Search Results (94)

An amino acid-derived 2-thiohydantoin, 5-(2-methylsulfanylethyl)-3-prop-2-enyl-2-sulfanylideneimidazolidin-4-one, obtained from l-methionine, was synthesized in a two-step reaction protocol with allyl isothiocyanate. The compound was obtained in an 82% yield and was fully structurally characterized by NMR and IR spectroscopy. The crystal structure, molecular packing, and intermolecular interactions were characterized by X-ray diffraction analysis. Full article

The aim of this study was to prevent the development of microorganisms in the refrigerated storage of tench by releasing allyl isothiocyanate (AITC) produced by black mustard seeds. Tench reared in an aquaculture centre were sacrificed and the fillets were separated. Different amounts of defatted mustard seed (300, 400 and 500 mg) were added to hermetic polypropylene trays. Microbiological, sensory, and gas chromatography with MS detection analysis were done. AITC release increased progressively until the third day of storage, significantly delaying the development of microorganisms in samples with higher mustard seed content. The tasting panel detected positive aromas at the beginning of the study, but these decreased and negative aromas appeared. The mustard seed treatment resulted in a higher positive aroma at the end of the storage, reducing rotting and ammonia odours. A total of 31 volatile compounds were detected and grouped into hydrocarbon, alcohol, benzenoid, isothiocyanate, ketone, acetate, aldehyde, and others. Butylated hydroxytoluene, an indicator of bacterial contamination, was the major aromatic compound found during storage. The release of AITC resulted in fewer organic compounds with negative aromas appearing during storage. PCA analysis allowed us to classify the assays during storage according to their volatile profiles, confirming the differences observed between treatments. Thus, adding mustard seed to fish packaging could be a viable alternative to extending the product’s shelf life and ensuring food safety. Full article

Allyl isothiocyanate (AITC) is a naturally occurring, pungent compound abundant in cruciferous vegetables and functions as a repellent for various organisms. The antibacterial effect of AITC against various bacteria has been reported, but there are no reports on the effect on Streptococcus mutans, a major bacterium contributing to dental caries. In this study, we investigated the inhibitory effect and mechanism of AITC on the survival and growth of S. mutans. AITC showed an antibacterial effect in a time- and concentration-dependent manner. In addition, bacterial growth was delayed in the presence of AITC, and there were almost no bacteria in the presence of 0.1% AITC. In a biofilm assay, the amount of biofilm formation with 0.1% AITC was significantly decreased compared to the control. RNA sequencing analysis showed that the expression of 39 genes (27 up-regulation and 12 down-regulation) and 38 genes (24 up-regulation and 14 down-regulation) of S. mutans was changed during the survival and the growth, respectively, in the presence of AITC compared with the absence of AITC. Protein–protein interaction analysis revealed that AITC mainly interacted with genes of unknown function in S. mutans. These results suggest that AITC may inhibit cariogenicity of S. mutans through a novel mechanism. Full article

Tillage is a major factor influencing soil biological communities, particularly earthworms, which play a key role in soil structure and nutrient cycling. To address soil degradation, less-intensive tillage practices are increasingly being adopted globally and have shown positive effects on earthworm populations when applied consistently over extended periods. However, understanding of the earthworm population dynamics in the period following the implementation of changes in tillage practices remains limited. This three-year field study (2021–2023) investigates earthworm populations during the early transition phase (4–6 years) following the conversion from conventional ploughing to conservation (<8 cm depth, with residue retention) and no-tillage systems in a temperate arable system in central Slovenia. Earthworms were sampled annually in early October from three adjacent fields, each following the same three-year crop rotation (maize—winter cereal + cover crop—soybeans), using a combination of hand-sorting and allyl isothiocyanate (AITC) extraction. Results showed that reduced tillage practices significantly increased both earthworm biomass and abundance compared to conventional ploughing. However, a significant interaction between tillage and year was observed, with a sharp decline in earthworm abundance and mass in 2022, likely driven by a combination of 2022 summer tillage prior to cover crop sowing and extreme drought conditions. Juvenile earthworms were especially affected, with their proportion decreasing from 62% to 34% in ploughed plots and from 63% to 26% in conservation tillage plots. Despite interannual fluctuations, no-till showed the lowest variability in earthworm population. Long-term monitoring is essential to disentangle management and environmental effects and to inform resilient soil management strategies. Full article

