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.

Figure optionsDownload as PowerPoint slide