ArticleChemical research in toxicology2019
Isoflavones as Ah Receptor Agonists in Colon-Derived Cell Lines: Structure-Activity Relationships.
Article in Chemical research in toxicology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 29 citations in OpenAlex.
- Anticancer Potential of Isoflavones: A Narrative Overview of Mechanistic Insights and Experimental Evidence from the Past Ten Years.Biomedicines · 2025Review
- Minimalistic Peptide Nanocarriers for Multiple Cancer Drugs.ACS applied bio materials · 2025Article
- Chrysin: A Comprehensive Review of Its Pharmacological Properties and Therapeutic Potential.Pharmaceuticals (Basel, Switzerland) · 2025Review
- The protective role of anti-parkinsonian drugs in pancreatic cancer risk: A comprehensive case-control study in Taiwan.Cancer science · 2025Article
- Article
- Unlocking the Potential: How Flavonoids Affect Angiogenesis, Oxidative Stress, Inflammation, Proliferation, Invasion, and Alter Receptor Interactions in Endometriosis.Food science & nutrition · 2025Review
- Harnessing the Anti-Inflammatory Properties of Polyphenols in the Treatment of Inflammatory Bowel Disease.International journal of biological sciences · 2024Review
- Structure-activity relationships among mono- and dihydroxy flavones as aryl hydrocarbon receptor (AhR) agonists or antagonists in CACO2 cells.Chemico-biological interactions · 2022Review
- Substrate-Driven Differences in Tryptophan Catabolism by Gut Microbiota and Aryl Hydrocarbon Receptor Activation.Molecular nutrition & food research · 2021Article
- Plant Occurring Flavonoids as Modulators of the Aryl Hydrocarbon Receptor.Molecules (Basel, Switzerland) · 2021Review
- Flavonoids: structure-function and mechanisms of action and opportunities for drug development.Toxicological research · 2021Review
- Hydroxylated Chalcones as Aryl Hydrocarbon Receptor Agonists: Structure-Activity Effects.Toxicological sciences : an official journal of the Society of Toxicology · 2021Article
- The Potential Role of Phytonutrients Flavonoids Influencing Gut Microbiota in the Prophylaxis and Treatment of Inflammatory Bowel Disease.Frontiers in nutrition · 2021Review
- How Ah Receptor Ligand Specificity Became Important in Understanding Its Physiological Function.International journal of molecular sciences · 2020Review
- Dopamine is an aryl hydrocarbon receptor agonist.The Biochemical journal · 2020Article
- Molecular Mechanism for Attractant Signaling to DHMA by E. coli Tsr.Biophysical journal · 2020Article
- Divergent Effects of Daidzein and its Metabolites on Estrogen-Induced Survival of Breast Cancer Cells.Cancers · 2020Article
- Soy Isoflavones Accelerate Glial Cell MigrationFrontiers in endocrinology · 2020Article
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
Abstract
Many of the protective responses observed for flavonoids in the gastrointestinal track resemble aryl hydrocarbon receptor (AhR)-mediated effects. Therefore, we examined the structure-activity relationships of isoflavones and isomeric flavone and flavanones as AhR ligands on the basis of their induction of CYP1A1, CYP1B1, and UGT1A1 gene expression in colon cancer Caco2 cells and young adult mouse colonocyte (YAMC) cells. Caco2 cells were significantly more Ah-responsive than YAMC cells, and this was due, in part, to flavonoid-induced cytotoxicity in the latter cell lines. The structure-activity relationships for the flavonoids were complex and both response and cell context specific; however, there was significant variability in the AhR activities of the isomeric substituted isoflavones and flavones. For example, 4',5,7-trihydroxyisoflavone (genistein) was AhR-inactive whereas 4',5,7-trihydroxyflavone (apigenin) induced CYP1A1, CYP1B1, and UGT1A1 in Caco2 cells. In contrast, both 5,7-dihydroxy-4-methoxy substituted isoflavone (biochanin A) and flavone (acacetin) induced all three AhR-responsive genes; 4',5,7-trimethoxyisoflavone was a potent AhR agonist, and the isomeric flavone was AhR-inactive. These results coupled with simulation studies modeling flavonoid interaction within the AhR binding pocket demonstrate that the orientation of the substituted phenyl ring at C-2 (flavones) or C-3 (isoflavones) on the common 4-
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