Modulation of membrane physical properties by natural insecticidal ketones.

Autor: Miguel V; Universidad Nacional de Córdoba, Facultad de Ciencias Exactas, Físicas y Naturales, Departamento de Química, Cátedra de Química Biológica, Córdoba, Argentina; Instituto de Investigaciones Biológicas y Tecnológicas (IIBYT), CONICET, Córdoba, Argentina., Sánchez-Borzone ME; Universidad Nacional de Córdoba, Facultad de Ciencias Exactas, Físicas y Naturales, Departamento de Química, Cátedra de Química Biológica, Córdoba, Argentina; Instituto de Investigaciones Biológicas y Tecnológicas (IIBYT), CONICET, Córdoba, Argentina., Mariani ME; Universidad Nacional de Córdoba, Facultad de Ciencias Exactas, Físicas y Naturales, Departamento de Química, Cátedra de Química Biológica, Córdoba, Argentina; Instituto de Investigaciones Biológicas y Tecnológicas (IIBYT), CONICET, Córdoba, Argentina., García DA; Universidad Nacional de Córdoba, Facultad de Ciencias Exactas, Físicas y Naturales, Departamento de Química, Cátedra de Química Biológica, Córdoba, Argentina; Instituto de Investigaciones Biológicas y Tecnológicas (IIBYT), CONICET, Córdoba, Argentina. Electronic address: dagarcia@unc.edu.ar.
Jazyk: angličtina
Zdroj: Biophysical chemistry [Biophys Chem] 2021 Feb; Vol. 269, pp. 106526. Date of Electronic Publication: 2020 Dec 14.
DOI: 10.1016/j.bpc.2020.106526
Abstrakt: The insecticidal activity of Mentha oil and its main components has been tested and established for various insects/pests. Several mint ketones have demonstrated to act on GABA A receptors (GABA A -R), a transmembrane channel target of several important insecticides whose activity can be modulated by surface-active compounds and by changes in the physical properties of the lipid membrane. In the present work, we analyze the capacity of monoterpenic ketones most commonly found in Mentha species, pulegone and menthone, to interact with DPPC membranes by molecular dynamics (MD) simulations and Langmuir monolayers. The experimental results indicate that the presence of menthone and pulegone in the subphase modify the interfacial characteristics of DPPC isotherms. The changes were reflected as expansion of the isotherms and disappearance or bringing forward of DPPC phase transition. MD simulation corroborate these results and indicate that both ketones are located at the region of the carbonyl group, at the interface with the acyl chains. Ketone intercalation between lipid molecules would induce an increasing intermolecular interaction, diminishing the film elasticity and causing an ordering effect. Our results suggest that the insecticidal activity of both ketones could involve their interaction with lipid molecules causing disturbance of the cell membrane as postulated for several larvicide compounds, or at least modulating the receptor surrounding.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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