AAPH-mediated antioxidant reactions of secoisolariciresinol and SDG

Abstract

Secoisolariciresinol (SECO 1) is the major lignan found in flaxseed (Linum usitatissimum L.) and is present in a polymer that contains secoisolariciresinol diglucoside (SDG 2). SECO, SDG and the polymer are known to have a number of health benefits, including reduction of serum cholesterol levels, delay in the onset of type II diabetes and decreased formation of breast, prostate and colon cancers. The health benefits of SECO and SDG may be partially attributed to their antioxidant properties. To better understand their antioxidant properties, SECO and SDG were oxidized using 2,2′-azobis(2-amidinopropane), an in vitro model of radical scavenging. The major lignan radical-scavenging oxidation products and their formation over time were determined. SDG was converted to four major products (11–14), which were the result of a phenoxyl radical intermediate. One of these products (13), a dimer of SDG, decomposed under the reaction conditions to form two of the other major products, 12 and 14. SECO was converted to five major products (6–10), two of which (6 and 7) were also the result of a phenoxyl radical intermediate. The remaining products (8, 9 and 10) were the result of an unexpected alkoxyl radical intermediate. The phenol oxidation products were stable under the reaction conditions, whereas two of the alcohol oxidation products (8 and 9) decomposed. In general, only one phenol group on the lignans was oxidized, suggesting that the number of phenols per molecule may not predict radical scavenging antioxidant ability of lignans. Finally, SECO is a superior antioxidant to SDG, and it may be that the additional alcohol oxidation pathway contributes to its greater antioxidant ability.