Methylophiopogonanone B
(Synonyms: 甲基麦冬黄烷酮B) 目录号 : GC36599
An isoflavone with diverse biological activities
Cas No.:74805-91-7
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
Methylophiopogonanone B is an isoflavone that has been found in O. japonicus and has diverse biological activities.1,2,3,4 It increases Rho activity in normal human epidermal melanocytes (NHEMs) when used at a concentration of 1 ?M.1 Methylophiopogonanone B inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia with an IC50 value of 7.8 ?M.2 It reduces hydrogen peroxide-induced production of reactive oxygen species (ROS), apoptosis, and decreases in superoxide dismutase (SOD) activity in human umbilical vein endothelial cells (HUVECs) when used at concentrations of 40 and 50 ?M.3 It is cytotoxic to SMMC-7721 and HeLa cancer cells (IC50s = 34.6 and 6 ?g/ml, respectively).4
1.Ito, A., Kanamaru, A., and Tada, A.A novel agent, methylophiopogonanone B, promotes Rho activation and tubulin depolymerizationMol. Cell. Biochem.297(1-2)121-129(2007) 2.Li, N., Zhang, J.-Y., Zeng, K.-W., et al.Anti-inflammatory homoisoflavonoids from the tuberous roots of Ophiopogon japonicusFitoterapia83(6)1042-1045(2012) 3.Wang, L., Zhou, Y., Qin, Y., et al.Methylophiopogonanone B of radix ophiopogonis protects cell from H2O2-induced apoptosis through the NADPH oxidase pathway in HUVECsMol. Med. Rep.20(4)3691-3700(2019) 4.Wang, K.-W., Zhang, H., Shen, L.-W., et al.Novel steroidal saponins from Liriope graminifolia (Linn.) baker with anti-tumor activitiesCarbohydr. Res.346(2)253-258(2011)
| Cas No. | 74805-91-7 | SDF | |
| 别名 | 甲基麦冬黄烷酮B | ||
| Canonical SMILES | O=C1[C@H](CC2=CC=C(OC)C=C2)COC3=C(C)C(O)=C(C)C(O)=C13 | ||
| 分子式 | C19H20O5 | 分子量 | 328.36 |
| 溶解度 | DMSO: 10 mM | 储存条件 | Store at -20°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 | 3.0454 mL | 15.2272 mL | 30.4544 mL |
| 5 mM | 0.6091 mL | 3.0454 mL | 6.0909 mL |
| 10 mM | 0.3045 mL | 1.5227 mL | 3.0454 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。
Methylophiopogonanone B of Radix Ophiopogonis protects cells from H2O2‑induced apoptosis through the NADPH oxidase pathway in HUVECs
Mol Med Rep 2019 Oct;20(4):3691-3700.PMID:31485606DOI:10.3892/mmr.2019.10625.
Methylophiopogonanone B (MO‑B), which belongs to a group of homoisoflavonoids, present in Ophiopogon japonicus, has been identified as an active component with antioxidative and anti‑tumor properties. The present study investigated whether MO‑B may exert protective effects on human umbilical vein endothelial cells (HUVECs) against H2O2‑induced injury in vitro, and whether the MO‑B effects may be modulated by the NADPH pathway. HUVECs were treated with MO‑B in the presence or absence of H2O2. Malondialdehyde (MDA), reactive oxygen species (ROS) levels, and superoxide dismutase (SOD) activity were analyzed to evaluate cell injury and the antioxidative potential of MO‑B. The results revealed that MO‑B inhibited the production of MDA and ROS, but enhanced SOD activity. Furthermore, MO‑B could alleviate H2O2‑induced apoptosis in HUVECs, which is consistent with the expression of apoptosis‑associated genes and proteins in cells, including Bax/Bcl‑2 and caspase‑3. To explore the potential mechanism, the present study investigated the effects of MO‑B on NADPH‑related signaling via the analysis of neutrophil cytochrome b light chain (p22phox) expression, which is the membrane‑associated subunit of NADPH oxidase. MO‑B could improve the survival of endothelial cells and therefore may be a potential drug in the treatment of cardiovascular diseases.
