Oxypeucedanin
(Synonyms: 氧化前胡素) 目录号 : GC39006
Oxypeucedanin 是从 Angelica dahurica 中分离出来的呋喃香豆素衍生物。Oxypeucedanin 是一种选择性的开放通道阻滞剂，可抑制 hKv1.5 通道电流，IC50 值为 76 nM。Oxypeucedanin 延长心脏动作电位持续时间 (APD)，是一种潜在的抗心律失常试剂。Oxypeucedanin 通过抑制癌细胞迁移来诱导细胞凋亡 (apoptosis )。
Cas No.:737-52-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oxypeucedanin is a furocoumarin derivative isolated from Angelica dahurica. Oxypeucedanin is a selective open-channel blocker, inhibits the hKv1.5 current with an IC50 value of 76 nM. Oxypeucedanin prolongs cardiac action potential duration (APD), is a potential antiarrhythmic agent for atrial fibrillation[1]. Oxypeucedanin induces cell apoptosis through inhibition of cancer cell migration[2].
[1]. Eun JS, et al. Effects of oxypeucedanin on hKv1.5 and action potential duration.Biol Pharm Bull. 2005 Apr;28(4):657-60. [2]. Yu Liu, et al. Oxypeucedanin hydrate monoacetate isolated from Angelica dahurica induces apoptosis in Caco-2 colon carcinoma cells through the mediation of PI3K-signalling pathway and inhibition of cancer cell migration
| Cas No. | 737-52-0 | SDF | |
| 别名 | 氧化前胡素 | ||
| Canonical SMILES | CC1(C)C(O1)COC2=C(C=CO3)C3=CC(O4)=C2C=CC4=O | ||
| 分子式 | C16H14O5 | 分子量 | 286.28 |
| 溶解度 | Soluble 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 | 3.4931 mL | 17.4654 mL | 34.9308 mL |
| 5 mM | 0.6986 mL | 3.4931 mL | 6.9862 mL |
| 10 mM | 0.3493 mL | 1.7465 mL | 3.4931 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities
Plants (Basel) 2021 Jul 30;10(8):1577.PMID:34451622DOI:10.3390/plants10081577.
The present review comprehensively gathered phytochemical, bioactivity, and pharmacokinetic reports on a linear furanocoumarin, namely Oxypeucedanin. Oxypeucedanin (OP), which structurally contains an epoxide ring, has been majorly isolated from ethyl acetate-soluble partitions of several genera, particularly Angelica, Ferulago, and Prangos of the Apiaceae family; and Citrus, belonging to the Rutaceae family. The methanolic extract of Angelica dahurica roots has been analytically characterized as the richest natural OP source. This naturally occurring secondary metabolite has been described to possess potent antiproliferative, cytotoxic, anti-influenza, and antiallergic activities, as assessed in preclinical studies. In order to explore potential drug candidates, Oxypeucedanin, its derivatives, and semi-synthetically optimized analogues can be considered for the complementary assessments of biological assays.
Oxypeucedanin is a Mechanism-based Inactivator of CYP2B6 and CYP2D6
Curr Drug Metab 2021;22(11):882-892.PMID:34191696DOI:10.2174/1389200222666210629114830.
Background: Herbal medicine Angelica dahurica is widely employed for the treatment of rheumatism and pain relief in China. Oxypeucedanin is a major component in the herb. Objectives: The objectives of this study are aimed at the investigation of mechanism-based inactivation of CYP2B6 and CYP2D6 by Oxypeucedanin, characterization of the reactive metabolites associated with the enzyme inactivation, and identification of the P450s participating in the bioactivation of Oxypeucedanin. Methods: Oxypeucedanin was incubated with liver microsomes or recombinant CYPs2B6 and 2D6 under designed conditions, and the enzyme activities were measured by monitoring the generation of the corresponding products. The resulting reactive intermediates were trapped with GSH and analyzed by LC-MS/MS. Results: Microsomal incubation with Oxypeucedanin induced a time-, concentration-, and NADPH-dependent inhibition of CYPs2B6 and 2D6 with kinetic values of KI/kinact 1.82 μM/0.07 min-1 (CYP2B6) and 8.47 μM/0.044 min-1 (CYP2D6), respectively. Ticlopidine and quinidine attenuated the observed time-dependent enzyme inhibitions. An epoxide and/or γ-ketoenal intermediate(s) derived from Oxypeucedanin was/were trapped in microsomal incubations. CYP3A4 was the primary enzyme involved in the bioactivation of Oxypeucedanin. Conclusion: Oxypeucedanin was a mechanism-based inactivator of CYP2B6 and CYP2D6. An epoxide and/or γ- ketoenal intermediate(s) may be responsible for the inactivation of the two enzymes.
Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier
Aging (Albany NY) 2022 Aug 18;14(16):6626-6641.PMID:35985771DOI:10.18632/aging.204235.
