Glycycoumarin
(Synonyms: 甘草香豆素) 目录号 : GC36163Glycycoumarin 是一种甘草中主要的生物活性香豆素。Glycycoumarin 通过激活自噬,抑制内质网应激介导的 JNK 和 GSK-3 介导的线粒体途径,来抑制肝细胞脂性凋亡。Glycycoumarin 能直接靶向 T-LAK 细胞源蛋白激酶发挥抗肝癌活性 。
Cas No.:94805-82-0
Sample solution is provided at 25 µL, 10mM.
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Glycycoumarin is a major bioactive coumarin of licorice. Glycycoumarin inhibits hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress-mediated JNK and GSK-3-mediated mitochondrial pathway. Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase [1] [2].
[1]. Zhang E, et al. Glycycoumarin inhibits hepatocyte lipoapoptosis through activation of autophagy and inhibition of ER stress/GSK-3-mediated mitochondrial pathway. Sci Rep. 2016 Nov 30;6:38138. [2]. Song X, et al. Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase. Oncotarget. 2016 Oct 4;7(40):65732-65743.
Cas No. | 94805-82-0 | SDF | |
别名 | 甘草香豆素 | ||
Canonical SMILES | O=C1C(C2=CC=C(O)C=C2O)=CC3=C(OC)C(C/C=C(C)\C)=C(O)C=C3O1 | ||
分子式 | C21H20O6 | 分子量 | 368.38 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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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 |
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Pharmacological Activities and Pharmacokinetics of Glycycoumarin
Rev Bras Farmacogn 2022 Dec 16;1-13.PMID:36567915DOI:10.1007/s43450-022-00342-x.
Glycycoumarin is a representative coumarin compound with significant pharmacological activities isolated from Glycyrrhiza uralensis Fisch., Fabaceae. Studies have shown that Glycycoumarin has many biological activities, such as anti-tumor, liver protection, antispasmodic, antibacterial, and antivirus. However, the poor solubility of Glycycoumarin in water and the accompanying reactions of the phase I (hydroxylation) and II (glucuronidation) metabolism limit its druggability, which manifests as low absorption in the body after oral administration and low free drug concentration, ultimately leading to low bioavailability. Therefore, a comprehensive review of the pharmacological effects and pharmacokinetics of Glycycoumarin is presented to provide a reference for further research and application as a therapeutic agent. Supplementary information: The online version contains supplementary material available at 10.1007/s43450-022-00342-x.
Protective effects of Glycycoumarin on liver diseases
Phytother Res 2020 Jun;34(6):1191-1197.PMID:31840883DOI:10.1002/ptr.6598.
Licorice, an edible and medicinal plant, has long been used to treat various diseases, including liver diseases. Glycycoumarin (GCM) is a representative coumarin compound in licorice with favorable bioavailability feature. Recent studies by us demonstrated that GCM is highly effective against alcoholic liver disease, nonalcoholic fatty liver disease, acetaminophen-induced hepatotoxicity, and liver cancer through mechanisms involved in activation of Nrf2 antioxidant system, stimulation of AMPK-mediated energy homeostasis, induction of autophagy degradation process, and inhibiting oncogenic kinase T-lymphokine-activated killer cell-originated protein kinase activity. In this review, we summarize the findings on the hepatoprotective effect of GCM, discuss the signaling pathways underlying GCM-induced protective effect on liver diseases, and propose the issues that need to be addressed to promote further development of GCM as a clinically useful hepatoprotective agent.
Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway
Oxid Med Cell Longev 2020 Apr 22;2020:1675957.PMID:32377290DOI:10.1155/2020/1675957.
