An isoflavonoid with diverse biological activities
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Irigenin

Item No. 34676

Technical Information
Formal Name
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
CAS Number
548-76-5
Molecular Formula
C18H16O8
Formula Weight
Purity
≥98%
Formulation
A solid
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:4): 0.20 mg/mlDMSO: 10 mg/ml
λmax
268 nm
SMILES
O=C1C(C2=CC(OC)=C(OC)C(O)=C2)=COC3=CC(O)=C(C(O)=C13)OC
InChi Code
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
InChi Key
TUGWPJJTQNLKCL-UHFFFAOYSA-N
Origin
Plant/Belamcanda chinensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Irigenin is a polyketide synthase-derived isoflavonoid that has been found in B. chinensis rhizomes and has diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoform CYP1A (IC50 = 1.2 µM) and induces a 2-fold increase in NADPH quinone reductase activity in Hepa-1c1c7 cells when used at a concentration of 7.8 µM.2 Irigenin inhibits LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2; Item No. 14010), as well as increases in the levels of inducible nitric oxide synthase (iNOS) and COX-2, in RAW 264.7 cells.3 In vivo, irigenin (10 and 20 mg/kg) increases survival and reduces cardiac apoptosis, fibrosis, and levels of TNF-α, IL-6, IL-18, and IL-1β in a mouse model of cardiotoxicity induced by doxorubicin (Item No. 15007).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Raju, K.S.R., Kadian, N., Taneja, I., et alPhytochemical analysis of isoflavonoids using liquid chromatography coupled with tandem mass spectrometry. Phytochem. Rev. 14(3), 469–498 (2015).

    2. Wollenweber, E., Stevens, J.F., Klimo, K., et alCancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica. Planta Med. 69(1), 15-20 (2003).

    3. Ahn, K.S., Noh, E.J., Cha, K.-H., et alInhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E2 production in murine macrophage RAW 264.7 cells. Life Sci. 78(20), 2336-2342 (2006).

    4. Guo, L., Zheng, X., Wang, E., et alIrigenin treatment alleviates doxorubicin (DOX)-induced cardiotoxicity by suppressing apoptosis, inflammation and oxidative stress via the increase of miR-425. Biomed. Pharmacother. 125, 109784 (2020).