Isoscopoletin
(Synonyms: 异莨菪亭,6-Hydroxy-7-methoxycoumarin) 目录号 : GC36342
A coumarin with diverse biological activities and an active metabolite of scoparone
Cas No.:776-86-3
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isoscopoletin is a coumarin that has been found in D. fragrans and has diverse biological activities and is an active metabolite of scoparone .1,2,3,4,5 It is formed from scoparone by the cytochrome P450 (CYP) isoform Cyp2c29 in mouse liver microsomes.5 Isoscopoletin is cytotoxic to A549 lung, MCF-7 breast, and HepG2 liver cancer cells (IC50s = 5.25, 8.58, and 4.76 ?M, respectively).1 It is active against Gram-positive and Gram-negative bacteria, including S. aureus and E. coli, respectively, as well as the plant pathogenic fungus A. niger, in agar diffusion assays.2 Isoscopoletin inhibits 15-lipoxygenase (15-LO; IC50 = 15.1 ?M) and reduces paw thickness in a rat model of carrageenan-induced paw edema when administered at a dose of 0.1 mg/kg.3,4
1.Zhao, D.-D., Zhao, Q.-S., Liu, L., et al.Compounds from Dryopteris fragrans (L.) Schott with cytotoxic activityMolecules19(3)3345-3355(2014) 2.Nazir, S., Li, B., Tahir, K., et al.Antimicrobial activity of five constituents isolated from Ranunculus muricatusJ. Med. Plants Res.7(47)3438-3443(2013) 3.Deng, S., Palu, A.K., West, B.J., et al.Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in TahitiJ. Nat. Prod.70(5)859-862(2007) 4.Selim, Y.A., and Ouf, N.H.Anti-inflammatory new coumarin from the Ammi majus LOrg. Med. Chem. Lett.2(1)1(2012) 5.Meyer, R.P., Hagemeyer, C.E., Knoth, R., et al.Oxidative hydrolysis of scoparone by cytochrome P450 CYP2C29 reveals a novel metaboliteBiochem. Biophys. Res. Commun.285(1)32-39(2001)
| Cas No. | 776-86-3 | SDF | |
| 别名 | 异莨菪亭,6-Hydroxy-7-methoxycoumarin | ||
| Canonical SMILES | O=C1C=CC2=CC(O)=C(OC)C=C2O1 | ||
| 分子式 | C10H8O4 | 分子量 | 192.17 |
| 溶解度 | Soluble 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 5.2037 mL | 26.0186 mL | 52.0373 mL |
| 5 mM | 1.0407 mL | 5.2037 mL | 10.4075 mL |
| 10 mM | 0.5204 mL | 2.6019 mL | 5.2037 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。
Scoparone as a therapeutic drug in liver diseases: Pharmacology, pharmacokinetics and molecular mechanisms of action
Pharmacol Res 2020 Oct;160:105170.PMID:32877694DOI:10.1016/j.phrs.2020.105170.
Scoparone is an active and efficious ingredient of herbal medicine Artemisia capillaris Thunb, which has been used clinically in traditional Chinese medicine formula (e.g. Yin-Chen-Hao decoction) for the treatment of hepatic dysfunction, cholestasis and jaundice for over thousand years. More recently, scoparone has received increasing attention due to its multiple properties. In this comprehensive review, we provide the first summary of the pharmacological effects and pharmacokinetic characteristics of scoparone, and discuss future research prospects. The results implicated that scoparone possesses a wide spectrum of pharmacological activities, including anti-inflammatory, antioxidant, anti-apoptotic, anti-fibrotic and hypolipidemic properties. Pharmacokinetic studies have addressed that Isoscopoletin and scopoletin are major primary metabolites of scoparone. Moreover, hepatic dysfunction might promote bioavailability of scoparone due to limited intrinsic clearance. On the other hand, the bioavailability of multi-component including scoparone in certain TCM formula can also be enhanced by applying this formula at a high dose on account of their interacted effects. In view of good pharmacological actions, scoparone is anticipated to be a potential drug candidate for various liver diseases, such as acute liver injury, fulminant hepatitis, alcohol-induced hepatotoxicity, non-alcoholic fatty liver disease and fibrosis. However, further studies are warranted to clarify its molecular mechanisms and targets, elucidate its toxicity, and identify its interplay with other active ingredients of classical TCM formula in clinical settings.
Metabolism of Scoparone in Experimental Animals and Humans
Planta Med 2019 Apr;85(6):453-464.PMID:30736072DOI:10.1055/a-0835-2301.
