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Details

Stereochemistry ACHIRAL
Molecular Formula C18H16O8
Molecular Weight 360.3148
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IRIGENIN

SMILES

COC1=CC(=CC(O)=C1OC)C2=COC3=C(C2=O)C(O)=C(OC)C(O)=C3

InChI

InChIKey=TUGWPJJTQNLKCL-UHFFFAOYSA-N
InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3

HIDE SMILES / InChI
Irigenin is an O-methylated isoflavone. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris Kemaonensis; which are used in traditional Chinese and Tibetan medicine. Irigenin has been identified as a potential anti-inflammatory compound; reducing inflammatory Nitric Oxide and Prostaglandin production. Irigenin has also been investigated in cell models for lung cancer.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Alkylated benzoquinones from Iris kumaonensis.
2002 Dec
Analysis of DNA in endometrial cancer cells treated with phyto-estrogenic compounds using comparative genomic hybridisation microarrays.
2005 May
Isolation and purification of isoflavonoids from Rhizoma Belamcandae by two-dimensional preparative high-performance liquid chromatography with column switch technology.
2009 Oct
Patents

Sample Use Guides

In a pharmacokinetic study, rats were orally dosed with 50 mg/kg bw of extract from Rhizoma Belamcandae; which corresponds to 27.0 mg/kg of irigenin. A maximum plasma concentration (405.08 ng/mL) of Irigenin was achieved within half an hour, suggesting rapid absorption through the stomach.
Route of Administration: Oral
RAW 264.7 cells were transfected wit hpNF-kB-SEAP-NPT plasmid to introduce the SEAP reporter gene for NF-kB activity. Irigenin was isolated from extracts of the rhizomes of B. chinensis. Cells were stimulated with 100 ng/mL of lipopolysaccharide (LPS) for 18 hours to induce iNOS. Irigenin was then added to cell cultures in doses of 3, 10, or 30 microM. After 18 hours of Irigenine treatment, cultures were assayed (using the Griess Method) for effects on Nitrous Oxide production, PGE2 production, and iNOS enzyme activity. Irigenin significantly reduced NO production and PGE2 production. Furthermore, Irigenin inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COS-2) and mRNAs without appreciable cytotoxic effects. Irigenin also appears to have lowered the NF-kB activity in the cells, as measured by electrophoretic mobility shift assay. These results suggest that Irrigenin may be interesting as an anti-inflammatory molecule.
Name Type Language
IRIGENIN
MI  
Common Name English
IRIGENIN [MI]
Common Name English
5,7-DIHYDROXY-3-(3-HYDROXY-4,5-DIMETHOXYPHENYL)-6-METHOXY-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
3',5,7-TRIHYDROXY-4',5',6-TRIMETHOXYISOFLAVONE
Common Name English
Code System Code Type Description
MERCK INDEX
m6404
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Irigenin
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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MESH
C509874
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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PUBCHEM
5464170
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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FDA UNII
6O4NX37350
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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ECHA (EC/EINECS)
208-958-3
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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CAS
548-76-5
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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EPA CompTox
DTXSID90203285
Created by admin on Fri Dec 15 19:40:00 GMT 2023 , Edited by admin on Fri Dec 15 19:40:00 GMT 2023
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