4-hydroxy-3-methoxy-trans-stilbene/MOPEG sulfate potassium salt/2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol/4-hydroxy-3-methoxystilbene/4-hydroxy-3-methoxyphenylethylene glycol 4-sulfate potassium salt/NOREPINEPHRINE METABOLITE-D3 POTASSIUM SALT/MHPG SULFATE POTASSIUM SALT/(E)-isoeugenol/Phenol, 2-methoxy-4-[(1E)-1-propen-1-yl]-/Isoeugenol/4-hydroxy-3-methoxy-phenylglycol4-sulfate/trans-4-hydroxy-3-methoxystilbene/2-Methoxy-4-[(1E)-1-propen-1-yl]phenol/3-Methoxy-4-Hydroxyphenylglycol Sulfate/4-HYDROXY-3-METHOXYPHENYLGLYCOL*4-SULFAT E POTASSIUM/MOPEG SULFATE/(E)-2-methoxy-4-(prop-1-enyl)phenol/4-HYDROXY-3-METHOXYPHENYLGLYCOL SULFATE POTASSIUM SALT/MHPG SULFATE/2-Methoxy-4-[(1E)-1-propen-1-yl]phenol
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This increase in the prevalence of drug-resistant pathogens occurs at a time when the discovery and development of new antimicrobial agents occur slowly. In this context, the objective of this study was to investigate the antifungal activity of isoeugenol, a phenylpropanoid, by in vitro and in silico assays against Penicillium citrinum strains.
MATERIAL AND METHOD:
For in silico analysis, the software PASS online, Molinspiration and Osiris were used. For the determination of Minimum Inhibitory Concentration (MIC) and Minimal Fungicide Concentration (MFC) of isoeugenol and voriconazole were carried out using the broth microdilution technique. PASS online has shown that isoeugenol has the opportunity to present antiseptic, antifungal, antibacterial, antimycobacterial activities. Molinspiration showed that the phytoconstituent has good potential for oral bioavailability.
In the analysis with the Osiris program, it was demonstrated that isoeugenol has low irritant and tumorigenic risk. The MIC of isoeugenol varied between 256 and 32 µg/mL, MIC50 of 64 µg/mL and MIC90 was 128 µg/mL. The MFC50, MFC90 and MFC of the isoeugenol for P. citrinum species were 64, 256 and 518 μg/mL, respectively. After analysis, it was verified that the isoeugenol have bactericidal effect against the strains of P. citrinum. After these results, it is important to discover the mechanism of action involved in the antifungal action of the compound, as well as in vitro and in vivo toxicity tests.
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Antifungal activity; Antimicrobian activity; Bioavailability; In silico analysis; Isoeugenol; Phenylpropanoids; Toxicity.
In Silico and In Vitro Investigation of the Antifungal Activity of Isoeugenol against Penicillium citrinum.
Ferreira SB1, Dantas TB1, de Figuerêdo Silva D1, Ferreira PB1, de Melo TR1, de Oliveira Lima E1.
Pathogenic bacteria can spread between individuals or between food items via the surfaces they share. Limiting the survival of pathogens on surfaces, therefore, presents an opportunity to limit at least one route of how pathogens spread. In this study, we propose that a simple coating with the essential oil isoeugenol can be used to circumvent the problem of bacterial transfer via surfaces.
METHODS AND RESULTS:
Two commonly used materials, stainless steel and polyethylene, were coated by physical adsorption, and the coatings were characterized by Raman spectroscopy, atomic force microscopy and water contact angle measurements. We quantified and visualized the colonization of coated and uncoated surfaces by three bacteria: Staphylococcus aureus, Listeria monocytogenes and Pseudomonas fluorescens. No viable cells were detected on surfaces coated with isoeugenol.
The isoeugenol coating prepared with simple adsorption proved effective in preventing biofilm formation on stainless steel and polyethylene surfaces. The result was caused by the antibacterial effect of isoeugenol, as the coating did not diminish the adhesive properties of the surface.
SIGNIFICANCE AND IMPACT OF THE STUDY:
Our study demonstrates that a simple isoeugenol coating can prevent biofilm formation of S. aureus, L. monocytogenes and P. fluorescens on two commonly used surfaces.
© 2017 The Society for Applied Microbiology.
Listeria monocytogenes ; Pseudomonas fluorescens ; Staphylococcus aureus ; biofilm; essential oil; isoeugenol; polyethylene; stainless steel
Antibacterial isoeugenol coating on stainless steel and polyethylene surfaces prevents biofilm growth.
Nielsen CK1, Subbiahdoss G1, Zeng G1, Salmi Z2, Kjems J1, Mygind T3, Snabe T3, Meyer RL1,4.
Isoeugenol is widely used by the cosmetic and fragrance industries, but it also represents a known cause of skin sensitization adverse effects. Although devoid of a structural alert, isoeugenol has been classified as prehapten in virtue of the presence of a pre-Michael acceptor domain. Isoeugenol oxidation could theoretically lead to the generation of reactive toxic quinones, and photoinduced oxidative degradation of isoeugenol was reported to generate strongly thiol reactive byproducts. Nonetheless, the isoeugenol degradation product responsible for increased reactivity was found to be elusive. In the present study, an aged isoeugenol sample was subjected to reactivity-guided experiments to trap elusive thiol reactive species with a fluorescent nucleophile, viz. dansyl cysteamine (DCYA). The results herein presented demonstrate that photo-oxidation of isoeugenol led to the formation of a dimeric 7,4′-oxyneolignan with strong chemical reactivity, capable of nucleophilic substitution with thiols. The results were confirmed by isolation, structural characterization, and further NMR reactivity studies. Isoeugenol is already well-known as moderately reactive in thiol depletion assays, and was herein demonstrated to be capable of converting to more potent electrophilic species upon degradation, thus acting as a prehapten. The application of the reactivity-guided strategy described herein was shown to serve as an effective tool to investigate elusive skin sensitizers.
Is Isoeugenol a Prehapten? Characterization of a Thiol-Reactive Oxidative Byproduct of Isoeugenol and Potential Implications for Skin Sensitization.
Ahn J1, Avonto C1, Chittiboyina AG1, Khan IA1,2.
2020 Apr 20