A novel agent, Methylophiopogonanone B, promotes Rho activation and tubulin depolymerization
Mol Cell Biochem 2007 Mar;297(1-2):121-9.PMID:17029007DOI:10.1007/s11010-006-9336-y.
Cytoskeletal reorganization, including reconstruction of actin fibers and microtubules, is essential for various biological processes, such as cell migration, proliferation and dendrite formation. We show here that Methylophiopogonanone B (MOPB) induces cell morphological change via melanocyte dendrite retraction and stress fiber formation. Since members of the Rho family of small GTP-binding proteins act as master regulators of dendrite formation and actin cytoskeletal reorganization, and activated Rho promotes dendrite retraction and stress fiber formation, we studied the effects of MOPB on the small GTPases using normal human epidermal melanocytes and HeLa cells. In in vitro binding assay, MOPB significantly increased GTP-Rho, but not GTP-Rac or GTP-CDC42. Furthermore, a Rho inhibitor, a Rho kinase inhibitor and a small GTPase inhibitor each blocked MOPB-induced stress fiber formation. The effect of MOPB on actin reorganization was blocked in a Rho dominant negative mutant. These results suggest MOPB acts via the Rho signaling pathway, and it may directly or indirectly activate Rho. Quantitative Western blot analysis indicated that MOPB also induced microtubule destabilization and tubulin depolymerization. Thus, MOPB appears to induce Rho activation, resulting in actin cytoskeletal reorganization, including dendrite retraction and stress fiber formation.
Investigation of the effective components inhibited macrophage foam cell formation in Ophiopogonis Radix
J Ethnopharmacol 2022 Jan 30;283:114678.PMID:34563614DOI:10.1016/j.jep.2021.114678.
Ethnopharmacological relevance: Ophiopogonis Radix, the commonly used traditional Chinese medicine in clinic for treating cardiovascular diseases, is returned to the stomach, lung and heart meridian. It is reported to nourish yin, moisten lung and is used to treat heart yin deficiency syndromes and asthenia of heart and lung, which indicated that Ophiopogonis Radix may have a protective effect on heart disorders. Atherosclerosisis is an important process in the development of cardiovascular diseases and abnormal lipid deposition induced macrophage foam cells is its crucial foundation. Our previous study showed the extract of Ophiopogonis Radix (EOR) ameliorates atherosclerosis in vitro. However, it may protect against cardiovascular diseases through inhibiting macrophage foam cell formation and its potential effective components and mechanisms are still unclear. Aim of the study: Our study aimed to investigate the effect of Ophiopogonis Radix on macrophage foam cell formation and its potential active constituents and mechanisms. Materials and methods: Ox-LDL induced macrophage cells were employed to evaluate the effect of Ophiopogonis Radix on macrophage foam cell formation. Then the potential active constituents inhibited formation of macrophage foam cells were screened by biospecific cell extraction and its underlying mechanisms were also explored by Western blot. Results: The extract of Ophiopogonis Radix was found to significantly inhibit macrophage foam cell formation, evidenced by the decrease of TG and TC and Oil Red O staining analysis in macrophage cells, which indicated that EOR reduced the formation of macrophage foam cells. At the same time, EOR was showed to increase antioxidant capacity in macrophage cells. After treatment with EOR, two potential active components interacted with macrophage foam cells specifically were identified to inhibit macrophage foam cell formation including methylophiopogonanone A and Methylophiopogonanone B. Methylophiopogonanone A was then proved to decrease the expression of CD36, Lox-1 and SREBP2, increase the expression of ABCA1 obviously, while the expression of ABCG1 and SREBP1 had no changes. Conclusions: In our study, Ophiopogonis Radix was found to protect against atherosclerosis through suppressing ox-LDL induced macrophage foam cell formation and two potential compounds were identified by biospecific cell extraction including methylophiopogonanone A and Methylophiopogonanone B. Moreover, methylophiopogonanone A was proved to inhibit foam cells through reducing uptake, synthesis and increasing efflux, which may provide guidance and reference for application of Ophiopogonis Radix and investigation of the effective components of TCMs.
