Staphylococcus aureus membrane-damaging activities of four phenolics (original) (raw)
Related papers
Microbiological Research, 2014
Cationic amino acid-based surfactants are known to interact with the lipid bilayer of cell membranes resulting in depolarization, lysis and cell death through a disruption of the membrane topology. A range of cationic surfactant analogues derived from l-Phenylalanine (C 1 -C 20 ) and l-Tyrosine (C 8 -C 14 ) esters have been synthesized and screened for their antibacterial activity. The esters were more active against gram positive than gram negative bacteria. The activity increased with increasing chain length, exhibiting a cut-off effect at C 12 for gram positive and C 8 /C 10 for gram negative bacteria. The cut-off effect for gram negative bacteria was observed at a lower alkyl chain length. The CMC was correlated with the MIC, inferring that micellar activity contribute to the cut-off effect in antibacterial activity. The interaction of the cationic surfactants with the phospholipid vesicles (1,2-dipalmitoyl-sn-glycero-3-phosphocholine, DPPC) in the presence of 1-anilino-8-naphthalene sulfonate (ANS) and 1,6-diphenyl-1,3,5-hexatriene (DPH) as fluorescence probes showed that an increase in ionic interaction causes an increase in antibacterial activity. Increase in hydrophobic interaction increases the antibacterial activity only to a certain chain length, attributing to the cut-off effect. Therefore, both electrostatic and hydrophobic interactions, involving the polar and nonpolar moieties are of paramount importance for the bactericidal properties.
Molecules (Basel, Switzerland), 2014
Monolayers composed of bacterial phospholipids were used as model membranes to study interactions of the naturally occurring phenolic compounds 2,5-dihydroxybenzaldehyde and 2-hydroxy-5-methoxybenzaldehyde, and the plant essential oil compounds carvacrol, cinnamaldehyde, and geraniol, previously found to be active against both Gram-positive and Gram-negative pathogenic microorganisms. The lipid monolayers consist of 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine (DPPE), 1,2-dihexa- decanoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (DPPG), and 1,1',2,2'-tetratetradecanoyl cardiolipin (cardiolipin). Surface pressure-area (π-A) and surface potential-area (Δψ-A) isotherms were measured to monitor changes in the thermodynamic and physical properties of the lipid monolayers. Results of the study indicated that the five compounds modified the three lipid monolayer structures by integrating into the monolayer, forming aggregates of antimicrobial -lipid complexes, reducing the...
Antimicrobial properties of phenolic acid alkyl esters
Czech Journal of Food Sciences
The series of phenolic acid (2-, 3-, 4-monohydroxy- and 2,4-, 2,5-dihydroxy) alkyl esters (methyl, ethyl, propyl, and butyl) were prepared, and their antimicrobial activities were determined. The antimicrobial activity against the tested microorganisms Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus brasiliensis was investigated and expressed by minimum inhibitory concentration (MIC) in the range of 1.2–20 mM. The inhibitory activity of higher esters of phenolic acids was found to be higher than that of methyl esters and acids. The minimum inhibitory concentration (MIC) of tested compounds was compared with that of 4-hydroxybenzoic acid and its esters (parabens).
Pharmaceutics
Background: Carvacrol, a mono-terpenoid phenol found in herbs, such as oregano and thyme, has excellent antibacterial properties against Streptococcus pyogenes. However, its mechanism of bactericidal activity on S. pyogenes has not been elucidated. Objectives: This study investigated the bactericidal mechanism of carvacrol using three strains of S. pyogenes. Methods: Flow cytometry (FCM) experiments were conducted to determine carvacrol’s membrane permeabilization and cytoplasmic membrane depolarization activities. Protoplasts of S. pyogenes were used to investigate carvacrol’s effects on the membrane, followed by gel electrophoresis. The carvacrol-treated protoplasts were examined by transmission electron microscopy (TEM) to observe ultrastructural morphological changes. The fluidity of the cell membrane was measured by steady-state fluorescence anisotropy. Thin-layer chromatographic (TLC) profiling was conducted to study the affinity of carvacrol for membrane phospholipids. Result...
