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Details

Stereochemistry RACEMIC
Molecular Formula C21H24O6
Molecular Weight 372.4117
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARCTIGENIN, (±)-

SMILES

COC1=CC(C[C@@H]2[C@@H](CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC=C1O

InChI

InChIKey=NQWVSMVXKMHKTF-JKSUJKDBSA-N
InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H24O6
Molecular Weight 372.4117
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26446917

Arctigenin is a plant lignan extracted from Arctium lappa that has been shown to have estrogenic properties. In ER-positive MCF-7 cells, arctigenin efficiently inhibited 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced cell migration and invasion. Arctigenin confers anti-metastatic effects by inhibiting MMP-9 and uPA via the Akt, NF-κB and MAPK signaling pathways on breast cancer, regardless of ER expression. Intake of arctigenin could be an effective supplement for breast cancer patients. Arctigenin is a phenylpropanoid dibenzylbutyrolactone lignan compound possessing antitumor, anti-inflammatory, anti-influenza, antioxidant, antibacterial, and hypoglycaemic activities. Arctigenin exhibited significant antiproliferative activity against CCRF-CEM cells after 72 h treatment with IC50 values of 1.21 ± 0.15 um. It arrested CCRF-CEM cells in the S phase. It induced apoptosis in CCRF-CEM cells in a concentration- and time-dependent manner. Arctigenin is a good candidate for the development of novel agents against T-cell lymphoma. Arctigenin has been found to act as an agonist of adiponectin receptor 1 (AdipoR1). Arctigenin is an antagonist of MR and effectively decreases the Na/K-ATPase 1 gene expression, thus highlighting its potential as an anti-hypertensive drug lead compound.

CNS Activity

Curator's Comment: Arctigenin can cross the blood-brain barrier and in the brain it interacts with kainate sensitive ionotropic glutamate receptors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.21 µM [IC50]
Target ID: CHEMBL1075388
17.34 µM [IC50]
3.9 µM [IC50]
2.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.
1996 Jan 5
Arctigenin inhibits lipopolysaccharide-induced iNOS expression in RAW264.7 cells through suppressing JAK-STAT signal pathway.
2011 Aug
Patents

Sample Use Guides

GBS-01, an extract from the fruit of Arctium lappa L., an orally administered drug rich in Arctigenin, was given orally at escalating doses from 3.0 g (containing 1.0 g burdock fruit extract) to 12.0 g q.d.
Route of Administration: Oral
Arctigenin decreased human rheumatoid arthritis fibroblast-like synoviocytes cell viability by 23, 30, and 38% at the dose of 10, 20, and 30 uM, respectively. The half maximal inhibitory concentration (IC50) of Arctigenin on RAFLSs was about 38 uM. Moreover, 9, 15, and 21% of RAFLSs are induced apoptosis by 10, 20, and 30 uM of Arctigenin.
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:18:27 GMT 2023
Edited
by admin
on Sat Dec 16 06:18:27 GMT 2023
Record UNII
2FD8L150E7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARCTIGENIN, (±)-
Common Name English
2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)DIHYDRO-3-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, TRANS-
Systematic Name English
2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)DIHYDRO-3-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3R,4R)-REL-
Systematic Name English
(±)-ARCTIGENIN
Common Name English
ARCTIGENIN, TRANS-((±)-
Common Name English
Code System Code Type Description
PUBCHEM
64981
Created by admin on Sat Dec 16 06:18:27 GMT 2023 , Edited by admin on Sat Dec 16 06:18:27 GMT 2023
PRIMARY
CAS
144901-91-7
Created by admin on Sat Dec 16 06:18:27 GMT 2023 , Edited by admin on Sat Dec 16 06:18:27 GMT 2023
PRIMARY
FDA UNII
2FD8L150E7
Created by admin on Sat Dec 16 06:18:27 GMT 2023 , Edited by admin on Sat Dec 16 06:18:27 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE