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Selective Synthesis and Biological Evaluation of Sulfate-Conjugated Resveratrol Metabolites

2010; American Chemical Society; Volume: 53; Issue: 13 Linguagem: Inglês

10.1021/jm100274c

1520-4804

Juma Hoshino, Eun‐Jung Park, Tamara P. Kondratyuk, Laura E. Marler, John M. Pezzuto, Richard B. van Breemen, Shunyan Mo, Yongchao Li, Mark Cushman,

Genomics, phytochemicals, and oxidative stress

Five resveratrol sulfate metabolites were synthesized and assessed for activities known to be mediated by resveratrol: inhibition of tumor necrosis factor (TNF) α induced NFκB activity, cylcooxygenases (COX-1 and COX-2), aromatase, nitric oxide production in endotoxin-stimulated macrophages, proliferation of KB or MCF7 cells, induction of quinone reductase 1 (QR1), accumulation in the sub-G1 phase of the cell cycle, and quenching of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical. Two metabolites showed activity in these assays; the 3-sulfate exhibited QR1 induction, DPPH free radical scavenging, and COX-1 and COX-2 inhibitory activities and the 4′-sulfate inhibited NFκB induction, as well as COX-1 and COX-2 activities. Resveratrol and its 3′-sulfate and 4-sulfate inhibit NO production by NO scavenging and down-regulation of iNOS expression in RAW 264.7 cells. Resveratrol sulfates displayed low antiproliferative activity and negligible uptake in MCF7 cells.