(±)-Praeruptorin A是ciskhellactone（CKL）的二酯化产物，是紫草根中的主要活性成分，具有显著的抗高血压作用，通常通过作为钙通道阻滞剂发挥作用。
Cas No.:73069-25-7
Sample solution is provided at 25 µL, 10mM.
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(±)-Praeruptorin A (PA) is the di-esterified product of ciskhellactone (CKL) and the major active ingredient in Peucedani Radix and exhibits dramatically anti-hypertensive effect typically through acting as a calcium channel blocker. (±)-Praeruptorin A is revealed anti-inflammatory activity typically by inhibiting the activation of NF-B pathway[1]. (±)-Praeruptorin A also shows great therapeutic potential for the treatment of allergic asthma[2].
In vitro, (±)-Praeruptorin A (0-40μM; 24h) dose-dependently inhibited the LPS (1μg/mL)-induced increases in the mRNA and protein expression levels of inflammatory factors, including TNF-α, IL-1β, IL-6, IL-8, MCP-2, and VCAM-1, in HUVECs[3]. (±)-Praeruptorin A (0-50μM; 24h) dose-dependently inhibited the proliferation, migration, and invasion of HeLa and SiHa cells, accompanied by the downregulation of Matrix Metalloproteinase-2 (MMP-2) and Extracellular signal-Regulated Kinase 1/2 (ERK1/2) signaling-related expression[4]. (±)-Praeruptorin A (0-30μM; 24h) dose-dependently inhibited the migration and invasion of hepatocellular carcinoma cell[5].
In vivo, treatment with (±)-Praeruptorin A (30, 60, 120mg/kg/d; p.o.; 5 days) dose-dependently reduced airway hyperresponsiveness and eosinophilic airway inflammation in mice with allergic asthma, improved lung pathological injury, decreased the levels of interleukin (IL)-4, IL-5, IL-13, and LTC4 in bronchoalveolar lavage fluid as well as serum immunoglobulin E (IgE) levels, and inhibited pulmonary eotaxin production and mRNA expression, IκBα degradation, NF-κB nuclear translocation, NF-κB DNA-binding activity, and RelA/p65 phosphorylation[6]. (±)-Praeruptorin A (2mg/kg; i.v.; once) reduced serum IL-6 levels and the expression of Fas, Bax, and Bcl-2, increased the Bcl-2/Bax ratio, and alleviated inflammatory cell infiltration in rats subjected to 30min of ischemia followed by 120min of reperfusion[7].
References:
[1] Song, Yue-Lin et al. “Metabolic characterization of (±)-praeruptorin A in vitro and in vivo by high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry and time-of-flight mass spectrometry.” Journal of pharmaceutical and biomedical analysis vol. 90 (2014): 98-110.
[2] Xiong, Youyi et al. “Effects of (±)-praeruptorin A on airway inflammation, airway hyperresponsiveness and NF-κB signaling pathway in a mouse model of allergic airway disease.” European journal of pharmacology vol. 683,1-3 (2012): 316-24.
[3] Chang H, Zhang J, Yang C, Qi Z. Pd-Ia exerts anti-inflammatory effects by activating PPAR-α in human umbilical vein endothelial cells. J Transl Sci. 2019;5:1-7.
[4] Wu, Min-Hua et al. “Praeruptorin A Inhibits Human Cervical Cancer Cell Growth and Invasion by Suppressing MMP-2 Expression and ERK1/2 Signaling.” International journal of molecular sciences vol. 19,1 10. 21 Dec. 2017.
[5] Wang, Qiongxiao et al. “The traditional uses, pharmacology, and phytochemistry of Peucedanum praeruptorum Dunn.” Frontiers in pharmacology vol. 15 1352657. 3 Apr. 2024.
[6] Xiong, Youyi et al. “Effects of (±)-praeruptorin A on airway inflammation, airway hyperresponsiveness and NF-κB signaling pathway in a mouse model of allergic airway disease.” European journal of pharmacology vol. 683,1-3 (2012): 316-24.
[7] Chang, Tian-Hui et al. “Effects of dl-praeruptorin A on interleukin-6 level and Fas, bax, bcl-2 protein expression in ischemia-reperfusion myocardium.” Acta pharmacologica Sinica vol. 23,9 (2002): 769-74.