Evaluation of cell membrane integrity as a potential antimicrobial target for plant products
BMC Complementary & Alternative Medicine, 2014
Abstract Background: There is urgent need to discover new antimicrobial compounds with diverse chemical structures and mechanisms of action due to increasing new and re-emerging infectious diseases. Additionally, appearance of undesirable side effects of certain antibiotics and increasing resistance to antibiotics in current clinical use is also a cause for concern. Bacterial cell membranes are a possible target for developing new antibacterial drugs since membrane-based efflux pump systems play an important role in bacterial pathogenicity and antimicrobial resistance in bacteria. Hence, the objective of our study was to evaluate bacterial membrane integrity of two species of bacteria; Staphylococcus aureus and Pseudomonas aeruginosa, in the presence of ethanolic leaf extracts of two plant species Callistemon citrinus and Vernonia adoensis from Zimbabwe. Methods: Bacterial efflux pump inhibition using both leaf extracts was determined by monitoring the transport of Rhodamine 6 G (R6G) across the cell membrane and IC50 values were obtained. Membrane permeabilizing properties of both extracts were also evaluated using the membrane potential sensitive dye 3’3 dipropylthiadicarbocyanine (diSC3-5). Haemolysis effect of both extracts on sheep erythrocytes was also investigated. Results: Both extracts inhibited bacterial efflux pumps which resulted in the accumulation of R6G inside the cell. The IC50 values for C. citrinus and V.adoensis against S. aureus were 1.44 mg/ml and 1.61 mg/ml, respectively. Both leaf extracts however, showed similar IC50 values of 1.64 mg/ml against P. aeruginosa. Both plant extracts showed some significant effects on permeability of the bacterial membrane when a 24-28% increase of diSC3-5 dye release was observed for S. aureus and 45–53% of dye was released from P. aeruginosa cell membrane after a 60 minute incubation period. In addition, both extracts exhibited haemolytic effects on sheep erythrocytes at concentrations greater than 2.5 mg/ml. Conclusions: These plant extracts may provide new lead compounds for developing potential efflux pump inhibitors (EPIs) or permeabilising agents that could aid the transport of antibacterial agents into bacterial cells. Keywords: Bacterial efflux pumps, Membrane permeability, C. citrinus, V. adoensis
Food Control, 2013
Minimal inhibitory concentrations (MICs) of seven synthetic phenolic compounds, five commonly used as antioxidants (TBHQ, BHA, BHT, propyl gallate and octyl gallate) and two as antimicrobials (propyl 4hydroxybenzoate and n-heptyl 4-hydroxybenzoate) were assessed against several strains of two Grampositive (Staphylococcus aureus and Bacillus cereus) and one Gram-negative (Pseudomonas fluorescens) bacteria, by using a standardized microdilution assay (ISO 20776-1, 2006). Octyl gallate was the most effective compound against the three genera/species of bacteria considered simultaneously (with the exception of four strains of B. cereus, which were resistant for this compound) with MIC values ( 100 mg/ ml) lower than the concentrations usually used as antioxidants. TBHQ and n-heptyl 4-hydroxybenzoate were also effective in the control of S. aureus at very low concentrations (MIC of 3.1 mg/ml and 12.5 mg/ml, respectively). Propyl 4-hydroxybenzoate was the most inhibitory phenolic compound against all strains of B. cereus and both tested parabens (propyl-and heptyl-) were not effective for P. fluorescens (MIC > 1600 mg/ml). B. cereus was the bacterial genera that showed more intra-species variation, distinguishing two clearly groups of sensitivity among the strains to octyl gallate and n-heptyl 4hydroxybenzoate ("sensitive" with mean MICs of 42.8 and 4.2 mg/ml, respectively; and "resistant" with MICs >1600 and >800 mg/ml, respectively). According to all that, octyl gallate would be an interesting phenolic compound for the food industry, not only because of its recognized antioxidant properties but also because of their effectivity as antimicrobial against S. aureus, B. cereus and P. fluorescens.
