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Carcinogenesis Advance Access published online on March 7, 2006
Carcinogenesis, doi:10.1093/carcin/bgi366
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© The Author 2006. Published by Oxford University Press. All rights reserved. For permissions, please email: journals.permissions@oxfordjournals.org
Received July 27, 2005
Revised January 12, 2006
Accepted February 6, 2006

MOLECULAR EPIDEMIOLOGY AND CANCER PREVENTION

Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NF{kappa}B and AP-1 activity

Stephen S. Hecht 1 *, Chuanshu Huang 2, Gary D. Stoner 3, Jingxia Li 2, Patrick M. J. Kenney 4, Shana J. Sturla 1, and Steven G. Carmella 1

1 The Cancer Center, University of Minnesota, Minneapolis, MN 55455
2 Nelson Institute of Environmental Medicine, New York University School of Medicine, Tuxedo, NY 10987
3 Department of Internal Medicine and Comprehensive Cancer Center, The Ohio State University, Columbus, OH 43210
4 Pace Analytical Services, Inc., St. Paul, MN 55144

* To whom correspondence should be addressed.
Stephen S. Hecht, E-mail: hecht002{at}umn.edu


  Abstract

Dietary freeze-dried black raspberries inhibit tumor induction by N-nitrosomethylbenzylamine in the rat esophagus, but the constituents responsible for this chemopreventive activity have not been identified. We fractionated freeze-dried black raspberries and used mouse epidermal JB6 Cl 41 cells stably transfected with either a nuclear factor kappa B (NF{kappa}B)- or an activator protein 1 (AP-1)-luciferase reporter, and treated with racemic anti-benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), to assess the inhibitory effects of the fractions. The ethanol and water extracts of the freeze-dried black raspberries had inhibitory activity and these extracts were fractionated by HPLC to give several bioactive fractions. Further HPLC analysis yielded multiple subfractions, some of which inhibited BPDE-induced NF{kappa}B activity. Major constituents of the most active subfractions were identified by their spectral properties and by comparison to standards as cyanidin 3-O-glucoside, cyanidin 3-O-(2G-xylosylrutinoside), and cyanidin 3-O-rutinoside. Analysis of freeze-dried black raspberries indicated that these three components comprised about 3.4% of the material by dry weight. Consistent with these results, standard cyanidin-3-O-glucoside and cyanidin chloride were also good inhibitors of BPDE-induced NF{kappa}B activity. The results of this study demonstrate that cyanidin glycosides of freeze-dried black raspberries are bioactive compounds which could account for at least some of the chemopreventive activity observed in animal models.


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