Norwogonin
(Synonyms: 去甲汉黄芩素; 5,7,8-Trihydroxyflavone) 目录号 : GC45990
A polyhydroxy flavone with diverse biological activities
Cas No.:4443-09-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Norwogonin is a polyhydroxy flavone that has been found in S. baicalensis and has diverse biological activities, including antioxidant, antiviral, and anticancer properties.1,2,3 It scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl radicals with IC50 values of 1.24 and 35.61 μg/ml, respectively, in cell-free assays.1 Norwogonin inhibits cytopathic effects induced by enterovirus 71 (EV71) in infected Vero cells (IC50 = 31.83 μg/ml).2 It reduces the viability of MDA-MB-231, BT-549, HCC70, and HCC1806 triple-negative breast cancer (TNBC) cells (IC50s = 32.24, 56.2, 39.05, and 37.3 μM, respectively) but not the non-tumorigenic cell lines MCF-10A and AG11132 (IC50s = >100 μM for both).3 Norwogonin induces cell cycle arrest at the G1 and G2/M phases and increases apoptosis in MDA-MB-231 cells in a concentration-dependent manner.
|1. Sarian, M.N., Ahmed, Q.U., Mat So'ad, S.Z., et al. Antioxidant and antidiabetic effects of flavonoids: A structure-activity relationship based study. Biomed. Res. Int. 2017:8386065, (2017).|2. Choi, H.J., Song, H.-H., Lee, J.-S., et al. Inhibitory effects of Norwogonin, Oroxylin A, and Mosloflavone on Enterovirus 71. Biomol. Ther. (Seoul) 24(5), 552-558 (2016).|3. Abd El-Hafeez, A.A., Khalifa, H.O., Mahdy, E.A.M., et al. Anticancer effect of nor-wogonin (5, 7, 8-trihydroxyflavone) on human triple-negative breast cancer cells via downregulation of TAK1, NF-κB, and STAT3. Pharmacol. Rep. 71(2), 289-298 (2019).
| Cas No. | 4443-09-8 | SDF | |
| 别名 | 去甲汉黄芩素; 5,7,8-Trihydroxyflavone | ||
| Canonical SMILES | O=C1C=C(C2=CC=CC=C2)OC3=C(O)C(O)=CC(O)=C31 | ||
| 分子式 | C15H10O5 | 分子量 | 270.2 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.1 mg/ml,Ethanol: 0.1 mg/ml | 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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| 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 | 3.701 mL | 18.5048 mL | 37.0096 mL |
| 5 mM | 0.7402 mL | 3.701 mL | 7.4019 mL |
| 10 mM | 0.3701 mL | 1.8505 mL | 3.701 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。
Norwogonin attenuates hypoxia-induced oxidative stress and apoptosis in PC12 cells
BMC Complement Med Ther 2021 Jan 7;21(1):18.PMID:33413359DOI:10.1186/s12906-020-03189-8.
Background: Norwogonin is a natural flavone with three phenolic hydroxyl groups in skeletal structure and has excellent antioxidant activity. However, the neuroprotective effect of Norwogonin remains unclear. Here, we investigated the protective capacity of Norwogonin against oxidative damage elicited by hypoxia in PC12 cells. Methods: The cell viability and apoptosis were examined by MTT assay and Annexin V-FITC/PI staining, respectively. Reactive oxygen species (ROS) content was measured using DCFH-DA assay. Lactate dehydrogenase (LDH), malondialdehyde (MDA) and antioxidant enzyme levels were determined using commercial kits. The expression of related genes and proteins was measured by real-time quantitative PCR and Western blotting, respectively. Results: We found that Norwogonin alleviated hypoxia-induced injury in PC12 cells by increasing the cell viability, reducing LDH release, and ameliorating the changes of cell morphology. Norwogonin also acted as an antioxidant by scavenging ROS, reducing MDA production, maintaining the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx), and decreasing the expression levels of HIF-1α and VEGF. In addition, Norwogonin prevented cell apoptosis via inhibiting the expression levels of caspase-3, cytochrome c and Bax, while increasing the expression levels of Bcl-2 and the ratio of Bcl-2/Bax. Conclusions: Norwogonin attenuates hypoxia-induced injury in PC12 cells by quenching ROS, maintaining the activities of antioxidant enzymes, and inhibiting mitochondrial apoptosis pathway.