In this study, in order to overcome the fragility and cost disadvantages of PHB-based films, PHB was blended with PCL. Additionally, allyl isothiocyanate (AITC) was incorporated as an active component. The resulting PHB, PCL, and PHB/PCL composite films with/without allyl isothiocyanate (AITC) prepared via the casting method were analyzed for their physicochemical, thermal, mechanical, barrier, morphological properties and antimicrobial and antioxidant activities. While neat PHB films showed the highest tensile strength (TS) of 19.82 MPa and the lowest elongation at break (EB) of 1.13%, PHB/PCL blend films exhibited lower TS (15.34 MPa) and higher EB values (21.33%). AITC addition decreased TS significantly while showing no significant impact on EB. PHB/PCL blend films had the highest water vapor permeability (WVP) values, possibly due to their increased porosity, while neat PCL- and PHB-based films showed better oxygen and water vapor barrier properties, respectively. DSC analysis showed that PHB and PCL films had a crystalline phase, while in the case of PHB/PCL blend films, both polymers maintained their characteristic melting behaviors. The addition of AITC affected the thermal stability by increasing the melting temperature of the PHB films and decreasing the melting temperature of the PCL films. SEM analyses revealed that PHB and PHB-A films had a homogeneous structure, while irregular spherical structures and cracks were also observed in PCL and PCL-A films. The incorporation of AITC into the film samples (PHB-A, PCL-A, and PHB/PCL-A) brought remarkable antimicrobial (from 16.25 mm to 37.25 mm of inhibition zones) and antioxidant activity (from 281.85 to 286.41 mg trolox equivalent/1 g film sample, as measured by CUPRAC), while no activity was observed in the control films without AITC (PHB, PCL, and PHB/PCL). In conclusion, new AITC-activated PHB-, PCL-, and PHB/PCL-based films were successfully designated with additional functionalities and showed valuable potential to be used in active biodegradable food packaging applications. Full article

The preservation of chilled fresh pork is an issue that has widely drawn significant attention. A novel microcapsule was developed in this study, specifically a composite plant essential oil microcapsule (CEO mps) prepared using gum arabic (GA) and an inclusion compound of allyl isothiocyanate (AITC) with β-cyclodextrin (β-CD), in which AITC is encapsulated within the cavity of β-CD molecules. In this formulation, AITC functions as an antibacterial agent, while the essential oils provide antioxidant properties that further enhance bacterial inhibition. The encapsulation ratio of AITC to β-CD was optimized at 1:1, with nuclear magnetic resonance (NMR) hydrogen spectroscopy confirming that AITC was incorporated into β-CD through its wider cavity. The morphology and structure of CEO mps were characterized using Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), and laser particle size analysis, and these were compared to those of AITC mps—microcapsules prepared with GA and β-CD as wall materials and AITC as the core material. The results indicated that CEO mps exhibited superior appearance and physical stability in comparison to AITC mps. The release rate of CEO mps was evaluated using gas chromatography–mass spectrometry (GC/MS), revealing sustained release characteristics. On day 12, cumulative releases for AITC, eugenol, cuminal, and thymol were 61.82%, 57.96%, 44.34%, and 38.65%. Finally, the efficacy of CEO mps in preserving chilled pork was assessed by measuring pH levels, total volatile base nitrogen (TVB-N), color parameters (L*, a*, b*), thiobarbituric acid-reactive substances (TBARSs), water loss, and total microbial counts. The results demonstrated that CEO mps significantly inhibited microbial growth in chilled pork, reduced TBARS and TVB-N values, and helped preserve meat color integrity, thereby effectively extending shelf life by approximately six days. Overall, the experimental findings confirmed that the developed CEO mps possess both antibacterial and antioxidant properties, thereby improving both the shelf life and organoleptic quality of chilled pork. Full article

