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Metabolism of Thymol and <i>trans</i>-Anethole in Larvae of <i>Spodoptera litura</i> and <i>Trichoplusia ni</i> (Lepidoptera:  Noctuidae)

Claus M. PaßreiterInstitut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany, Faculty of Agricultural Sciences, University of British Columbia, Vancouver BC, Canada V6T 1Z4, and Departments of Earth and Ocean Sciences and Chemistry, University of British Columbia, Vancouver BC, Canada V6T 1Z4Joanne A. P. WilsonInstitut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany, Faculty of Agricultural Sciences, University of British Columbia, Vancouver BC, Canada V6T 1Z4, and Departments of Earth and Ocean Sciences and Chemistry, University of British Columbia, Vancouver BC, Canada V6T 1Z4Raymond J. AndersenInstitut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany, Faculty of Agricultural Sciences, University of British Columbia, Vancouver BC, Canada V6T 1Z4, and Departments of Earth and Ocean Sciences and Chemistry, University of British Columbia, Vancouver BC, Canada V6T 1Z4Murray B. IsmanInstitut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany, Faculty of Agricultural Sciences, University of British Columbia, Vancouver BC, Canada V6T 1Z4, and Departments of Earth and Ocean Sciences and Chemistry, University of British Columbia, Vancouver BC, Canada V6T 1Z4
2004en
ABI

Abstract

Metabolism of the monoterpenoid thymol and the phenylpropanoid trans-anethole, both constituents of essential oils, was investigated following topical and oral administration of the compounds to the tobacco cutworm (Spodoptera litura) and the cabbage looper (Trichoplusia ni). In both species and irrespective of route, administration of thymol resulted in the excretion of its 3-O-beta-glucoside, whereas trans-anethole was hydroxylated on the side chain methyl group. Both metabolites were isolated and their structures elucidated by interpretation of their mass and NMR spectra. Previous experiments indicated that trans-anethole synergized the toxicity of thymol in S. litura, but analyses of feces indicated that metabolism of thymol was not significantly suppressed when the two compounds were orally coadministered to T. ni larvae.

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DOI
10.1021/jf035386m

Citations and references

Cited by 20 references
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