Insights into the Relationships Between Herbicide Activities, Molecular Structure and Membrane Interaction of Cinnamon and Citronella Essential Oils Components

Int J Mol Sci. 2019 Aug 16;20(16):4007. doi: 10.3390/ijms20164007.

Abstract

Since the 50's, the massive and "environmental naïve" use of synthetic chemistry has revolutionized the farming community facing the dramatic growth of demography. However, nowadays, the controversy grows regarding the long-term harmful effects of these products on human health and the environment. In this context, the use of essential oils (EOs) could be an alternative to chemical products and a better understanding of their mode of biological action for new and optimal applications is of importance. Indeed, if the biocidal effects of some EOs or their components have been at least partly elucidated at the molecular level, very little is currently known regarding their mechanism of action as herbicides at the molecular level. Here, we showed that cinnamon and Java citronella essential oils and some of their main components, i.e.,, cinnamaldehyde (CIN), citronellal (CitA), and citronellol (CitO) could act as efficient herbicides when spread on A. thaliana leaves. The individual EO molecules are small amphiphiles, allowing for them to cross the mesh of cell wall and directly interact with the plant plasma membrane (PPM), which is one of the potential cellular targets of EOs. Hence, we investigated and characterized their interaction with biomimetic PPM while using an integrative biophysical approach. If CitO and CitA, maintaining a similar chemical structure, are able to interact with the model membranes without permeabilizing effect, CIN belonging to the phenylpropanoid family, is not. We suggested that different mechanisms of action for the two types of molecules can occur: while the monoterpenes could disturb the lipid organization and/or domain formation, the phenylpropanoid CIN could interact with membrane receptors.

Keywords: Essential oils; plant plasma membrane; structure/activity relationships.

MeSH terms

  • Acrolein / analogs & derivatives
  • Acrolein / chemistry
  • Acrolein / metabolism
  • Acyclic Monoterpenes / chemistry
  • Acyclic Monoterpenes / metabolism
  • Aldehydes / chemistry
  • Aldehydes / metabolism
  • Arabidopsis / drug effects*
  • Arabidopsis / metabolism
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Cinnamomum zeylanicum / chemistry*
  • Cymbopogon / chemistry*
  • Herbicides / chemistry*
  • Herbicides / metabolism
  • Oils, Volatile / chemistry*
  • Oils, Volatile / metabolism
  • Plant Leaves / drug effects
  • Plant Leaves / metabolism

Substances

  • Acyclic Monoterpenes
  • Aldehydes
  • Herbicides
  • Oils, Volatile
  • Acrolein
  • citronellol
  • citronellal
  • cinnamaldehyde