Genistein
(Synonyms: 染料木素; NPI 031L) 目录号 : GC14102
染料木黄酮是一种异黄酮，属于类黄酮化合物，存在于多种植物中。
Cas No.:446-72-0
Sample solution is provided at 25 µL, 10mM.
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| Cell experiment [1]: | |
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Cell lines |
Primary calvaria osteoblasts in mice |
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Preparation Method |
Osteoblasts were incubated with varying concentrations of Genistein and different assays viz. cell proliferation, differentiation, calcium deposition, cell cycle progression, antioxidant ability, and osteogenic gene expression were performed. |
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Reaction Conditions |
1、5 and 10 µM Genistein for 9 days |
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Applications |
Results revealed that Genistein markedly induced cell growth and osteoblast differentiation depending upon dose. Antioxidant ability of Genistein, which reduced the H2O2- induced intracellular oxidative stress in osteoblasts. Genistein treatment upregulated the expression of osteoblastic genes of Runt-related transcription factor 2 (Runx2), bone morphogenetic proteins 2 (BMP2), and osteocalcin. |
| Animal experiment [2]: | |
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Animal models |
Adult male Wistar rats |
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Preparation Method |
Eight groups of adult male Wistar rats, fed with either standard chow diet or high-fat diet, were treated with BPA (50µg/kg/day), genistein (10mg/kg/day), and BPA plus genistein for 35 weeks, respectively. Metabolic parameters in serum and liver were determined; the hematoxylin/eosin and oil Red O staining were used to observe liver histologically |
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Dosage form |
10mg/kg/day genistein for 35 weeks |
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Applications |
No difference of body weight gain, total energy intake, liver weight/body weight or body fat percentage in both STD- and HFD-fed sub-groups was observed after treatment with BPA, genistein, or BPA plus genistein. Genistein alleviated lipid metabolism disorder and decreased the mRNA and protein expression of PPARγ, and increased the protein expression of LC3II in liver of HFD-fed rats. |
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References: [1]: Siddiqui S, Mahdi AA, et,al. Genistein contributes to cell cycle progression and regulates oxidative stress in primary culture of osteoblasts along with osteoclasts attenuation. BMC Complement Med Ther. 2020 Sep 11;20(1):277. doi: 10.1186/s12906-020-03065-5. PMID: 32917180; PMCID: PMC7488498. |
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Genistein is an isoflavone belonging to the flavonoid group of compounds and is found in a number of plants. It's a tyrosine kinase inhibitor.
Results revealed that Genistein markedly induced cell growth and osteoblast differentiation depending upon dose. Antioxidant ability of GS, which reduced the H2O2- induced intracellular oxidative stress in osteoblasts. GS treatment upregulated the expression of osteoblastic genes of Runt-related transcription factor 2 (Runx2), bone morphogenetic proteins 2 (BMP2), and osteocalcin[7]. Pre-treatment with genistein did not affect insulin-induced tyrosine kinase activity of the insulin receptor or activation of protein kinase B. On the other hand, genistein acted as a direct inhibitor of insulin-induced glucose uptake in 3T3-L1 adipocytes with an IC(50) of 20 microM[4]. Migration of inflammatory cells is also inhibited by genistein through diminishing adherence of leukocytes to endothelial cells[5].Genistein decreases NF-kappa B DNA binding and abrogates NF-kappa B activation by DNA-damaging agents, H2O2 and tumor necrosis factor-alpha, in prostate cancer cells regardless of androgen sensitivity. Genistein reduces phosphorylation of the inhibitory protein I kappa B alpha and blocks the nuclear translocation of NF-kappa B, prohibiting DNA binding and preventing NF-kappa B activation[6]. Genistein decreases NF-kappa B DNA binding and abrogates NF-kappa B activation by DNA-damaging agents, H2O2 and tumor necrosis factor-alpha, in prostate cancer cells regardless of androgen sensitivity. Genistein reduces phosphorylation of the inhibitory protein I kappa B alpha and blocks the nuclear translocation of NF-kappa B, prohibiting DNA binding and preventing NF-kappa B activation [1].
