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Modulation of membrane physical properties by natural insecticidal ketones
V Miguel1, M E Sánchez-Borzone1, M E Mariani1
1Universidad 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.
Biophysical Chemistry
|December 21, 2020
Summary
Menthol and pulegone, found in mint oil, interact with cell membranes. This interaction may explain their insecticidal activity by disrupting membrane function or modulating receptors.
Area of Science:
- Biochemistry
- Molecular Biology
- Insect Toxicology
Background:
- Mentha oil components exhibit insecticidal properties.
- Mint ketones like pulegone and menthone target GABAA receptors (GABAA-R).
- Insecticide activity can be influenced by membrane properties and surface-active compounds.
Purpose of the Study:
- To investigate the interaction of pulegone and menthone with dipalmitoylphosphatidylcholine (DPPC) membranes.
- To elucidate the molecular mechanisms underlying the insecticidal activity of these monoterpenic ketones.
Main Methods:
- Molecular dynamics (MD) simulations were employed to model ketone-membrane interactions.
- Langmuir monolayers were used to experimentally assess the effects of ketones on DPPC membrane characteristics.
Main Results:
- Menthone and pulegone altered DPPC interfacial characteristics, expanding isotherms and shifting phase transitions.
- MD simulations confirmed ketone intercalation at the carbonyl group, near the acyl chain interface.
- This intercalation increased intermolecular interactions, reduced film elasticity, and induced ordering within the membrane.
Conclusions:
- Pulegone and menthone interact with lipid membranes, potentially disrupting cellular function.
- Their insecticidal effects may stem from membrane disturbance or modulation of the receptor environment.
- These findings offer insights into the mode of action for mint-derived insecticides.
