Effect of the Chemical Composition of Free-Terpene Hydrocarbons Essential Oils on Antifungal Activity

Abstract

In this study, Carum carvi L. essential oil (CEO) and Origanum majorana L. essential oil (MEO) was steam-distillated under reduced pressure. We henceforth obtained three fractions for each essential oil: CF1, CF2, CF3, MF1, MF2, and MF3. Then, these fractions were characterized using the gas chromatography–mass spectrometry (GC-MS) technique. The results indicated that some fractions were rich in oxygenated compounds (i.e., CF2, CF3, MF2, and MF3) with concentrations ranging from 79.21% to 98.56%. Therefore, the influence of the chemical composition of the essential oils on their antifungal activity was studied. For this purpose, three food spoilage fungi were isolated, identified, and inoculated in vitro, in order to measure the antifungal activity of CEO, MEO, and their fractions. The results showed that stronger fungi growth inhibitions (FGI) (above 95%) were found in fractions with higher percentages of oxygenated compounds, especially with (−)-carvone and terpin-4-ol as the major components. Firstly, this work reveals that the free-terpenes hydrocarbons fractions obtained from MEO present higher antifungal activity than the raw essential oil against two families of fungi. Then, it suggests that the isolation of (−)-carvone (97.15 ± 5.97%) from CEO via vacuum distillation can be employed successfully to improve antifungal activity by killing fungi (FGI = 100%). This study highlights that separation under reduced pressure is a simple green method to obtain fractions or to isolate compounds with higher biological activity useful for pharmaceutical products or natural additives in formulations.

Hexosomal Dispersion: A Nano-Based Approach to Boost the Antifungal Potential of Citrus Essential Oils against Plant Fungal Pathogens

“…The oxygenated hydrocarbon composition is higher in C. lemon and C. aurantifolia , with percentages of 33.53% and 14.59%, respectively. High concentrations of oxygenated hydrocarbons in C. lemon and C. aurantifolia could be attributed to the strong antifungal activities of these oils [ 21 ]. They could synergistically increase the effect of limonene and other monoterpene hydrocarbons [ 22 ].…”

Discovering Penicillium polonicum with High-Lytic Capacity on Helianthus tuberosus Tubers: Oil-Based Preservation for Mold Management

“…The GC analysis showed an increase in the proportion of oxygenated compounds in caraway fractions in comparison to hydrocarbons, therefore, caraway oil could be considered to be highly oxygenated while clove oil is moderately oxygenated. Previously, oxygenated compounds have been reported to have bioactive inhibitory effects against several fungal strains, including numerous Penicillium strains, such activity of the oil could be attributed to the oxygenated carvone that possessed higher antifungal activity, as well as antioxidant activity [ 40 , 41 , 42 ]. Such compounds could also inhibit the rate of primary and the secondary oxidation product formation.…”

“…Such compounds could also inhibit the rate of primary and the secondary oxidation product formation. Furthermore, the physical nature of the rich oxygenated essential oils, for example, their low molecular weight combined with a lipophilic character, allow them to penetrate the cell membrane more quickly compared to other substances [ 41 , 43 ]. Clove oil also showed good potential in inhibiting the growth of Penicillium polonium .…”

Effect of Carum carvi essential oil on ERG6 gene expression and virulence factors in Candida albicans

“…Carum carvi EO contains rich oxygenated compounds, such as carvone and limonene, affecting the integrity of the fungal cell membrane. It has been shown that free-terpene hydrocarbons containing oxygenated compounds with low molecular weights are able to penetrate through the cell membrane after combining with lipophilic molecules [ 36 ]. Furthermore, phenolic compounds with OH group and aromatic structure have been identified to contribute to the deactivation of fungal enzymes [ 36 ].…”

“…It has been shown that free-terpene hydrocarbons containing oxygenated compounds with low molecular weights are able to penetrate through the cell membrane after combining with lipophilic molecules [ 36 ]. Furthermore, phenolic compounds with OH group and aromatic structure have been identified to contribute to the deactivation of fungal enzymes [ 36 ]. Our findings revealed that C. carvi EO could successfully inhibit extracellular proteinase and phospholipase activities in C. albicans .…”