Synthesis and in vitro evaluation of peracetyl and deacetyl glycosides of eugenol, isoeugenol and dihydroeugenol acting against food-contaminating bacteria

Resende, Déborah Braga; Martins, Heloísa Helena de Abreu; Souza, Thiago Belarmino de; Carvalho, Diogo Teixeira; Píccoli, Roberta Hilsdorf; Schwan, Rosane Freitas; Dias, Disney Ribeiro

doi:10.1016/j.foodchem.2017.06.056

Cited by 19 publications

(14 citation statements)

References 18 publications

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“…In recent years, various applications of essential oil components (EOCs) have been studied extensively due to market preferences for natural chemicals and growing concerns about the health and environmental safety of synthetic chemicals . Due to their antimicrobial activity, EOCs have emerged as suitable alternatives to synthetic pesticides, food preservatives, cosmetics, or pharmaceutical products, and essential oils and their components are in high demand in a number of industries …”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4][5][6][7] Due to their antimicrobial activity, EOCs have emerged as suitable alternatives to synthetic pesticides, food preservatives, cosmetics, or pharmaceutical products, and essential oils and their components are in high demand in a number of industries. [8][9][10][11][12][13][14] However, due to their high hydrophobicity, volatility and reactivity, EOCs quickly lose activity, limiting their practical application. 15 Formulation technologies for overcoming these drawbacks include nanoemulsions, 16 β-cyclodextrin encapsulation, 17 and various polymer-based films.…”

Section: Introductionmentioning

confidence: 99%

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The efficacy of essential oil components loaded into montmorillonite against Aspergillus niger and Staphylococcus aureus

Bernardos

Božík

Álvarez

et al. 2019

Flavour & Fragrance J

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Essential oil components (EOCs) are potent natural antimicrobial agents, but their high volatility and reactivity limit their potential applications. Here, we report the preparation of a series of nanomaterials containing EOCs (i.e., allyl isothiocyanate, carvacrol, cinnamaldehyde, diallyl disulphide, eugenol and thymol). The materials were prepared by simple adsorption of the EOCs onto a montmorillonite nanoclay. The antimicrobial activities of these materials were assessed against Aspergillus niger and Staphylococcus aureus as typical models of agricultural fungal pathogens and foodborne bacterial pathogens, respectively. In addition, the activities of the encapsulated EOCs were compared with those of the corresponding free forms with or without Tween‐80 in two types of assays: microdilution assays for determining the minimum inhibitory concentration (MIC) and agar‐based assays mimicking surface treatment. Enhanced antifungal activity of the encapsulated form was observed for all EOCs. In addition, against S. aureus, the MICs of all EOCs were remarkably lower in encapsulated form than in free form. These results indicate that EOCs encapsulated in low‐cost nanoclays have favourable potential as antimicrobials compared with the pure compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The efficacy of essential oil components loaded into montmorillonite against Aspergillus niger and Staphylococcus aureus

Bernardos

Božík

Álvarez

et al. 2019

Flavour & Fragrance J

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“…Four of our samples (3a, 3e, 3f, 3s) are matching the samples tested in antibacterial assays so far. [29][30][31] Eugenyl acetate (3a) was tested in a disc diffusion method on a set of seven Gram-positive and nine Gram-negative bacteria. 30 The results have shown notable antimicrobial effect against all sixteen bacteria tested, with a superior performance when compared to pure eugenol.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…[29][30][31] Eugenyl acetate (3a) was tested in a disc diffusion method on a set of seven Gram-positive and nine Gram-negative bacteria. 30 The results have shown notable antimicrobial effect against all sixteen bacteria tested, with a superior performance when compared to pure eugenol. 30 Even when different methodologies were employed, two crucial and completely opposed observations can be made; our results have shown that derivatives have never exceeded the activity of the parent compound and that all were inactive against Gram-negative bacteria taken into consideration.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Synthesis, Antimicrobial Activity and in silico Studies on Eugenol Eters

Lazarević

Kolarević

Stojanović

et al. 2018

ACSi

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The results presented herein represent our continued study based on the modification of phenolic functionality in molecules originated from natural sources by acylation. A small focused library of nineteen eugenyl esters, with four of which are new compounds, is reported. All compounds were subjected to in vitro antimicrobial testing. In silico studies were carried out calculating physico-chemical, pharmacokinetic and toxicological properties, providing more data as additional guidance for further research.

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Synthesis and Structure‐Activity Relationship Studies of Novel Aryl Sulfonamides and Their Activity against Human Breast Cancer Cell Lines

Azevedo-Barbosa

Ferreira-Silva

Vale

et al. 2022

Chemistry & Biodiversity

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A series of structural analogs of aryl sulfonamide hybrid compounds were synthesised and their cytotoxic activity was evaluated against three human breast cancer cell lines (MCF‐7, MDA‐MB‐231 and Hs 578T). The compounds were designed through electronic, hydrophobic and steric modifications using the chemical structure of N‐{4‐[(2‐hydroxy‐3‐methoxy‐5‐propylphenyl)sulfamoyl]phenyl}acetamide (referred to as compound 7) as a starting point to then assess a structure‐activity relationship (SAR) study. From the data generated, we observed that compounds 9, 10 and 11 (which have modifications in the substituents of the aryl sulfonamide), efficiently reduced the cell viability of MCF‐7 and MDA‐MB‐231 cell cultures. Based on initial data, we selected compounds 10 and 11 for further investigations into their antiproliferative and/or cytotoxic profile against MDA‐MB‐231 cells, and we noted that compound 10 was the most promising compound in the series. Compound 10 promoted morphological changes and altered the dynamics of cell cycle progression in MDA‐MB‐231 cells, inducing arrest in G1/S transition. Taken together, these results show that the dihydroeugenol‐aryl‐sulfonamide hybrid compound 10 (which has an electron withdrawing nitro group) displays promising antiproliferative activity against MDA‐MB‐231 cell lines.

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Synthesis and in vitro evaluation of peracetyl and deacetyl glycosides of eugenol, isoeugenol and dihydroeugenol acting against food-contaminating bacteria

Cited by 19 publications

References 18 publications

The efficacy of essential oil components loaded into montmorillonite against Aspergillus niger and Staphylococcus aureus

The efficacy of essential oil components loaded into montmorillonite against Aspergillus niger and Staphylococcus aureus

Synthesis, Antimicrobial Activity and in silico Studies on Eugenol Eters

Synthesis and Structure‐Activity Relationship Studies of Novel Aryl Sulfonamides and Their Activity against Human Breast Cancer Cell Lines

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