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Irigenin

Catalog Number: EVT-337242

CAS Number: 548-76-5

Molecular Formula: C18H16O8

Molecular Weight: 360.3 g/mol

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Product Introduction

Description

Irigenin is an isoflavonoid compound that has been isolated from the rhizome of Belamcanda chinensis, a plant known for its various pharmacological effects. Research has shown that irigenin exhibits anti-inflammatory, antioxidant, anti-apoptotic, and anticancer properties, making it a compound of interest in the treatment of various diseases, including cancer, neurotoxicity, liver disease, and acute lung injury1 3 5 6 7 8.

Applications in Various Fields

Anti-inflammatory Applications

Irigenin has demonstrated significant anti-inflammatory effects in murine macrophage cells, suggesting its potential as a treatment for inflammatory diseases1.

Cancer Therapy

Irigenin has shown promise as an anticancer agent in various types of cancer, including lung cancer, gastric cancer, liver cancer, and glioblastoma, by affecting cell cycle, apoptosis, and metastasis2 3 6 7.

Neuroprotection

The neuroprotective effects of irigenin against neurotoxicity induced by 1-methyl-4-phenylpyridinium (MPP+) suggest its potential application in neurodegenerative diseases5.

Treatment of Liver Diseases

Irigenin's ability to induce apoptosis and cell cycle arrest in liver cancer cells indicates its potential as a therapeutic agent for liver diseases7.

Acute Lung Injury

The compound's efficacy in reducing inflammation and apoptosis in a model of acute lung injury points to its potential use in respiratory conditions8.

Cardiovascular Protection

Irigenin's protective effects on endothelial cells under oxidative stress conditions suggest its potential in preventing cardiovascular diseases9.

Material Science

The structural and optical properties of irigenin have been studied, indicating potential applications in flexible organic electronics due to its optical band gap10.

Properties

CAS Number

548-76-5

Product Name

Irigenin

IUPAC Name

5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one

Molecular Formula

C18H16O8

Molecular Weight

360.3 g/mol

InChI

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

SMILES

COC1=CC(=CC(=C1OC)O)C2=COC3=CC(=C(C(=C3C2=O)O)OC)O

Synonyms

irigenin

Canonical SMILES

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

Mechanism of Action

Irigenin's anti-inflammatory effects are attributed to its ability to inhibit the production of nitric oxide (NO) and prostaglandin E2 (PGE2) by downregulating the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). This is achieved through the suppression of nuclear factor-kappaB (NF-kappaB) activation in macrophage cells1. In the context of cancer, irigenin has been shown to inhibit metastasis in lung cancer cells by blocking the interaction between Fibronectin Extra Domain A (EDA) and integrins, which is crucial for the epithelial to mesenchymal transition (EMT) of tumor cells2. Additionally, irigenin sensitizes gastric cancer cells to apoptosis induced by tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) by upregulating pro-apoptotic molecules3. In liver cancer cells, irigenin induces mitochondrial apoptosis and cell cycle arrest, leading to the inhibition of cancer progression7. Furthermore, irigenin has been found to protect against neurotoxicity by activating the Keap1/Nrf2 pathway, which is involved in the cellular response to oxidative stress5. In glioblastoma, irigenin's anticancer effects are mediated through the suppression of YAP/β-catenin signaling6. Lastly, irigenin's protective role in acute lung injury is linked to the inactivation of the mitogen-activated protein kinase (MAPK) signaling pathway8.

Method of Synthesis or Extraction

Irigenin can be synthesized or extracted from natural sources. The most commonly used methods for the synthesis of irigenin include chemical synthesis and microbial transformation. Chemical synthesis involves the use of chemical reactions to produce irigenin from simple starting materials. Microbial transformation involves the use of microorganisms to convert precursor compounds into irigenin.
The extraction of irigenin from natural sources involves the use of solvents to isolate the compound from plant material. The efficiency and yield of each method depend on various factors, including the quality of the starting material, the extraction method, and the purification process. Environmental and safety considerations are also important factors to consider when choosing a method for the synthesis or extraction of irigenin.

Chemical Structure and Biological Activity

Irigenin has a unique chemical structure that consists of a flavone backbone with a hydroxyl group at position 5 and a methoxy group at position 7. This structure is responsible for the biological activity of irigenin, which has been shown to have anti-inflammatory, anti-cancer, and anti-oxidant properties.
The mechanism of action of irigenin involves the modulation of various cellular pathways, including the NF-κB pathway, the MAPK pathway, and the PI3K/Akt pathway. Irigenin has been shown to inhibit the activation of these pathways, which can lead to the suppression of inflammation and the induction of apoptosis in cancer cells.

Biological Effects

Irigenin has been shown to have various biological effects on cell function and signal transduction. It has been shown to inhibit the production of pro-inflammatory cytokines, such as TNF-α and IL-6, and to reduce the expression of inflammatory enzymes, such as COX-2 and iNOS.
Irigenin has also been shown to have potential therapeutic and toxic effects. It has been studied for its potential use in the treatment of various diseases, including cancer, inflammation, and neurodegenerative disorders. However, irigenin can also have toxic effects at high doses, including hepatotoxicity and nephrotoxicity.

Future Perspectives and Challenges

The use and study of irigenin face various limitations, including the lack of standardized methods for its synthesis and extraction, the limited understanding of its pharmacokinetics and pharmacodynamics, and the potential toxic effects at high doses. Possible solutions and improvements include the development of standardized methods for the synthesis and extraction of irigenin, the use of advanced analytical techniques to study its pharmacokinetics and pharmacodynamics, and the identification of safer and more effective analogs of irigenin.
Future trends and prospects in the application of irigenin in scientific research include the development of novel therapeutic agents based on its unique chemical structure and biological activity, the identification of new targets for its biological activity, and the integration of irigenin into sustainable and environmentally friendly manufacturing processes.

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