Parasitic nematodes, particularly those in the Rhabditidae family, are vital components of belowground ecosystems, contributing to pest regulation and sustainable agriculture. This study investigated the chemotactic responses of three nematode species—Phasmarhabditis papillosa, Oscheius myriophilus, and O. onirici—to volatile organic compounds (VOCs) emitted by Brassica nigra roots under herbivory by Delia radicum larvae. Using a chemotaxis assay, the effects of five VOCs (dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, phenylethyl isothiocyanate, and benzonitrile) were tested at two concentrations (pure and 0.03 ppm) and two temperatures (18 °C and 22 °C). The results revealed that VOCs and temperature significantly influenced nematode responses, while nematode species and VOC concentration showed limited effects. Benzonitrile consistently demonstrated strong chemoattractant properties, particularly for O. myriophilus and O. onirici. Conversely, allyl isothiocyanate exhibited potent nematicidal effects, inhibiting motility and causing mortality. Dimethyl disulfide and dimethyl sulfide elicited moderate to strong attractant responses, with species- and temperature-dependent variations. Significant interactions between VOCs, temperature, and nematode species highlighted the complexity of these ecological interactions. These findings emphasize the ecological roles of VOCs in mediating nematode behavior and their potential applications in sustainable pest management. Benzonitrile emerged as a promising candidate for nematode-based biocontrol strategies, while allyl isothiocyanate showed potential as a direct nematicidal agent. The study underscores the importance of integrating chemical cues into pest management systems to enhance agricultural sustainability and reduce reliance on chemical pesticides. Full article

Allyl isothiocyanate (AITC) is a low-molecular-weight natural chemical predominantly obtained from the autolysis of sinigrin, a glucosinolate found in cruciferous vegetables like mustard, horseradish, and wasabi. AITC has sparked widespread interest due to its various biological actions, which include strong antioxidant, anti-inflammatory, antibacterial, and anticancer capabilities. This compound offers promising potential in several fields, particularly in food preservation, medicine, and enhancing food quality through natural means. AITC’s effectiveness against a broad spectrum of microorganisms, including foodborne pathogens and spoilage agents, makes it an attractive natural alternative to synthetic preservatives. The potential to extend the shelf life of perishable foods makes AITC an important tool for food production, meeting rising customer demand for natural additives. In addition to its antimicrobial effects, AITC demonstrates significant anti-inflammatory activity, reducing levels of pro-inflammatory cytokines and modulating key signaling pathways, which could make it valuable in managing chronic inflammatory conditions. Furthermore, emerging research highlights its potential in cancer prevention and treatment, as AITC has been demonstrated to induce apoptosis and inhibit cell increase in several cancer cell lines, offering a natural approach to chemoprevention. This review delves into the chemical structure, metabolism, and bioavailability of freshly produced AITC, providing a comprehensive overview of its beneficial properties. Challenges related to AITC’s volatility, dosage optimization, and regulatory considerations are also discussed, alongside future research directions to enhance the stability and efficacy of AITC-based formulations. The findings underscore AITC’s role as a versatile bioactive compound with known potential to support human health and the sustainable food industry. Full article

The present study aimed to investigate the ability of an aqueous extract derived from mustard seed meal to counteract the effects of E. coli endotoxin lipopolysaccharide (LPS) on the intestinal epithelium. Caco-2 cells were cultured together with HT29-MTX and used as a cellular model to analyze critical intestinal parameters, such as renewal, integrity, innate immunity, and signaling pathway. Byproducts of mustard seed oil extraction are rich in soluble polysaccharides, proteins, allyl isothiocyanates, and phenolic acids, which are known as powerful antioxidants with antimicrobial and antifungal properties. Cells were seeded at a ratio of nine (Caco-2) to one (HT29-MXT) and treated for 2 h with mustard meal extract (ME, dilution 1/50) and zinc oxide (ZnO, 50 μM) after reaching 80–100% confluence. Then, they were challenged with 5 μg/mL E. coli-LPS and incubated for another 4 h. The results show that LPS did not alter the cell viability but decreased proliferation compared to the control, ME and ZnO treatments. LPS altered the cell membrane integrity and monolayer permeability by decreasing the transepithelial electrical resistance and tight-junction protein expression. In addition, LPS increased the activity of LDH and the expression of Toll-like receptors. The mechanisms by which LPS induces these disturbances involves the overexpression of PKC, p38 MAPK, and NF-κB signaling molecules. The pretreatment with mustard meal and ZnO succeeded in counteracting the impairment of epithelial renewal, the damage of the membrane integrity and permeability as well as in restoring the gene expression of tight-junction proteins. Full article