Introduction: Acute lung injury (ALI) is commonly accompanied by a severe inflammatory reaction process, and effectively managing inflammatory reactions is an important therapeutic approach for alleviating ALI. Macrophages play an important role in the inflammatory response, and this role is proinflammatory in the early stages of inflammation and anti-inflammatory in the late stages. Oxypeucedanin is a natural product with a wide range of pharmacological functions. This study aimed to determine the effect of Oxypeucedanin on lipopolysaccharide (LPS)-induced ALI. Methods and results: In this study, the following experiments were performed based on LPS-induced models in vivo and in vitro. Using myeloperoxidase activity measurement, ELISA, qRT-PCR, and Western blotting, we found that Oxypeucedanin modulated the activity of myeloperoxidase and decreased the expression levels of inflammatory mediators such as TNF-α, IL-6, IL-1β, MPO, COX-2 and iNOS in LPS-induced inflammation models. Meanwhile, Oxypeucedanin inhibited the activation of PI3K/AKT and its downstream NF-κB and MAPK signaling pathways. In addition, Oxypeucedanin significantly decreased the pulmonary vascular permeability, which was induced by LPSs, and the enhanced expression of tight junction proteins (Occludin and Claudin 3). Conclusions: In conclusion, this study demonstrated that the anti-inflammatory mechanism of Oxypeucedanin is associated with the inhibition of the activation of PI3K/AKT/NF-κB and MAPK signaling pathways and the maintenance of the integrity of the lung air-blood barrier.
Enantioseparation and determination of Oxypeucedanin and its application to a stereoselective analysis in Angelica Dahuricae Radix and pharmacokinetic study of rats
J Chromatogr B Analyt Technol Biomed Life Sci 2022 Sep 1;1207:123355.PMID:35839628DOI:10.1016/j.jchromb.2022.123355.
In this study, a new enantioseparation method was established for the quantitative analysis of the Oxypeucedanin enantiomers by using cellulose tris(3,5-dichlorophenyl carbamate) stationary phase column Chiralpak IC. For this method, enantiomeric separation of Oxypeucedanin was achieved with the mobile phase consisting of acetonitrile-water (60:40, v/v) at a flow rate of 0.5 mL/min by changing the type and proportion of mobile phase. And the quantitative determination of racemic Oxypeucedanin in Angelica Dahuricae Radix (in vitro) and rat plasma (in vivo) were performed on above-mentioned condition by High PerformanceLiquid Chromatography combined with diode arrangement detector (HPLC-DAD) and mass spectrometry (HPLC-MS/MS). The precision, repeatability, stability, recovery were within the acceptance criteria. And the method was validated in the concentration range of 1-400 μg/mL for the two enantiomers in vitro and 0.2-600 ng/mL in vivo. After validation, the established method was successfully applied to the stereoselective analysis of racemic Oxypeucedanin in Angelica dahurica from different regions and the stereoselective pharmacokinetic investigation in rat. Results showed that the (+)-oxypeucedanin was at a relative high level in Angelica dahuricae Radix and (-)-oxypeucedanin performed a higher plasma concentration, which demonstrated the difference of Oxypeucedanin enantiomers both in vitro and in vivo.
Preclinical Pharmacokinetics and Bioavailability of Oxypeucedanin in Rats after Single Intravenous and Oral Administration
Molecules 2022 Jun 2;27(11):3570.PMID:35684506DOI:10.3390/molecules27113570.
Oxypeucedanin, a furanocoumarin extracted from many traditional Chinese herbal medicines, has a variety of pharmacological effects. However, the independent pharmacokinetic characteristics and bioavailability of this compound remains elusive. In this study, a rapid, sensitive, and selective method using ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC/MS/MS) was developed for evaluating the intravenous and oral pharmacokinetics of Oxypeucedanin. After intravenous administration of Oxypeucedanin (2.5, 5, and 10 mg/kg), and intragastric administration of Oxypeucedanin (20 mg/kg), blood samples were collected periodically from the tail vein. The plasma concentration-time curves were plotted, and the pharmacokinetic parameters were calculated using a non-compartmental model analysis. After intravenous administration of Oxypeucedanin (single dosing at 2.5, 5, and 10 mg/kg) to rats, the pharmacokinetics fit the linear kinetics characteristics, which showed that some parameters including average elimination half-life (T1/2Z of 0.61~0.66 h), mean residence time (MRT of 0.62~0.80 h), apparent volume of distribution (VZ of 4.98~7.50 L/kg), and systemic clearance (CLZ of 5.64~8.55 L/kg/h) are dose-independent and the area under concentration-time curve (AUC) increased in a dose-proportional manner. Single oral administration of Oxypeucedanin (20 mg/kg) showed poor and slow absorption with the mean time to reach the peak concentration (Tmax) of 3.38 h, MRT of 5.86 h, T1/2Z of 2.94 h, and a mean absolute bioavailability of 10.26% in rats. These results provide critical information for a better understanding of the pharmacological effect of Oxypeucedanin, which will facilitate its research and development.