Antioxidant activity and mechanism of the abietane-type diterpene ferruginol

The antioxidant activity of the abietane-type diterpene ferruginol was evaluated by comparison with that of carnosic acid, (+/-)--tocopherol and dibutylhydroxytoluene using 2,2-diphenyl-1-picrylhydrazyl, -carotene bleaching and linoleic acid assays. Ferruginol had the lowest antioxidant activity of this group using the 2,2-diphenyl-1-picrylhydrazyl and -carotene methods in polar solvent buffer. However, ferruginol exhibited stronger activity than carnosic acid and -tocopherol for linoleic acid oxidation under non-solvent conditions. Five peaks corresponding to ferruginol derivatives were detected through GC-MS analysis of the reaction between ferruginol and methyl linoleate. The three reaction products were identified as dehydroferruginol, 7-hydroxyferruginol and sugiol, and the other two peaks were assumed to be 7-hydroxyferruginol and the quinone methide derivative of ferruginol. The time course of the reaction suggests that the quinone methide was produced early in the reaction and reacted further to produce dehydroferruginol, 7-hydroxyferruginol and sugiol. Thus, we inferred that quinone methide formation was a key step in the antioxidant reaction of ferruginol.