A high-resolution mass spectrometry-based methodology for characterization and identification of Methylophiopogonanone B metabolites from cryopreserved hepatocytes and liver microsomes
Biomed Chromatogr 2023 Apr;37(4):e5574.PMID:36527223DOI:10.1002/bmc.5574.
Methylophiopogonanone B (MOB), one of the homoisoflavonoids isolated from Ophiopogon japonicus, has been demonstrated to possess antioxidative and antitumor activities. The aim of this work was to investigate the metabolism of MOB using liver microsomes and hepatocytes. MOB was individually incubated with rat, monkey, and human hepatocytes to generate the metabolites. To investigate the bioactivation pathways, MOB was incubated with liver microsomes in the presence of glutathione (GSH). All the metabolites were detected and identified using LC with a quadrupole Orbitrap mass spectrometer. Under the current conditions, nine metabolites were identified in hepatocyte incubations. Of these metabolites, M7 derived from hydroxylation was identified as the most abundant metabolite in hepatocyte incubation. MOB was metabolized via demethylation, hydroxylation, and glucuronidation. In liver microsomes, five GSH conjugates were detected and identified. MOB was subjected to bioactivation through demethylation yielding M9, which further formed quinone-methide and ortho-quinone intermediates, followed by GSH conjugation. This work is the first to study the metabolism of MOB, which will help us understand its disposition and efficacy.
Interactions of the major effective components in Shengmai formula with breast cancer resistance protein at the cellular and vesicular levels
Biomed Pharmacother 2021 Jan;133:110939.PMID:33232930DOI:10.1016/j.biopha.2020.110939.
Shengmai Formula (SMF) is one of the traditional Chinese medicine representative formulas and is widely used for the treatment of cardio- and cerebrovascular disease. Previous studies demonstrated that the major effective ingredients in SMF can interact with each other based on some uptake transporters. However, the role of the efflux transporter breast cancer resistance protein (BCRP) in these interactions involving SMF remains unclear. The purpose of this study was to investigate the interactions of the major active components of SMF with BCRP and the compatibility mechanism of these complex components in SMF based on BCRP. We selected 4 main fractions, including ginseng total saponins (GTS), ophiopogon total saponins (OTS), ophiopogon total flavonoids (OTF), and fructus schisandrae total lignans (STL), and 12 bioactive components, including ginsenosides Re, Rd, Rb1, and Rg1, ophiopogonins D and D', methylophiopogonanones A and B, schizandrins A and B, and schizandrols A and B to explore the interactions of SMF with BCRP in LLC-PK1 and LLC-PK1/BCRP cells and BCRP membrane vesicles. The results showed that ginsenosides Re and Rg1, Methylophiopogonanone B, and schizandrin A can be transported by BCRP into LLC-PK1/BCRP cells. Schisandrol B exhibited a markedly inhibitory effect on the transport function of BCRP and can significantly inhibit the uptake of Methylophiopogonanone B and schizandrin A into LLC-PK1/BCRP cells. In "Inside-Out" BCRP membrane vesicles, BCRP mediated the transport of ginsenosides Re and Rg1, Methylophiopogonanone B, and schizandrin A, with Km values of 111.9 ± 31.26 μM, 82.01 ± 16.72 μM, 57.06 ± 8.789 μM, and 37.19 ± 6.512 μM, respectively. GTS, STL, ginsenosides Rd and Rb1, and schisandrol B were potent inhibitors of BCRP and showed different degrees of inhibition on the transport of ginsenosides Re and Rg1, Methylophiopogonanone B, and schizandrin A via BCRP. In conclusion, GTS, STL, ginsenosides Rd and Rb1, and schizandrol B are potential inhibitors of BCRP. Ginsenosides Re and Rg1, Methylophiopogonanone B, and schizandrin A are potential substrates of BCRP, and their transport, which is mediated by BCRP, may be inhibited by potential inhibitors in SMF. There are potential interactions of these main effective components of SMF at the cellular and vesicular levels that are mediated by BCRP. The interplay of these bioactive components based on BCRP may be an important compatibility mechanism in SMF.