(±)-Praeruptorin A是ciskhellactone（CKL）的二酯化产物，是紫草根中的主要活性成分，具有显著的抗高血压作用，通常通过作为钙通道阻滞剂发挥作用。(±)-Praeruptorin A通过抑制NF-B通路的激活而显示出抗炎活性[1]。(±)-Praeruptorin A还具有治疗过敏性哮喘的巨大潜力[2]。
体外实验中，(±)-Praeruptorin A（0-40μM；24h）剂量依赖性抑制了1μg/ml LPS诱导的HUVECs细胞中TNF-α、IL-1β、IL-6、IL-8、MCP-2和VCAM-1等炎症因子mRNA和蛋白表达水平的增加[3]。(±)-Praeruptorin A（0-50μM；24h）剂量依赖性抑制HeLa和SiHa细胞的增殖、迁移和侵袭，并下调胞内MMP-2、ERK1/2相关信号的表达[4]。(±)-Praeruptorin A（0-30μM；24h）剂量依赖性抑制人肝癌细胞系的迁移和侵袭[5]。
体内实验中，(±)-Praeruptorin A（30，60，120mg/kg/d；口服；5天）可剂量依赖性地降低过敏性哮喘模型小鼠的气道高反应性和嗜酸性粒细胞性气道炎症，改善肺部病理损伤，降低支气管肺泡灌洗液中白细胞介素（IL）-4、IL-5、IL-13 和LTC4的水平以及血清中免疫球蛋白（Ig）E的水平，并抑制肺组织中嗜酸性粒细胞趋化蛋白的生成及其mRNA表达、IκBα的降解、NF-κB的核转位、NF-κB的DNA结合活性以及RelA/p65的磷酸化[6]。(±)-Praeruptorin A（2mg/kg；静脉注射；单次给药）可降低大鼠30分钟缺血后120分钟再灌注模型中的血清IL-6水平以及Fas、Bax和Bcl-2的表达，提高Bcl-2/Bax比值，并减轻炎症细胞浸润[7]。
| Cell experiment [1]: | |
Cell lines | HUVECs |
Preparation Method | Cells were treated with 1μg/ml LPS and 0-40μM (±)-Praeruptorin A for 24h. Relative expression of TNF-α and IL-1β, IL-6, IL-8, MCP-2 and VCAM-1 were detected by quantitative real-time PCR analysis and ELISA analysis. |
Reaction Conditions | 10, 20, 40μM; 24h |
Applications | (±)-Praeruptorin A dose-dependently inhibited the LPS (1μg/mL)-induced increases in the mRNA and protein expression levels of inflammatory factors, including TNF-α, IL-1β, IL-6, IL-8, MCP-2, and VCAM-1. |
| Animal experiment [2]: | |
Animal models | Female BALB/c mice |
Preparation Method | Mice were assigned randomly to one of the following six experimental groups: control, three different doses of (±)-Praeruptorin A (30, 60 and 120mg/kg), model and dexamethasone. All mice, except for those in the control group, were sensitized on days 0 and 14 by intra-peritoneal injection of 10μg ovalbumin dissolved in saline containing 200μg aluminium hydroxide gel in a total volume of 0.2ml; mice in control group received alum only. On day 28, all ovalbumin-sensitized mice were aerosol challenged with 1% ovalbumin in phosphate-buffered saline in an exposure chamber by a nebulizer for 20min per day for 5 consecutive days; mice in control group received only phosphatebuffered saline aerosol. One hour before every airway challenge, mice in (±)-Praeruptorin A groups were administered intragastrically with (±)-Praeruptorin A dissolved in 0.5% sodium carboxymethyl cellulose solution at a dose of 30, 60 and 120mg/kg, respectively; mice in dexamethasone group were injected with dexamethasone dissolved in 0.9% sodium chloride at a dose of 3mg/kg; mice in control and model group were intragastrically administered with 0.5% sodium carboxymethyl cellulose solution for parallel manipulation. |
Dosage form | 30, 60, 120mg/kg/d; p.o.; 5d |
Applications | Treatment of mice with (±)-Praeruptorin A decreased the lung resistance (RL) in a murine model of allergic airway disease. (±)-Praeruptorin A inhibited the increase in the numbers of total leukocytes, eosinophils, neutrophils, and lymphocytes in model mice. Levels of inflammatory mediators and IgE in mice were significantly decreased by the treatment of (±)-Praeruptorin A in a dose-dependent manner. (±)-Praeruptorin A inhibited eotaxin protein/mRNA expression, IκBα degradation, NF-κB nuclear translocation, NF-κB DNA-binding activity, and RelA/p65 phosphorylation in lung tissue. |
References: | |
| Cas No. | 73069-25-7 | SDF | |
| 别名 | (±)-白花前胡甲素 | ||
| 化学名 | [(9R,10S)-10-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate | ||
| Canonical SMILES | C/C([H])=C(C(O[C@](C1(C)C)([H])[C@](OC(C)=O)([H])C2=C(O1)C=CC(C=C3)=C2OC3=O)=O)/C | ||
| 分子式 | C21H22O7 | 分子量 | 386.40 |
| 溶解度 | ≥ 30mg/mL in DMSO | 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 | 2.588 mL | 12.94 mL | 25.8799 mL |
| 5 mM | 517.6 μL | 2.588 mL | 5.176 mL |
| 10 mM | 258.8 μL | 1.294 mL | 2.588 mL |
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| % DMSO % % Tween 80 % saline | ||||||||||
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