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Clinical Research

Suppression of Estrogen Biosynthesis by Procyanidin Dimers in Red Wine and Grape Seeds

Elizabeth T. Eng, JingJing Ye, Dudley Williams, Sheryl Phung, Roger E. Moore, Mary K. Young, Ugis Gruntmanis, Glenn Braunstein and Shiuan Chen
Elizabeth T. Eng
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JingJing Ye
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Dudley Williams
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Sheryl Phung
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Roger E. Moore
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Mary K. Young
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Ugis Gruntmanis
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Glenn Braunstein
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Shiuan Chen
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DOI:  Published December 2003
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Abstract

In breast cancer, in situ estrogen production has been demonstrated to play a major role in promoting tumor growth. Aromatase is the enzyme responsible for the conversion of androgen substrates into estrogens. This enzyme is highly expressed in breast cancer tissue compared with normal breast tissue. A wine extract fraction was recently isolated from red wine that exhibited a potent inhibitory action on aromatase activity. Using UV absorbance analysis, high-performance liquid chromatography profiling, accurate mass-mass spectrometry, and nanospray tandem mass spectrometry, most of the compounds in our red wine fraction were identified as procyanidin B dimers that were shown to be aromatase inhibitors. These chemicals have been found in high levels in grape seeds. Inhibition kinetic analysis on the most potent procyanidin B dimer has revealed that it competes with the binding of the androgen substrate with a Ki value of 6 μm. Because mutations at Asp-309, Ser-378, and His-480 of aromatase significantly affected the binding of the procyanidin B dimer, these active site residues are thought to be important residues that interact with this phytochemical. The in vivo efficacy of procyanidin B dimers was evaluated in an aromatase-transfected MCF-7 breast cancer xenograft model. The procyanidin B dimers were able to reduce androgen-dependent tumor growth, indicating that these chemicals suppress in situ estrogen formation. These in vitro and in vivo studies demonstrated that procyanidin B dimers in red wine and grape seeds could be used as chemopreventive agents against breast cancer by suppressing in situ estrogen biosynthesis.

Footnotes

  • Grant support: This work was supported by NIH-National Center for Complementary and Alternative Medicine predoctoral fellowship F31 AT00059 (to E. T. E.), NIH Grants ES08258 and CA44735 (to S. C.), and the California Breast Cancer Research Program 4PB-0115 (to S. C.).

  • The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked advertisement in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

  • Present address: Dudley Williams, Allergan Inc., 2525 Dupont Drive, Mail Stop: TL-2B, Irvine, California 92612.

  • Requests for reprints: Shiuan Chen, Department of Surgical Science, Beckman Research Institute of the City of Hope, 1450 East Duarte Road, Duarte, California 91010. Phone: (626) 359-8111, ext. 63454; Fax: (626) 301-8972; E-mail: schen{at}coh.org

  • Received July 16, 2003.
  • Revision received September 8, 2003.
  • Accepted September 22, 2003.
  • ©2003 American Association for Cancer Research.
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Cancer Research: 63 (23)
December 2003
Volume 63, Issue 23
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Suppression of Estrogen Biosynthesis by Procyanidin Dimers in Red Wine and Grape Seeds
Elizabeth T. Eng, JingJing Ye, Dudley Williams, Sheryl Phung, Roger E. Moore, Mary K. Young, Ugis Gruntmanis, Glenn Braunstein and Shiuan Chen
Cancer Res December 1 2003 (63) (23) 8516-8522;

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Suppression of Estrogen Biosynthesis by Procyanidin Dimers in Red Wine and Grape Seeds
Elizabeth T. Eng, JingJing Ye, Dudley Williams, Sheryl Phung, Roger E. Moore, Mary K. Young, Ugis Gruntmanis, Glenn Braunstein and Shiuan Chen
Cancer Res December 1 2003 (63) (23) 8516-8522;
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