Rhapontigenin
(Synonyms: 丹叶大黄素) 目录号 : GC13470
Rhapontigenin（丹叶大黄素）是一种有效的细胞色素P4501A1选择性灭活剂，IC50为0.4μM，对P4501A1的选择性分别是P4501A2和P4501B1的400倍和23倍。
Cas No.:500-65-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
Cell lines | PC3 cells |
Preparation Method | PC3 cells were transfected with HA-tagged ubiquitin (HA-Ub). At 24h post-transfection, cells were pre-treated with 0, 2.5, 5, 10, 20μM Rhapontigenin for 30min, followed by TGF-β stimulation overnight. After 24h, the cells were treated with 10μM MG132 for 4h and cell lysates were extracted for immunoprecipitation (IP). HA-Ub-conjugated HIF-1α was detected using anti-HA antibodies. |
Reaction Conditions | 0, 2.5, 5, 10, 20μM; 30min |
Applications | Rhapontigenin inhibited HIF-1α expression in a dose-dependent manner. Rhapontigenin inhibited TGF-β-induced expression of N-cadherin, vimentin, and CA9. |
| Animal experiment [2]: | |
Animal models | Sprague-Dawley rats |
Preparation Method | Thirty-six Sprague-Dawley rats were randomly divided into 6 groups. Appropriate amount of Rhapontigenin (RPG) was dissolved in DMSO and sterile water (1:9 v/v) and then further diluted with saline. To induce myocardial infarction in rats, isoproterenol (ISO) solution was prepared in saline and injected subcutaneously (85mg/kg) daily for 2 consecutive days. Animal study: Group I (control), Group II (ISO treatment), Group III (1.0mg/kg/day RPG and ISO treatment), Group IV (2.5mg/kg/day RPG and ISO treatment), Group V (5.0mg/kg/day RPG and ISO treatment) and Group VI (treated with RPG 5.0mg/kg/day). RPG solution was injected via tail vein, ISO is given by subcutaneous injection. After 8 days, the body weight of the animals was recorded and euthanized, and then the heart was removed. After 5h of coronary artery occlusion, blood was collected from the vena cava and centrifuged at 3,000 rpm for 30min at 4°C to collect serum, which was then stored at –20°C for measurement of various parameters. |
Dosage form | 1, 2.5, 5mg/kg/day for 8 days; i.v. |
Applications | Rhapontigenin treatment improved myocardial infarction area, heart/body mass index, Creatinine kinase (CK), lactate dehydrogenase (LD), and cardiac troponin-T (CTT) in rats. Rhapontigenin treatment significantly downregulated the expression levels of TNF-α, IL-6, MD, SOD, p38, and iNOS. |
References: [1]Yeh Y H, Wang S W, Yeh Y C, et al. Rhapontigenin inhibits TGF-β-mediated epithelial mesenchymal transition via the PI3K/AKT/mTOR pathway and is not associated with HIF-1α degradation[J]. Oncology Reports, 2016, 35(5): 2887-2895. [2]Fan Y. Cardioprotective effect of rhapontigenin in isoproterenol-induced myocardial infarction in a rat model[J]. Pharmacology, 2019, 103(5-6): 291-302. | |
Rhapontigenin is a potent and selective inactivator of cytochrome P4501A1 with an IC50 of 0.4μM. It is 400-fold and 23-fold more selective for P4501A1 than P4501A2 and P4501B1, respectively[1]. Rhapontigenin is a natural analog of resveratrol and has anticancer, antioxidant, antifungal and antibacterial activities[2, 3].
In vitro, treatment of PC3 cells with Rhapontigenin (0, 2.5, 5, 10, 20μM) for 30min inhibited the expression of HIF-1α protein in a concentration-dependent manner and reduced the protein levels of epithelial-mesenchymal transition (EMT)-related markers N-cadherin, vimentin and the HIF-1α target gene anhydrous carbonate IX (CA9)[4]. Rhapontigenin (0-250μg/mL) treated HepG2 cells for 24h, inhibited cell viability in a concentration-dependent manner, with an IC50 of 115μg/mL[5].
