Peroxidase-catalyzed synthesis of neolignan and its anti-inflammatory activity

Abstract

Different peroxidases were used to catalyze the synthesis of neolignan. Horseradish peroxidase (type I, Sigma) was employed successfully to catalyze the formation of magnolol by the phenolic oxidative coupling of allyphenol. The effects of organic co-solvents, pH, addition rate of H 2O 2, and the ratio of enzyme/substrate on the yields of dimer were studied. After the peroxidase-catalyzed reaction was performed, different neolignans were isolated and identified as magnolol ( 3), the trimeric ortho– ortho-coupled product dunnianol ( 4), the ortho- O-coupled product isomagnolol ( 5), and the Pummerer's ketone derivative ( 6). The inhibitory activities of magnolol against cyclo-oxygenase and lipoxygenase were also reported.