Twice acting antioxidants: synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Two new organochalcogen-containing zingerone derivatives, 4-(4-hydroxy-3-methoxyphenyl): 4-(phenylseleno)-2-butanone (2b) and 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylthio)-2-butanone (2c) were prepared and evaluated for their antioxidant properties. DPPH and lipid peroxidation studies show that 2b and 2c have significantly improved antioxidant activity over dehydrozingerone (1) despite having similar electron transfer capacity. We speculate that the improved activity of 2b and 2c is partly due to the ability of these compounds to act twice as phenolic antioxidants through a mechanism that eliminates phenylselenyl or phenylthiyl radicals. (C) 2015 Elsevier Ltd. All rights reserved.