Glabrone
(Synonyms: 光果甘草酮) 目录号 : GC36146
Glabrone 是从甘草根中分离的一种异黄酮。Glabrone 具有抗流感活性和显著的 PPAR-γ 配体结合活性。
Cas No.:60008-02-8
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
Glabrone is an isoflavone isolated from Glycyrrhiza glabra roots. Glabrone exhibits anti-influenza activity and significant PPAR-γ ligand-binding activity[1][2]. PPAR-γ
[1]. Grienke U, et al. Computer-guided approach to access the anti-influenza activity of licorice constituents. J Nat Prod. 2014 Mar 28;77(3):563-70. [2]. Kuroda M, et al. Phenolics from Glycyrrhiza glabra roots and their PPAR-gamma ligand-binding activity. Bioorg Med Chem. 2010 Jan 15;18(2):962-70.
| Cas No. | 60008-02-8 | SDF | |
| 别名 | 光果甘草酮 | ||
| Canonical SMILES | O=C1C(C2=CC=C3C(C=CC(C)(C)O3)=C2O)=COC4=CC(O)=CC=C14 | ||
| 分子式 | C20H16O5 | 分子量 | 336.34 |
| 溶解度 | DMSO : 25 mg/mL (74.33 mM; Need ultrasonic) | 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 | 2.9732 mL | 14.8659 mL | 29.7318 mL |
| 5 mM | 0.5946 mL | 2.9732 mL | 5.9464 mL |
| 10 mM | 0.2973 mL | 1.4866 mL | 2.9732 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。
Glabrone as a specific UGT1A9 probe substrate and its application in discovering the inhibitor glycycoumarin
Eur J Pharm Sci 2021 Jun 1;161:105786.PMID:33684484DOI:10.1016/j.ejps.2021.105786.
UDP-glucuronosyltransferase 1A9 (UGT1A9) is one of the most important UGT isoforms, and plays an important role in the metabolic elimination of therapeutic drugs via glucuronidation. Herbal medicines affecting the activity of UGT1A9 may influence the metabolism of related drugs, thus causing herb-drug interactions and even adverse effects. However, few methods are available to evaluate the activity of UGT1A9. In this study, a natural product Glabrone was discovered as an isoform-specific probe substrate for UGT1A9. The Vmax and Km values of Glabrone were 362.6 nmol/min/mg protein and 17.2 μM for human liver microsomes (HLMs), and 382.3 nmol/min/mg protein and 16.6 μM for recombinant human UGT1A9, respectively. Glabrone 7-O-glucuronide, the UGT1A9 metabolite of Glabrone, was prepared by using a plant glucuronosyltransferase UGT88D1, and the structure was identified by NMR spectroscopy. Using Glabrone as a probe, we established a rapid HPLC method to screen UGT1A9 inhibitors from 54 natural products isolated from the Chinese herbal medicine licorice. Among them, glycycoumarin was found as a potent UGT1A9 inhibitor with an IC50 value of 6.04 μM. In rats, the pretreatment of glycycoumarin (4 mg/kg, i.p.) for 3 days could remarkably increase the plasma concentrations of dapagliflozin while decrease the concentrations of dapagliflozin-O-glucuronide after administration of dapagliflozin (1 mg/kg, i.v.), which is mainly metabolized by UGT1A9. The results indicated the potential risk of herb-drug interactions between licorice and UGT1A9-metabolizing drugs.
Glabrol impurity exacerbates glabridin toxicity in zebrafish embryos by increasing myofibril disorganization
J Ethnopharmacol 2022 Apr 6;287:114963.PMID:34971733DOI:10.1016/j.jep.2021.114963.
Ethnopharmacological relevance: Glabridin, extracted from Glycyrrhiza glabra L., is widely used for the treatment of hyperpigmentation because of its anti-inflammatory and antioxidant activities and its ability to inhibit melanin synthesis. This led to the strict regulation of its quality and safety. However, traditional quality control methods used for plant extracts cannot reflect the product quality owing to multiple unknown impurities, which necessitates the further analysis of impurities. Aim of the study: The study identified the toxic impurities of glabridin and their toxicological mechanism. Materials and methods: In total, 10 glabridin samples from different sources were quantified using high-performance liquid chromatography. Sample toxicities were evaluated using zebrafish and cell models. To identify impurities, samples with different toxicity were analyzed by ultra-high-performance liquid chromatography coupled with quadrupole-Orbitrap mass spectrometry. The toxicity of related impurities was verified in the zebrafish model. Phalloidin stain was used to evaluate subtle changes in myofibril alignment. Results: Although glabridin content in the samples was similar, there were significant differences in toxicity. The results were verified using four different mammalian cell lines. Higher contents of Glabrone and glabrol were identified in the sample with the highest toxicity. In the zebrafish model, the addition of glabrol reduced the LC50 of glabridin to 9.224, 6.229, and 5.370 μM at 48, 72, and 96 h post-fertilization, respectively, whereas Glabrone did not have any toxic effect. Phalloidin staining indicated that a glabrol impurity exacerbates the myotoxicity of glabridin in zebrafish embryos. Conclusion: Glabrol, but not Glabrone, was identified as a key impurity that increased glabridin toxicity. This finding indicates that controlling glabrol content is necessary during glabridin product production.