No difference of body weight gain, total energy intake, liver weight/body weight or body fat percentage in both STD- and HFD-fed sub-groups was observed after treatment with BPA, genistein, or BPA plus genistein. Genistein alleviated lipid metabolism disorder and decreased the mRNA and protein expression of PPARγ, and increased the protein expression of LC3II in liver of HFD-fed rats[2]. Cultivation of the tiny clusters of cells scattered throughout the pancreas, also known as pancreatic islets, were isolated from three to five day-old animals (rats) with genistein, resulting in a rapid and more enhanced insulin exudation in a dose-dependent manner, genistein substantially increased insulin secretion in pancreatic islets of adult mice as well[3].
References:
[1]: Peterson G, Barnes S. Genistein inhibits both estrogen and growth factor-stimulated proliferation of human breast cancer cells. Cell Growth Differ. 1996 Oct;7(10):1345-51. PMID: 8891338
[2]: Ding S, Zuo X, et,al. Environmentally Relevant Dose of Bisphenol A Does Not Affect Lipid Metabolism and Has No Synergetic or Antagonistic Effects on Genistein's Beneficial Roles on Lipid Metabolism. PLoS One. 2016 May 12;11(5):e0155352. doi: 10.1371/journal.pone.0155352. PMID: 27171397; PMCID: PMC4865196.
[3]: Jonas JC, Plant TD, et,al. Multiple effects and stimulation of insulin secretion by the tyrosine kinase inhibitor genistein in normal mouse islets. Br J Pharmacol. 1995 Feb;114(4):872-80. doi: 10.1111/j.1476-5381.1995.tb13285.x. PMID: 7773549; PMCID: PMC1510214.
[4]: Bazuine M, van den Broek PJ, et,al. Genistein directly inhibits GLUT4-mediated glucose uptake in 3T3-L1 adipocytes. Biochem Biophys Res Commun. 2005 Jan 14;326(2):511-4. doi: 10.1016/j.bbrc.2004.11.055. PMID: 15582607.
[5]: MacGregor CA, Canney PA, et,al. A randomised double-blind controlled trial of oral soy supplements versus placebo for treatment of menopausal symptoms in patients with early breast cancer. Eur J Cancer. 2005 Mar;41(5):708-14. doi: 10.1016/j.ejca.2005.01.005. PMID: 15763646.
[6]: Davis JN, Kucuk O, et,al. Genistein inhibits NF-kappa B activation in prostate cancer cells. Nutr Cancer. 1999;35(2):167-74. doi: 10.1207/S15327914NC352_11. PMID: 10693171.
[7]: Siddiqui S, Mahdi AA, et,al. Genistein contributes to cell cycle progression and regulates oxidative stress in primary culture of osteoblasts along with osteoclasts attenuation. BMC Complement Med Ther. 2020 Sep 11;20(1):277. doi: 10.1186/s12906-020-03065-5. PMID: 32917180; PMCID: PMC7488498.
