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Antifeedant and Phytotoxic Activity of the Sesquiterpene p-Benzoquinone Perezone and Some of its Derivatives

Burgueño-Tapia, Eleuterio, Castillo, Lucia, González-Coloma, Azucena, Joseph-Nathan, Pedro
Journal of chemical ecology 2008 v.34 no.6 pp. 766-771
sesquiterpenoids, antifeeding activity, benzoquinones, Spodoptera littoralis, phytotoxicity, Lactuca sativa, Myzus persicae, Leptinotarsa decemlineata, structure-activity relationships, root growth, chemical constituents of plants, pest resistance, root radicle
The sesquiterpene p-benzoquinone perezone (1), isolated from Perezia adnata var. alamani (Asteraceae), and its non-natural derivatives isoperezone (2), dihydroperezone (3), dihydroisoperezone (4), and anilidoperezone (5) were tested as antifeedants against the herbivorous insects Spodoptera littoralis, Leptinotarsa decemlineata, and Myzus persicae. Compounds 1-5 exhibited strong antifeedant activity against L. decemlineata and M. persicae, and elicited a low response by S. littoralis. Antifeedant activity on L. decemlineata and M. persicae increased when the hydroxyl group at C-3 in perezone (1) was changed to C-6 to give isoperezone (2). The same effect was found with hydrogenation of the double bond of the alkyl chain of (1) to yield dihydroperezone (3). In contrast, hydrogenation of this double bond in isoperezone (2) to give dihydroisoperezone (4) led to a reduction in antifeedant activity. Determination of the phytotoxic activity of 1-5 revealed that 3 had a significant inhibition effect on Lactuca sativa radicle length growth.