Isothiocyanates (ITCs), found in edible plants such as cruciferous vegetables, are a group of reactive organo-sulfur phytochemicals produced by the hydrolysis of precursors known as glucosinolates. ITCs have been studied extensively both in vivo and in vitro to define their therapeutic potential for the treatment of chronic health conditions. Therapeutically, they have shown an intrinsic ability to inhibit oxidative and inflammatory phenotypes to support enhanced health. This review summarizes the current evidence supporting the observation that the antioxidant and anti-inflammatory activities of ITCs temper the pathogenic effects of a group of reactive metabolites called advanced glycation end products (AGEs). AGE exposure has significantly increased across the lifespan due to health risk factors that include dietary intake, a sedentary lifestyle, and comorbid conditions. By contributing to a chronic cycle of inflammatory stress through the aberrant activation of the transmembrane receptor for AGE (RAGE), increased AGE bioavailability is associated with chronic disease onset, progression, and severity. This review debates the potential molecular mechanisms by which ITCs may inhibit AGE bioavailability to reduce RAGE-mediated pro-oxidant and pro-inflammatory phenotypes. Bringing to light the molecular impact that ITCs may have on AGE biogenesis may stimulate novel intervention strategies for reversing or preventing the impact of lifestyle factors on chronic disease risk. Full article

This study aimed to enhance the properties and compostability of active poly(lactic acid) (PLA) films by incorporating β-cyclodextrin (β-CD) inclusion complexes with allyl isothiocyanate (AITC). Films were prepared using melt extrusion and characterized based on their structural, chemical, morphological, thermal, and barrier properties. These inclusion complexes improved the thermal stability and moisture absorption of films, enhancing disintegration under composting conditions. The release of AITC in the vapor phase was responsive to relative humidity, maintaining the antimicrobial functionality at low values and releasing effectively at higher humidity levels, with a maximum release at 100%. Incorporating 5% and 10% β-CD:AITC complexes accelerated disintegration under composting conditions, reducing the time by 5 days for disintegration compared to pure PLA, achieving up to 90% in 23 days. These results, with a general improvement in functional properties, suggest that PLA films with β-CD:AITC are promising for developing sustainable, biodegradable antimicrobial packaging solutions for food applications. Full article

Biofumigation was proposed as an alternative to synthetic pesticides for the disinfection of agricultural soils, in view of the biocidal effect of isothiocyanates (ITCs) released by some vegetal species, like Brassicaceae. However, biofumigation also presents limitations; thus, a novel and viable alternative could be the direct introduction of ITCs into agricultural soils as components loaded into biodegradable hydrogels. Thus, in this work, ITCs-based microemulsions were developed, which can be loaded into porous polymer-based hydrogel beads based on sodium alginate (ALG) or sodium carboxymethyl cellulose (CMC). Three ITCs (ethyl, phenyl, and allyl isothiocyanate) and three different surfactants (sodium dodecylsulfate, Brij 35, and Tween 80) were considered. The optimal system was characterized with attenuated ATR-FTIR spectroscopy and differential scanning calorimetry to study how the microemulsion/gels interaction affects the gel properties, such as the equilibrium water content or free water index. Finally, loading and release profiles were studied by means of UV–Vis spectrophotometry. It was found that CMC hydrogel beads showed a slightly more efficient profile of micelles’ release in water with respect to ALG beads. For this reason, and due to the enhanced contribution of Fe(III) to their biocidal properties, CMC-based hydrogels are the most promising in view of the application on real agricultural soils. Full article

Reactions with allyl-, acetyl-, and phenylisothiocyanate have been studied on the basis of 3-amino-4,6-dimethylpyridine-2(1H)-one, 3-amino-4-phenylpyridine-2-one, and 3-amino-4-(thiophene-2-yl)pyridine-2(1H)-one (benzoyl-)isothiocyanates, and the corresponding thioureide derivatives 8-11a-c were obtained. Twelve thiourea derivatives were obtained and studied for their anti-diabetic activity against the enzyme α-glucosidase in comparison with the standard drug acarbose. The comparison drug acarbose inhibits the activity of α-glucosidase at a concentration of 15 mM by 46.1% (IC₅₀ for acarbose is 11.96 mM). According to the results of the conducted studies, it was shown that alkyl and phenyl thiourea derivatives 8,9a-c, in contrast to their acetyl–(benzoyl) derivatives and 10,11a-c, show high antidiabetic activity. Thus, 1-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-phenylthiourea 9a has the highest inhibitory activity against the enzyme α-glucosidase, exceeding the activity of the comparison drug acarbose, which inhibits the activity of α-glucosidase by 56.6% at a concentration of 15 mm (IC₅₀ = 9,77 mM). 1-(6-methyl-2-oxo 4-(thiophen-2-yl)-1,2-dihydropyridin-3-yl)-3-phenylthiourea 9c has inhibitory activity against the enzyme α-glucosidase, comparable to the comparison drug acarbose, inhibiting the activity of α-glucosidase at a concentration of 15 mm per 41.2% (IC₅₀ = 12,94 mM). Compounds 8a, 8b, and 9b showed inhibitory activity against the enzyme α-glucosidase, with a lower activity compared to acarbose, inhibiting the activity of α-glucosidase at a concentration of 15 mM by 23.3%, 26.9%, and 35.2%, respectively. The IC₅₀ against α-glucosidase for compounds 8a, 8b, and 9b was found to be 16.64 mM, 19.79 mM, and 21.79 mM, respectively. The other compounds 8c, 10a, 10b, 10c, 11a, 11b, and 11c did not show inhibitory activity against α-glucosidase. Thus, the newly synthesized derivatives of thiourea based on 3-aminopyridine-2(1H)-ones are promising candidates for the further modification and study of their potential anti-diabetic activity. These positive bioanalytical results will stimulate further in-depth studies, including in vivo models. Full article

