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

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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.

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Acknowledgments

This work was supported by grants CTQ2006-15597-C02-01/PPQ, CSIC-CNRST, SIP-IPN, CONACYT and CYTED, and L. Castillo by AECI. We gratefully acknowledge S. Carlin for language revision.

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Authors and Affiliations

  1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Tomás, México, D.F., 11340, México

    Eleuterio Burgueño-Tapia

  2. Instituto de Ciencias Agrarias, CCMA, CSIC, Serrano 115-bis, 28006, Madrid, España

    Lucia Castillo & Azucena González-Coloma

  3. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D.F., 07000, México

    Pedro Joseph-Nathan

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  1. Eleuterio Burgueño-Tapia
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  2. Lucia Castillo
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  3. Azucena González-Coloma
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  4. Pedro Joseph-Nathan
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Correspondence to Pedro Joseph-Nathan.

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Burgueño-Tapia, E., Castillo, L., González-Coloma, A. et al. Antifeedant and Phytotoxic Activity of the Sesquiterpene p-Benzoquinone Perezone and Some of its Derivatives. J Chem Ecol 34, 766–771 (2008). https://doi.org/10.1007/s10886-008-9495-2

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  • DOI: https://doi.org/10.1007/s10886-008-9495-2

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