染料木黄酮是一种异黄酮,属于类黄酮化合物,存在于多种植物中。 It'；是一种酪氨酸激酶抑制剂。
结果表明,Genistein 显着诱导细胞生长和成骨细胞分化,具体取决于剂量。 GS 的抗氧化能力,可降低 H2O2 诱导的成骨细胞细胞内氧化应激。 GS 处理上调了 Runt 相关转录因子 2 (Runx2)、骨形态发生蛋白 2 (BMP2) 和骨钙素[7] 的成骨细胞基因的表达。用染料木黄酮预处理不影响胰岛素诱导的胰岛素受体酪氨酸激酶活性或蛋白激酶 B 的激活。另一方面,染料木黄酮作为具有 IC 的 3T3-L1 脂肪细胞中胰岛素诱导的葡萄糖摄取的直接抑制剂(50) 20 microM[4]。染料木黄酮还通过减少白细胞与内皮细胞的粘附来抑制炎症细胞的迁移[5]。染料木黄酮降低 NF-kappa B DNA 结合并消除 DNA 损伤剂 H2O2 对 NF-kappa B 的激活和肿瘤坏死因子-α,在前列腺癌细胞中,无论雄激素敏感性如何。 Genistein 可降低抑制蛋白 I kappa B α 的磷酸化并阻断 NF-kappa B 的核转位,从而抑制 DNA 结合并阻止 NF-kappa B 激活[6]。无论雄激素敏感性如何,Genistein 都会降低 NF-kappa B DNA 结合并消除 DNA 损伤剂、H2O2 和肿瘤坏死因子-α 对 NF-kappa B 的激活。 Genistein 降低抑制蛋白 I kappa B α 的磷酸化并阻断 NF-kappa B 的核转位,从而抑制 DNA 结合并阻止 NF-kappa B 激活[1]。
在用 BPA、染料木黄酮或 BPA 加染料木黄酮治疗后,在 STD 和 HFD 喂养的亚组中,体重增加、总能量摄入、肝脏重量/体重或体脂百分比没有差异。 Genistein减轻脂代谢紊乱,降低PPARγ的mRNA和蛋白表达,并增加HFD喂养大鼠肝脏中LC3II的蛋白表达[2]。散布在胰腺各处的微小细胞簇（也称为胰岛）的培养是从三到五天大的动物（大鼠）中分离出来的染料木黄酮,导致以剂量依赖的方式快速和增强胰岛素渗出,染料木素显着增加成年小鼠胰岛的胰岛素分泌[3]。
| Cas No. | 446-72-0 | SDF | |
| 别名 | 染料木素; NPI 031L | ||
| 化学名 | 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one | ||
| Canonical SMILES | C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O | ||
| 分子式 | C15H10O5 | 分子量 | 270.24 |
| 溶解度 | ≥ 55.6mg/mL in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.7004 mL | 18.5021 mL | 37.0041 mL |
| 5 mM | 0.7401 mL | 3.7004 mL | 7.4008 mL |
| 10 mM | 0.37 mL | 1.8502 mL | 3.7004 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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2.
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An Overview on Genistein and its Various Formulations
Drug Res (Stuttg)2019 Jun;69(6):305-313.PMID: 30517965DOI: 10.1055/a-0797-3657
Genistein is the natural isoflavone and a phytoestrogen with a broad range of pharmacological properties, such as tyrosine and topoisomerase inhibition. It also induces apoptosis and cell proliferation inhibition, differentiates cancer cells. Added health benefits include the reduction of osteoporosis by suppressing osteoclasts and lymphocyte functions, decreased the risk of cardiovascular attacks and relieved postmenopausal problems. Genistein traditionally used in Chinese and Ayurvedic medicine and are found to be associated with lower risk of breast, prostate and lung cancer. Numerous factors comprising genetic, epigenetic and transcriptomic alterations are evidenced to be responsible for breast, prostate and lung cancer. In present review, an overview on genistein, the various analytical methods and drug delivery approaches to determine genistein in the formulations are discussed. It may help to develop novel formulations with better solubility and bioavailability of genistein. The tumor cell scan may be targeted to form a stable genistein formulation.
Cannabinoid receptor 1 antagonist genistein attenuates marijuana-induced vascular inflammation
Cell2022 May 12;185(10):1676-1693.e23.PMID: 35489334DOI: 10.1016/j.cell.2022.04.005
Epidemiological studies reveal that marijuana increases the risk of cardiovascular disease (CVD); however, little is known about the mechanism. ¦¤9-tetrahydrocannabinol (¦¤9-THC), the psychoactive component of marijuana, binds to cannabinoid receptor 1 (CB1/CNR1) in the vasculature and is implicated in CVD. A UK Biobank analysis found that cannabis was an risk factor for CVD. We found that marijuana smoking activated inflammatory cytokines implicated in CVD. In silico virtual screening identified genistein, a soybean isoflavone, as a putative CB1 antagonist. Human-induced pluripotent stem cell-derived endothelial cells were used to model ¦¤9-THC-induced inflammation and oxidative stress via NF-¦ʂ signaling. Knockdown of the CB1 receptor with siRNA, CRISPR interference, and genistein attenuated the effects of ¦¤9-THC. In mice, genistein blocked ¦¤9-THC-induced endothelial dysfunction in wire myograph, reduced atherosclerotic plaque, and had minimal penetration of the central nervous system. Genistein is a CB1 antagonist that attenuates ¦¤9-THC-induced atherosclerosis.
