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Eupatilin is a naturally occurring lipophilic flavonoid isolated from Artemisia species, acting as a PPARα agonist, and possessing anti-apoptotic, anti-oxidative and anti-inflammatory activities.
| Targets |
Eupatilin acts as an agonist/activator of PPARα [1]
Eupatilin exerts PPARα agonistic effects [2] |
|---|---|
| ln Vitro |
Eupatilin is a PPARα agonist. Eupatilin (10, 30, 100 μM) reduces IL-4 expression and degranulation in RBL-2H3 cells [1]. Eupatilin (50-100 μM) showed a modest reduction in HaCaT cell viability. Eupatilin (10, 30, 50, 100 μM) promotes PPARα transactivation and expression in HaCaT cells. Eupatilin (10, 30, and 50 μM) reduced TNFα-induced MMP-2/-9 expression in HaCaT cells. Eupatilin suppresses TNFα-induced p65 translocation, IκBα phosphorylation, AP-1, and MAPK signaling via PPARα [2]. Eupatilin (10-50 μM) shows no cytotoxic effects on ARPE19 cells. Eupatilin (10, 25, 50 μM) decreases H2O2-induced ROS generation in ARPE19 cells while increasing oxidation-induced cell viability. Eupatilin (50 μM) reduces H2O2-induced cell viability while activating PI3K/Akt receptors in RPE cells [3].
Eupatilin (10 μM, 20 μM, 40 μM) inhibited TNFα-induced MMP-1 and MMP-9 expression in HaCaT cells. It suppressed TNFα-mediated activation of NF-κB signaling pathway by inhibiting IκBα phosphorylation and p65 nuclear translocation, and upregulated PPARα expression as well as promoted its nuclear translocation [2] Eupatilin (5 μM, 10 μM, 20 μM) increased superoxide dismutase (SOD) and catalase (CAT) activities, reduced malondialdehyde (MDA) level, and suppressed reactive oxygen species (ROS) production and DNA damage in H2O2-challenged human retinal pigment epithelial cells. It also decreased Bax/Bcl-2 ratio, caspase-3 activation, and PARP cleavage to inhibit H2O2-induced apoptosis [3] |
| ln Vivo |
The oxazolone-induced Balb/c model exhibits improved symptoms similar to atopic dermatitis (AD) when euphemilin (1.5% or 3.0%) is administered. In the model induced by oxazolone, euphemaline significantly decreased serum IgE levels, IL-4 levels, and the mRNA expression of TNFα, IFNγ, IL-1β, TSLP, IL-33, and IL-25 induced by oxazolone. Eupatilin also raises the loricin and filaggrin mRNA expression among the compounds produced by oxazolone [1].
Eupatilin (20 mg/kg, 40 mg/kg) significantly reduced atopic dermatitis-like symptoms (erythema, edema, scaling, pruritus) in oxazolone-induced Balb/c mice. It decreased epidermis and dermis thickness, inhibited infiltration of inflammatory cells (eosinophils, mast cells, lymphocytes) into skin lesions, and downregulated expression of pro-inflammatory cytokines (IL-4, IL-5, IL-13, TNFα, IFNγ) and chemokines (CCL11, CCL22) in skin and serum. It also upregulated PPARα expression and suppressed NF-κB activation in skin tissues [1] |
| Cell Assay |
HaCaT cells were cultured and treated with TNFα (10 ng/mL) alone or combined with Eupatilin (10 μM, 20 μM, 40 μM) for 24 hours. Cell lysates were subjected to Western blot for detecting MMP-1, MMP-9, PPARα, phosphorylated IκBα, and nuclear p65, while quantitative real-time PCR was used to measure mRNA levels of MMP-1, MMP-9, and PPARα [2]
Human retinal pigment epithelial cells were seeded and pretreated with Eupatilin (5 μM, 10 μM, 20 μM) for 2 hours, followed by H2O2 (200 μM) exposure for 24 hours. Cell viability was assessed by CCK-8 assay, ROS production by fluorescent probe, SOD/CAT activities and MDA level by assay kits, and apoptosis by flow cytometry and Western blot (Bax, Bcl-2, caspase-3, PARP) [3] |
| Animal Protocol |
6-8 weeks old Balb/c mice were sensitized with 1% oxazolone on day 0 and 7, then challenged with 0.5% oxazolone every other day from day 14 to 28. Eupatilin was dissolved in 10% DMSO, 40% polyethylene glycol, 50% saline, and administered intragastrically at 20 mg/kg or 40 mg/kg once daily from day 14 to 28. Mice were sacrificed on day 29, and skin tissues, serum, and lymph nodes were collected for histological, immunohistochemical, and cytokine analysis [1]
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Eupatilin's known human metabolites include Jaceosidine. |
| References |
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| Additional Infomation |
Eupatilin is a trimethoxyflavonoid with a flavonoid structure in which hydroxyl groups are substituted at C-5 and C-7, and methoxy groups are substituted at C-6, C-3', and C-4'. It was isolated from citrus (Citrus reticulata) and sage (Salvia tomentosa) and has anti-inflammatory, anti-ulcer, and antitumor activities. Eupatilin can function as an antiulcer drug, an EC 1.13.11.34 (arachidonic acid 5-lipoxygenase) inhibitor, an antitumor drug, an anti-inflammatory drug, and a metabolite. It is a trimethoxyflavonoid and a dihydroxyflavonoid.
It has been reported that Eupatilin exists in Artemisia princeps, Achillea setacea, and other organisms with relevant data. Eupatilin exerts its anti-inflammatory effect by activating PPARα and inhibiting NF-κB, showing potential efficacy in the treatment of atopic dermatitis[1]. Eupatilin’s PPARα agonist activity helps to inhibit the TNFα-induced MMP signaling pathway in keratinocytes, suggesting its potential application value in inflammatory skin diseases [2]. Eupatilin exhibits antioxidant and anti-apoptotic properties in human retinal pigment epithelial cells, suggesting its potential application in oxidative stress-related ocular diseases [3]. |
| Molecular Formula |
C18H16O7
|
|---|---|
| Molecular Weight |
344.3154
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| Exact Mass |
344.089
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| CAS # |
22368-21-4
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| PubChem CID |
5273755
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
583.6±50.0 °C at 760 mmHg
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| Melting Point |
236 °C
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| Flash Point |
214.7±23.6 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.627
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| LogP |
2.46
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
520
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
DRRWBCNQOKKKOL-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3
|
| Chemical Name |
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
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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 |
| 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 : ~33.33 mg/mL (~96.80 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.26 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 25.0 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: ≥ 2.5 mg/mL (7.26 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9043 mL | 14.5214 mL | 29.0428 mL | |
| 5 mM | 0.5809 mL | 2.9043 mL | 5.8086 mL | |
| 10 mM | 0.2904 mL | 1.4521 mL | 2.9043 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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