The purpose of this study was to investigate the inhibitory/bactericidal activity and cell membrane effects of the hydrodistilled essential oil of Inula helenium L. roots against Staphylococcus aureus. Additionally, detailed chemical investigation was done in order to pinpoint the most active oil constituents and also the parts of these molecules responsible for their antimicrobial effect. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined using the broth microdilution method. The membrane-active nature of this oil was investigated by measuring the culture turbidity, leakage of phosphates, and 260-nm-absorbing material, together with lysis of the exposed cells. Finally, the effect of the oil on the cells was visualized using scanning electron microscopy (SEM). The chemical composition of the essential oil was analyzed using gas chromatography-mass spectrometry (GC-MS) and preparative medium-pressure liquid chromatography (MPLC). Chemical modification of the oil was performed using catalytic hydrogenation (H(2), Pd/C) and reduction with NaBH(4). The MIC and MBC values were 0.01 μl mL(-1) and 0.02 μl mL(-1), respectively. Membrane damage was demonstrated through increased permeability (phosphates and nucleic acid leakage), followed by lysis of the exposed cells, captured on SEM images. The most active constituents were alantolactone, isoalantolactone, and diplophyllin. The essential oil showed very potent antistaphylococcal activity, with obvious membrane-damaging effects. Sesquiterpene lactones were found to be the most active principles of the oil, whose eudesmane core olefinic bonds, along with the α,β-methylene-lactone ring, are essential structural parts responsible for the exhibited antimicrobial activity.
. Fatty and volatile oils of the gypsywort lycopus europaeus L. and the gaussian-like distribution of its wax alkanes. JAOCS, 89 (12), 2165-2185.
Fatty and volatile oils of the gypsywort lycopus europaeus L. and the gaussian-like distribution of its wax alkanes
AbstractThe detailed analyses of the volatile essential oil and lipid profiles of the aerial parts from the blooming and fruit-forming stages of both ripe and unripe fruit of Lycopus europaeus (Lamiaceae) are presented. Both of these profiles are distinguished by components with a restricted occurrence in the Plant Kingdom. These rare compounds include (E)-hotrienol in the volatiles, numerous unusual fatty acids (such as very long chain, oddnumbered and branched-chain) in the bound lipids and a high amount of iso-and anteiso-alkanes in the epicuticular waxes. Furthermore, a Gaussian-like distribution of the relative amounts of the epicuticular wax alkanes was observed. These normal distributions could be interpreted as the end result of the work of elongase enzyme systems where the Gaussian parameter μ should match the length of the "ideal" fatty acid biosynthesised and σ would represent the error of this enzyme system. These curve parameters were shown to have a close relationship with ACL and CPI values usually utilised to describe the natural distribution of wax alkanes. The screening of L. europaeus essential oil for its in vitro antimicrobial activity showed that this oil possesses selectivity towards two gram-negative strains, E. coli and K. pneumoniae. europaeus essential oil for its in vitro antimicrobial activity showed that this oil possesses selectivity towards two Gram negative strains, E. coli and K. pneumoniae.
The small combinatorial library approach enabled the first unequivocal identification of long-chain 3-methyl-2-alkanones as plant secondary metabolites, and, also, allowed determination of not only a single compound and biological properties, but those of a group of structurally related compounds.
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