Licoflavonol
(Synonyms: 甘草黄酮醇) 目录号 : GC36450
Licoflavonol 是乌拉甘草中的一种小型黄酮类化合物，能作为沙门氏菌 T3SS 的抑制剂。
Cas No.:60197-60-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Licoflavonol, a minor flavone from the roots of Glycyrrhiza uralensis, is an inhibitor of the Salmonella type III secretion system (T3SS)[1][2].
[1]. Qiao X, et al. Simultaneous determination of five minor coumarins and flavonoids in Glycyrrhiza uralensis by solid-phase extraction and high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Planta Med. 2014 Feb;80(2-3):237-42. [2]. Guo Z, et al. Licoflavonol is an inhibitor of the type three secretion system of Salmonella enterica serovar Typhimurium. Biochem Biophys Res Commun. 2016 Sep 2;477(4):998-1004.
| Cas No. | 60197-60-6 | SDF | |
| 别名 | 甘草黄酮醇 | ||
| Canonical SMILES | O=C1C(O)=C(C2=CC=C(O)C=C2)OC3=CC(O)=C(C/C=C(C)\C)C(O)=C13 | ||
| 分子式 | C20H18O6 | 分子量 | 354.35 |
| 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。 |
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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 | 2.8221 mL | 14.1103 mL | 28.2207 mL |
| 5 mM | 0.5644 mL | 2.8221 mL | 5.6441 mL |
| 10 mM | 0.2822 mL | 1.411 mL | 2.8221 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。
Licoflavonol Reduces Aβ Secretion by Increasing BACE1 Phosphorylation to Facilitate BACE1 Degradation
Mol Nutr Food Res 2019 Feb;63(3):e1800474.PMID:30365228DOI:10.1002/mnfr.201800474.
Scope: In the previous study, Glycyrrhiza uralensis Fisch extract (GUE) inhibited Aβ secretion by inhibiting β-site APP-cleaving enzyme 1 (BACE1) transcription, and the active compounds semilicoisoflavone B (SB) and Licoflavonol (LF) inhibited Aβ secretion. SB corresponds to the same mechanism as GUE, but LF has a different mechanism. In this study, the mechanism underlying inhibition of Aβ by LF is investigated. Methods and results: The effects of LF on Aβ, sAPPα, and sAPPβ secretion are evaluated by ELISA, and the effect of LF on BACE1 expression is detected by western blotting. It is found that the effect of LF on Aβ secretion is due to promotion of BACE1 protein degradation, and that the effect of LF on Aβ and BACE1 expression is attenuated after cotreatment with the lysosome inhibitor chloroquine. In a subsequent mechanistic study, it is found that LF increases BACE1 phosphorylation to increase its interactions with ADP ribosylation factor-binding proteins 1 and 3 (GGA1 and GGA3, respectively) and eventually facilitate BACE1 delivery to lysosomes for degradation. Conclusion: This study is the first to demonstrate that the BACE1 phosphorylation inducer LF can modulate BACE1 trafficking and lead to facilitating degradation of BACE1, eventually decreasing Aβ secretion.
Licoflavonol is an inhibitor of the type three secretion system of Salmonella enterica serovar Typhimurium
Biochem Biophys Res Commun 2016 Sep 2;477(4):998-1004.PMID:27387231DOI:10.1016/j.bbrc.2016.07.018.
As an important food-borne human pathogen, Salmonella enterica serovar Typhimurium depends on its type III secretion system (T3SS) as a major virulence factor to cause disease all over the world. The T3SS secretes effector proteins to facilitate invasion into host cells. In this study, twenty prenylated flavonoids (1-20) were screened for their anti-T3SS activity, revealing that several analogs exhibited strong inhibitory effects on the secretion of Salmonella pathogenicity island 1 (SPI-1)-associated effector proteins without affecting the growth of bacteria and the secretion of the flagellar protein FliC. Among the flavonoids 1-20, Licoflavonol (20) exhibited a strong inhibitory effect on the secretion of the SPI-1 effector proteins via regulating the transcription of the SicA/InvF genes, and the transportation of the effector protein SipC. In summary, Licoflavonol, a novel natural inhibitor of Salmonella T3SS, could be a promising candidate for novel type of anti-virulence drugs.
