Methylophiopogonanone A
(Synonyms: 麦冬高异黄酮A) 目录号 : GN10454
甲基麦冬酮 A (MOA) 是一种从草药麦冬中分离出来的具有丰富生物活性的同型异黄酮，被认为是麦冬相关草药制剂质量控制的关键化学指标。
Cas No.:74805-92-8
Sample solution is provided at 25 µL, 10mM.
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Methylophiopogonanone A (MOA), an abundantly bioactive homoisoflavonoid isolated from the herbal medicine Ophiopogonis Radix, has been considered as the key chemical index for the quality control of Ophiopogonis Radix related herbal formulations [1]. Methylophiopogonanone A inhibited hUGTs effect of 4-HN-335 O-glucuronidation with IC50 values ranged from 1.23 ± 0.09 μμ (for UGT1A1) to 8.30 ± 0.72 μμ (for UGT2B7) [2].
Modern pharmacological studies have demonstrated that Methylophiopogonanone A held a variety of pharmacological effects, including anti-oxidative, anti-inflammatory, anti-tumour, anti-hyperlipidemia effects and the potentials for attenuating myocardial apoptosis and improving cerebral ischemia/reperfusion injury [3,4,5,6].
Methylophiopogonanone A dose-dependently inhibited hUGT1A1-catalysed NHPN-O-glucuronidation in HeLa-UGT1A1 cells, with the apparent IC50 value of 1.54 ± 0.17 μM [2]. Methylophiopogonanone A (2.5-10 μM) treatment significantly reversed the decreased TER values when compared with the model group, which indicated that Methylophiopogonanone A had a protective effect on hypoxic BBB damage [5]. In H9C2 cells subjected to H/R, pretreatment with Methylophiopogonanone A (10 μmol/L) significantly decreased apoptosis and cleaved caspase-3 expression, elevated the Bcl-2/Bax ratio and restored NO production [6].
Pretreatment with Methylophiopogonanone A (10 mg.kg-1.d-1, po.) significantly reduced the infarct size (by 60.7%) and myocardial apoptosis (by 56.8%), and improved cardiac function, in I/R mice [6]. Cerebral water contents were less in the Methylophiopogonanone A (2.5 mg/kg and 5.0 mg/kg) treatment groups than those in the model group in MCAO rats [5].
References:
[1]. Zheng Y, Fan C, Liu M, Chen Y, Lu Z, Xu N, Huang H, Zeng H, Liu S, Cao H, Liu J. Overall quality control of the chemical and bioactive consistency of ShengMai Formula. Journal of pharmaceutical and biomedical analysis. 2020 Sep 10;189:113411.
[2]. Zhou Q H, Zhu G H, Song Y Q, et al. Methylophiopogonanone A is a naturally occurring broad‐spectrum inhibitor against human UDP‐glucuronosyltransferases: Inhibition behaviours and implication in herb‐drug interactions[J]. Basic & Clinical Pharmacology & Toxicology, 2021, 129(6): 437-449.
[3]. Li, Z., Wu, Y. Y., & Yu, B. X. (2020). Methylophiopogonanone A, an Ophiopogon homoisoflavonoid, alleviates high-fat diet-induced hyperlipidemia: assessment of its potential mechanism. Brazilian Journal of Medical and Biological Research, 53.
[4]. Dang, N. H., Chung, N. D., Tuan, H. M., Hiep, N. T., & Dat, N. T. (2017). Cytotoxic homoisoflavonoids from Ophiopogon japonicus tubers. Chemical and Pharmaceutical Bulletin, 65(2), 204-207.
[5]. Lin, M., Sun, W., Gong, W., Zhou, Z., Ding, Y., & Hou, Q. (2015). Methylophiopogonanone a protects against cerebral ischemia/reperfusion injury and attenuates blood-brain barrier disruption in vitro. PLoS One, 10(4), e0124558.
[6]. He, F., Xu, B. L., Chen, C., Jia, H. J., Wu, J. X., Wang, X. C., ... & Cheng, J. (2016). Methylophiopogonanone A suppresses ischemia/reperfusion-induced myocardial apoptosis in mice via activating PI3K/Akt/eNOS signaling pathway. Acta Pharmacologica Sinica, 37(6), 763-771.
甲基麦冬酮 A (MOA) 是一种从草药麦冬中分离出来的具有丰富生物活性的同型异黄酮，被认为是麦冬相关草药制剂质量控制的关键化学指标[1]。甲基麦冬酮 A 抑制 4-HN-335 O-葡萄糖醛酸化的 hUGTs 效应，IC50 值范围为 1.23 ± 0.09 μμ（对于 UGT1A1）至 8.30 ± 0.72 μμ（对于 UGT2B7）[2]。
现代药理研究表明，甲基麦冬酮A具有多种药理作用，包括抗氧化、抗炎、抗肿瘤、抗高血脂等作用，具有减轻心肌细胞凋亡、改善脑缺血/再灌注损伤的潜力 < sup>[3,4,5,6].
