Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NFkappaB and AP-1 activity. Carcinogenesis 2006 Aug;27(8):1617-26
Date
03/09/2006Pubmed ID
16522666Pubmed Central ID
PMC3017344DOI
10.1093/carcin/bgi366Scopus ID
2-s2.0-33747874879 (requires institutional sign-in at Scopus site) 78 CitationsAbstract
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 (NFkappaB)- 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 NFkappaB 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-(2(G)-xylosylrutinoside) and cyanidin 3-O-rutinoside. Analysis of freeze-dried black raspberries indicated that these three components comprised approximately 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 NFkappaB 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.
Author List
Hecht SS, Huang C, Stoner GD, Li J, Kenney PM, Sturla SJ, Carmella SGMESH terms used to index this publication - Major topics in bold
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxideAnimals
Anthocyanins
Carcinogens
Cells, Cultured
Chromatography, High Pressure Liquid
Epidermis
Freeze Drying
Fruit
Glucosides
Mice
NF-kappa B
Plant Extracts
Rosaceae
Transcription Factor AP-1
