The influence of ergosterol on the action of the hop oil and its major terpenes on model fungi membranes. Towards understanding the mechanism of action of phytocompounds for food and plant protection.

The aim of this work was to find the correlation between the content of ergosterol in fungi membrane and the action of the hop essential oil, myrcene and humulene on its properties. To reach this goal, the monolayers and bilayers composed of phosphatidylcholine, phosphatidyethanol amine and ergosterol, differing in the concentration of sterol, were used as model membrane systems. The impact of the essential oil and its major terpenes on one component ergosterol film was also investigated. It was found that pure isolated terpenes, in contrast to the hop oil being the mixture of them, do not incorporate into pure ergosterol membrane, however, they cause the loss of monolayer material from the interface. These results are in contrast to the effect of these terpenes on phospholipid films reported previously and they may suggest a strong effect of ergosterol on the behavior of terpenes in the mixed systems. Surprisingly, for model membranes, the effect of myrcene was qualitatively similar to the effect of the hop oil and ergosterol was found to regulate the incorporation of both these substances into the film. In contrast, very strong correlation between ergosterol content and the action of humulene was found. Namely, the ability of humulene to change model membrane properties was found to increase with ergosterol concentration. Additionally, the differentiating effect of ergosterol on humulene action in membranes was much more pronounced than for myrcene or the hop oil. Interestingly, at the highest ergosterol level the influence of humulene was even stronger than the effect of the hop oil. This is very important finding suggesting that ergosterol may regulate the sensitivity of particular membrane to the impact of humulene. Summarizing, ergosterol substantially differentiates the effect of the hop oil, myrcene and humulene on the lipid systems and it can be the molecule important for antifungal effect of the essential oil and terpenes.

The influence of the essential oil extracted from hops on monolayers and bilayers imitating plant pathogen bacteria membranes.

Many plant-derived compounds possess antimicrobial, antioxidant and even anticancer activities. Therefore, they are considered as substances that can be used instead of synthetic compounds in various applications. In this work, the essential oil from hop cones was extracted and analyzed, and then its effects on model bacteria membranes were studied to verify whether the hop essential oils could be used as ecological pesticides. The experiments involved surface pressure-area measurements, penetration studies and Brewster angle microscopy (BAM) imaging of lipid monolayers as well as hydrodynamic diameter, zeta potential, steady-state fluorescence anisotropy and Cryo-Transmission Electron Microscopy (cryo-TEM) measurements of liposomes. Finally the bactericidal tests on plant pathogen bacteria Pseudomonas syringae pv. lachrymans PCM 1410 were performed. The obtained results showed that the components of the essential oils from hop cones incorporate into lipid monolayers and bilayers and alter their fluidity. However, the observed effect is determined by the system composition, its condensation and the oil concentration. Interestingly, at a given dose, the effect of the essential oil on membranes was found to stabilize. Moreover, BAM images proved that hop oil prevents the formation of a large fraction of a condensed phase at the interface. Both the studies on model membranes as well as the in vitro tests allow one to conclude that the hop essential oil could likely be considered as the candidate to be used in agriculture as a natural pesticide.