Irigenin
(Synonyms: 野鸢尾黄素) 目录号 : GC38801
An isoflavonoid with diverse biological activities
Cas No.:548-76-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Irigenin is a polyketide synthase-derived isoflavonoid that has been found in B. chinensis rhizomes and has diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoform CYP1A (IC50 = 1.2 ?M) and induces a 2-fold increase in NADPH quinone reductase activity in Hepa-1c1c7 cells when used at a concentration of 7.8 ?M.2 Irigenin inhibits LPS-induced production of nitric oxide (NO) and prostaglandin E2 , as well as increases in the levels of inducible nitric oxide synthase (iNOS) and COX-2, in RAW 264.7 cells.3 In vivo, irigenin (10 and 20 mg/kg) increases survival and reduces cardiac apoptosis, fibrosis, and levels of TNF-α, IL-6, IL-18, and IL-1β in a mouse model of cardiotoxicity induced by doxorubicin .4
1.Raju, K.S.R., Kadian, N., Taneja, I., et al.Phytochemical analysis of isoflavonoids using liquid chromatography coupled with tandem mass spectrometryPhytochem. Rev.14(3)469–498(2015) 2.Wollenweber, E., Stevens, J.F., Klimo, K., et al.Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanicaPlanta Med.69(1)15-20(2003) 3.Ahn, K.S., Noh, E.J., Cha, K.-H., et al.Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E2 production in murine macrophage RAW 264.7 cellsLife Sci.78(20)2336-2342(2006) 4.Guo, L., Zheng, X., Wang, E., et al.Irigenin treatment alleviates doxorubicin (DOX)-induced cardiotoxicity by suppressing apoptosis, inflammation and oxidative stress via the increase of miR-425Biomed. Pharmacother.125109784(2020)
| Cas No. | 548-76-5 | SDF | |
| 别名 | 野鸢尾黄素 | ||
| Canonical SMILES | O=C1C(C2=CC(OC)=C(OC)C(O)=C2)=COC3=CC(O)=C(OC)C(O)=C13 | ||
| 分子式 | C18H16O8 | 分子量 | 360.31 |
| 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 | 2.7754 mL | 13.8769 mL | 27.7539 mL |
| 5 mM | 0.5551 mL | 2.7754 mL | 5.5508 mL |
| 10 mM | 0.2775 mL | 1.3877 mL | 2.7754 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。
Irigenin, a novel lead from Iris confusa for management of Helicobacter pylori infection with selective COX-2 and HpIMPDH inhibitory potential
Sci Rep 2022 Jul 6;12(1):11457.PMID:35794127DOI:10.1038/s41598-022-15361-w.
The development of new natural drugs for Helicobacter pylori (H. pylori) management has recently received significant attention. Iris confusa (I. confusa) was long used for the treatment of bacterial infections and gastritis. This study aimed at evaluating its effect on management of H. pylori infection and exploring its bioactive metabolites. The inhibitory potential of the polar (PF), non-polar (NPF) fractions and the isolated compounds against H. pylori using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay in addition to their cyclooxygenases (COX-1 and COX-2), and nitric oxide (NO) inhibitory activities were assessed. The most biologically active compound was tested for its selective H. pylori inosine-5'-monophosphate dehydrogenase (HpIMPDH) inhibitory potential. Chromatographic purification of PF and NPF allowed isolation of tectoridin, orientin, Irigenin, tectorigenin, isoarborinol and stigmasterol. The PF exhibited significant anti-H. pylori (MIC 62.50 µg/mL), COX-1, COX-2 (IC50 of 112.08 ± 0.60 and 47.90 ± 1.50 µg/mL respectively, selectivity index SI of 2.34), and NO (IC50 47.80 ± 0.89 µg/mL) inhibitory activities, while Irigenin was the most potent isolated compound. Irigenin was found to have a promising activity against HpIMPDH enzyme (IC50 of 2.07 ± 1.90 μM) with low activity against human hIMPDH2 (IC50 > 10 μM) than clarithromycin, assuring its selectivity. Overall, I. confusa and its isolated compounds may serve as a potential source of plant-based drugs for H. pylori control. This study scientifically validated the claimed anti-bacterial activity of I. confusa and revealed Irigenin potential as a novel lead exhibiting anti H. pylori activity in a first record.
Irigenin inhibits glioblastoma progression through suppressing YAP/β-catenin signaling
Front Pharmacol 2022 Nov 30;13:1027577.PMID:36532767DOI:10.3389/fphar.2022.1027577.
Glioblastoma (GBM) is the most malignant glioma in brain tumors with low survival and high recurrence rate. Irigenin, as an isoflavone compound extracted from Shegan, has shown many pharmacological functions such as antioxidant, anti-inflammatory and anti-tumor. However, the effects of Irigenin on GBM cells and the related molecular mechanisms remain unexplored. In this study, we found that Irigenin inhibited the proliferation of GBM cells in a dose-dependent manner by several assays in vitro. Subsequently, we found that Irigenin arrested cell cycle at G2/M phase and induced apoptosis of GBM cells in vitro. In addition, Irigenin inhibited the migration of GBM cells. Mechanically, we found that Irigenin treatment decreased the expression of YAP (yes-associated protein), suppressed β-catenin signaling. Furthermore, overexpression of YAP partially restored the anti-tumor effects of Irigenin on GBM cells in vitro. Finally, we found that Irigenin inhibited the growth of tumor in GBM xenograft mice model through inactivation of YAP. Taken together, these results suggest that Irigenin exerts its anticancer effects on GBM via inhibiting YAP/β-catenin signaling, which may provide a new strategy for the treatment of GBM.
