Icariin Inhibitor CAS No. 489-32-7

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Chemical Characteristic

Product Name	Icariin
CAS No.	489-32-7
Molecular Weight	676.66
Formula	C₃₃H₄₀O₁₅
Chemical 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
Smiles	c1(c(c(=O)c2c(o1)c(c(cc2O)OC1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)CC=C(C)C)OC1[C@H](O)[C@H](O)[C@@H](O)[C@@H](O1)C)c1ccc(cc1)OC
Chemical Structure

Biological activities

Icariin is a flavonol glycoside obtained from the aerial part of the plant Herba Epimedii, which is commonly used in Chinese medicine.^[1] Icariin is used in the treatment of osteoporosis and prevention of osteonecrosis through stimulation of bone formation and inhibition of bone resorption. Other than that, Icariin shows cardiovascular protective effects, neuroprotective activity, and antidepressant activity in animal studies. Icariin has beneficial effects on erectile function through inhibitory function on PDE5. In vitro tests show that Icariin inhibits PDE5A1, A2, and A3 with an IC50 value of 1.0, 0.75, and 1.1 mM, respectively.^[2] Icariin also increases penile nNOS and smooth muscle content in Icariin-treated animals with improved functional outcomes.^[3] Icariin has effect on bone formation. In vitro tests, Icariin stimulates the proliferation of rat bone marrow stromal cells, enhances the osteogenic differentiation of marrow stromal cells and osteoblasts by promoting alkaline phosphatase activity, osteoalcin secretion and calcium deposition level.^[4] Icariin and Icariin?? glycosides have structural similarities to estrogen so that Icariin and Icariin?? glycosides have binding capabilities to estrogen receptors that regulate bone remodeling in bone cell through estrogen receptor pathway.^[5] In cardiovascular protective effects, Icariin upregulates the expression of eNOS which enhanced the production of bioactive NO both in short-term and long-term through the activation of NF-ΚB in human umbilical vein endothelial cells in in vitro tests. The protective effective of Icariin on endothelial cells is correlated to cardiovascular protective effects. In neuroprotection, Icariin increases Superoxide Dismutase (SOD) activity and decreases MDA and Aβ(1-40) content in the hippocampus in rats treated with aluminium. In the aspect of antidepressant activity, experimental mice treated with Icariin show shorter immobility time than mice in control group in the forced swimming test. Moreover, Icarrin possesses antidepressant properties via mediation of neurochemical and neuroendocrine systems. Icariin induces decreases in brain monoamine oxidase A and B activities, serum corticotropin-releasing factor levels, and increases in brain monoamine neurotransmitter levels in the mice that are treated with Icariin.

Protocols

In vitro, Icariin is dissolved in DMSO or solvent system composed of n-hexane, n-butanol, methanol, distilled water in proportion of 1:4:2:6 (v/v).

References

[1] Xin ZC, Kim E, Tian ZJ, Ling GT, Guo YL. Icariin on relaxation effect of corpus cavernosum smooth muscle. Chin Sci Bull. 2001, 46: 1186??190. [2] Ning H, Xin ZC, Lin G, Banie L, Lue TF, Lin CS. Effects of Icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells. Urology. 2006,68(6): 1350-1354. [3] Alan W. Shindel, MD, Zhong-Chen Xin, et al. Erectogenic and Neurotrophic Effects of Icariin, a Purified Extract of Horny Goat Weed (Epimedium spp.) In Vitro and In Vivo. J Sex Med. 2010, 7(4 Pt 1): 1518??528. [4] Chen KM, Ge BF, Ma HP, Liu XY, Bai MH, Wang Y. Icariin, a ?avonoid from the herb Epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells. Pharmazie 2005:60: 939??42. [5] Zhang G, Qin L, Hung WY, Shi YY, Leung PC, Yeung HY, Leung KS. Flavonoids derived from herbal Epimedium Brevicornum Maxim prevent OVX-induced osteoporosis in rats independent of its enhancement in intestinal calcium absorption. Bone 2006, 38: 818??25.

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