Mechanism of action of various terpenes and phenylpropanoids against Escherichia coli and Staphylococcus aureus

Abstract

Foodborne, disease-causing microorganisms are increasingly resistant to commercial antibiotics. Thus, there is a need for the development of new agents capable of acting efficiently in the control of these pathogens. Terpenoids and phenylpropanoids stand out for having high biological activity and a broad spectrum of action. The objectives of thi study were to evaluate the antibacterial potential of limonene, β-citronellol, carvone, carvacrol, eugenol and trans-cinnamaldehyde and to investigate the mechanism of activity of these compounds against the bacteria Escherichia coli and Staphylococcus aureus. The terpene and phenylpropanoid compoundswere purchased and their antibacterial potential was assessed by macrodilution. The mechanism of action was verified by tests of potassium ion efflux, salt tolerance, extravasation of cellular contents, absorption of crystal violet and morphological changes analyzed by electron microscopy. Bacteriostatic and bactericidal effects caused by the compounds carvone, carvacrol, eugenol and transcinemaldehyde were observed in both species; antibacterial activity against only S. aureus was observed for β-citronelol and limonene. Reduced salt tolerance was found for strains of E. coli treated with carvacrol and S. aureus treated with β-citronelol. There was extravasation of cellular materials induced by treatments with carvone, carvacrol, eugenol and trans-cinnamaldehyde in both microorganisms. The absorption of crystal violet increased for E. coli after incubation with each treatment. Deleterious effects and morphological changes were observed. Therefore, the monoterpenes and phenylpropanoids under study are potentially applicable for antimicrobial use against E. coli and S. aureus, and the mechanism of action involves changes in membrane permeability without cell lysis.

Potential of Marine Terpenoids against SARS-CoV-2: An In Silico Drug Development Approach

“…Generally, terpenoids are more diverse groups of secondary metabolites that exhibited a broad−spectrum inhibition with multiple types of mode of action during the treatment against several diseases [ 71 , 72 , 73 , 74 , 75 , 76 ]. Most plant and marine terpenoids showed potent antiviral activity in cell lines; however actual mode of inhibition is still under investigation [ 77 , 78 , 79 ].…”

“…At this stage, more computational investigation, drug chemistry, and SAR analysis may help to explore more drug-action information. In addition, like virucidal activity, terpenoids showed potent antibacterial activity by disturbing membrane permeability and cell morphology, reducing salt tolerance, inhibiting biofilm pathways, and targeting the cell membrane synthesis pathways [ 75 , 83 ]. Similarly, it showed potential antiparasitic/antimalarial activity by binding with hemin part of infected erythrocytes like the mainstream chloroquine [ 73 , 84 ], anticancer by disruption of microtubules, suppress the cyclin D1, apoptosis, and cell cycle arrest [ 74 , 85 ], treat neuro−disorder by inhibiting the neurotransmitters GABA and cannabinoid receptor-2 [ 86 , 87 ], antidiabetic potency by activating the α-adrenoreceptors to increase the release of an opioid peptide β-endorphin [ 72 , 73 , 88 ].…”

“…Most plant and marine terpenoids showed potent antiviral activity in cell lines; however actual mode of inhibition is still under investigation [77][78][79]. Especially, terpenoids showed virucidal activity against the various viruses by Generally, terpenoids are more diverse groups of secondary metabolites that exhibited a broad−spectrum inhibition with multiple types of mode of action during the treatment against several diseases [71][72][73][74][75][76]. Most plant and marine terpenoids showed potent antiviral activity in cell lines; however actual mode of inhibition is still under investigation [77][78][79].…”

A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria

“…Hence, the mechanisms need to be investigated independently. Regarding the phenylpropanoids, it is well known that small aromatic compounds disrupt the cell wall barrier in both Gram-positive and Gram-negative bacteria [ 19 ], so this should be investigated as a possible mechanism for compound 1 of the current study.…”

Bioactive properties of the aromatic molecules of spearmint (Mentha spicataL.) essential oil: a review

“…and E. coli. 48,50 Besides, carvone can be used as a precursor to produce an antibacterial coating that prevents bacterial infections arising from medical implants and devices. Chan et al proposed a single-step plasma polymerization of carvone to produce a moderately hydrophobic antibacterial coating ( ppCar) with an average roughness of <1 nm.…”