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Effects of carvone compounds on glutathione S-transferase activity in A/J mice

Zheng, G.Q., Kenney, P.M., Lam, L.K.T.
Journal of agricultural and food chemistry 1992 v.40 no.5 pp. 751-755
carvone, glutathione transferase, enzyme activity
The monoterpene d-carvone is present in a large number of commonly used essential oils. Recently, it has been found to induce the activity of detoxifying enzymes and inhibit nitrosamine-induced carcinogenesis. To explore the structure-activity relationship, a series of carvone compounds were tested for their ability to induce increased activity of glutathione S-transferase in several tissues of A/J mice. The parent compound d-carvone exhibited the highest activity as an inducer in all of the tissues. The alpha,beta-unsaturated ketone system in d-carvone appeared to be critical for the high enzyme-inducing activity, which proved the hypothesis that many anticarcinogenic enzyme inducers are Michael reaction acceptors containing olefinic bonds conjugated with electron-withdrawing groups. The effects of the carvone compounds on the tissue glutathione level were also determined. Several compounds were found to elevate GSH level significantly in the mouse forestomach, while d-carvone decreased GSH level in most of the tissues. Since the anticarcinogenic activity has been found to correlate with the ability to induce increased activity of detoxifying enzymes, carvone compounds can be a class of potential chemopreventive agents.