Genistein
Genistein is an isoflavone and phytoestrogen that was originally found in Genista but has since been found in many other plant sources, including soy. Genistein exhibits anti-resorptive, anti-osteoporotic, antioxidative, anti-obesity, anti-diabetic, anti-hyperlipidemic, neuroprotective, anti-inflammatory, anticancer, and anti-metastatic activities. Genistein inhibits osteoclast formation in macrophages and induces phase II enzymes such as superoxide dismutase, heme oxygenase 1 (HO-1) and Nrf2 in other cellular models. In high fat diet fed animal models, genistein decreases body weight, liver weight, lipid levels, and insulin dysregulation by inhibiting S6K1 signaling. In animal models of cerebral occlusion, genistein decreases infarct volume and neuronal apoptosis, increases activation of ERK1/2, and improves neurological and survival outcomes. In cellular models of Alzheimer’s disease, genistein increases PKC signaling and inhibits amyloid-β (Aβ)-induced neurotoxicity. In other cellular models, this compound decreases activation of NF-κB and expression of IL-1β, IL-6, and IL-8 in an AMPK-dependent manner. In colon cancer cells, genistein induces G2/M phase cell cycle arrest and apoptosis, decreases the mitochondrial membrane potential, and inhibits cellular proliferation. In hepatocellular carcinoma cells, genistein decreases production of matrix metalloproteinase 9 (MMP9) and inhibits cellular invasion; it also downregulates hedgehog (Hh) signaling.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18926601
| Cas No. |
446-72-0 |
|---|---|
| Purity |
≥98% |
| Formula |
C15H10O5 |
| Formula Wt. |
270.24 |
| Chemical Name |
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1- benzopyran-4-one |
| IUPAC Name |
5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one |
| Synonym |
Prunetol; Genisteol |
| Melting Point |
297-298°C(slight dec.) |
| Solubility |
Soluble in acetone or methanol. DMSO to 100 mM, ethanol to 2 mg/mL. Insoluble in water. |
| Appearance |
Pale yellow crystalline powder |
Lee SH, Kim JK, Jang HD. Genistein inhibits osteoclastic differentiation of RAW 264.7 cells via regulation of ROS production and scavenging. Int J Mol Sci. 2014 Jun 12;15(6):10605-21. PMID: 24927148.
Wang S, Wei H, Cai M, et al. Genistein attenuates brain damage induced by transient cerebral ischemia through up-regulation of ERK activity in ovariectomized mice. Int J Biol Sci. 2014 Apr 8;10(4):457-65. PMID: 24719563.
Li J, Li J, Yue Y, et al. Genistein suppresses tumor necrosis factor α-induced inflammation via modulating reactive oxygen species/Akt/nuclear factor κB and adenosine monophosphate-activated protein kinase signal pathways in human synoviocyte MH7A cells. Drug Des Devel Ther. 2014 Mar 17;8:315-23. PMID: 24669186.
Wu J, Xu J, Han S, et al. Effects of genistein on apoptosis in HCT-116 human colon cancer cells and its mechanism. Wei Sheng Yan Jiu. 2014 Jan;43(1):1-5. PMID: 24564102.
Wang SD, Chen BC, Kao ST, et al. Genistein inhibits tumor invasion by suppressing multiple signal transduction pathways in human hepatocellular carcinoma cells. BMC Complement Altern Med. 2014 Jan 16;14:26. PMID: 24433534.
Fan P, Fan S, Wang H, et al. Genistein decreases the breast cancer stem-like cell population through Hedgehog pathway. Stem Cell Res Ther. 2013;4(6):146. PMID: 24331293.
Arunkumar E, Karthik D, Anuradha CV. Genistein sensitizes hepatic insulin signaling and modulates lipid regulatory genes through p70 ribosomal S6 kinase-1 inhibition in high-fat-high-fructose diet-fed mice. Pharm Biol. 2013 Jul;51(7):815-24. PMID: 23627466.
Luo S, Lan T, Liao W, et al. Genistein inhibits Aβ₂₅₋₃₅ -induced neurotoxicity in PC12 cells via PKC signaling pathway. Neurochem Res. 2012 Dec;37(12):2787-94. PMID: 22949092.
