Bioactivity and morphological changes of bacterial cells after exposure to 3-(p-chlorophenyl)thio citronellal

Goldbeck, Júlia Coswig; Victoria, Francine Novack; Motta, Amanda de Souza da; Savegnago, Lucielli; Jacob, Raquel G.; Perin, Gelson; Lenardão, Eder J.; Silva, Wladimir Padilha da

doi:10.1016/j.lwt.2014.05.036

Cited by 31 publications

(15 citation statements)

References 30 publications

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“…Coriander seeds oil also has more activity against Gram-positive bacteria than Gram-negative bacteria, which is attributed to differences in cell wall structure of Gram-positive and Gram-negative bacteria. This was consistent with the research results ( Ijaz Hussain et al., 2008 ; Karakaya et al., 2012 ; Goldbeck et al., 2014 ). The outer membrane of Gram-negative bacteria has a highly hydrophilic surface that prevents the penetration of hydrophobic compounds ( Rivera Calo et al., 2015 ).…”

Section: Resultssupporting

confidence: 94%

“…Bacteria were largely destroyed and the integrity of the cell wall and their appearance were almost completely destroyed. Many researchers have reported that the possible mechanisms of the essential oils and their derivatives include cell wall destruction, cytoplasmic membrane damage, damage to membrane proteins, intracellular content leakage, and cytoplasmic coagulation ( Goldbeck et al, 2014 ; Swamy et al., 2016 ). Based on the analysis of SEM images, it seems that the cell wall and the membrane of pathogenic bacteria are the main targets of the essential oils.…”

Section: Resultsmentioning

confidence: 99%

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Microwave-assisted hydrodistillation extraction of essential oil from coriander seeds and evaluation of their composition, antioxidant and antimicrobial activity

Ghazanfari

Mortazavi

Yazdi

et al. 2020

Heliyon

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Coriander seeds essential oil is used in food preparation, perfume, cosmetics and pharmaceuticals. In this study, extraction of essential oil from coriander seeds was done by hydrodistillation (HD) and microwave assisted hydrodistillation (MAHD) methods. Chemical composition, total phenol contents, antimicrobial and antioxidant properties of essential oils were measured and the results were compared between HD and MAHD methods. Scanning electron microscopy (SEM) results showed that the essential oils had inhibitory effect on the bacterial membrane and cell wall. Results showed that total phenol contents and antioxidant activity increased under heat and microwave conditions. Coriander seeds essential oil had a very strong effect on Candida albicans . Gram-positive bacteria were more sensitive to the essential oil of coriander seeds than Gram-negative bacteria. The essential oil extracted by MAHD showed better antimicrobial activity, higher phenols yield and antioxidant activity. According to the results of GC-MS, linalool was the most common constituent of both essential oils.

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Section: Resultssupporting

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Microwave-assisted hydrodistillation extraction of essential oil from coriander seeds and evaluation of their composition, antioxidant and antimicrobial activity

Ghazanfari

Mortazavi

Yazdi

et al. 2020

Heliyon

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“…Distorted bacterial membrane with no enclosed DNA was later visualized upon the longer incubation period, in accordance with the amount of released proteins and nucleic acids quantified in the supernatant. Additionally, severe damages at the surface including cell rupture and alterations in cellular morphology as demonstrated in SEM micrographs of both 630 and R20291 strains were consistent with the damages previously observed in other bacteria ( Hartmann et al, 2010 ; Goldbeck et al, 2014 ; Hong et al, 2015 ). These data suggested that AA potentially acts on cell membrane and causes substantial membrane rupture on C. difficile.…”

