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Experimental Therapeutics, Molecular Targets, and Chemical Biology

Milk Thistle and Prostate Cancer: Differential Effects of Pure Flavonolignans from Silybum marianum on Antiproliferative End Points in Human Prostate Carcinoma Cells

Paula R. Davis-Searles, Yuka Nakanishi, Nam-Cheol Kim, Tyler N. Graf, Nicholas H. Oberlies, Mansukh C. Wani, Monroe E. Wall, Rajesh Agarwal and David J. Kroll
Paula R. Davis-Searles
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Yuka Nakanishi
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Nam-Cheol Kim
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Tyler N. Graf
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Nicholas H. Oberlies
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Mansukh C. Wani
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Monroe E. Wall
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Rajesh Agarwal
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DOI: 10.1158/0008-5472.CAN-04-4662 Published May 2005
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Abstract

Extracts from the seeds of milk thistle, Silybum marianum, are known commonly as silibinin and silymarin and possess anticancer actions on human prostate carcinoma in vitro and in vivo. Seven distinct flavonolignan compounds and a flavonoid have been isolated from commercial silymarin extracts. Most notably, two pairs of diastereomers, silybin A and silybin B and isosilybin A and isosilybin B, are among these compounds. In contrast, silibinin is composed only of a 1:1 mixture of silybin A and silybin B. With these isomers now isolated in quantities sufficient for biological studies, each pure compound was assessed for antiproliferative activities against LNCaP, DU145, and PC3 human prostate carcinoma cell lines. Isosilybin B was the most consistently potent suppressor of cell growth relative to either the other pure constituents or the commercial extracts. Isosilybin A and isosilybin B were also the most effective suppressors of prostate-specific antigen secretion by androgen-dependent LNCaP cells. Silymarin and silibinin were shown for the first time to suppress the activity of the DNA topoisomerase IIα gene promoter in DU145 cells and, among the pure compounds, isosilybin B was again the most effective. These findings are significant in that isosilybin B composes no more than 5% of silymarin and is absent from silibinin. Whereas several other more abundant flavonolignans do ultimately influence the same end points at higher exposure concentrations, these findings are suggestive that extracts enriched for isosilybin B, or isosilybin B alone, might possess improved potency in prostate cancer prevention and treatment.

  • Silymarin
  • Silibinin
  • Prostate Cancer
  • Topoisomerases
  • Chemoprevention

Footnotes

  • Note: Supplementary data for this article are available at Cancer Research Online (http://cancerres.aacrjournals.org/).

  • N-C. Kim is currently at the Experimental Toxicology Program, Lovelace Respiratory Research Institute, 2425 Ridgecrest Drive Southeast, Albuquerque, NM 87108.

    M.E. Wall died on July 6, 2002.

  • Received December 31, 2004.
  • Revision received February 24, 2005.
  • Accepted March 8, 2005.
  • ©2005 American Association for Cancer Research.
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Cancer Research: 65 (10)
May 2005
Volume 65, Issue 10
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Milk Thistle and Prostate Cancer: Differential Effects of Pure Flavonolignans from Silybum marianum on Antiproliferative End Points in Human Prostate Carcinoma Cells
Paula R. Davis-Searles, Yuka Nakanishi, Nam-Cheol Kim, Tyler N. Graf, Nicholas H. Oberlies, Mansukh C. Wani, Monroe E. Wall, Rajesh Agarwal and David J. Kroll
Cancer Res May 15 2005 (65) (10) 4448-4457; DOI: 10.1158/0008-5472.CAN-04-4662

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Milk Thistle and Prostate Cancer: Differential Effects of Pure Flavonolignans from Silybum marianum on Antiproliferative End Points in Human Prostate Carcinoma Cells
Paula R. Davis-Searles, Yuka Nakanishi, Nam-Cheol Kim, Tyler N. Graf, Nicholas H. Oberlies, Mansukh C. Wani, Monroe E. Wall, Rajesh Agarwal and David J. Kroll
Cancer Res May 15 2005 (65) (10) 4448-4457; DOI: 10.1158/0008-5472.CAN-04-4662
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