Novel flavanone naringenin derivative with anti-inflammatory activity

Naringenin is a flavonoid with several biological activities already reported but with few biological applications in the pharmaceutical field. In this work, a new flavanone, called carboxymidamide (DCHA), synthesized through the condensation reaction between naringenin and aminoguanidine is structurally confirmed through spectroscopic analysis of nuclear magnetic resonance, mass spectrometry and Fourier transform infrared. DCHA was not toxic to human fibroblasts and inhibited macrophage activation in vitro. In vivo, it suppressed leukocyte migration in lipopolysaccharide (LPS)-induced peritonitis and reduced zymosan-induced paw edema. Molecular docking simulations of DCHA in the active site of the enzymes inducible nitric oxide synthase, cyclooxygenase-2 and phosphodiesterase type 4 indicate that the anti-inflammatory activity of this new flavanone can be explained by the inhibition of these target enzymes. This is the first work to present the synthesis of a flavonoid derivative with aminoguanidine that showed a high anti-inflammatory potential. (author)