Norwogonin flavone suppresses the growth of human colon cancer cells via mitochondrial mediated apoptosis, autophagy induction and triggering G2/M phase cell cycle arrest
J BUON 2020 May-Jun;25(3):1449-1454.PMID:32862589doi
Purpose: Colorectal cancer is one of the deadly malignancies and is one of the top three most common cancers and the third leading cause of cancer-related deaths. The main objective of the study was to investigate the anticancer effects of Norwogonin - a naturally occurring plant flavone. We also examined its effects on programmed cell death, autophagy and cell cycle phase distribution. Methods: Cell viability of colon cancer cells was evaluated by MTT assay while apoptotic studies were carried out by fluorescence microscopy using acridine orange (AO)/ethidium bromide (EB) and Comet assays. Transmission electron microscopy (TEM) was used to study formation of autophagosomes reminiscent of autophagy. Furthermore, western blot assay was used to study the effects of Norwogonin on apoptosis-related protein expressions including Bax, Bcl-2 and autophagy-related proteins. Effects on cell cycle were evaluated by flow cytometry. Results: The results showed that Norwogonin causes substantial reduction in the viability of the human colorectal carcinoma cells in a dose-dependent manner, exhibiting an IC50 of 15.5 µM in cancer cells and IC50 of 90 µM in normal cell lines. The AO/EB staining assay showed that Norwogonin suppresses the viability of cancer cells via induction of apoptotic cell death which was associated with increase in Bax and decrease in Bcl-2 levels. Comet assay results also confirmed that Norwogonin induces apoptosis. Norwogonin also led to induction of autophagy along with triggering G2/M phase cell cycle arrest. Conclusions: In conclusion, the current study shows that Norwogonin has a potential to inhibit in vitro colorectal cancer cells growth by triggering apoptosis, autophagy and cell cycle arrest and as such could be developed as a possible anticancer agent.
Inhibitory Effects of Norwogonin, Oroxylin A, and Mosloflavone on Enterovirus 71
Biomol Ther (Seoul) 2016 Sep 1;24(5):552-8.PMID:27257010DOI:10.4062/biomolther.2015.200.
Severe complications associated with EV71 infections are a common cause of neonatal death. Lack of effective therapeutic agents for these infections underlines the importance of research for the development of new antiviral compounds. In the present study, the anti-EV71 activity of Norwogonin, oroxylin A, and mosloflavone from Scutellaria baicalensis Georgi was evaluated using a cytopathic effect (CPE) reduction method, which demonstrated that all three compounds possessed strong anti-EV71 activity and decreased the formation of visible CPEs. Norwogonin, oroxylin A, and mosloflavone also inhibited virus replication during the initial stage of virus infection, and they inhibited viral VP2 protein expression, thereby inhibiting viral capsid protein synthesis. However, ribavirin has a relatively weaker efficacy compared to the other drugs. Therefore, these findings provide important information that will aid in the utilization of Norwogonin, oroxylin A, and mosloflavone for EV71 treatment.
Multi-material basis and multi-mechanisms of the Dahuang Zhechong pill for regulating Treg/Th1 balance in hepatocellular carcinoma
Phytomedicine 2022 Jun;100:154055.PMID:35344716DOI:10.1016/j.phymed.2022.154055.
Background: Dahuang Zhechong pill (DHZCP) improves the inhibitory immune status of mice with hepatocellular carcinoma (HCC) by regulating Treg/Th1 balance. Hypothesis/purpose: To study the multi-material basis and multi-mechanisms of DHZCP against HCC by regulating Treg/Th1 balance in vitro and in vivo. Methods: UPLC-MS/MS was used to detect the dynamic changes in 29 characteristic components of different polar parts of DHZCP. H&E and TUNEL were used to check pathological condition in HCC mice. The number of CD4+T, CD8+T, Treg, Th1, and Th1-like Treg cells was counted by flow cytometry. TGF-β, IL-10, IFN-γ, and TNF-α content were detected by ELISA. α-Ketoglutarate and glutamine levels were detected by Trace1310/TSQ8000 GC-MS/MS. p-Smad2, and p-Smad3 protein levels were detected by WB, mRNA expression of Smad2, alanine-serine-cysteine transporter-2, glutaminase, and glutamate dehydrogenase were detected by RT-PCR. Simca-p multivariate data analysis software was used to evaluate the relationship between the different polar parts of DHZCP and the proportion of Treg cells. Results: Water-soluble (PW) and ethyl acetate (PE) polar parts of DHZCP affected the HCC immune system by inhibiting the differentiation of Tregs, reversing the balance of Treg/Th1, and significantly reduced the tumor volume and weight. However, petroleum ether and n-butanol polar parts had no above actions. The changes in emodin, chrysophanol, aloe vera emodin, emodin-8-O-β-D-glycoside, gallic acid, naringenin, baicalein, wogonin, Norwogonin, apigenin, chrysin, glycyrrhizin, formononetin, and palmitic acid were closely related to the changes of Treg cells, which is the main material basis of DHZCP inhibition of Treg differentiation. Additionally, PW mainly inhibit the differentiation of Treg cells by affecting the metabolism of hepatoma cells, improving tumor microenvironment acidity, and glutamine depletion. However, PE inhibited the differentiation of Treg cells mainly by regulating the TGF-β/Smad pathway. Conclusion: In this study, accurate analysis of multi-component was combined with pharmacodynamic evaluations to identify the pharmacodynamic substances of DHZCP in regulating Treg/Th1 balance, and clarified the multi-target mechanism of DHZCP to improve tumor immunity. The study style offers a novel approach for pharmacological research on TCM.
Convergent synthesis of moslosooflavone, isowogonin and Norwogonin from chrysin
Nat Prod Commun 2015 Mar;10(3):387-8.PMID:25924511doi
A convergent synthesis route of moslooflavone, isowogonin and norwogoninis reported,starting from chrysin, an easily available flavone, by methylation, bromination, methoxylation and demethylation procedures. This synthetic route is convenient and can give the three rare flavones in good yield.