ArticleChemical research in toxicology2016
Hop (Humulus lupulus L.) Extract and 6-Prenylnaringenin Induce P450 1A1 Catalyzed Estrogen 2-Hydroxylation.
Article in Chemical research in toxicology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 48 citations in OpenAlex.
- 6-Prenylnaringenin-Its Beneficial Biological Effects and Possible Applications.International journal of molecular sciences · 2025Review
- Wild Hops in Breadmaking Among Bulgarians: From History to Modern Perspectives and Future Potentials.Foods (Basel, Switzerland) · 2025Article
- Identifying behavior regulatory leverage over mental disorders transcriptomic network hubs toward lifestyle-dependent psychiatric drugs repurposing.Human genomics · 2025Article
- DESIGNER fraction concept unmasks minor bioactive constituents in red clover (Trifolium pratense L.).Phytochemistry · 2023Article
- Breast cancer prevention with liquiritigenin from licorice through the inhibition of aromatase and protein biosynthesis in high-risk women's breast tissue.Scientific reports · 2023Article
- An Updated Review of the GenusPlants (Basel, Switzerland) · 2022Review
- Dietary Phytoestrogens and Their Metabolites as Epigenetic Modulators with Impact on Human Health.Antioxidants (Basel, Switzerland) · 2021Review
- The Antifungal Mechanism of Isoxanthohumol fromInternational journal of molecular sciences · 2021Article
- Synthetic production of prenylated naringenins in yeast using promiscuous microbial prenyltransferases.Metabolic engineering communications · 2021Article
- Plant Occurring Flavonoids as Modulators of the Aryl Hydrocarbon Receptor.Molecules (Basel, Switzerland) · 2021Review
- 6-Prenylnaringenin from Hops Disrupts ERα-Mediated Downregulation ofChemical research in toxicology · 2020Article
- Flavonoids as Phytoestrogenic Components of Hops and Beer.Molecules (Basel, Switzerland) · 2020Review
- Composition and In Vitro Effects of Cultivars ofNutrients · 2019Article
- The Multiple Biological Targets of Hops and Bioactive Compounds.Chemical research in toxicology · 2019Review
- Chemical Diversity and Biological Activity of African Propolis.Progress in the chemistry of organic natural products · 2019Article
- Evidence for Chemopreventive and Resilience Activity of Licorice:Cancer prevention research (Philadelphia, Pa.) · 2018Article
- Highly Cancer Selective Antiproliferative Activity of Natural Prenylated Flavonoids.Molecules (Basel, Switzerland) · 2018Article
- Article
- Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops.Molecules (Basel, Switzerland) · 2018Review
- Red Clover Aryl Hydrocarbon Receptor (AhR) and Estrogen Receptor (ER) Agonists Enhance Genotoxic Estrogen Metabolism.Chemical research in toxicology · 2017Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
Humulus lupulus L. (hops) is a popular botanical dietary supplement used by women as a sleep aid and for postmenopausal symptom relief. In addition to its efficacy for menopausal symptoms, hops can also modulate the chemical estrogen carcinogenesis pathway and potentially protect women from breast cancer. In the present study, an enriched hop extract and the key bioactive compounds [6-prenylnarigenin (6-PN), 8-prenylnarigenin (8-PN), isoxanthohumol (IX), and xanthohumol (XH)] were tested for their effects on estrogen metabolism in breast cells (MCF-10A and MCF-7). The methoxyestrones (2-/4-MeOE1) were analyzed as biomarkers for the nontoxic P450 1A1 catalyzed 2-hydroxylation and the genotoxic P450 1B1 catalyzed 4-hydroxylation pathways, respectively. The results indicated that the hop extract and 6-PN preferentially induced the 2-hydroxylation pathway in both cell lines. 8-PN only showed slight up-regulation of metabolism in MCF-7 cells, whereas IX and XH did not have significant effects in either cell line. To further explore the influence of hops and its bioactive marker compounds on P450 1A1/1B1, mRNA expression and ethoxyresorufin O-dealkylase (EROD) activity were measured. The results correlated with the metabolism data and showed that hop extract and 6-PN preferentially enhanced P450 1A1 mRNA expression and increased P450 1A1/1B1 activity. The aryl hydrocarbon receptor (AhR) activation by the isolated compounds was tested using xenobiotic response element (XRE) luciferase construct transfected cells. 6-PN was found to be an AhR agonist that significantly induced XRE activation and inhibited 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) induced XRE activity. 6-PN mediated induction of EROD activity was also inhibited by the AhR antagonist CH223191. These data show that the hop extract and 6-PN preferentially enhance the nontoxic estrogen 2-hydroxylation pathway through AhR mediated up-regulation of P450 1A1, which further emphasizes the importance of standardization of botanical extracts to multiple chemical markers for both safety and desired bioactivity.
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