The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
Open accessAbstract
Chemoprotective phytochemicals exhibit multiple activities and interact with several cellular receptors, including the aryl hydrocarbon (Ah) receptor (AhR). In this study we investigated the AhR agonist/antagonist activities of the following flavonoids: chrysin, phloretin, kaempferol, galangin, naringenin, genistein, quercetin, myricetin, luteolin, baicalein, daidzein, apigenin, and diosmin. We also investigated the AhR-dependent activities of cantharidin and emodin (in herbal extracts) in Ah-responsive MCF-7 human breast cells, HepG2 human liver cancer cells, and mouse Hepa-1 cells transiently or stably transfected with plasmids expressing a luciferase reporter gene linked to multiple copies of a consensus dioxin-responsive element. The AhR agonist activities of the compounds (1 and 10 micro M) were as high as 25% of the maximal response induced by 5 nM 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), and their potencies were dependent on cell context. Galangin, genistein, daidzein, and diosmin were active only in Hepa-1 cells, and cantharidin induced activity only in human HepG2 and MCF-7 cells. Western blot analysis confirmed that baicalein and emodin also induced CYP1A1 protein in the human cancer cell lines. The AhR antagonist activities of four compounds inactive as agonists in MCF-7 and HepG2 cells (kaempferol, quercetin, myricetin, and luteolin) were also investigated. Luteolin was an AhR antagonist in both cell lines, and the inhibitory effects of the other compound were dependent on cell context. These data suggest that dietary phytochemicals exhibit substantial cell context-dependent AhR agonist as well as antagonist activities. Moreover, because phytochemicals and other AhR-active compounds in food are present in the diet at relatively high concentrations, risk assessment of dietary toxic equivalents of TCDD and related compounds should also take into account AhR agonist/antagonist activities of phytochemicals.
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Cites
Dioxin binding activities of polymorphic forms of mouse and human arylhydrocarbon receptors.
Ema, M., Ohe, N., Suzuki, M., Mimura, J., Sogawa, K., Ikawa, S., & Fujii-Kuriyama, Y. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)46990-6 · Cited by 329
Cited by
Van den Berg, M., Birnbaum, L. S., Denison, M., De Vito, M., Farland, W., Feeley, M., Fiedler, H., Hakansson, H., Hanberg, A., Haws, L., et al. (2006) · Toxicological Sciences · doi:10.1093/toxsci/kfl055 · Cited by 3,785
Self-citationDietary polyphenols, oxidative stress and antioxidant and anti-inflammatory effects
Zhang, H., & Tsao, R. (2016) · Current Opinion in Food Science · doi:10.1016/j.cofs.2016.02.002 · Cited by 1,519
The Search for Endogenous Activators of the Aryl Hydrocarbon Receptor
Nguyen, L. P., & Bradfield, C. A. (2008) · Chemical Research in Toxicology · doi:10.1021/tx7001965 · Cited by 709
Shanle, E. K., & Xu, W. (2011) · Chemical Research in Toxicology · doi:10.1021/tx100231n · Cited by 522
Fritsche, E., Schäfer, C., Calles, C., Bernsmann, T., Bernshausen, T., Wurm, M., Hübenthal, U., Cline, J. E., Hajimiragha, H., Schroeder, P., et al. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0701764104 · Cited by 437
Metadata
- Authors
- Zhang, S., Qin, C., & Safe, S. H.
- Venue
- Environmental Health Perspectives
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-12
- Volume
- 111
- Issue
- 16
- Pages
- 1877-1882
- ISSN
- 0091-6765 (ISSN-L)
- 1552-9924
- OpenAlex
- W2029588268
- Cited by
- 340
- References
- 1
- FWCI
- 7.78
- Type
- journal article
- Language
- en
- Open access
- gold
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- Zhang, S., Qin, C., & Safe, S. H. (2003). Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. Environmental Health Perspectives. https://doi.org/10.1289/ehp.6322
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