Cited by 1,359Essential Oils and Antimicrobial ActivityAntimicrobial agents and applicationsAntimicrobial Peptides and Activities

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Mechanisms of Antibacterial Action of Three Monoterpenes

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Trombetta, Domenico, Castelli, Francesco, Sarpietro, Maria Grazia, Venuti, Vincenza, Cristani, Mariateresa, Daniele, Claudia, Saija, Antonella, Mazzanti, Gabriela, Bisignano, Giuseppe·2005·Antimicrobial Agents and Chemotherapy

DOI 10.1128/aac.49.6.2474-2478.2005PMC PMC1140516

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Abstract

In the present paper, we report the antimicrobial efficacy of three monoterpenes [linalyl acetate, (+)menthol, and thymol] against the gram-positive bacterium Staphylococcus aureus and the gram-negative bacterium Escherichia coli. For a better understanding of their mechanisms of action, the capability of these three monoterpenes to damage biomembranes was evaluated by monitoring the release, following exposure to the compounds under study, of the water-soluble fluorescent marker carboxyfluorescein from unilamellar vesicles with different lipidic compositions (phosphatidylcholine, phosphatidylcholine/phosphatidylserine [9:1], phosphatidylcholine/stearylamine [9:1], and phosphatidylglycerol/cardiolipin [9:1]). Furthermore, the interaction of the terpenes tested with dimyristoylphosphatidylcholine multilamellar vesicles as model membranes was monitored by means of differential scanning calorimetry. Finally, the results were related to the relative lipophilicity and water solubility of the compounds examined. Taken together, our findings lead us to speculate that the antimicrobial effect of (+)menthol, thymol, and linalyl acetate may result, at least partially, from a perturbation of the lipid fraction of microorganism plasma membrane, resulting in alterations of membrane permeability and in leakage of intracellular materials. Besides being related to physicochemical characteristics of the drugs (such as lipophilicity and water solubility), this effect seems to be dependent on lipid composition and net surface charge of microbial membranes. Furthermore, the drugs might cross the cell membranes, penetrating into the interior of the cell and interacting with intracellular sites critical for antibacterial activity.

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Authors: Trombetta, D., Castelli, F., Sarpietro, M. G., Venuti, V., Cristani, M., Daniele, C., Saija, A., Mazzanti, G., & Bisignano, G.
Affiliations: University of Messina (IT)
University of Catania (IT)
Department of Pharmacology of Natural Substances and General Physiology, University of Rome “La Sapienza,” Rome, Italy
Sapienza University of Rome (IT)
ORCID: Trombetta, Domenico
Castelli, Francesco
Sarpietro, Maria Grazia
Cristani, Mariateresa
Saija, Antonella
Bisignano, Giuseppe
Venue: Antimicrobial Agents and Chemotherapy
Publisher: American Society for Microbiology
Published: 2005-06
Volume: 49
Issue: 6
Pages: 2474-2478
ISSN: 0066-4804 (ISSN-L)
1098-6596
DOI: 10.1128/aac.49.6.2474-2478.2005
PMC: PMC1140516
OpenAlex: W2164168857
Cited by: 1,359
References: 27
Citations by year: 2026: 74 · 2025: 87 · 2024: 102 · 2023: 91 · 2022: 129 · 2021: 130 · 2020: 127 · 2019: 94 · 2018: 88 · 2017: 73 · 2016: 73 · 2015: 47 · 2014: 54 · 2013: 41 · 2012: 43
FWCI: 21.81
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: journals.asm.org/non-commercial-tdm-license (tdm)
Locations: Antimicrobial Agents and Chemotherapy (publishedVersion)
Europe PMC (PubMed Central) (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
IRIS Research product catalog (Sapienza University of Rome) (submittedVersion)
Topics: Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Antimicrobial agents and applications
Life Sciences › Immunology and Microbiology › Microbiology › Antimicrobial Peptides and Activities
Keywords: monoterpenes, linalyl acetate, menthol, thymol, antibacterial mechanism, Staphylococcus aureus, Escherichia coli, membrane damage, membrane permeability, lipid vesicles, membrane lipid composition, membrane surface charge, lipophilicity, water solubility, antimicrobial activity
MeSH terms: Anti-Bacterial Agents, Calorimetry, Differential Scanning, Cell Membrane, Cell Membrane Permeability, Escherichia coli, Fluoresceins, Lipids, Liposomes, Menthol, Microbial Sensitivity Tests, Staphylococcus aureus, Thymol, Monoterpenes

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