Background: Melanoma is a malignant skin tumor and quercetin has been reported to inhibit metastasis. A quercetin glycoside and 7 methylquercetins were synthesized from rutin to investigate structure-activity relationships. Materials and Methods: We evaluated the anti-proliferative and anti-migration activity of quercetin glycoside and 7 methylquercetins in murine B16 melanoma cells by commercially available kits. We also examined the effect of these compounds on growth of human fibroblast cells to evaluate cytotoxicity. Results: 3-O-methylquercetin (2) exhibited 30, 38, 45% migration activity at 25, 12.5, 6.25 μM respectively. Furthermore, 3,4',7-O-trimethylquercetin (5) and 3,4'-O-dimethylquercetin (3) inhibited migration more potent than 2 with no cytotoxicity. 3-hydroxymethylquercetin and quercetin glycoside exhibited no anti-migration activity. Furthermore, the 3 and 4 inhibited melanoma proliferation with no cytotoxicity. Conclusion: The methoxyl group at the C-3 position plays an important role in inhibiting the migration of B16 melanoma cells.
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