Protective effects of Irigenin against 1-methyl-4-phenylpyridinium-induced neurotoxicity through regulating the Keap1/Nrf2 pathway
Phytother Res 2021 Mar;35(3):1585-1596.PMID:33118665DOI:10.1002/ptr.6926.
The rhizome of Belamcanda chinensis possesses antiinflammatory and antioxidant activities. However, the effect of Irigenin, isolated from the rhizome of B. chinensis, on 1-methyl-4-phenylpyridinium (MPP+ )-induced neurotoxicity is unknown. MTT assay showed that MPP+ exposure dose dependently inhibited the viability of mouse microglia BV-2 cells, whereas Irigenin suppressed MPP+ -induced viability reduction. The production of nitric oxide, prostaglandin E2, tumor necrosis factor-α and interleukin-6 were increased by MPP+ treatment, which were abolished by Irigenin treatment. Irigenin-attenuated MPP+ -induced increase of malondialdehyde content and activities of superoxide dismutase, catalase and glutathione peroxidase in BV-2 cells. Irigenin treatment also repressed apoptosis, caspase-3/7 activity and Cytochrome C expression in MPP+ -challenged BV-2 cells. Interestingly, Irigenin activated the Keap1/Nrf2 pathway in MPP+ -induced BV-2 cells. Nrf2 knockdown attenuated the effects of Irigenin on MPP+ -induced viability reduction, inflammation, oxidative stress and apoptosis in BV-2 cells. In conclusion, Irigenin alleviated MPP+ -induced neurotoxicity in BV-2 cells through regulating the Keap1/Nrf2 pathway.
Irigenin reduces the expression of caspase-3 and matrix metalloproteinases, thus suppressing apoptosis and extracellular matrix degradation in TNF-α-stimulated nucleus pulposus cells
Chem Biol Interact 2021 Nov 1;349:109681.PMID:34600870DOI:10.1016/j.cbi.2021.109681.
Irigenin, an isoflavonoid isolated from the rhizome of Belamcanda chinensis, possess various pharmacological effects. However, the effect and mechanism of Irigenin on intervertebral disc degeneration (IDD) remain unclear. The potential targets of Irigenin or disease were predicted using PharmMapper or GeneCards databases, respectively. The overlapping targets were inputted into the String database to establish protein-protein interaction (PPI) network. The overlapping targets were also submitted to DAVID webserver to perform gene ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analyses. Nucleus pulposus (NP) cells were exposed to 10 ng/mL tumor necrosis factor-α (TNF-α) to establish a cell model of IDD. Cell viability, LDH content, apoptosis and caspase-3 activity were evaluated by CCK-8, LDH release, TUNEL, and caspase-3 activity assays, respectively. The expression of collagen II, aggrecan, matrix metalloproteinase (MMP)-2, MMP-3, MMP-9, and MMP-13 were detected by qRT-PCR and western blot analyses. The network analysis revealed that MMP-2, MMP-3, MMP-9, MMP-13, caspase-3 (CASP3), vitamin D receptor (VDR), insulin-like growth factor 1 (IGF1), and transforming growth factor beta2 (TGFB2) play key roles in the effect of Irigenin against IDD. TNF-α stimulation inhibited cell viability and increased LDH content, apoptosis, caspase-3 expression and caspase-3 activity in NP cells, which were reversed by Irigenin treatment. TNF-α stimulation inhibited the expression of collagen II and aggrecan and upregulated MMPs (MMP-2, MMP-3, MMP-9, and MMP-13) in NP cells, while such changes were abolished by Irigenin treatment. In conclusion, Irigenin suppressed apoptosis and ECM degradation in TNF-α-stimulated NP cells by reducing the expression of caspase-3 and MMPs.
UGT1A1 and UGT1A9 Are Responsible for Phase II Metabolism of Tectorigenin and Irigenin In Vitro
Molecules 2022 Jun 26;27(13):4104.PMID:35807350DOI:10.3390/molecules27134104.
Tectorigenin and Irigenin are biologically active isoflavones of Belamcanda chinensis (L.) DC. Previous studies indicated that both compounds could be metabolized in vivo; however, the kinetic parameters of enzymes involved in the metabolization of tectorigenin and Irigenin have not been identified. The aim of this study was to investigate UGTs involved in the glucuronidation of tectorigenin and Irigenin and determine enzyme kinetic parameters using pooled human liver microsomes (HLMs) and recombinant UGTs. Glucuronides of tectorigenin and Irigenin were identified using high-performance liquid chromatography (HPLC) coupled with mass spectrometry and quantified by HPLC using a response factor method. The results showed that tectorigenin and Irigenin were modified by glucuronidation in HLMs. One metabolite of tectorigenin (M) and two metabolites of Irigenin (M1 and M2) were detected. Chemical inhibition and recombinant enzyme experiments revealed that several enzymes could catalyze tectorigenin and Irigenin glucuronidation. Among them, UGT1A1 and UGT1A9 were the primary enzymes for both tectorigenin and Irigenin; however, the former mostly produced Irigenin glucuronide M1, while the latter mostly produced Irigenin glucuronide M2. These findings suggest that UGT1A1 and UGT1A9 were the primary isoforms metabolizing tectorigenin and Irigenin in HLMs, which could be involved in drug-drug interactions and, therefore, should be monitored in clinical practice.