Abstract
Sesamol (3,4-methylenedioxyphenol) is a potent antioxidative constituent of sesame product. It is well known that sesame, seeds of Sesamum indicum and its oil products are used for healthy foods from ancient times. Until now many beneficial activities of sesamol itself have been reported. Sesamol is now recognized as one of the promising food-functional compounds. Phytophenols and related phenolics including sesamol have attracted much attention as potent antioxidants. These antioxidative phenols are very oxidizable due to their chemical property. In this investigation, several phenols having potent antioxidant activity were oxidized with oxygen in the presence of a catalytic amount of Fe ions. Among the obtained oxidation products, the product from sesamol showed a remarkable cytotoxic activity. To clarify the cytotoxic principle of the product, assay-guided fractionation and subsequent isolation of the oxidation compound of sesamol was carried out. After all, structure analysis of the isolated compounds revealed that they are novel dimeric, trimeric and terrameric compounds of sesamol. The cytotoxic activity of these oligomeric compounds was evaluated by a flow cytometric analysis, results indicating that the toxic oligomers of sesamol promoted apoptosis to cell death.