In vivo, Rhapontigenin (1, 2.5, 5mg/kg/day) was injected into the tail vein to treat rats with myocardial infarction for 8 days, which improved the myocardial infarction area, heart/body mass index, creatine kinase (CK), lactate dehydrogenase (LD) and cardiac troponin-T (CTT) in rats, and significantly downregulated the expression levels of TNF-α, IL-6, MDA, SOD, p38 and iNOS[6]. Rhapontigenin (1-5mg/kg) was orally treated with hyperlipidemic rats for 4 weeks, which dose-dependently improved the pathological characteristics of degenerative fatty liver in rats and significantly reduced serum lipid levels[7].
References:
[1] Chun Y J, Ryu S Y, Jeong T C, et al. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin[J]. Drug Metabolism and Disposition, 2001, 29(4): 389-393.
[2] Chen D, Liu J R, Cheng Y, et al. Metabolism of rhaponticin and activities of its metabolite, rhapontigenin: a review[J]. Current Medicinal Chemistry, 2020, 27(19): 3168-3186.
[3] Sun Y, Liang X, Cheng H, et al. Review of characteristics, pharmacology, determination and pharmacokinetics of rhaponticin[J]. Mini-Reviews in Organic Chemistry, 2017, 14(1): 24-34.
[4] Yeh Y H, Wang S W, Yeh Y C, et al. Rhapontigenin inhibits TGF-β-mediated epithelial mesenchymal transition via the PI3K/AKT/mTOR pathway and is not associated with HIF-1α degradation[J]. Oncology Reports, 2016, 35(5): 2887-2895.
[5] Roupe K A, Helms G L, Halls S C, et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: Applications to metabolism, pharmacokinetics and anti-cancer studies[J]. J. Pharm. Pharm. Sci, 2005, 8(3): 374-386.
[6] Fan Y. Cardioprotective effect of rhapontigenin in isoproterenol-induced myocardial infarction in a rat model[J]. Pharmacology, 2019, 103(5-6): 291-302.
[7] Jo S P, Kim J K, Lim Y H. Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet[J]. Planta medica, 2014, 80(13): 1067-1071.
Rhapontigenin（丹叶大黄素）是一种有效的细胞色素P4501A1选择性灭活剂，IC50为0.4μM，对P4501A1的选择性分别是P4501A2和P4501B1的400倍和23倍[1]。Rhapontigenin是白藜芦醇的天然类似物，具有抗癌、抗氧化、抗真菌和抗菌活性[2, 3]。
在体外，Rhapontigenin（0, 2.5, 5, 10, 20μM）处理PC3细胞30min，以浓度依赖性方式抑制HIF-1α蛋白的表达，降低了上皮间质转化（EMT）相关标记物N-钙粘蛋白、波形蛋白和HIF-1α靶基因无水碳酸IX（CA9）的蛋白质水平[4]。Rhapontigenin（0-250μg/mL）处理HepG2细胞24h，浓度依赖性地抑制了细胞活力，IC50为 115μg/mL[5]。
在体内，Rhapontigenin（1, 2.5, 5mg/kg/day）通过尾静脉注射治疗心肌梗死大鼠8天，改善了大鼠心肌梗死面积、心脏/体重指数、肌酸激酶（CK）、乳酸脱氢酶（LD）和心肌肌钙蛋白-T（CTT），显著下调了TNF-α、IL-6、MDA、SOD、p38和iNOS的表达水平[6]。Rhapontigenin（1-5mg/kg）通过口服治疗高脂血症大鼠4周，剂量依赖性地改善了大鼠退化性脂肪肝的病理特征，显著降低了血清脂质水平[7]。
| Cas No. | 500-65-2 | SDF | |
| 别名 | 丹叶大黄素 | ||
| 化学名 | 5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol | ||
| Canonical SMILES | COc1ccc(/C=C\c2cc(O)cc(O)c2)cc1O | ||
| 分子式 | C15H14O4 | 分子量 | 258.3 |
| 溶解度 | ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide | 储存条件 | 4°C, protect from light |
| 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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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.8715 mL | 19.3573 mL | 38.7147 mL |
| 5 mM | 0.7743 mL | 3.8715 mL | 7.7429 mL |
| 10 mM | 0.3871 mL | 1.9357 mL | 3.8715 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 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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| % DMSO % % Tween 80 % saline | ||||||||||
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计算结果:
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2.
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