Antifeedant and phytotoxic activity of the sesquiterpene p-benzoquinone perezone and some of its derivatives

Eleuterio Burgueño-Tapia, Lucia Castillo, Azucena González-Coloma, Pedro Joseph-Nathan

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)766-771
Number of pages6
JournalJournal of Chemical Ecology
Volume34
Issue number6
DOIs
StatePublished - Jun 2008

Keywords

  • Antifeedant
  • Isoperezone
  • Perezone
  • Phytotoxicity

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