Computer-guided approach to access the anti-influenza activity of licorice constituents
J Nat Prod 2014 Mar 28;77(3):563-70.PMID:24313801DOI:10.1021/np400817j.
Neuraminidase (NA), a key enzyme in viral replication, is the first-line drug target to combat influenza. On the basis of a shape-focused virtual screening, the roots of Glycyrrhiza glabra (licorice) were identified as plant species with an accumulation of constituents that show 3D similarities to known influenza NA inhibitors (NAIs). Phytochemical investigation revealed 12 constituents identified as (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-2-propen-1-one (1), 3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-ol (2), biochanin B (3), glabrol (4), Glabrone (5), hispaglabridin B (6), licoflavone B (7), licorice glycoside B (8), licorice glycoside E (9), liquiritigenin (10), liquiritin (11), and prunin (12). Eleven of these constituents showed significant influenza virus NA inhibition in a chemiluminescence (CL)-based assay. Additional tests, including (i) a cell-based cytopathic effect inhibition assay (general antiviral activity), (ii) the evaluation of cytotoxicity, (iii) the inhibition of the NA of Clostridium perfringens (CL- and fluorescence (FL)-based assay), and (iv) the determination of self-fluorescence and quenching, provided further perspective on their anti-influenza virus potential, revealing possible assay interference problems and false-positive results. Compounds 1, 3, 5, and 6 showed antiviral activity, most likely caused by the inhibition of NA. Of these, compounds 1, 3, and 6 were highly ranked in shape-focused virtual screening.
Phenolics from Glycyrrhiza glabra roots and their PPAR-gamma ligand-binding activity
Bioorg Med Chem 2010 Jan 15;18(2):962-70.PMID:20022509DOI:10.1016/j.bmc.2009.11.027.
Bioassay-guided fractionation of the EtOH extract of licorice (Glycyrrhiza glabra roots), using a GAL-4-PPAR-gamma chimera assay method, resulted in the isolation of 39 phenolics, including 10 new compounds (1-10). The structures of the new compounds were determined by analysis of their spectroscopic data. Among the isolated compounds, 5'-formylglabridin (5), (2R,3R)-3,4',7-trihydroxy-3'-prenylflavane (7), echinatin, (3R)-2',3',7-trihydroxy-4'-methoxyisoflavan, kanzonol X, kanzonol W, shinpterocarpin, licoflavanone A, glabrol, shinflavanone, gancaonin L, and Glabrone all exhibited significant PPAR-gamma ligand-binding activity. The activity of these compounds at a sample concentration of 10microg/mL was three times more potent than that of 0.5microM troglitazone.
High-performance liquid chromatographic profile and 1H quantitative nuclear magnetic resonance analyses for quality control of a Xinjiang licorice extract
Biosci Biotechnol Biochem 2020 Oct;84(10):2128-2138.PMID:32614708DOI:10.1080/09168451.2020.1785272.
Various pharmacological properties of Xinjiang licorice flavonoids have been reported recently. We have investigated constituents corresponding to distinct peaks on the high-performance liquid chromatography (HPLC) profile of a flavonoid-rich extract from licorice, and identified 13 flavonoids, including licochalcone A (1), licochalcone B (3), Glabrone (4), and echinatin (5), by isolating them and then performing high-resolution electrospray ionization mass spectrometry and 1H nuclear magnetic resonance (NMR) spectral analyses. We then applied the 1H quantitative NMR (qNMR) method for analysis of major flavonoids, 1 and 3-5 in the extract. The 1H qNMR results were supported by 13C NMR analysis. The results demonstrated the utility of the combination of HPLC profiling and qNMR analyses for quality control of Xinjiang licorice. Additionally, we observed a moderate inhibitory effect of the most abundant constituent, licochalcone A (1), on acetylcholine esterase activity, suggesting utility as a seed for drug development.