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Licochalcone B

Alias: LicoB Lico-B Lico BLicochalcone-B
Cat No.:V24107 Purity: ≥98%
Licochalcone B,a naturally occuring chalcone compound isolated from the root ofGlycyrrhiza inflate, is an inhibitor of phosphorylation of NF-kappaB p65 in LPS signaling pathway.
Licochalcone B
Licochalcone B Chemical Structure CAS No.: 58749-23-8
Product category: Beta Amyloid
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Licochalcone B, a naturally occuring chalcone compound isolated from the root of Glycyrrhiza inflate, is an inhibitor of phosphorylation of NF-kappaB p65 in LPS signaling pathway. It also inhibits amyloid β (Aβ42) self-aggregation (IC50=2.16 μM) and disaggregate pre-formed Aβ42 fibrils, reduce metal-induced Aβ42 aggregation through chelating metal ions.
Licochalcone B is a retrochalcone flavonoid isolated primarily from the roots of licorice (Glycyrrhiza inflata and Glycyrrhiza uralensis). It has a molecular formula of C16H14O5 and a molecular weight of 286.28 g/mol. This natural compound has attracted significant attention due to its diverse pharmacological properties, including anti-inflammatory, antioxidant, antiviral, and anticancer effects. It has been shown to have antitumor, antimetastatic, cardioprotective, antioxidant, antiapoptotic, and anti-inflammatory effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Licochalcone B targets multiple pathways. It has been shown to inhibit LPS-induced phosphorylation at serine 276 and the transcriptional activation of NF-κB. By inhibiting NF-κB, a master regulator of the inflammatory response, licochalcone B reduces the expression of pro-inflammatory genes. It also inhibits amyloid β self-aggregation with an IC50 of 2.16 μM, suggesting potential activity against Alzheimer's disease.
ln Vitro
Aβ42 aggregation is inhibited and Aβ42 pre-fibril formation is fragmented by licochalcone B (IC50: 2.16 μM) [1]. In SH-SY5Y cells, licochalcone B (0–12 μM, 48 h) decreases ROS generation and safeguards the cell culture medium H2O2. causes cellular apoptosis. In RAW264.7 cells, licochalcone B (10 μM, 1 h) suppresses the activation of NF-κB triggered by LPS [2]. Licochalcone B (0–20 μM, 24 or 48 h) suppresses the development of human NSCLC cells, while licochalcone B (10 μM, 1 h) inhibits LPS-induced NF-κB p65 serine 276 phosphorylation [3].
In vitro, licochalcone B inhibits LPS-induced phosphorylation at serine 276 and the transcriptional activation of NF-κB. This leads to a reduction in the production of pro-inflammatory cytokines. It also inhibits amyloid β self-aggregation with an IC50 of 2.16 μM. These in vitro activities confirm its anti-inflammatory and potential neuroprotective properties.
ln Vivo
Licochalcone B (1–25 mg/kg, gavage) reduces the oxidative stress and hepatotoxicity that CCl4[5] causes in mice.
In vivo, licochalcone B has demonstrated antitumor and antimetastatic effects. It has been shown to inhibit the adhesion, invasion, and metastasis of human malignant bladder cancer T24 cells. These in vivo activities highlight its potential as an anticancer agent. Its cardioprotective and antioxidant effects also suggest potential therapeutic applications in cardiovascular diseases.
Enzyme Assay
Non-cell-based assays for licochalcone B would typically involve measuring its ability to inhibit NF-κB DNA binding using an electrophoretic mobility shift assay (EMSA). Amyloid β aggregation assays can be performed using Thioflavin T fluorescence to measure the inhibition of fibril formation.
Cell Assay
Western Blot Analysis[2]
Cell Types: RAW264.7 Cell
Tested Concentrations: 10. µM
Incubation Duration: 1 hour
Experimental Results: Inhibits phosphorylation of NF-κB at serine 276 but not at serine 536.
Cellular assays for licochalcone B are performed using immune cells such as macrophages. The cells are stimulated with LPS, and the levels of pro-inflammatory cytokines are measured by ELISA. The activation of NF-κB is measured by Western blotting for phosphorylated proteins or by immunofluorescence for NF-κB nuclear translocation. In cancer cells, the compound's effect on cell adhesion, invasion, and metastasis is assessed using appropriate assays.
Animal Protocol
Animal/Disease Models: CCl4[5] induced mice
Doses: 1, 5, 25 mg/kg
Route of Administration: po (oral gavage).
Experimental Results: SOD and GSH levels increased, and GSSG levels diminished.
In vivo animal models for licochalcone B would typically involve tumor xenograft models in immunodeficient mice for studying its anticancer effects. For its anti-inflammatory effects, models such as LPS-induced sepsis or carrageenan-induced paw edema could be used. The compound would be administered orally or intraperitoneally, and its effects on tumor growth or inflammation would be measured.
ADME/Pharmacokinetics
Licochalcone B has a molecular weight of 286.28 g/mol and a molecular formula of C16H14O5. It is a lipophilic compound that is soluble in DMSO, acetone, chloroform, and ethyl acetate, but only slightly soluble in water. Detailed PK parameters such as half-life and bioavailability are not extensively detailed in the provided search results.
Toxicity/Toxicokinetics
Detailed toxicological data for licochalcone B are not provided in the search results. As a natural product, it is generally considered to have a good safety profile, but thorough toxicological studies would be required for therapeutic development. The compound is intended for research use only and is not for human consumption.
References

