Miquelianin (Quercetin 3-O-glucuronide)
(Synonyms: 槲皮素3-O-葡萄糖酸苷,Quercetin 3-O-glucuronide; Quercetin 3-glucuronide) 目录号 : GC44795
Miquelianin (Quercetin 3-O-glucuronide)是槲皮素在体内的主要代谢产物,也是羰基还原酶1(CBR1)的抑制剂。
Cas No.:22688-79-5
Sample solution is provided at 25 µL, 10mM.
Miquelianin (Quercetin 3-O-glucuronide) is the main metabolite of quercetin in the body and is also a carbonyl reductase 1 (CBR1) inhibitor [1]. Miquelianin effectively scavenges reactive oxygen species (ROS), inhibits inflammatory responses mediated by the NF-κB signaling pathway, and improves cellular metabolic homeostasis by activating the PI3K/Akt pathway [2]. Miquelianin is primarily used in experimental studies of oxidative, anti-inflammatory, neuroprotective, and metabolic regulatory mechanisms [3-4].
In MDCK cells, Miquelianin can effectively inhibit the replication of H1N1-UI182 virus, as manifested by a significant decrease in the expression of viral nucleoprotein (NP) and a significant reduction in cytopathic effect (CPE) observed under a microscope [5]. In C3H10T1/2 cells, Miquelianin (5μM, 10μM; 24h) can reduce intracellular lipid accumulation by promoting lipolysis and fatty acid β-oxidation and inhibiting lipid droplet formation, thereby exerting metabolic regulation and anti-fatty degeneration effects [6].
In atopic dermatitis (AD) mice model, Oral administration of Miquelianin (4mg/mL, 10mg/mL; po; 21d) can significantly reduce serum IgE levels and the expression of Th2-related cytokines (such as IL-4 and IL-5) in the spleen, thereby inhibiting excessive Th2 immune responses [7]. In HFD-fed mice model, Miquelianin (12.8mg/kg, 25.6mg/kg; ig; 12weeks) extract promotes white-to-beige fat conversion via blocking AMPK/DRP1/mitophagy and modulating gut microbiota [8].
References:
[1]. Terao J, Yamaguchi S, Shirai M, et al. Protection by quercetin and quercetin 3-O-β-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein[J]. Free Radical Research, 2001, 35(6): 925-931.
[2]. Wang T, Lv L, Feng H, et al. Unlocking the potential: quercetin and its natural derivatives as promising therapeutics for sepsis[J]. Biomedicines, 2024, 12(2): 444.
[3]. Bakirhan N K, Sener S O, Baran M Y, et al. An Electrochemical Approach for a Flavonoid: Miquelianin via Carbon-Based Electrodes and Its Analysis from Calystegia silvatica[J]. Journal of AOAC International, 2025: qsaf032.
[4]. Schepetkin I A, Ramstead A G, Kirpotina L N, et al. Therapeutic potential of polyphenols from Epilobium angustifolium (Fireweed)[J]. Phytotherapy research, 2016, 30(8): 1287-1297.
[5]. Li H, Shen B, Bi Y, et al. Miquelianin inhibits IAV infection via the MAPK signaling pathway both in vitro and in vivo[J]. Frontiers in Immunology, 2025, 16: 1532336.
[6]. Wang Z, Xue C, Yang T, et al. Miquelianin, a main functional flavonoid of lotus leaf, induces thermogenic signature via p38‐PINK1‐PARKIN‐mediated mitophagy and mimicking NRF2 signaling during brown adipocyte differentiation[J]. Food Frontiers, 2023, 4(4): 1831-1844.
[7]. Choi D W, Jung S Y, Kim G D, et al. Miquelianin inhibits allergic responses in mice by suppressing CD4+ T cell proliferation[J]. Antioxidants, 2021, 10(7): 1120.
[8]. Wang Z, Yang T, Zeng M, et al. Miquelianin in Folium Nelumbinis extract promotes white-to-beige fat conversion via blocking AMPK/DRP1/mitophagy and modulating gut microbiota in HFD-fed mice[J]. Food and Chemical Toxicology, 2023, 181: 114089.