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.
Influence of the pKa value on the antioxidant activity of licorice flavonoids under solvent-mediated effects
Arch Pharm (Weinheim) 2023 Apr;356(4):e2200470.PMID:36707412DOI:10.1002/ardp.202200470.
Licorice flavonoids (LCFs) have been widely used in food care and medical treatment due to their significant antioxidant activities. However, the molecular mechanism of their antioxidant activity remains unclear. Therefore, network pharmacology, ADMET, density functional theory (DFT), molecular docking, and molecular dynamics (MD) simulation were employed to explore the molecular mechanism of the antioxidant effects of LCF. The network pharmacology and ADMET studies showed that the active molecules of kumatakenin (pKa = 6.18), Licoflavonol (pKa = 6.86), and topazolin (pKa = 6.21) in LCF are key antioxidant components and have good biosafety. Molecular docking and MD simulation studies demonstrated that active molecules interacted with amino acid residues in target proteins to form stable protein-ligand complexes and exert their antioxidant effects. DFT studies showed that the antioxidant activity of LCF could be significantly modulated under the solvent-mediated effect. In addition, based on the derivation of the Henderson-Hasselbalch and van't Hoff formulas, the functional relationships between the reaction-free energy (ΔG) of LCF and the pH and pKa values were established. The results showed that active molecules with larger pKa values will be more conducive to the improvement of their antioxidant activity under solvent-mediated effects. In conclusion, this study found that increasing the pKa value of LCF would be an effective strategy to improve their antioxidant activity under the effect of solvent mediation. The pKa value of an LCF will be a direct standard to evaluate its solvent-mediated antioxidant activity. This study will provide theoretical guidance for the development of natural antioxidants.
Investigation of the mechanisms and experimental verification of Shao yao gan cao decoction against Sphincter of Oddi Dysfunction via systems pharmacology
Math Biosci Eng 2022 Sep 14;19(12):13374-13398.PMID:36654051DOI:10.3934/mbe.2022626.
This study explored the chemical and pharmacological mechanisms of Shao Yao Gan Cao decoction (SYGC) in the treatment of Sphincter of Oddi Dysfunction (SOD) through ultra-high-performance liquid chromatography coupled with Quadrupole Exactive-Orbitrap high-resolution mass spectrometry (UHPLC-Q Exactive-Orbitrap HR-MS), network pharmacology, transcriptomics, molecular docking and in vivo experiments. First, we identified that SYGC improves SOD in guinea pigs by increased c-kit expression and decreased inflammation infiltration and ring muscle disorders. Then, a total of 649 SOD differential genes were found through RNA sequencing and mainly enriched in complement and coagulation cascades, the B cell receptor signaling pathway and the NF-kappa B signaling pathway. By combining UHPLC-Q-Orbitrap-HRMS with a network pharmacology study, 111 chemicals and a total of 52 common targets were obtained from SYGC in the treatment of SOD, which is also involved in muscle contraction, the B cell receptor signaling pathway and the complement system. Next, 20 intersecting genes were obtained among the PPI network, MCODE and ClusterOne analysis. Then, the molecular docking results indicated that four active compounds (glycycoumarin, Licoflavonol, echinatin and homobutein) and three targets (AURKB, KIF11 and PLG) exerted good binding interactions, which are also related to the B cell receptor signaling pathway and the complement system. Finally, animal experiments were conducted to confirm the SYGC therapy effects on SOD and verify the 22 hub genes using RT-qPCR. This study demonstrates that SYGC confers therapeutic effects against an experimental model of SOD via regulating immune response and inflammation, which provides a basis for future research and clinical applications.