Study of lipophilicity of alpha-asarone derivatives and their deterrent activity against the Colorado potato beetle

• Authors: Bożena Łozowicka , Piotr Kaczyński , Jan Nawrot
• Languages of publication: EN

Abstracts

EN

Five positional isomers and thirty derivatives of alpha-asarone wereobtained as a bioactive set of substances, and their deterrent activity against the Colorado potato beetle was studied. The lipophilicity values of thirty-six compounds were determined by using experimental, chromatographic and theoretical methods. The logk w values for all compounds were determined by reversed-phase high-performance liquid chromatography using five different columns. The octan-1-ol/water partition coefficients values were determined experimentally as a measure of lipophilicity. For the purpose of comparison, theoretical lipophilic parameters for all compounds were calculated with the use of chemical programs. The experimental, chromatographic and calculated values were compared using linear regression analysis. The most significant correlations were found between the chromatographic lipophilicities using methanol/water for all tested columns and calculated values. It has been found that 13 compounds have the lowest lipophilicities, which correspond to deterrent activity. The presented results show that the computational method is useful for determining the lipophilicity of a series of homologues, but not for positional isomers. In addition, this study shows that determination of lipophilicity using HPLC with various stationary phases is practical and reasonable for all alpha-asarone derivatives. [...]

Keywords

EN

Lipophilicity; Alpha-asarone derivative; Antifeedant activity; Colorado potato beetle

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 12
• Pages: 2120-2133

Dates

published

1 - 12 - 2013

online

26 - 9 - 2013

Contributors

author

Bożena Łozowicka

• Institute of Plant Protection - National Research Institute, Regional Experimental Station, BiaŁystok, 15-195, Poland

author

Piotr Kaczyński

• Institute of Plant Protection - National Research Institute, Regional Experimental Station, BiaŁystok, 15-195, Poland

author

Jan Nawrot

• Institute of Plant Protection - National Research Institute, Department of Entomology, Poznań, 60-318, Poland

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Identifiers

DOI

10.2478/s11532-013-0336-y