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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=C(OC)C(O)=CC(=C1)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
Antimutagenic and anti-oxidant activities of isoflavonoids from Belamcanda chinensis (L.) DC.
2010-02
Isolation and purification of isoflavonoids from Rhizoma Belamcandae by two-dimensional preparative high-performance liquid chromatography with column switch technology.
2009-10
Quality evaluation of Rhizoma Belamcandae (Belamcanda chinensis (L.) DC.) by using high-performance liquid chromatography coupled with diode array detector and mass spectrometry.
2009-03-13
Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines.
2009-01-08
The rapid identification of isoflavonoids from Belamcanda chinensis by LC-NMR and LC-MS.
2008-10
Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E(2) production in murine macrophage RAW 264.7 cells.
2006-04-11
Analysis of DNA in endometrial cancer cells treated with phyto-estrogenic compounds using comparative genomic hybridisation microarrays.
2005-05
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
2005-03
Phytoestrogens derived from Belamcanda chinensis have an antiproliferative effect on prostate cancer cells in vitro.
2004-12
[Study on the fingerprints of Belamcanda chinensis (L.) DC by capillary electrophoresis].
2004-05
Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica.
2003-01
Alkylated benzoquinones from Iris kumaonensis.
2002-12
Isoflavonoids from the rhizomes of Belamcanda chinensis and their effects on aldose reductase and sorbitol accumulation in streptozotocin induced diabetic rat tissues.
2002-06
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
3',5,7-TRIHYDROXY-4',5',6-TRIMETHOXYISOFLAVONE
Preferred 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
Code System Code Type Description
MERCK INDEX
m6404
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
Irigenin
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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MESH
C509874
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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PUBCHEM
5464170
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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FDA UNII
6O4NX37350
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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ECHA (EC/EINECS)
208-958-3
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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CAS
548-76-5
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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EPA CompTox
DTXSID90203285
Created by admin on Mon Mar 31 19:52:47 GMT 2025 , Edited by admin on Mon Mar 31 19:52:47 GMT 2025
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