Antibacterial Activity of Long-Chain Fatty Alcohols against Staphylococcus aureus

Togashi, Naoko; Shiraishi, Akiko; Nishizaka, Miki; Matsuoka, K.; Endo, Kazutoyo; Hamashima, Hajime; Inoué, Yoshihiro

doi:10.3390/12020139

Cited by 140 publications

(94 citation statements)

References 22 publications

(23 reference statements)

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“…The greatest growth inhibition activity is seen in long-chained fatty alcohols with an aliphatic carbon chain of 12 or 13 carbon atoms. The fatty alcohols with aliphatic chains of fewer than 7 carbon atoms have no activity, and alcohols with chains longer than 17 carbon atoms have very low antimicrobial effect [31]. Considering the structure of fatty alcohols identified in the chloroform extracts of E. palmatum, it can be presumed that these compounds contribute to the observed antimicrobial activity.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

et al. 2013

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The chemical composition, antimicrobial and antioxidant activity of Eryngium palmatum, an endemic plant species from the Balkan Peninsula, were investigated. The flavonoids apigenin (9.5±0.3 mg g−1) and apigenin 7-O-glucoside (2.4±0.1 mg g−1) were determined in a methanol extract of aerial parts using HPLC analysis. The methanol extract of roots contained catechin (5.0±0.1 mg g−1), epicatechin (2.9±0.1 mg g−1), chlorogenic acid (1.6±0.0 mg g−1), gallic acid (0.9±0.0 mg g−1) and rosmarinic acid (0.9±0.2 mg g−1). GC-FID and GCMS analysis of a chloroform extract of aerial parts showed that the main volatile constituents were falcarinol, linoleic acid, hexadecanoic acid and methyl linoleate (comprising 32.6%; 24.4%; 19.9; 13.2% of the volatile fraction, respectively), while octanoic acid, tetradecanol and dodecanol dominated in the chloroform extract of the roots (34.9%; 25.8%; 22.2% of the volatile fraction, respectively). Investigation of antimicrobial activity by broth microdilution showed that the methanol and chloroform extracts of aerial parts and roots exerted a significant effect (MIC 3.5–15.6 μg mL−1) against tested Gram-positive and Gram-negative bacteria. The methanol extracts of aerial parts or roots exerted moderate ferric reducing antioxidant power, DPPH radical scavenging activity and hydroxyl radical scavenging activity.

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Section: Antimicrobial Activitymentioning

confidence: 99%

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

et al. 2013

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“…For example, antibacterial activity of long-chain fatty alcohols against S. aureus varied with the length of the aliphatic carbon chain 30 . The amount of absorption on bacteria surface and membrane damaging ability of C16:1 fatty acid Ca salt will be evaluated to explain the bactericidal ability of these fatty acid Ca salts.…”

Section: Bactericidal Properties Of C16:1 Fatty Acid Ca Saltmentioning

confidence: 99%

Palmitoleic Acid Calcium Salt: A Lubricant and Bactericidal Powder from Natural Lipids

et al. 2015

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“…1-Decanol, a model surfactant, partitions into the membrane due to its amphipathic properties (20,54) and induces depolarization independently of lipid II. We reasoned that if the modified culture conditions did not influence membrane properties, then 1-decanol would maintain its depolarization activity across all conditions.…”

Section: Effect Of Telavancin On Bacterial Membrane Potentialmentioning

confidence: 99%

Telavancin Disrupts the Functional Integrity of the Bacterial Membrane through Targeted Interaction with the Cell Wall Precursor Lipid II

Lunde

Hartouni

Janc

et al. 2009

Antimicrob Agents Chemother

159

125

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The increasing prevalence of serious infections caused by gram-positive bacteria, including those caused by methicillin (meticillin)-resistant Staphylococcus aureus (MRSA), highlights the need for new agents with enhanced antimicrobial properties (2,10,21,26,35). One promising approach has been the development of lipoglycopeptide antibiotics, semisynthetic derivatives of glycopeptides that contain hydrophobic substituents and that possess improved antimicrobial properties (1,4,13,32,39). Telavancin, a lipoglycopeptide derivative of vancomycin, exhibits enhanced potency in vitro, concentration-dependent bactericidal activity, and activity both in vitro and in vivo against organisms that display reduced susceptibility to vancomycin (17,18,23,24,28,31,33,36,42). Telavancin has been evaluated in phase III clinical trials for the treatment of complicated skin and skin structure infections and hospitalacquired pneumonia (46,53).The bactericidal action of telavancin results from a mechanism that includes the inhibition of cell wall synthesis and the disruption of essential membrane barrier functions (25). Telavancin possesses the glycopeptide core of vancomycin, which binds with a high affinity to the acyl-D-alanyl-D-alanine (DAla-D-Ala) terminus of cell wall precursors through a network of hydrogen bonds and hydrophobic packing interactions (3, 45). Inhibition of cell wall synthesis by telavancin therefore involves binding to late-stage peptidoglycan precursors, including membrane-embedded lipid II. These interactions prevent both the polymerization of the precursor into peptidoglycan and subsequent cross-linking events. Telavancin also binds to bacterial membranes and causes membrane depolarization and increased membrane permeability. The mechanism by which telavancin binds to and disrupts the function of the bacterial membrane has not been determined.The present study was undertaken to further explore the interaction of telavancin with the bacterial membrane. Using a flow cytometry assay optimized for the accurate measurement of membrane potential in bacteria, we demonstrate that telavancin causes pronounced, concentration-dependent depolarization in S. aureus cells. Isolates of S. aureus expressing important and emerging resistance phenotypes, such as MRSA, heterogeneous vancomycin-intermediate S. aureus (hVISA), vancomycin-intermediate S. aureus (VISA), and daptomycinnonsusceptibile MRSA, are equally susceptible to depolarization by telavancin. We provide evidence, through multiple lines of investigation, that membrane disruption by telavancin requires binding to the bacterial specific target, lipid II. Finally, we demonstrate that telavancin does not lyse bacteria during the time course that membrane effects are assayed. Importantly, the latter observation indicates that telavancin-induced membrane depolarization is not a consequence of a weakened * Corresponding author. Mailing address:

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Antibacterial Activity of Long-Chain Fatty Alcohols against Staphylococcus aureus

Cited by 140 publications

References 22 publications

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

Composition, antimicrobial and antioxidant activity of the extracts of Eryngium palmatum Pančić and Vis. (Apiaceae)

Palmitoleic Acid Calcium Salt: A Lubricant and Bactericidal Powder from Natural Lipids

Telavancin Disrupts the Functional Integrity of the Bacterial Membrane through Targeted Interaction with the Cell Wall Precursor Lipid II

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