甲基麦冬酮 A 剂量依赖性地抑制 HeLa-UGT1A1 细胞中 hUGT1A1 催化的 NHPN-O-葡萄糖醛酸化，表观 IC50 值为 1.54 ± 0.17 μM [2]。与模型组相比，甲基麦冬酮 A (2.5-10 μM) 处理显着逆转了降低的 TER 值，这表明甲基麦冬酮 A 对缺氧性 BBB 损伤具有保护作用[5]。在经过 H/R 处理的 H9C2 细胞中，用 Methylophiopogonanone A (10 μmol/L) 预处理可显着降低细胞凋亡和裂解的 caspase-3 表达，提高 Bcl-2/Bax 比率并恢复 NO 产生[6].
使用甲基麦冬花酮 A（10 mg.kg-1.d-1，口服）预处理可显着减少 I/R 患者的梗塞面积（减少 60.7%）和心肌细胞凋亡（减少 56.8%），并改善心脏功能小鼠[6]。甲基麦冬酮A（2.5 mg/kg和5.0 mg/kg）治疗组MCAO大鼠脑水含量低于模型组[5]。
| Cell experiment [1]: | |
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Cell lines |
Mouse brain endothelial bEND.3 cells, Human monocytic THP-1 cells |
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Preparation Method |
Cells were seeded at 5×105 cells per well on 24 well plates. After 12 hours, cells were incubated in a hypoxia chamber with Dulbecco＊s modified Eagle＊s medium (no glucose) supplemented with 10% (v/v) fetal bovine serum at 37～C in a 5% (v/v) CO2/ 95% (v/v) N2 for 12 hours, and then incubated under normal conditions at 37～C for another 24 hours. Before hypoxia, cells were treated with Methylophiopogonanone A (2.5, 5.0 or 10 uM), and control cells were cultured under normal conditions with vehicle. After stimulation, cells were lysated with an ultrasonic lysis instrument, and supernatants were collected for ICAM-1 and VCAM-1 ELISA detection. Human monocytic THP-1 cells were cultured in RPMI 1640 medium supplemented with 10% (v/v) fetal bovine serum at 37～C in a humidified atmosphere of 5% (v/v) CO2. Cells were seeded at 5×105 cells per well on 24 well plates, and stimulated with PMA (200 nM) or PMA (200 nM) + Methylophiopogonanone A (2.5, 5.0 or 10 uM) for 24 hours. After stimulation, cell culture supernatants were collected for MMP-9 ELISA detection, the MMP-9 ELISA was performed according to the protocols of human MMP-9 quantikine ELISA kit. |
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Reaction Conditions |
2.5, 5.0 or 10 µM for 24 hours |
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Applications |
The level of ICAM-1 and VCAM-1 were significantly enhanced in OGD/R-induced bEnd.3 cells (model group) when compared with the control group. MO-A treatment significantly inhibited the increase of ICAM-1 and VCAM-1 induced by OGD/R-treatment. |
| Animal experiment [1]: | |
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Animal models |
Sprague-Dawley rats |
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Preparation Method |
Middle cerebral artery occlusion (MCAO) was induced using the intraluminal suture method. To evaluate the neuroprotective effect of Methylophiopogonanone A (dissolved in normal saline with PH = 8.0), except for sham operation rats (Control), MCAO rats were randomly divided into 4 groups: MCAO with vehicle (model), and MCAO treated with 1.25, 2.50 or 5.00 mg/kg Methylophiopogonanone A twice per day. After 2 h reperfusion, the rats were treated intravenously with Methylophiopogonanone A for 7 days. Control rats were treated with equal volumes of saline. |
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Dosage form |
1.25, 2.50 or 5.00 mg/kg Methylophiopogonanone A twice per day for 7 days |
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Applications |
The infarct area of each treatment group was observed by 2,3,5-triphenyltetrazolium chloride (TTC) staining. Infarct volume was analyzed, and the results showed that there was no infarct in sham animals, but significant ischemic injury following transient MCAO (model group). TTC staining revealed that MO-A (2.5 mg/kg, 5.0 mg/kg) significantly reduced infarct volume when compared with the model group. |
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References: [1]: Lin M, Sun W, Gong W, et al. Methylophiopogonanone a protects against cerebral ischemia/reperfusion injury and attenuates blood-brain barrier disruption in vitro[J]. PLoS One, 2015, 10(4): e0124558. |
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| Cas No. | 74805-92-8 | SDF | |
| 别名 | 麦冬高异黄酮A | ||
| 化学名 | (3R)-3-(1,3-benzodioxol-5-ylmethyl)-5,7-dihydroxy-6,8-dimethyl-2,3-dihydrochromen-4-one | ||
| Canonical SMILES | CC1=C(C2=C(C(=C1O)C)OCC(C2=O)CC3=CC4=C(C=C3)OCO4)O | ||
| 分子式 | C19H18O6 | 分子量 | 342.34 |
| 溶解度 | ≥ 86.7mg/mL 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 | 2.9211 mL | 14.6054 mL | 29.2107 mL |
| 5 mM | 0.5842 mL | 2.9211 mL | 5.8421 mL |
| 10 mM | 0.2921 mL | 1.4605 mL | 2.9211 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。
Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
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