A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity.

Highly oxidized lignans produced during the cytochrome P-450 metabolism in the cells show biological activities significantly different from those of their parent natural compounds. Lignans precursors of mammalian enterolignans were treated with a methyltrioxorhenium/hydrogen peroxide catalytic system to afford new compounds oxidized at benzylic as well as in arylic positions. The evaluation of the antioxidant and apoptogenic activity by in vivo protocols of these compounds showed some interesting structure-activity relationships related to the oxidation degree of the molecules.