ArticleChirality2011
Enantiomers of naringenin as pleiotropic, stereoselective inhibitors of cytochrome P450 isoforms.
Article in Chirality, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
23 citing papers in PubMed, 76 citations in OpenAlex.
- Repeated Intake of Grapefruit Juice Inhibits CYP2B6, CYP2C9, CYP2C19, and CYP3A4 while Lingonberry Powder Does Not Induce Major CYP Enzymes in Humans.Clinical pharmacology and therapeutics · 2026Article
- Article
- Synthetic and semi-synthetic antioxidants in medicine and food industry: a review.Frontiers in pharmacology · 2025Review
- Flavouring Group Evaluation 413 (FGE.413): Naringenin.EFSA journal. European Food Safety Authority · 2024Article
- Flavonoids as CYP3A4 Inhibitors In Vitro.Biomedicines · 2024Review
- Health consequences of exposure to aircraft contaminated air and fume events: a narrative review and medical protocol for the investigation of exposed aircrew and passengers.Environmental health : a global access science source · 2023Article
- Possible Side Effects of Polyphenols and Their Interactions with Medicines.Molecules (Basel, Switzerland) · 2023Review
- Article
- First purified recombinant CYP75B including transmembrane helix with unexpected high substrate specificity to (2R)-naringenin.Scientific reports · 2022Article
- Comprehensive Investigation of Stereoselective Food Drug Interaction Potential of Resveratrol on Nine P450 and Six UGT Isoforms in Human Liver Microsomes.Pharmaceutics · 2021Article
- Binding mechanism of naringenin with monoamine oxidase - B enzyme: QM/MM and molecular dynamics perspective.Heliyon · 2021Article
- Potential Herb-Drug Interactions in the Management of Age-Related Cognitive Dysfunction.Pharmaceutics · 2021Review
- Cell-free biosensors for rapid detection of water contaminants.Nature biotechnology · 2020Article
- Perspective: The Potential Effects of Naringenin in COVID-19.Frontiers in immunology · 2020Article
- Scientific Opinion of Flavouring Group Evaluation 410 (FGE.410): 4',5,7-trihydroxyflavanone from chemical group 25 (phenol derivatives containing ring-alkyl, ring-alkoxy, and side-chains with an oxygenated functional group).EFSA journal. European Food Safety Authority · 2017Article
- Does consumption of red grapefruit juice alter naringenin concentrations in milk produced by breastfeeding mothers?PloS one · 2017Article
- Synthesis of Triphenylethylene Bisphenols as Aromatase Inhibitors That Also Modulate Estrogen Receptors.Journal of medicinal chemistry · 2016Article
- Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities.Journal of medicinal chemistry · 2015Article
- Effect of simvastatin and naringenin coadministration on rat liver DNA fragmentation and cytochrome P450 activity: an in vivo and in vitro study.Journal of physiology and biochemistry · 2014Article
- Inhibition of cytochrome p450 enzymes by the e- and z-isomers of norendoxifen.Drug metabolism and disposition: the biological fate of chemicals · 2013Article
Corrections and comments
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
Abstract
Interactions between naringenin and the cytochrome P450 (CYP) system have been of interest since the first demonstration that grapefruit juice reduced CYP3A activity. The effects of naringenin on other CYP isoforms have been less investigated. In addition, it is well known that interactions with enzymes are often stereospecific, but due to the lack of readily available pure naringenin enantiomers, the enantioselectivity of its effects has not been characterized. We isolated pure naringenin enantiomers by chiral high-performance liquid chromatography and tested the ability of (R)-,(S)- and rac-naringenin to inhibit several important drug-metabolizing CYP isoforms using recombinant enzymes and pooled human liver microsomes. Naringenin was able to inhibit CYP19, CYP2C9, and CYP2C19 with IC50 values below 5 μM. No appreciable inhibition of CYP2B6 or CYP2D6 was observed at concentrations up to 10 μM. Whereas (S)-naringenin was 2-fold more potent as an inhibitor of CYP19 and CYP2C19 than (R)-naringenin, (R)-naringenin was 2-fold more potent for CYP2C9 and CYP3A. Chiral flavanones like naringenin are difficult to separate into their enantiomeric forms, but enantioselective effects may be observed that ultimately impact clinical effects. Inhibition of specific drug metabolizing enzymes by naringenin observed in vitro may be exploited to understand pharmacokinetic changes seen in vivo.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.