.2007.03.002. PMID 17499557.
7. Zhang ZB, Yang QT (September 2006). "The testosterone mimetic properties of icariin". Asian J. Androl. 8 (5): 601–5. doi:10.1111/j.1745-7262.2006.00197.x. PMID 16751992.
8. Xie J, Sun W, Duan K, Zhang Y (June 2007). "Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities". Nat. Prod. Res. 21 (7): 600–5. doi:10.1080/14786410701369680. PMID 17613817.
9. Zhao F, Tang YZ, Liu ZQ (December 2007). "Protective effect of icariin on DNA against radical-induced oxidative damage". J. Pharm. Pharmacol. 59 (12): 1729–32. doi:10.1211/jpp.59.12.0016. PMID 18053336.
10. Pan Y, Kong L, Xia X, Zhang W, Xia Z, Jiang F (December 2005). "Antidepressant-like effect of icariin and its possible mechanism in mice". Pharmacol. Biochem. Behav. 82 (4): 686–94. doi:10.1016/j.pbb.2005.11.010. PMID 16380159.
11. Pan Y, Zhang WY, Xia X, Kong LD (December 2006). "Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats". Biol. Pharm. Bull. 29 (12): 2399–403. doi:10.1248/bpb.29.2399. PMID 17142971.
12. Pan Y, Kong LD, Li YC, Xia X, Kung HF, Jiang FX (May 2007). "Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats". Pharmacol. Biochem. Behav. 87 (1): 130–40. doi:10.1016/j.pbb.2007.04.009. PMID 17509675.
13. Luo Y, Nie J, Gong QH, Lu YF, Wu Q, Shi JS (August 2007). "Protective effects of icariin against learning and memory deficits induced by aluminium in rats". Clin. Exp. Pharmacol. Physiol. 34 (8): 792–5. doi:10.1111/j.1440-1681.2007.04647.x. PMID 17600559.
14. Zheng M, Qu L, Lou Y (May 2008). "Effects of icariin combined with Panax notoginseng saponins on ischemia reperfusion-induced cognitive impairments related with oxidative stress and CA1 of hippocampal neurons in rat". Phytother Res. 22 (5): 597–604. doi:10.1002/ptr.2276. PMID 18398927.