Journal Article

Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit <i>anti</i>-benzo[<i>a</i>]pyrene-7,8-diol-9,10-epoxide induced NFκB and AP-1 activity

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

in Carcinogenesis

Volume 27, issue 8, pages 1617-1626
ISSN: 0143-3334
Published online March 2006 | e-ISSN: 1460-2180 | DOI:
Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NFκB and AP-1 activity

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  • Clinical Cytogenetics and Molecular Genetics


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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 (NFκB)- 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 NFκB activity. Major constituents of the most active subfractions were identified by their spectral properties and in comparison with 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 ∼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 NFκB 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.

Journal Article.  5135 words.  Illustrated.

Subjects: Clinical Cytogenetics and Molecular Genetics

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