Recovery of antioxidant activity from carnosol quinone: antioxidants obtained from a water-promoted conversion of carnosol quinone

Carnosol is one of the main antioxidants in sage and rosemary. Although carnosol quinone is the antioxidation product of carnosol and has a very weak antioxidant activity, its treatment in water-containing solvent restored its strong antioxidant activity. HPLC analysis of the water-stimulated recovery reaction of the antioxidant activity revealed that the strong activity was due to the reproduced carnosol. The analysis also showed that an almost equal amount of quinone derivatives of rosmanol (rosmanol quinone) was produced in the reaction along with the carnosol. The rosmanol was formed by the addition of 1 equiv of water and the following isomerization from carnosol quinone in the water-containing solvent. The formed rosmanol was also found to be oxidized by the remaining carnosol quinone to produce rosmanol quinone. At the same time, carnosol quinone was reduced to afford carnosol. This redox phenomenon is an important part of the mechanism for the recovery of the antioxidant activity from carnosol quinone under the water-containing conditions.