Section: Discussionsupporting

confidence: 88%

Antimicrobial Effect of Asiatic Acid Against Clostridium difficile Is Associated With Disruption of Membrane Permeability

et al. 2018

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Antibiotic resistance is a major concern in Clostridium difficile, the causative agent of antibiotic-associated diarrhea. Reduced susceptibility to first- and second-line agents is widespread, therefore various attempts have been made to seek alternative preventive and therapeutic strategies against this pathogen. In this work, the antimicrobial properties of asiatic acid were evaluated against C. difficile. Asiatic acid displayed substantial inhibitory effects on 19 C. difficile isolates collected from different sources with minimal inhibitory concentrations ranging from 10 to 20 μg/ml. Time kill analysis and minimal bactericidal concentration revealed potential bactericidal activity of this compound. Asiatic acid induced membrane damages and alterations in morphological ultrastructure in C. difficile, thereby causing the leakage of intracellular substances. Moreover, asiatic acid also displayed an inhibitory effect on cell motility, but did not interfere with biofilm formation and spore germination. Analysis of drug combination showed no synergistic effect between asiatic acid and vancomycin/metronidazole. Altogether, asiatic acid exhibited strong antimicrobial activity against vegetative cells and could serve as an alternative resource for tackling C. difficile.

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“…Interestingly, compound 5a , having a phenylthio group in the α-position, inhibited B. cereus selectively, presenting MIC and MBC values of 0.48 mM and 0.59 mM, respectively. The antibacterial activity of 3-( p -chlorophenyl)thio citronellal, a close-related compound to 3a , was recently studied by us [ 27 ] and it showed inhibitory activity against Gram-positive L. monocytogenes and S. aureus (MIC of 2.1 mM) and Gram-negative bacteria S. Typhimurium, S. dysenteriae, E. coli , and P. fluorescens (MIC of 4.2 mM).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal

et al. 2017

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Background: The main constituents of Cymbopogonnardus (L) Rendle and C. citratus (DC) Stapfessential oils are (R)-citronellal and citral, respectively. Organochalcogen compounds can boost the biological activities of natural products. Methods: Several chalcogen-containing nitrones derived from (R)-citronellal and citral were prepared and evaluated for their antimicrobial and antioxidant activities. The antimicrobial activity was evaluated by the disc diffusion test and the antioxidant properties were evaluated in vitro by DPPH (1,1-diphenyl-2-picryl-hydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), and FRAP (ferric ion reducing antioxidant power) assays. Results: In the antimicrobial assay, (E)-N,3,7-trimethyl-3-(phenylthio)oct-6-en-1-imine oxide 5c exhibited halos between 21.5 mm (Escherichia coli O157:H7) and 26.0 mm (Listeria monocytogenes), while (E)-N,3,7-trimethyloct-6-en-1-imine oxide 5d presented halos between 22.5 mm (E. coli O157:H7) and 31.0 mm (L. monocytogenes). (E)-N,3,7-Trimethyl-2-(phenylthio)oct-6-en-1-imine oxide 5a showed the lowest minimal inhibitory concentration (MIC) value against Bacillus cereus (0.48 mM), and 5c was the most potent bactericide, with a minimal bactericidal concentration (MBC) of 0.52 mM for E. coli O157:H7. In the antioxidant assays, 5c, 5d, and 10 ((E)-3,7-dimethyl-2-(phenylselanyl)oct-6-enal oxime) were the most actives in the DPPH, ABTS, and FRAP assays, respectively. Conclusions: The presence of a phenylthio group in the nitrone increases its antimicrobial activity against Gram-positive and Gram-negative foodborne pathogens in the disk diffusion test and the antioxidant activity in vitro.

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Bioactivity and morphological changes of bacterial cells after exposure to 3-(p-chlorophenyl)thio citronellal

Cited by 31 publications

References 30 publications

Microwave-assisted hydrodistillation extraction of essential oil from coriander seeds and evaluation of their composition, antioxidant and antimicrobial activity

Microwave-assisted hydrodistillation extraction of essential oil from coriander seeds and evaluation of their composition, antioxidant and antimicrobial activity

Antimicrobial Effect of Asiatic Acid Against Clostridium difficile Is Associated With Disruption of Membrane Permeability

Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal

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