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Title

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

AuthorsBurgueño-Tapia, Eleuterio; Castillo, Lucía; González-Coloma, Azucena ; Joseph-Nathan, Pedro
KeywordsPerezone
Isoperezone
Antifeedant
Phytotoxicity
Issue Date2008
PublisherSpringer
CitationJournal of Chemical Ecology 34: 766-771 (2008)
AbstractThe 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.
Description6 pages, figures, and tables statistics.
Publisher version (URL)http://dx.doi.org/10.1007/s10886-008-9405-2
URIhttp://hdl.handle.net/10261/28389
DOI10.1007/s10886-008-9495-2
ISSN0098-0331
Appears in Collections:(IRN) Artículos
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