ArticleToxicological sciences : an official journal of the Society of Toxicology2018
Structure-Dependent Modulation of Aryl Hydrocarbon Receptor-Mediated Activities by Flavonoids.
Article in Toxicological sciences : an official journal of the Society of Toxicology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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Who cites it
56 citing papers in PubMed, 101 citations in OpenAlex.
- Aryl hydrocarbon receptor pharmacology-mechanisms, ligands, and therapeutic potential.Pharmacological reviews · 2026Review
- Propolis as a potential modulator of aryl hydrocarbon receptor signaling in inflammation.European cytokine network · 2026Review
- Modified Jiaoqi powder ameliorates ulcerative colitis through gut microbiota-tryptophan metabolism-AhR signaling modulating-ILC2/ILC3 balance.Frontiers in microbiology · 2026Article
- Impact of Hericium erinaceus and Ganoderma lucidum metabolites on AhR activation in neuronal HT-22 cells.Pharmacological reports : PR · 2025Article
- Minimalistic Peptide Nanocarriers for Multiple Cancer Drugs.ACS applied bio materials · 2025Article
- The aryl hydrocarbon receptor: a new frontier in male reproductive system.Reproductive biology and endocrinology : RB&E · 2025Review
- Hepatoprotective Effect of Kaempferol-A Review.Molecules (Basel, Switzerland) · 2025Review
- Nootkatone (NK), a grapefruit-derived sesquiterpenoid, suppresses UVB-induced damage by regulating NRF2-HO-1 and AhR-CYP1A1 signaling pathways in HaCaT cells.Food science and biotechnology · 2025Article
- Article
- Therapeutic Expedition of Luteolin against Brain-related Disorders: An Updated Review.Combinatorial chemistry & high throughput screening · 2025Review
- Therapeutic Potential of Nutritional Aryl Hydrocarbon Receptor Ligands in Gut-Related Inflammation and Diseases.Biomedicines · 2024Review
- Quercetin and Thyroid.Antioxidants (Basel, Switzerland) · 2024Article
- Differential Interactions of Flavonoids with the Aryl Hydrocarbon Receptor In Silico and Their Impact on Receptor Activity In Vitro.Pharmaceuticals (Basel, Switzerland) · 2024Article
- Aryl hydrocarbon receptor: current perspectives on key signaling partners and immunoregulatory role in inflammatory diseases.Frontiers in immunology · 2024Review
- The Antioxidative Effects of Flavones in Hypertensive Disease.Biomedicines · 2023Review
- Regulatory Mechanism of the IL-33-IL-37 Axis via Aryl Hydrocarbon Receptor in Atopic Dermatitis and Psoriasis.International journal of molecular sciences · 2023Review
- Inhibition of Cancer Development by Natural Plant Polyphenols: Molecular Mechanisms.International journal of molecular sciences · 2023Review
- Molecular Docking of Natural Compounds for Potential Inhibition of AhR.Foods (Basel, Switzerland) · 2023Article
- Flavone and Hydroxyflavones Are Ligands That Bind the Orphan Nuclear Receptor 4A1 (NR4A1).International journal of molecular sciences · 2023Article
- Apigenin improves cytotoxicity of antiretroviral drugs against HTLV-1 infected cells through the modulation of AhR signaling.NeuroImmune pharmacology and therapeutics · 2023Article
Corrections and comments
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Authors and funding
13 authors at 1 institution in 1 country.
Funding
Abstract
Dietary flavonoids are used in treatment of multiple diseases, and their antiinflammatory effects in the intestine are due, in part, to interactions with gut microflora and possibly due to modulation of aryl hydrocarbon receptor (AhR) signaling. In this study, we investigated the structure-dependent AhR activity of 14 flavonoids in Caco2 colon cancer cells using induction of CYP1A1 and UGT1A1 gene expression as endpoints. A major structural determinant for AhR activation was the number of hydroxyl groups where pentahydroxyflavonoids (with the exception of morin) > hexahydroxyflavonoids > tetra-/trihydroxyflavonoids, and some of the latter compounds such as apigenin exhibited AhR antagonist activity for induction of CYP1A1. Simulations suggest that while quercetin and apigenin interact primarily with the same residues, the strength of interactions between specific AhR residues with CYP1A1 agonist, quercetin, in comparison with CYP1A1 antagonist, apigenin, is different; thus, such interactions are presumably indicative of potential switches for modulating CYP1A1 activity. The structure-dependent effects of the hydroxyl flavonoids on induction of UGT1A1 were similar to that observed for induction of CYP1A1 except that luteolin and apigenin induced UGT1A1 levels similar to that observed for TCDD, whereas both compounds were AhR antagonists for CYP1A1. Thus, the effects of the flavonoids in Caco2 cells on Ah-responsiveness and interactions with butyrate were both ligand structure- and response-dependent and these activities are consistent with hydroxyflavonoids being selective AhR modulators.
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