Genistein: Its role in metabolic diseases and cancer
Crit Rev Oncol Hematol2017 Nov;119:13-22.PMID: 29065980DOI: 10.1016/j.critrevonc.2017.09.004
Genistein is an isoflavone present in soy and is known to have multiple molecular effects, such as the inhibition of inflammation, promotion of apoptosis, and modulation of steroidal hormone receptors and metabolic pathways. Since these molecular effects impact carcinogenesis, cancer propagation, obesity, osteoporosis, and metabolic syndromes, genistein plays an important role in preventing and treating common disorders. The role of genistein has not been adequately evaluated in all these clinical settings. This review summarizes some of the known molecular effects of genistein and its potential role in health maintenance and treatment.
Genistein: Dual Role in Women's Health
Nutrients2021 Aug 30;13(9):3048.PMID: 34578926DOI: 10.3390/nu13093048
Advanced research in recent years has revealed the important role of nutrients in the protection of women's health and in the prevention of women's diseases. Genistein is a phytoestrogen that belongs to a class of compounds known as isoflavones, which structurally resemble endogenous estrogen. Genistein is most often consumed by humans via soybeans or soya products and is, as an auxiliary medicinal, used to treat women's diseases. In this review, we focused on analyzing the geographic distribution of soybean and soya product consumption, global serum concentrations of genistein, and its metabolism and bioactivity. We also explored genistein's dual effects in women's health through gathering, evaluating, and summarizing evidence from current in vivo and in vitro studies, clinical observations, and epidemiological surveys. The dose-dependent effects of genistein, especially when considering its metabolites and factors that vary by individuals, indicate that consumption of genistein may contribute to beneficial effects in women's health and disease prevention and treatment. However, consumption and exposure levels are nuanced because adverse effects have been observed at lower concentrations in in vitro models. Therefore, this points to the duplicity of genistein as a possible therapeutic agent in some instances and as an endocrine disruptor in others.
Genistein as Potential Therapeutic Candidate for Menopausal Symptoms and Other Related Diseases
Molecules2019 Oct 29;24(21):3892.PMID: 31671813DOI: 10.3390/molecules24213892
Plant-derived compounds have recently attracted greater interest in the field of new therapeutic agent development. These compounds have been widely screened for their pharmacological effects. Polyphenols, such as soy-derived isoflavones, also called phytoestrogens, have been extensively studied due to their ability to inhibit carcinogenesis. These compounds are chemically similar to 17¦estradiol, and mimic the binding of estrogens to its receptors, exerting estrogenic effects in target organs. Genistein is an isoflavone derived from soy-rich products and accounts for about 60% of total isoflavones found in soybeans. Genistein has been reported to exhibit several biological effects, such as anti-tumor activity (inhibition of cell proliferation, regulation of the cell cycle, induction of apoptosis), improvement of glucose metabolism, impairment of angiogenesis in both hormone-related and hormone-unrelated cancer cells, reduction of peri-menopausal and postmenopausal hot flashes, and modulation of antioxidant effects. Additionally, epidemiological and clinical studies have reported health benefits of genistein in many chronic diseases, such as cardiovascular disease, diabetes, and osteoporosis, and aid in the amelioration of typical menopausal symptoms, such as anxiety and depression. Although the biological effects are promising, certain limitations, such as low bioavailability, biological estrogenic activity, and effects on target organs, have limited the clinical applications of genistein to some extent. Moreover, studies report that modification of its molecular structure may eliminate the biological estrogenic activity and its effects on target organs. In this review, we summarize the potential benefits of genistein on menopause symptoms and menopause-related diseases like cardiovascular, osteoporosis, obesity, diabetes, anxiety, depression, and breast cancer.