[1]. Licochalcone B, a chalcone derivative from Glycyrrhiza inflata, as a multifunctional agent for the treatment of Alzheimer's disease. Nat Prod Res. 2018 Oct 22:1-4.

[2]. Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-kappaB p65 in LPS signaling pathway. Int Immunopharmacol. 2009 Apr;9(4):499-507.

[3]. Licochalcone B inhibits growth and induces apoptosis of human non-small-cell lung cancer cells by dual targeting of EGFR and MET. Phytomedicine. 2019 Oct;63:153014.

[4]. Licochalcone B specifically inhibits the NLRP3 inflammasome by disrupting NEK7-NLRP3 interaction. EMBO Rep. 2022 Feb 3;23(2):e53499.

[5]. Hepatoprotective effects of licochalcone B on carbon tetrachloride-induced liver toxicity in mice. Iran J Basic Med Sci. 2016 Aug;19(8):910-915.

Additional Infomation
Licochalcone B is a chalcone compound. It has been reported to exist in licorice (Glycyrrhiza uralensis), euphorbia helioscopia, and other organisms with relevant data. See also: Root (part) of inflated licorice (Glycyrrhiza inflata).
Licochalcone B is a retrochalcone flavonoid from licorice root. It has diverse pharmacological properties, including anti-inflammatory, antioxidant, antiviral, and anticancer effects. It inhibits LPS-induced NF-κB activation and amyloid β self-aggregation (IC50 = 2.16 μM). It has the CAS number 58749-23-8 and is supplied for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H14O5
Molecular Weight
286.28
Exact Mass
286.084
CAS #
58749-23-8
Related CAS #
58749-23-8;
PubChem CID
5318999
Appearance
Light yellow to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
550.5±50.0 °C at 760 mmHg
Melting Point
196-197ºC
Flash Point
208.5±23.6 °C
Vapour Pressure
0.0±1.5 mmHg at 25°C
Index of Refraction
1.684
LogP
2.57
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
4
Heavy Atom Count
21
Complexity
373
Defined Atom Stereocenter Count
0
SMILES
COC1=C(C=CC(=C1O)O)/C=C/C(=O)C2=CC=C(C=C2)O
InChi Key
IOBDWJXFMVMVKI-XBXARRHUSA-N
InChi Code
InChI=1S/C16H14O5/c1-21-16-12(7-9-14(19)15(16)20)13(18)8-4-10-2-5-11(17)6-3-10/h2-9,17,19-20H,1H3/b8-4+
Chemical Name
(E)-1-(3,4-dihydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms
LicoB Lico-B Lico BLicochalcone-B
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~83.33 mg/mL (~291.08 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.27 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 3.4931 mL 17.4654 mL 34.9308 mL
5 mM 0.6986 mL 3.4931 mL 6.9862 mL
10 mM 0.3493 mL 1.7465 mL 3.4931 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.

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Working concentration mg/mL;

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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.
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