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Research article

Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially

Henry P. CIOLINO, Phillip J. DASCHNER, Grace Chao YEH
Biochemical Journal Jun 15, 1999, 340 (3) 715-722; DOI: 10.1042/bj3400715
Henry P. CIOLINO
Cellular Defense and Carcinogenesis Section, Basic Research Laboratory, Division of Basic Sciences, National Cancer Institute-Frederick Cancer Research and Development Center, National Institutes of Health, Building 560, Room 12-05, P. O. Box B, Frederick, MD, USA 21702-1201, U.S.A.
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Phillip J. DASCHNER
Intramural Research Support Program, SAIC, National Cancer Institute-Frederick Cancer Research and Development Center, National Institutes of Health, Building 560, Room 12-05, P. O. Box B, Frederick, MD, USA 21702-1201, U.S.A.
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Grace Chao YEH
Cellular Defense and Carcinogenesis Section, Basic Research Laboratory, Division of Basic Sciences, National Cancer Institute-Frederick Cancer Research and Development Center, National Institutes of Health, Building 560, Room 12-05, P. O. Box B, Frederick, MD, USA 21702-1201, U.S.A.
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Abstract

Transcriptional activation of the human CYP1A1 gene (coding for cytochrome P450 1A1) is mediated by the aryl hydrocarbon receptor (AhR). In the present study we have examined the effect of the common dietary polyphenolic compounds quercetin and kaempferol on the transcription of CYP1A1 and the function of the AhR in MCF-7 human breast cancer cells. Quercetin caused a time- and concentration-dependent increase in the amount of CYP1A1 mRNA and CYP1A1 enzyme activity in MCF-7 cells. The increase in CYP1A1 mRNA caused by quercetin was prevented by the transcription inhibitor actinomycin D. Quercetin also caused an increase in the transcription of a chloramphenicol reporter vector containing the CYP1A1 promoter. Quercetin failed to induce CYP1A1 enzyme activity in AhR-deficient MCF-7 cells. Gel retardation studies demonstrated that quercetin activated the ability of the AhR to bind to an oligonucleotide containing the xenobiotic-responsive element (XRE) of the CYP1A1 promoter. These results indicate that quercetin's effect is mediated by the AhR. Kaempferol did not affect CYP1A1 expression by itself but it inhibited the transcription of CYP1A1 induced by the prototypical AhR ligand 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), as measured by a decrease in TCDD-induced CYP1A1 promoter-driven reporter vector activity, and CYP1A1 mRNA in cells. Kaempferol also abolished TCDD-induced XRE binding in a gel-shift assay. Both compounds were able to compete with TCDD for binding to a cytosolic extract of MCF-7 cells. Known ligands of the AhR are, for the most part, man-made compounds such as halogenated and polycyclic aromatic hydrocarbons. These results demonstrate that the dietary flavonols quercetin and kaempferol are natural, dietary ligands of the AhR that exert different effects on CYP1A1 transcription.

  • chemoprevention
  • flavonoid, MCF-7 cells
  • 2,3,7,8-tetrachlorodibenzo-p-dioxin
  • xenobiotic-responsive element
  • The Biochemical Society, London © 1999
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June 1999

Volume: 340 Issue: 3

Biochemical Journal: 340 (3)
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Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially
Henry P. CIOLINO, Phillip J. DASCHNER, Grace Chao YEH
Biochemical Journal Jun 1999, 340 (3) 715-722; DOI: 10.1042/bj3400715
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Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially
Henry P. CIOLINO, Phillip J. DASCHNER, Grace Chao YEH
Biochemical Journal Jun 1999, 340 (3) 715-722; DOI: 10.1042/bj3400715

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Keywords

chemoprevention
flavonoid, MCF-7 cells
2,3,7,8-tetrachlorodibenzo-p-dioxin
xenobiotic-responsive element

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