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Article

Cranberry Phytochemicals: Isolation, Structure Elucidation, and Their Antiproliferative and Antioxidant Activities

Xiangjiu He^† and Rui Hai Liu*^†^‡

Department of Food Science, Stocking Hall, and Institute of Comparative and Environmental Toxicology, Cornell University, Ithaca, New York 14853-7201

J. Agric. Food Chem., 2006, 54 (19), pp 7069–7074

DOI: 10.1021/jf061058l

Publication Date (Web): August 29, 2006

†

Department of Food Science.

Corresponding author [telephone (607) 255-6235; fax (607) 254-4868; e-mail RL23@cornell.edu].

‡

Institute of Comparative and Environmental Toxicology.

Abstract

Bioactivity-guided fractionation of cranberries was used to determine the chemical identity of bioactive constituents. Twenty compounds were isolated using gradient solvent fractionation, silica gel and ODS columns, and preparative RP-HPLC. Their chemical structures were identified using HR-MS, 1D and 2D NMR, and X-ray diffraction analysis. Antiproliferative activities of isolated compounds against HepG2 human liver cancer and MCF-7 human breast cancer cells were evaluated. Among the compounds isolated, ursolic acid, quercetin, and 3,5,7,3‘,4‘-pentahydroxyflavonol-3-O-β-d-glucopyranoside showed potent antiproliferative activities against HepG2 cell growth, with EC₅₀ values of 87.4 ± 2.7, 40.9 ± 1.1, and 49.2 ± 4.9 μM, respectively. Ursolic acid, quercetin, and 3,5,7,3‘,4‘-pentahydroxyflavonol-3-O-β-d-glucopyranoside showed potent inhibitory activity toward the proliferation of MCF-7 cells, with EC₅₀ values of 11.7 ± 0.1, 137.5 ± 2.6, and 23.9 ± 3.9 μM, respectively. Quercetin, 3,5,7,3‘,4‘-pentahydroxyflavonol-3-O-β-d-glucopyranoside, 3,5,7,3‘,4‘-pentahydroxyflavonol-3-O-β-d-galactopyranoside, and 3,5,7,3‘,4‘-pentahydroxyflavonol-3-O-α-l-arabinofuranoside showed potent antioxidant activities, with EC₅₀ values of ≈10 μM. These results showed cranberry phytochemical extracts have potent antioxidant and antiproliferative activities.