Synthesis of genistein coupled with sugar derivatives and their inhibitory effect on nitric oxide production in macrophages

•Genistein was coupled with sugar derivatives.•Genistein derivatives showed variable inhibition of NO and TNF-α production.•7-O-(6″-deoxy-α-d-galactopyrane-6″-yl)-genistein was not cytotoxic.•7-O-(6″-Deoxy-α-d-galactopyrane-6″-yl)-genistein appears as promising anti-inflammatory agent.

The isoflavone genistein 1 and some derivatives modulate IL-12, TNF-α and NO production by macrophages and lung cancer cell lines, and improve the clinical signs of experimental autoimmune encephalomyelitis (EAE). Seven genistein derivatives connected at C-6 position of a sugar, such as d-glucose and d-galactose, were synthesized. The ability to modulate macrophage response was evaluated, showing variable inhibition capacity of NO and TNF-α production in J774.A1 and RAW 264.7. Five of the seven compounds were non-cytotoxic; compound 8 was more effective to inhibit NO and TNF-α production, without affecting cell viability.

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