| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
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Purity: =98.82%
| Targets |
NF-kappaB/NF-κB p65
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| ln Vitro |
Licochalcone D (10 μM; 1 h) significantly inhibits LPS-induced iNOS expression and NO production by blocking the phosphorylation and transactivation of NF-κB p65, which in turn inhibits LPS-induced protein regulatory A (PKA) activation. This indicates that Licochalcone D (10 μM; 24 h) negatively regulates lipopolysaccharide (LPS)-induced NF-κB activation. Proliferation of melanoma cells inhibits A375 cell migration, lowers the potential of the mitochondrial membrane, and raises ROS generation in A375 cells [2]. Licochalcone D (0–25 μM; 24 h) decreases MMP-2 and A375 cell migration as well as sterility.
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| ln Vivo |
In a xenograft model of oncinoblastoma B16F0 cells, licochalcone D (25 and 50 mg/kg; ig; once daily for one week) reduces the formation of tumors [2].
licochalcone D (LD) inhibits the tumor growth in a mouse xenograft model of murine melanoma B16F0 cells Based on the findings that LD induced A375 cell apoptosis in vitro, we used B16F0 tumor models to measure whether LD could suppress tumor progression in vivo. C57BL/6 mice bearing melanoma B16F0 cell-derived tumors were used as an in vivo model to evaluate the effects of LD. Compared with the control group, the tumor growth rates were obviously lower in mice treated with LD. The tumor growth inhibition rates were calculated to be 32.0 and 54.1% in the LD-treated groups (25 and 50 mg/kg), respectively (Fig. 9A and B)[2]. |
| Enzyme Assay |
Licorice root has been used as a traditional medicine for the treatment of gastric ulcer, bronchial asthma and inflammation. Licochalcone A is a major component of Xinjiang licorice, Glycyrrhiza inflata. Previously we showed that Licochalcone A significantly inhibited LPS-induced NF-kappaB transcriptional activation by abrogating the phosphorylation of NF-kappaB p65 at serine 276. Glycyrrhiza inflata contains not only Licochalcone A but also Licochalcone B, Licochalcone C, Licochalcone D, Echinatin and Isoliquiritigenin, harboring the common structure of chalcones. No chalcones had any effect on LPS-induced IkappaB degradation, nuclear translocation and DNA binding activity of NF-kappaB p65; however, we observed that Licochalcone B and Licochalcone D significantly inhibited LPS-induced phosphorylation at serine 276 and transcriptional activation of NF-kappaB, the same as Licochalcone A. Interestingly, we also found that Licochalcone A, Licochalcone B and Licochalcone D effectively inhibited LPS-induced activation of PKA, which is required for the phosphorylation of NF-kappaB p65 at serine 276. Consequently, Licochalcone B and Licochalcone D significantly reduced the LPS-induced production of NO, TNFalpha and MCP-1. On the other hand, Licochalcone C, Echinatin and Isoliquitigenin failed to inhibit LPS-induced NF-kappaB activation. These findings suggest that the anti-inflammatory effect of Glycyrrhiza inflata is ascribable to the potent inhibition of NF-kappaB by Licochalcone A, Licochalcone B and Licochalcone D[1].
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| Cell Assay |
Western Blot Analysis[1]
Cell Types: RAW264.7 Cell Tested Concentrations: 10 μM Incubation Duration: 1 h or 24 h (iNOS), 30 after LPS stimulation (1 μg/mL). min Experimental Results: Inhibits the phosphorylation of NF-κB at serine 276 but not at serine 536. Inhibits LPS-induced TNFα mRNA and MCP-1 mRNA expression. Strongly inhibits the expression of iNOS. Cell viability assay[2] Cell Types: A375 cells or SK-MEL-5 Tested Concentrations: 0, 1, 2.5, 5, 15, 30, 45, 60, 75 and 90 μM (A375) or 0, 20, 40, 60 and 80 μM (SK-MEL-5) Incubation Duration: 24 hrs (hours) Experimental Results: Inhibits the proliferation of A375 and SK-MEL-5 in a concentration-dependent manner. Apoptosis analysis [2] Cell Types: A375 Tested Concentrations: 0, 30, 60, 90 μM Incubation Duration: 24 h Experimental Results: The cells demonstrated obvious apoptotic characteristics after treatment. RT-PCR[2] Cell Types: A375 Tested Concentrations: 0, 30, 60 and 90 μM Incubation Duration: 24 h Experimental Results: Down-regulated Bcl-2 mRNA levels, up-regulated caspase-3, caspase-9 and Bax mRNA levels. Cell invasion experiment [2] Cell li |
| Animal Protocol |
Animal/Disease Models: C57BL/6 mice, B16F0 tumor model [2]
Doses: 25 and 50 mg/kg Route of Administration: intragastric (po) (po)administration, one time/day for one week Experimental Results: Dramatically diminished tumor growth rate, calculated at 25 and 50 mg/kg kg, the tumor growth inhibition rates were 32.0 and 54.1% respectively. |
| References |
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| Additional Infomation |
Licochalcone D has been reported in Glycyrrhiza inflata with data available.
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| Molecular Formula |
C21H22O5
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|---|---|
| Molecular Weight |
354.4
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| Exact Mass |
354.147
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| Elemental Analysis |
C, 71.17; H, 6.26; O, 22.57
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| CAS # |
144506-15-0
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| PubChem CID |
10473311
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| Appearance |
Light yellow to yellow solid powder
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| LogP |
4.216
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
523
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C(C(/C(/[H])=C(\[H])/C2C([H])=C([H])C(=C(C=2OC([H])([H])[H])O[H])O[H])=O)=C([H])C=1C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H]
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| InChi Key |
RETRVWFVEFCGOK-RMKNXTFCSA-N
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| InChi Code |
InChI=1S/C21H22O5/c1-13(2)4-5-15-12-16(8-10-18(15)23)17(22)9-6-14-7-11-19(24)20(25)21(14)26-3/h4,6-12,23-25H,5H2,1-3H3/b9-6+
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| Chemical Name |
(E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
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| Synonyms |
Licochalcone D; LicoD; Licochalcone-D; 144506-15-0; Licochalcone d [MI]; 2-Propen-1-one, 3-(3,4-dihydroxy-2-Methoxyphenyl)-1-[4-hydroxy-3-(3-Methyl-2-butenyl)p henyl]-, (E)-; 3P0SH94V09; (E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one; (2E)-3-(3,4-Dihydroxy-2-methoxyphenyl)-1-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-2-propen-1-one; 2-Propen-1-one, 3-(3,4-dihydroxy-2-methoxyphenyl)-1-(4-hydroxy-3-(3-methyl-2-butenyl)phenyl)-, (2E)-;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~352.71 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8217 mL | 14.1084 mL | 28.2167 mL | |
| 5 mM | 0.5643 mL | 2.8217 mL | 5.6433 mL | |
| 10 mM | 0.2822 mL | 1.4108 mL | 2.8217 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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