Nepodin
(Synonyms: 羊蹄素,Musizin) 目录号 : GC38567
A naphthol with diverse biological activities
Cas No.:3785-24-8
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
Nepodin is a naphthol that has been found in Rumex and has diverse biological activities.1,2,3,4 It inhibits COX-1 and COX-2 in vitro (IC50s = 27.43 and 32.28 μM, respectively).1 Nepodin inhibits C. albicans and S. aureus biofilm formation in a concentration-dependent manner when used at concentrations ranging from 1 to 10 μM.2 It is active against chloroquine-sensitive and -resistant P. falciparum strains (IC50s = 0.74 and 0.79 μg/ml for strains 3D7 and S20, respectively).3 Nepodin (250 mg/kg) suppresses parasitemia and increases survival time in a mouse model of P. berghei infection. It also increases skeletal muscle phosphorylation of AMPK, reduces serum and hepatic triglyceride and cholesterol levels, and improves insulin resistance in db/db diabetic mice.4
1.Grover, J., Kumar, V., Singh, V., et al.Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitorsEur. J. Med. Chem.8047-56(2014) 2.Lee, J.H., Kim, Y.G., Khadke, S.K., et al.Inhibition of biofilm formation by Candida albicans and polymicrobial microorganisms by nepodin via hyphal-growth suppressionACS Infect. Dis.5(7)1177-1187(2019) 3.Lee, K.H., and Rhee, K.H.Antimalarial activity of nepodin isolated from Rumex crispusArch. Pharm. Res.36(4)430-435(2013) 4.Ha, B.G., Yonezawa, T., Son, M.J., et al.Antidiabetic effect of nepodin, a component of Rumex roots, and its modes of action in vitro and in vivoBiofactors40(4)436-447(2014)
| Cas No. | 3785-24-8 | SDF | |
| 别名 | 羊蹄素,Musizin | ||
| Canonical SMILES | CC(C1=C(C)C=C2C=CC=C(O)C2=C1O)=O | ||
| 分子式 | C13H12O3 | 分子量 | 216.23 |
| 溶解度 | Methanol: soluble | 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 | 4.6247 mL | 23.1235 mL | 46.2471 mL |
| 5 mM | 0.9249 mL | 4.6247 mL | 9.2494 mL |
| 10 mM | 0.4625 mL | 2.3124 mL | 4.6247 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。
Evaluation of raw Nepodin extraction from Rumex japonicus and R. obtusifolius and their DNA polymorphisms
J Nat Med 2018 Jan;72(1):369-374.PMID:29063361DOI:10.1007/s11418-017-1143-0.
Nepodin, found in the roots of Rumex japonicus Houtt. (Polygonaceae), inhibits osteoclast differentiation and has an antidiabetic effect. We propose Nepodin as an ingredient of new functional foods or as a drug candidate for reducing the risk of reduced locomotion resulting from diseases such as osteoporosis. Although there are no previous reports of R. obtusifolius L., which is found throughout Japan, having roots containing Nepodin, we found Nepodin in the roots of this species. Therefore, R. obtusifolius as well as R. japonicus was considered a candidate raw material for Nepodin extraction. We also discuss the suitability of R. japonicus and R. obtusifolius as sources of raw Nepodin for cultivation on the Ryukyu Islands. In this study, all specimens on the Ryukyu Islands were identified as R. japonicus. Conversely, all specimens on mainland Japan were R. obtusifolius. The DNA sequence of the chloroplast trnL-trnF intergenic spacer region and partial nuclear internal transcribed spacer was consistent with the identification of R. japonicus and R. obtusifolius by morphological characteristics of the perianth segments. Therefore, to avoid erroneous identification and misuse of the plant species used for extraction of raw materials, it is preferable to develop DNA markers for these two regions. The content of Nepodin varied from undetectable to 0.34% of the fresh weight (%FW) in R. japonicus and from undetectable to 0.21%FW in R. obtusifolius. From a pharmacological perspective, as plants that might be suitable as raw materials for Nepodin extraction, it became clear that both R. japonicus and R. obtusifolius can be used with the same expected extraction efficiency. Based on our findings, R. obtusifolius could not be confirmed as inhabiting the Ryukyu Islands. For this reason, to conserve the endemic genetic characteristics of the Ryukyu Islands and to prevent genetic pollution by R. obtusifolius, only R. japonicus should be cultivated on the Ryukyu Islands.
Antimalarial activity of Nepodin isolated from Rumex crispus
Arch Pharm Res 2013 Apr;36(4):430-5.PMID:23440579DOI:10.1007/s12272-013-0055-0.
