Isoglycycoumarin
目录号 : GC36335
Isoglycycoumarin 是从Glycyrrhiza uralensis 根中提取的黄酮类化合物。Isoglycycoumarin 是一种高度选择性的人细胞色素 P450 2A6 (CYP2A6) 探针。
Cas No.:117038-82-1
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
Isoglycycoumarin is a flavonoid isolated from the roots of Glycyrrhiza uralensis. Isoglycycoumarin is a highly selective probe for human cytochrome P450 2A6 (CYP2A6)[1][2]. P450 2A6[2]
[1]. Li S, et al. Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities. Bioorg Med Chem Lett. 2010 Sep 15;20(18):5398-401. [2]. Wang Q, et al. The prenylated phenolic natural product isoglycycoumarin is a highly selective probe for human cytochrome P450 2A6. Eur J Pharm Sci. 2017 Nov 15;109:472-479.
| Cas No. | 117038-82-1 | SDF | |
| Canonical SMILES | COC1=C(CCC(C)(C)O2)C2=CC(O3)=C1C=C(C4=C(C=C(O)C=C4)O)C3=O | ||
| 分子式 | C21H20O6 | 分子量 | 368.38 |
| 溶解度 | Soluble in DMSO | 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 | 2.7146 mL | 13.5729 mL | 27.1459 mL |
| 5 mM | 0.5429 mL | 2.7146 mL | 5.4292 mL |
| 10 mM | 0.2715 mL | 1.3573 mL | 2.7146 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。
The prenylated phenolic natural product Isoglycycoumarin is a highly selective probe for human cytochrome P450 2A6
Eur J Pharm Sci 2017 Nov 15;109:472-479.PMID:28867491DOI:10.1016/j.ejps.2017.08.035.
Prenylated phenolic compounds are an important class of bioactive natural products. One major in vivo metabolic pathway of these compounds is hydroxylation at terminal methyl of the isoprenyl group. This study aims to identify the P450 isozyme catalyzing this metabolic reaction. In human liver microsomes, 16 out of 24 screened compounds could be metabolized into their hydroxylated derivatives. Chemical inhibition assays using 11 isozyme specific inhibitors indicated the hydroxylation reactions of 12 compounds were primarily catalyzed by cytochrome P450 2A6 (CYP2A6). In particular, CYP2A6 was the major enzyme participating in the metabolism of Isoglycycoumarin (IGCM). The product of IGCM was obtained and identified as licopyranocoumarin (4″-hydroxyl Isoglycycoumarin) using NMR spectroscopic analysis. The Km values for human liver microsomes and recombinant human CYP2A6 were 7.98 and 10.14μM, respectively. According to molecular docking analysis, the catalytic mechanism may involve cyclized isoprenyl group of IGCM entering the active cavity of CYP2A6. These results demonstrate that IGCM could serve as an ideal isozyme selective probe to evaluate CYP2A6 activities.
Metabolites identification of bioactive licorice compounds in rats
J Pharm Biomed Anal 2015 Nov 10;115:515-22.PMID:26311472DOI:10.1016/j.jpba.2015.08.013.
Licorice (Glycyrrhiza uralensis Fisch.) is one of the most popular herbal medicines worldwide. This study aims to identify the metabolites of seven representative bioactive licorice compounds in rats. These compounds include 22β-acetoxyl glycyrrhizin (1), licoflavonol (2), licoricidin (3), licoisoflavanone (4), Isoglycycoumarin (5), semilicoisoflavone B (6), and 3-methoxy-9-hydroxy-pterocarpan (7). After oral administration of 250mg/kg of 1 or 40mg/kg of 2-7 to rats, a total of 16, 43 and 31 metabolites were detected in the plasma, urine and fecal samples, respectively. The metabolites were characterized by HPLC/DAD/ESI-MS(n) and LC/IT-TOF-MS analyses. Particularly, two metabolites of 1 were unambiguously identified by comparing with reference standards, and 22β-acetoxyl glycyrrhizin-6″-methyl ester (1-M2) is a new compound. Compound 1 could be readily hydrolyzed to eliminate the glucuronic acid residue. The phenolic compounds (4-7) mainly undertook phase II metabolism (glucuronidation or sulfation). Most phenolic compounds with an isoprenyl group (chain or cyclized, 2-5) could also undertake hydroxylation reaction. This is the first study on in vivo metabolism of these licorice compounds.
Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities
Bioorg Med Chem Lett 2010 Sep 15;20(18):5398-401.PMID:20724155DOI:10.1016/j.bmcl.2010.07.110.
Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and Isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 microM, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode.
[Quality evaluation of Chinese licorice]
Yao Xue Xue Bao 1991;26(10):788-93.PMID:1823722doi
The contents of 12 compounds, viz. glycyrrhizinic acid, uralsaponin A, uralsaponin B, liquiritin, isoliquiritin, liquiritigenin, isoliquiritigenin, glycycoumarin, Isoglycycoumarin, licochalcone A, glycyrol and isoglycyrol, present in Chinese licorice, the roots and rhizomes of 8 Glycyrrhiza species collected from 15 districts in China, were determined by high performance liquid chromatographic method. The quality evaluation of Chinese licorice was discussed according to the results of the determinations.