The Keap1/Nrf2/ARE system is a central defensive mechanism against oxidative stress which plays a key role in the pathogenesis and progression of many diseases. Nrf2 is a redox-sensitive transcription factor controlling a variety of downstream antioxidant and cytodefensive genes. Nrf2 has a powerful anti-inflammatory activity mediated via modulating NF-κB. Therefore, pharmacological activation of Nrf2 is a promising therapeutic strategy for the treatment/prevention of several diseases that are underlined by both oxidative stress and inflammation. Coumarins are natural products with promising pharmacological activities, including antioxidant, anticancer, antimicrobial, and anti-inflammatory efficacies. Coumarins are found in many plants, fungi, and bacteria and have been widely used as complementary and alternative medicines. Some coumarins have shown an ability to activate Nrf2 signaling in different cells and animal models. The present review compiles the research findings of seventeen coumarin derivatives of plant origin (imperatorin, visnagin, urolithin B, urolithin A, scopoletin, esculin, esculetin, umbelliferone, fraxetin, fraxin, daphnetin, anomalin, wedelolactone, Glycycoumarin, osthole, hydrangenol, and isoimperatorin) as antioxidant and anti-inflammatory agents, emphasizing the role of Nrf2 activation in their pharmacological activities. Additionally, molecular docking simulations were utilized to investigate the potential binding mode of these coumarins with Keap1 as a strategy to disrupt Keap1/Nrf2 protein-protein interaction and activate Nrf2 signaling.
Glycycoumarin exerts anti-liver cancer activity by directly targeting T-LAK cell-originated protein kinase
Oncotarget 2016 Oct 4;7(40):65732-65743.PMID:27582549DOI:10.18632/oncotarget.11610.
Glycycoumarin (GCM) is a major bioactive coumarin compound isolated from licorice and the anti-cancer activity of GCM has not been scientifically addressed. In the present study, we have tested the anti-liver cancer activity of GCM using both in vitro and in vivo models and found for the first time that GCM possesses a potent activity against liver cancer evidenced by cell growth inhibition and apoptosis induction in vitro and tumor reduction in vivo. Mechanistically, GCM was able to bind to and inactivate oncogenic kinase T-LAK cell-originated protein kinase (TOPK), which in turn led to activation of p53 pathway. Our findings supported GCM as a novel active compound that contributed to the anti-cancer activity of licorice and TOPK could be an effective target for hepatocellular carcinoma (HCC) treatment.
Glycycoumarin from Glycyrrhizae Radix acts as a potent antispasmodic through inhibition of phosphodiesterase 3
J Ethnopharmacol 2006 May 24;105(3):409-14.PMID:16387459DOI:10.1016/j.jep.2005.11.017.
Glycyrrhizae Radix is used to treat abdominal pain as a component of Shakuyaku-kanzo-to, a traditional Chinese medicine formulation. We aim at clarifying the antispasmodic principles of Glycyrrhizae Radix, and consequently isolated Glycycoumarin as a potent relaxant on the carbamylcholine (CCh)-induced contraction of mouse jejunum. In this paper we investigated the effects and the action mechanism of Glycycoumarin on the contraction of mouse jejunum. Glycycoumarin inhibited the contraction induced by various types of stimulants, such as CCh, KCl, BaCl(2), and A23187 (calcium ionophore III) with IC(50) values of 2.93+/-0.94 micromol/l (1.08+/-0.35 microg/ml), 2.59+/-0.58 micromol/l (0.95+/-0.29 microg/ml), 4.09+/-1.82 micromol/l (1.51+/-0.67 microg/ml) and 7.39+/-5.19 micromol/l (2.72+/-1.91 microg/ml), respectively, with a potency similar to that of papaverine (a representative antispasmodic for smooth muscle). Furthermore, pretreatment with Glycycoumarin enhanced the relaxation induced by forskolin on CCh-evoked contraction, similar to that by pretreatment with IBMX, a non-specific inhibitor of phosphodiesterases (PDEs). Pretreatment with Glycycoumarin also enhanced the relaxation effect of rolipram, a specific inhibitor of PDE isozyme 4, as pretreatment with milrinone, a specific inhibitor of isozyme 3, did. Moreover, the effect of Glycycoumarin was associated with dose-dependent accumulation of cAMP, but not cGMP, in mouse jejunum. These results indicate that Glycycoumarin has an inhibitory effect on smooth muscle contraction induced by various types of stimulants through the inhibition of PDEs, especially isozyme 3, followed by the accumulation of intracellular cAMP.