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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

Molecular Formula C18H16O7
Molecular Weight 344.3154
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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, a pharmacologically active flavone derived from Artemisia plants, induces apoptosis in human gastric cancer (AGS) cells.
2005
In vitro metabolism of eupatilin by multiple cytochrome P450 and UDP-glucuronosyltransferase enzymes.
2007 Aug
Inhibitory effect of eupatilin and jaceosidin isolated from Artemisia princeps in IgE-induced hypersensitivity.
2007 Dec 15
Analysis of eupatilin-human serum albumin interactions by means of spectroscopic and computational modelling.
2007 May
DA-6034, a derivative of flavonoid, prevents and ameliorates dextran sulfate sodium-induced colitis and inhibits colon carcinogenesis.
2008 Feb
Eupatilin protects gastric epithelial cells from oxidative damage and down-regulates genes responsible for the cellular oxidative stress.
2008 Jun
The protective effect of eupatilin on indomethacin-induced cell damage in cultured feline ileal smooth muscle cells: involvement of HO-1 and ERK.
2008 Jun 19
Eupatilin exhibits a novel anti-tumor activity through the induction of cell cycle arrest and differentiation of gastric carcinoma AGS cells.
2009 Apr
TNF-α induces expression of urokinase-type plasminogen activator and β-catenin activation through generation of ROS in human breast epithelial cells.
2010 Dec 15
Impact of dietary polyphenols on carbohydrate metabolism.
2010 Mar 31
Effects of eupatilin and jaceosidin on cytochrome p450 enzyme activities in human liver microsomes.
2010 Sep 16
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:24 GMT 2023
Edited
by admin
on Sat Dec 16 01:37:24 GMT 2023
Record UNII
4D58O05490
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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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