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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
Structure of EUPATILIN

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
1.18 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Stillen

Approved Use

Unknown
Primary
Stillen

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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

DA-9601 (comprises 60 mg of Artemisia asiatica 95% ethanol extract) three times per day for 2 weeks
Route of Administration: Oral
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.
Name Type Language
EUPATILIN
WHO-DD  
Common Name English
NSC-122413
Code English
2-(3,4-DIMETHOXYPHENYL)-5,7-DIHYDROXY-6-METHOXYCHROMEN-4-ONE
Systematic Name English
Eupatilin [WHO-DD]
Common Name English
Code System Code Type Description
NSC
122413
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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EPA CompTox
DTXSID30176904
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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FDA UNII
4D58O05490
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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CHEBI
4932
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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PUBCHEM
5273755
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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WIKIPEDIA
EUPATILIN
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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EVMPD
SUB32923
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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SMS_ID
100000126353
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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MESH
C045325
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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CAS
22368-21-4
Created by admin on Sat Dec 16 01:37:24 GMT 2023 , Edited by admin on Sat Dec 16 01:37:24 GMT 2023
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