Miquelianin (Quercetin 3-O-glucuronide)是槲皮素在体内的主要代谢产物,也是羰基还原酶1(CBR1)的抑制剂 [1]。Miquelianin能有效清除活性氧(ROS),抑制NF-κB信号通路介导的炎症反应,并通过激活PI3K/Akt通路改善细胞代谢稳态 [2]。Miquelianin主要用于氧化、抗炎、神经保护和代谢调控机制的实验研究 [3-4]。
在MDCK细胞中,Miquelianin能有效抑制H1N1-UI182病毒的复制,表现为病毒核蛋白(NP)表达显著降低,显微镜下观察到的细胞病变效应(CPE)显著减轻 [5]。在C3H10T1/2细胞中,Miquelianin(5μM,10μM;24h)可通过促进脂肪分解和脂肪酸β-氧化,抑制脂滴形成,减少细胞内脂质蓄积,从而发挥代谢调节和抗脂肪变性作用 [6]。
在特应性皮炎(AD)小鼠模型中,口服Miquelianin(4mg/mL、10mg/mL;po;21d)可显著降低血清IgE水平和脾脏中Th2相关细胞因子(如IL-4和IL-5)的表达,从而抑制过度的Th2免疫反应 [7]。在HFD喂养的小鼠模型中,Miquelianin(12.8mg/kg,25.6mg/kg;ig;12周)提取物通过阻断AMPK/DRP1/线粒体自噬和调节肠道菌群,促进白色脂肪向米色脂肪转化 [8]。
| Cell experiment [1]: | |
Cell lines | MDCK cells |
Preparation Method | MDCK cells were cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% FBS, 100IU/mL penicillin, and 100μg/mL streptomycin at 37℃ and 5% CO2. When the cell density reached 70–80%, the supernatant was discarded, and different concentrations of the Miquelianin (6.25, 12.5, 25, 50, and 100μM) were plated in duplicate in five replicate wells. Virus-infected and uninfected cells were simultaneously treated with the working solution at different concentrations. Positive control wells (H1N1-UI182 virus only) and negative control wells (no H1N1-UI182 virus) were assigned to each plate. After 48 hours, cell viability was assessed using a CCK-8 assay. |
Reaction Conditions | 6.25-100μM; 48h |
Applications | Miquiline can effectively inhibit the replication of H1N1-UI182 virus, as manifested by a significant decrease in the expression of viral nucleoprotein (NP) and a significant reduction in cytopathic effect (CPE) observed under a microscope. |
| Animal experiment [2]: | |
Animal models | Atopic dermatitis (AD) mice model |
Preparation Method | To evaluate the anti-AD effects of oral Miquelianin treatment, the BALB/c mice were divided into five groups: naïve (TMA-non-exposed, n = 6), sham (untreated, n = 8), Miquelianin-4 (4mg/mL, n = 8), Miquelianin-10 (10mg/mL, n = 8), and Dex (1mg/mL, n = 6). Mice were sensitized on the shaved right flank with 50μL of 5% TMA in a mixed solvent (acetone/isopropyl myristate, 4:1 v/v) on day 0, and then 20μL of 2% TMA was applied to the surface of both ears on days 5, 8, 11, 14, 17, 20, 23, and 26. Miquelianin or Dex was administered orally daily from day 5 to 26. |
Dosage form | 4mg/mL, 10mg/mL; po; 21d |
Applications | Oral administration of Miquelianin can significantly reduce serum IgE levels and the expression of Th2-related cytokines (such as IL-4 and IL-5) in the spleen, thereby inhibiting excessive Th2 immune responses. |
References: | |
| Cas No. | 22688-79-5 | SDF | |
| 别名 | 槲皮素3-O-葡萄糖酸苷,Quercetin 3-O-glucuronide; Quercetin 3-glucuronide | ||
| Canonical SMILES | OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O2)=C(C3=CC=C(O)C(O)=C3)O4)=O)C4=C1 | ||
| 分子式 | C21H18O13 | 分子量 | 478.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml,PBS (pH 7.2): 2 mg/ml | 储存条件 | Store at 2-8°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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1 mg | 5 mg | 10 mg |
| 1 mM | 2.0903 mL | 10.4515 mL | 20.903 mL |
| 5 mM | 418.1 μL | 2.0903 mL | 4.1806 mL |
| 10 mM | 209 μL | 1.0452 mL | 2.0903 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) | ||||||||||
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度: mg/ml;
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1. 首先保证母液是澄清的;
2.
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