Icariin

Not to be confused with Icaridin.
Icariin
Systematic (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
Clinical data
Oral
Identifiers
489-32-7 
None
PubChem CID 5318997
ChemSpider 4477421 Yes
ChEBI CHEBI:78420 
ChEMBL CHEMBL553204 Yes
Chemical data
Formula C33H40O15
676.662 g/mol
  (what is this?)  (verify)

Icariin is a flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound is derived from several species of plants belonging to the genus Epimedium, Berberidaceae, 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 commonly used in Chinese herbal medicine to enhance erectile function,[2] as well as for several other indications.

It is thought that icariin is likely to be the primary 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 and improve sexual function. In particular, icariin has been demonstrated to act as a PDE5 inhibitor[3][4][5] and to enhance the production of bioactive nitric oxide,[6] as well as mimicking the effects of testosterone.[7] It also shows antioxidant,[8][9] antidepressant[10][11][12] and neuroprotective[13][14] effects in animal studies, as well as stimulating osteoblast activity in bone tissue which has been linked to a possible therapeutic role in the treatment of osteoporosis.[15][16][17][18][19][20]


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.
  15. ↑ Yin XX, Chen ZQ, Liu ZJ, Ma QJ, Dang GT (February 2007). "Icariine stimulates proliferation and differentiation of human osteoblasts by increasing production of bone morphogenetic protein 2". Chin. Med. J. 120 (3): 204–10. PMID 17355822.
  16. ↑ Zhang G, Qin L, Shi Y (July 2007). "Epimedium-derived phytoestrogen flavonoids exert beneficial effect on preventing bone loss in late postmenopausal women: a 24-month randomized, double-blind and placebo-controlled trial". J. Bone Miner. Res. 22 (7): 1072–9. doi:10.1359/jbmr.070405. PMID 17419678.
  17. ↑ Chen KM, Ge BF, Liu XY et al. (May 2007). "Icariin inhibits the osteoclast formation induced by RANKL and macrophage-colony stimulating factor in mouse bone marrow culture". Pharmazie 62 (5): 388–91. PMID 17557750.
  18. ↑ Huang J, Yuan L, Wang X, Zhang TL, Wang K (August 2007). "Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro". Life Sci. 81 (10): 832–40. doi:10.1016/j.lfs.2007.07.015. PMID 17764702.
  19. ↑ Zhang DW, Cheng Y, Wang NL, Zhang JC, Yang MS, Yao XS (January 2008). "Effects of total flavonoids and flavonol glycosides from Epimedium koreanum Nakai on the proliferation and differentiation of primary osteoblasts". Phytomedicine 15 (1-2): 55–61. doi:10.1016/j.phymed.2007.04.002. PMID 17482445.
  20. ↑ Qin L, Han T, Zhang Q et al. (July 2008). "Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula". J Ethnopharmacol 118 (2): 271–9. doi:10.1016/j.jep.2008.04.009. PMID 18501540.