Chemistry and physics of lipids, 2017
The increased biosynthesis of lysyl-phosphatidylglycerol in Staphylococcus aureus when cultured under conditions of mild acidity and the resultant increased proportion of this lipid in the plasma membrane of the bacterium, alters the physico-chemical properties of lipid bilayers in a manner which is itself dependent upon environmental pH. Clinically relevant strains of S. aureus, both methicillin susceptible and resistant, all exhibited increased lysyl-phosphatidylglycerol biosynthesis in response to mild environmental acidity, albeit to differing degrees, from ∼30% to ∼55% total phospholipid. Polar lipid extracts from these bacteria were analysed by (31)P NMR and reconstituted into vesicles and monolayers, which were characterised by zeta potential measurements and Langmuir isotherms respectively. A combination of increased lysyl-phosphatidylglycerol content and mild environmental acidity were found to synergistically neutralise the charge of the membranes, in one instance altering...
Free Radical Biology and Medicine, 2003
The effects of four catechins, (ϩ)-catechin (C), (Ϫ)-epicatechin (EC), (Ϫ)-epicatechin gallate (ECG), and (Ϫ)-epigallocatechin gallate (EGCG), on the physical properties of phospholipid model membranes and the correlation to their antioxidant and antibacterial capacities have been studied by using differential scanning calorimetry (DSC), fluorescence spectroscopy, infrared spectroscopy (IR), AAPH-induced oxidation, and leakage experiments. DSC data revealed that galloylated catechins, especially ECG, affected the physical properties of both the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) bilayers dramatically. Galloylated catechins showed higher phospholipid/ water partition coefficients than their homologues and were immersed in the phospholipid palisade intercalating within the hydrocarbon chains, ECG being at the deepest position. In contrast, nongalloylated catechins presented a shallow location close to the phospholipid/water interface. ECG also exhibited the highest antioxidant capacity against lipid peroxidation, which correlated with its strong effect on DPH fluorescence anisotropy (as observed by the increase of the lipid order of fluid PC bilayers) and with the presence of highly cooperative transitions as seen by DSC. We propose that the high antioxidant capacity of some galloylated catechins such as ECG could be partially due to the formation of membrane structures showing resistance to detergent solubilization and in which the phospholipids have tightly packed acyl chains and highly hydrated phosphate groups. Significantly, PE was found to be essential to the promotion of carboxyfluorescein leakage from bacterial model membranes by galloylated catechins, indicating that their bactericidal activity, at least at the membrane level, could be due to the specific effect of these catechins on PE.
Antimicrobial activity of phenolic acids against commensal, probiotic and pathogenic bacteria
Research in Microbiology, 2010
Phenolic acids (benzoic, phenylacetic and phenylpropionic acids) are the most abundant phenolic structures found in fecal water. As an approach towards the exploration of their action in the gut, this paper reports the antimicrobial activity of thirteen phenolic acids towards Escherichia coli, Lactobacillus spp., Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans. The growth of E. coli ATCC 25922 was inhibited by only four of the phenolic acids tested at a concentration of 1000 mg/mL, whereas pathogenic E. coli O157:H7 (CECT 5947) was susceptible to ten of them. The genetically manipulated E. coli lpxC/tolC strain was highly susceptible to phenolic acids. The growth of lactobacilli (Lactobacillus paraplantarum LCH7, Lactobacillus plantarum LCH17, Lactobacillus fermentum LPH1, L. fermentum CECT 5716, Lactobacillus brevis LCH23, and Lactobacillus coryniformis CECT 5711) and pathogens (S. aureus EP167 and C. albicans MY1055) was also inhibited by phenolic acids, but to varying extents. Only P. aeruginosa PAO1 was not susceptible to any of the phenolic compounds tested. Structureeactivity relationships of phenolic acids and some of their diet precursors [(þ)-catechin and (À)-epicatechin] were established, based on multivariate analysis of microbial activities. The antimicrobial properties of phenolic acids reported in this paper might be relevant in vivo.