Scoparone, a major constituent of the Chinese herbal medicine Yin Chen Hao, expresses beneficial effects in experimental models of various diseases. The intrinsic doses and effects of scoparone are dependent on its metabolism, both in humans and animals. We evaluated in detail the metabolism of scoparone in human, mouse, rat, pig, dog, and rabbit liver microsomes in vitro and in humans in vivo. Oxidation of scoparone to Isoscopoletin via 6-O-demethylation was the major metabolic pathway in liver microsomes from humans, mouse, rat, pig and dog, whereas 7-O-demethylation to scopoletin was the main reaction in rabbit. The scoparone oxidation rates in liver microsomes were 0.8 - 1.2 µmol/(min*g protein) in mouse, pig, and rabbit, 0.2 - 0.4 µmol/(min*g protein) in man and dog, and less than 0.1 µmol/(min*g) in rat. In liver microsomes of all species, Isoscopoletin was oxidized to 3-[4-methoxy-ρ-(3, 6)-benzoquinone]-2-propenoate and esculetin, which was formed also in the oxidation of scopoletin. Human CYP2A13 exhibited the highest rate of Isoscopoletin and scopoletin oxidation, followed by CYP1A1 and CYP1A2. Glucuronidation of Isoscopoletin and scopoletin was catalyzed by the human UGT1A1, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT1A10, and UGT2B17. Dog was most similar to man in scoparone metabolism. Isoscopoletin glucuronide and sulfate conjugates were the major scoparone in vivo metabolites in humans, and they were completely excreted within 24 h in urine. Scoparone and its metabolites did not activate key nuclear receptors regulating CYP and UGT enzymes. These results outline comprehensively the metabolic pathways of scoparone in man and key preclinical animal species.
Activity-guided isolation of scopoletin and Isoscopoletin, the inhibitory active principles towards CCRF-CEM leukaemia cells and multi-drug resistant CEM/ADR5000 cells, from Artemisia argyi
Planta Med 2006 Jul;72(9):862-4.PMID:16881019DOI:10.1055/s-2006-947165.
The ethyl acetate extract of Artemisia argyi leaves showed substantial inhibition in a cell proliferation assay using human CCRF-CEM leukaemia cells. Bioassay-guided fractionation of the extract led to the isolation of scopoletin and Isoscopoletin as the active principles. Their IC50 values were 2.6 and 4.0 microM, respectively. Additionally the two substances were tested against the multidrug resistant subline, CEM/ADR5000 where they both showed IC50 values of 1.6 microM. In contrast to the standard cytostatic drugs doxorubicin, vincristine, and paclitaxel, CEM/ADR5000 cells therefore did not exhibit cross-resistance to scopoletin and Isoscopoletin.
A new ionone derivative from Lycium intricatum Boiss. (Solanaceae)
Nat Prod Res 2022 Feb;36(3):687-694.PMID:32705905DOI:10.1080/14786419.2020.1797729.
Lycium intricatum Boiss also called 'Awsadj' is a subshrub belonging to the Solanaceae family and producing red berries. In the present work, we report the isolation of a new compound, ((1 R,3aR,7aS)-3a,7-dimethyl-1-((E)-prop-1-en-1-yl)-1,3a,4,7a-tetrahydroisobenzofuran-5(3H)-one (1)). Three known compounds were also isolated for the first time from L. intricatum, and identified as Isoscopoletin (2), 3,4,5-trimethoxybenzyl alcohol (3), and (+)-isolariciresinol (4). Compounds 1-4 were isolated from the extract of leaves using chromatographic techniques, and the structure of compound 1 was fully elucidated by NMR, MS and ECD experiments.
Anticancer activity of botanical compounds in ancient fermented beverages (review)
Int J Oncol 2010 Jul;37(1):5-14.PMID:20514391DOI:10.3892/ijo_00000647.
Humans around the globe probably discovered natural remedies against disease and cancer by trial and error over the millennia. Biomolecular archaeological analyses of ancient organics, especially plants dissolved or decocted as fermented beverages, have begun to reveal the preliterate histories of traditional pharmacopeias, which often date back thousands of years earlier than ancient textual, ethnohistorical, and ethnological evidence. In this new approach to drug discovery, two case studies from ancient Egypt and China illustrate how ancient medicines can be reconstructed from chemical and archaeological data and their active compounds delimited for testing their anticancer and other medicinal effects. Specifically, Isoscopoletin from Artemisia argyi, artemisinin from Artemisia annua, and the latter's more easily assimilated semi-synthetic derivative, artesunate, showed the greatest activity in vitro against lung and colon cancers. In vivo tests of these compounds previously unscreened against lung and pancreatic cancers are planned for the future.