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Licarin A

Alias: NSC-370989; NSC 370989; Licarin A
Cat No.:V24103 Purity: ≥98%
Licarin A ((+)-Licarin A) significantly reduces dinitrophenylhydrazine-human serum albumin (DNP-HSA)-stimulated RBL-2H3 cells.
Licarin A
Licarin A Chemical Structure CAS No.: 51020-86-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Licarin A ((+)-Licarin A) significantly reduces dinitrophenylhydrazine-human serum albumin (DNP-HSA)-stimulated RBL-2H3 cells. Has anti-allergy effects. Licarin A reduces TNF-α and PGD2 production, and COX-2 expression.
Licarin A is a naturally occurring neolignan compound found in various plants, including licorice (Glycyrrhiza uralensis), Aristolochia taliscana, Machilus thunbergii, and Myristica fragrans. It is a flavonoid known for its diverse biological activities, including anti-inflammatory, antioxidant, and potential anticancer properties. Licarin A's anti-inflammatory activity is mediated through the inhibition of PKCα/βII and p38 MAPK pathways, leading to decreased secretion of TNF-α and prostaglandin D2 (PGD2), as well as reduced COX-2 expression.
Biological Activity I Assay Protocols (From Reference)
Targets
Licarin A targets multiple pathways involved in inflammation. It inhibits the protein kinase C (PKC) α/βII isoforms and the p38 MAPK pathway. By inhibiting these signaling cascades, licarin A reduces the expression of COX-2 and the secretion of pro-inflammatory mediators such as TNF-α and prostaglandin D2 (PGD2). TNF-α is a key cytokine in the inflammatory response, and its reduction is a major contributor to licarin A's anti-inflammatory effects.
ln Vitro
Licanoside A is present in plants that are used as spices and traditional medicines to treat digestive and neurological conditions, such as Aristolochia, Runnan, and Myristica. Additionally, licorin A possesses anti-inflammatory properties [1]. Licarin A (5–20 μM) inhibits the p38 MAPK and PKCα/βII pathways to decrease TNF-α and prostaglandin D2 (PGD2) release. Treatment with licorin A tends to lower levels of phosphorylated PKCα/βII and p38 MAPK protein [1].
In vitro, licarin A demonstrates potent anti-inflammatory activity. It inhibits the PKCα/βII and p38 MAPK pathways, leading to a decrease in TNF-α secretion with an IC50 of 12.6 μM. It also reduces the secretion of prostaglandin D2 (PGD2) and the expression of COX-2. These in vitro activities confirm its mechanism of action as an inhibitor of these key inflammatory signaling pathways.
ln Vivo
Detailed in vivo activity data for licarin A are not extensively provided in the search results. However, its anti-inflammatory properties suggest potential for in vivo efficacy in models of inflammation. Its presence in plants used in folk medicines for various disorders also hints at its therapeutic potential. Further in vivo studies would be required to fully characterize its efficacy and pharmacokinetic profile.
Enzyme Assay
Non-cell-based assays for licarin A would typically involve enzyme inhibition assays for its targets. For PKCα/βII, the enzyme would be incubated with a substrate and ATP, and licarin A would be added at various concentrations. The kinase activity would be measured, and an IC50 would be determined. For p38 MAPK, a similar kinase assay would be used.
Cell Assay
Cellular assays for licarin A are performed using immune cells such as macrophages. The cells are stimulated with LPS to induce an inflammatory response. Licarin A is added at various concentrations, and the levels of TNF-α and PGD2 in the culture supernatant are measured by ELISA. The expression of COX-2 is measured by Western blotting or qPCR. These assays confirm the compound's anti-inflammatory activity.
Animal Protocol
In vivo animal models for licarin A would likely involve standard models of inflammation, such as the carrageenan-induced paw edema model in rats or the LPS-induced sepsis model in mice. The compound would be administered, and inflammatory markers and tissue damage would be assessed. These studies are essential for evaluating the compound's therapeutic potential.
ADME/Pharmacokinetics
Licarin A has a molecular weight of 326.15 g/mol and a molecular formula of C20H22O4. It is a lipophilic compound that is soluble in DMSO and other organic solvents. Detailed PK parameters such as half-life and bioavailability are not extensively detailed in the provided search results.
Toxicity/Toxicokinetics
Detailed toxicological data for licarin A 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]. Licarin A Is a Candidate Compound for the Treatment of Immediate Hypersensitivity via Inhibition of Rat Mast Cell Line RBL-2H3 Cells. J Pharm Pharmacol. 2015 Dec;67(12):1723-32.

Additional Infomation
(-)-Licarin A has been reported to be found in plants of the genera Aristolochia fordiana, Jackiella javanica, and other organisms with available data.
Licarin A is a natural neolignan with anti-inflammatory properties. It inhibits PKCα/βII and p38 MAPK pathways, decreasing TNF-α secretion (IC50 = 12.6 μM) and PGD2 secretion, as well as COX-2 expression. It is found in licorice and other plants and has the CAS number 51020-86-1. It is supplied for research purposes as a natural product standard.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H22O4
Molecular Weight
326.39
Exact Mass
326.151
CAS #
51020-86-1
Related CAS #
83377-50-8 (rotation +);51020-86-1 (rotation -);
PubChem CID
6442393
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
452.0±45.0 °C at 760 mmHg
Flash Point
227.2±28.7 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.596
LogP
4.19
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
24
Complexity
437
Defined Atom Stereocenter Count
2
SMILES
C/C=C/C1=CC2=C(C(=C1)OC)O[C@@H]([C@H]2C)C3=CC(=C(C=C3)O)OC
InChi Key
ITDOFWOJEDZPCF-FNINDUDTSA-N
InChi Code
InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m0/s1
Chemical Name
2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
Synonyms
NSC-370989; NSC 370989; Licarin A
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 : ≥ 50 mg/mL (~153.19 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0638 mL 15.3191 mL 30.6382 mL
5 mM 0.6128 mL 3.0638 mL 6.1276 mL
10 mM 0.3064 mL 1.5319 mL 3.0638 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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