Osteosarcoma is a highly malignant, painful cancer with poor treatment opportunities and a bad prognosis. Transient receptor potential ankyrin 1 (TRPA1) and vanilloid 1 (TRPV1) receptors are non-selective cation channels that have been of great interest in cancer, as their expression is increased in some malignancies. In our study we aim to characterize the expression and functionality of the TRPA1 and TRPV1 channels in human and mouse osteosarcoma tissues and in a mouse cell line. TRPA1/Trpa1 and TRPV1/Trpv1 mRNA expressions were demonstrated by PCR gel electrophoresis and RNAscope in situ hybridization. The function of these channels was confirmed by their radioactive ₄₅Ca²⁺ uptake in response to the TRPA1 agonist, Allyl-isothiocyanate (AITC), and TRPV1 agonist, capsaicin, in K7M2 cells. An ATP-based K2M7 cell viability luminescence assay was used to determine cell viability after AITC or capsaicin treatments. Both TRPA1/Trpa1 and TRPV1/Trpv1 were expressed similarly in human and mouse osteosarcoma tissues, while Trpa1 transcripts were more abundantly present in K7M2 cells. TRPA1 activation with 200 µM AITC induced a significant ₄₅Ca²⁺ influx into K7M2 cells, and the antagonist attenuated this effect. In accordance with the lower Trpv1 expression, capsaicin induced a moderate ₄₅Ca²⁺ uptake, which did not reach the level of statistical significance. Both AITC and capsaicin significantly reduced K7M2 cell viability, demonstrating EC₅₀ values of 22 µM and 74 µM. The viability-decreasing effect of AITC was significantly but only partially antagonized by HC-030031, but the action of capsaicin was not affected by the TRPV1 antagonist capsazepine. We provide here the first data on the functional expression of the TRPA1 and TRPV1 ion channels in osteosarcoma, suggesting novel diagnostic and/or therapeutic perspectives. Full article

In this study, changes in volatile compounds co-fermented by different Pichia kluyveri with Saccharomyces cerevisiae were analyzed using GC-IMS and compared with S. cerevisiae fermentation, to investigate the production of aroma in mulberry wine during the fermentation process. A total of 61 compounds were accurately identified, including 21 esters, 10 alcohols, 8 aldehydes, 6 ketones, and 19 other volatiles. Compared with the single strain fermentation (S. cerevisiae), the content of 2-methylpropyl acetate, allyl Isothiocyanate, ethyl crotonate, isobutyl propanoate, and butyl 2-methylbutanoate, co-fermentation groups (S. cerevisiae with different P. kluyveri) showed a significant decrease. Alcohols, aldehydes, ketones, and organic acid were lower in both the F(S-P1) and F(S-P2) groups than in the F(S) group throughout fermentation. The 2-methylpentanoic acid only was contained in the F(S) group. The co-fermentation with different P. kluyveri could also be well distinguished. The content of Benzaldehyde and 4-methylphenol in the F(S-P1) group was significantly lower than that in the F(S-P2) group. The PCA results revealed effective differentiation of mulberry wine fermented by different fermentation strains from GC-IMS. The result showed that P. kluyveri could establish a new flavor system for mulberry wine, which plays a crucial role in enhancing the flavor of fruit wine. Full article