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Structure Database (LMSD)

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Common Name

Irigenin

Systematic Name

5,7,3'-Trimethoxy-6,4',5'-trimethoxyisoflavone

Synonyms

LM ID

LMPK12050417

Formula

C₁₈H₁₆O₈

Exact Mass

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360.08452

Status

Curated

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Classification

Biological Context

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), 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 .⁴

This information has been provided by Cayman Chemical

References

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

2. Ahn, K.S., Noh, E.J., Cha, K.-H., et al. Inhibitory 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).

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

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