ArticleMolecules (Basel, Switzerland)2020
The Grapefruit Effect: Interaction between Cytochrome P450 and Coumarin Food Components, Bergamottin, Fraxidin and Osthole. X-ray Crystal Structure and DFT Studies.
Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 18 citations in OpenAlex.
- Rapid Structural Analysis of Natural Products Using MicroED.Small (Weinheim an der Bergstrasse, Germany) · 2026Article
- Molecular dynamics simulations elucidate the role of the F-F' loop in substrate entry into CYP3A4.Communications chemistry · 2026Article
- Efficacy, side effects, adherence, affordability, and procurement of dietary supplements for treating hypercholesterolemia: a narrative review.Journal of health, population, and nutrition · 2024Review
- Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pharmaceuticals (Basel, Switzerland) · 2023Article
- Aromatic Polyphenol π-π Interactions with Superoxide Radicals Contribute to Radical Scavenging and Can Make Polyphenols Mimic Superoxide Dismutase Activity.Current issues in molecular biology · 2022Review
- Retrieval of High Added Value Natural Bioactive Coumarins from Mandarin Juice-Making Industrial Byproduct.Molecules (Basel, Switzerland) · 2021Article
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8 authors at 1 institution in 1 country.
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Abstract
Coumarins are plant-derived secondary metabolites. The crystal structure of three coumarins-bergamottin, osthole and fraxidin-are described and we analyze intermolecular interactions and their role in crystal formation. Bergamottin is a furanocoumarin found in citrus plants, which is a strong inhibitor of the principal human metabolizing enzyme, cytochrome P450 3A4 (CYP3A4). The crystal structure determinations of three coumarins give us the geometrical parameters and reveal the parallel-displaced π-π stacking and hydrogen bonding intermolecular interactions used for molecular assembly in the crystal structure. A quite strong (less than 3.4 Å) stacking interaction of bergamottin appears to be a determining feature that distinguishes it from other coumarins studied in this work. Our DFT computational studies on the three natural products of the same coumarin family docked into the active site of CYP3A4 (PDB 4D78) show different behavior for these coumarins at the active site. When the substrate is bergamottin, the importance of π-π stacking and hydrogen bonding, which can anchor the substrate in place, appears fundamental. In contrast, fraxidin and osthole show carbonyl coordination to iron. Our docking calculations show that the bergamottin tendency towards π-π stacking is important and likely influences its interactions with the heme group of CYP3A4.
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