Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H16O7 |
Molecular Weight | 344.3154 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1OC)C2=CC(=O)C3=C(O)C(OC)=C(O)C=C3O2
InChI
InChIKey=DRRWBCNQOKKKOL-UHFFFAOYSA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25352757Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29353040 | https://www.ncbi.nlm.nih.gov/pubmed/19663482 | https://www.ncbi.nlm.nih.gov/pubmed/27698876 | https://www.drugs.com/international/stillen.html
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25352757
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29353040 | https://www.ncbi.nlm.nih.gov/pubmed/19663482 | https://www.ncbi.nlm.nih.gov/pubmed/27698876 | https://www.drugs.com/international/stillen.html
Eupatilin (5,7-dihydroxy-3',4',6-trimethoxyflavone) is the major lipophilic flavonoid from Artemísia umbellifórmis, mountain wormwood used for the production of the celebrated alpine liqueur genepy. Eupatilin is the active ingredient of Stillen, a herbal drug from the Asian wormwood Artemisia asiatica, developed in South Korea for the treatment of gastritis and peptic ulcer. Eupatilin has been shown to exert cytoprotective and antiapoptotic effects on gastric and esophageal epithelial primary cells and is endowed with antispasmodic and antimutagenic properties, while apoptotic and anti-proliferative activities have been demonstrated on cancer cells. Eupatilin has also been evaluated, with promising results, in several assays of relevance for inflammation and allergy. Thus, this flavonoid inhibits in vitro mast cell degranulation and histamine release, shows in vivo anti-allergic properties is an antioxidant, inhibits 5-lipoxygenase and the leukotrienes synthesis, decreases prostaglandin E2 production, and inhibits the activation of nuclear transcription factor NF-κB and the expression of cyclooxygenase-2 and different pro-inflammatory cytokines, such as interleukins (IL-4, IL-6, and IL-8) and tumor necrosis factor-R (TNF-R)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26225954 |
1.18 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Stillen Approved UseUnknown |
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Primary | Stillen Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Eupatilin attenuates bile acid-induced hepatocyte apoptosis. | 2006 Aug |
|
Effects of DA-6034, a flavonoid derivative, on mucin-like glycoprotein and ocular surface integrity in a rabbit model. | 2009 |
|
Eupatilin exhibits a novel anti-tumor activity through the induction of cell cycle arrest and differentiation of gastric carcinoma AGS cells. | 2009 Apr |
|
Impact of dietary polyphenols on carbohydrate metabolism. | 2010 Mar 31 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28960033
DA-9601 (comprises 60 mg of Artemisia asiatica 95% ethanol extract) three times per day for 2 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27698876
The 786 O human RCC cell line was used for activity evaluation. Cells were seeded into 96 well plates at 5x10^3 cells per well and cultured for 24 h at 37˚C to adhere. Following treatment with various concentrations of eupatilin (10, 20 and 40 μM) for 72 h, 10 μl of CCK 8 reagent was added to the cells, followed by incubation for 2 h at 37˚C. Subsequently, the optical density (OD) value was read at 450 nm using a Bio Rad ELISA microplate reader. Eupatilin significantly induced cell apoptosis and enhanced the production of reactive oxygen species (ROS) in 786 O cells.
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SUBSTANCE RECORD