The purpose of this study is to define the antimalarial activity of Rumex crispus. To identify an active compound that is isolated from R. crispus, bioassay-based chromatographic fractionation and purification is carried out from 70 % ethanol extract of R. crispus; then, an active compound, Nepodin, is identified by spectroscopic analysis. Anitmalarial activity is measured by PfNDH2 assay, cytotoxicity, and animal test. From NADH:quinone oxidoreductase enzyme (PfNDAH2) assay, Nepodin exhibited significant IC50 values that were 0.74 ± 0.07 and 0.79 ± 0.06 μg/ml against P. falciparum chloroquine-sensitive (3D7) and P. falciparum chloroquine-resistant (S20), respectively. Nepodin showed a potential selective inhibition (SI index: ratio of 50 % cytotoxic concentration to 50 % effective anti-plasmodial concentration) of 161.6 and 151.4 against P. falciparum 3D7 and P. falciparum S20. In the animal test, all groups of Nepodin treatment of 10, 50, and 250 mg/kg were active with a parasitemia suppression of 97.1 ± 3.3, 99.1 ± 3.7, and 99.1 ± 2.6 %, respectively. The survival time with Nepodin treatment was increased by 14.6 ± 2.5, 16.2 ± 1.5, and 19.8 ± 1.7 days at each dose, respectively. This study newly identified the plant R. crispus containing Nepodin, which is a potential antimalarial compound. It exhibited the inhibitory activity of PfNDH2 and prolonged the survival time on the group of Nepodin treatment; moreover, it inhibited the parasitemia in the animal test.
Antidiabetic effect of Nepodin, a component of Rumex roots, and its modes of action in vitro and in vivo
Biofactors 2014 Jul-Aug;40(4):436-47.PMID:24756979DOI:10.1002/biof.1165.
Many active components derived from edible natural resources such as plant extracts have recently attracted attention for their potential use as functional foods or drugs for preventing and treating metabolic diseases such as diabetes. To obtain a novel modulator of glucose metabolism, we conducted screening of a small compound library in cultured L6 myotubes. We identified Nepodin that stimulated glucose uptake dose-dependently in differentiated L6 myotubes. The stimulatory effect of Nepodin on glucose uptake was abrogated by a 5'-adenosine monophosphate-activated protein kinase (AMPK) inhibitor. In addition, Nepodin stimulated the phosphorylation of AMPK. Nepodin also stimulated the translocation of GLUT4 to the plasma membrane in L6 myoblasts transfected with a Glut4 cDNA-coding vector and in differentiated L6 myotubes. In in vivo study, Nepodin suppressed the increases in fasting blood glucose levels and improved the glucose intolerance of C57BL/KsJ-db/db mice, a type 2 diabetic animal model. Nepodin rescued the impaired phosphorylation of AMPK in the skeletal muscle of db/db mice. These results suggest that Nepodin has an antidiabetic effect, which is at least partly mediated by stimulation of GLUT4 translocation via AMPK activation by Nepodin.
Inhibition of Biofilm Formation by Candida albicans and Polymicrobial Microorganisms by Nepodin via Hyphal-Growth Suppression
ACS Infect Dis 2019 Jul 12;5(7):1177-1187.PMID:31055910DOI:10.1021/acsinfecdis.9b00033.
Candida albicans is an opportunistic pathogenic yeast and is responsible for candidiasis. It readily colonizes host tissues and implant devices, and forms biofilms, which play an important role in pathogenesis and drug resistance. In this study, the antibiofilm, antihyphal, and antivirulence activities of Nepodin, isolated from Rumex japonicus roots, were investigated against a fluconazole-resistant C. albicans strain and against polymicrobial-microorganism-biofilm formation. Nepodin effectively inhibited C. albicans biofilm formation without affecting its planktonic cell growth. Also, Rumex-root extract and Nepodin both inhibited hyphal growth and cell aggregation of C. albicans. Interestingly, Nepodin also showed antibiofilm activities against Candida glabrata, Candida parapsilosis, Staphylococcus aureus, and Acinetobacter baumannii strains and against dual biofilms of C. albicans and S. aureus or A. baumannii but not against Pseudomonas aeruginosa. Transcriptomic analysis performed by RNA-seq and qRT-PCR showed Nepodin repressed the expression of several hypha- and biofilm-related genes (ECE1, HGT10, HWP1, and UME6) and increased the expression of several transport genes (CDR4, CDR11, and TPO2), which supported phenotypic changes. Moreover, Nepodin reduced C. albicans virulence in a nematode-infection model and exhibited minimal cytotoxicity against the nematode and an animal cell line. These results demonstrate that Nepodin and Rumex-root extract might be useful for controlling C. albicans infections and multispecies biofilms.
Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of Nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitors
Eur J Med Chem 2014 Jun 10;80:47-56.PMID:24763362DOI:10.1016/j.ejmech.2014.04.033.
Nepodin and chrysophanol, isolated from Rumex nepalensis roots, showed significant cyclooxygenase (COX) inhibitory activity. To further optimize these lead molecules and study structure activity relationship (SAR), eighteen derivatives of Nepodin and nine derivatives of chrysophanol were synthesized and evaluated for COX-1 and COX-2 inhibitory potential. Among the synthesized compounds, four Nepodin (1f, 1g, 1h and 1i) and three chrysophanol (2e, 2f and 2h) derivatives displayed more pronounced COX-2 inhibition than their respective lead molecule. Further, compounds 1f, 1g, 2e and 2h exhibited better anti-inflammatory activity than ibuprofen in carrageenan-induced rat paw edema assay. Taking into account the in vitro and in vivo results, molecular docking and in silico prediction of ADMET properties of compounds were carried out respectively.