Search Results (20)

Volatile sulfur compounds (VSCs) are known to cause characteristic—and sometimes unpleasant—body odour. Human presence may influence the odour of indoor air; however, the contribution of skin-derived VSCs has not been thoroughly evaluated. This study aimed to elucidate the regional and whole-body dermal emission rates of VSCs—diallyl disulfide (DADS), allyl methyl sulfide (AMS), ethyl mercaptan (EMT), allyl mercaptan (AMT) and dimethyl trisulfide (DMTS)—by conducting simultaneous and multi-point measurements of dermal emissions from the human skin surface to assess their potential impact on indoor air quality. Dermal emission fluxes of VSCs were measured at 14 anatomical regions of 12 healthy young subjects using a passive flux sampler coupled with gas chromatography/mass spectrometry. These fluxes were converted to emission rates using regional body surface area, and the whole-body emission rates were subsequently used to estimate indoor air concentrations for comparison with the odour thresholds of each VSC. The results showed that although some regional differences in emission rates were observed among subjects, the large inter-individual variability ultimately led to no significant differences in whole-body emission rates of VSCs between males and females. Using the average whole-body emission rates across 12 subjects, the estimated indoor air concentrations of VSCs followed the descending order: EMT > AMT >> DMTS > AMS > DADS. The odour quotient was used to evaluate the impact of skin-derived VSCs on indoor air quality and indicated that EMT consistently contributes to indoor odour. Full article

Background: Metabolic Syndrome (MetS) is a multifactorial condition characterized by insulin resistance, dyslipidemia, hypertension, and abdominal obesity, which collectively increase the risk of type 2 diabetes mellitus and cardiovascular diseases. Lifestyle modification represents the first-line strategy in its management, whereas pharmacological interventions are complex and typically require long-term polypharmacotherapy. In this context, natural bioactive compounds with pleiotropic effects are gaining increasing attention. Among these, S-allyl cysteine (SAC), the major sulfur-containing compound derived from black garlic, has been identified as a promising candidate due to its well-documented antioxidant and anti-inflammatory properties. Methods: This narrative review examines the pathophysiological mechanisms underlying MetS and summarizes current evidence on the protective role of SAC against key pathological features of this condition, including oxidative stress, inflammation, glucose and lipid dysmetabolism, endothelial dysfunction, and gut microbiota alterations. Results: Preclinical studies indicate that SAC counteracts lipid accumulation, insulin resistance, endothelial dysfunction, and gut dysbiosis through multiple mechanisms, including hydrogen sulfide release, reactive oxygen species scavenging, inhibition of advanced glycation end products, and modulation of metabolic pathways. Conclusions: SAC emerges as a promising nutraceutical for the prevention and management of MetS and its complications. This underscores the broader relevance of nutraceuticals as promising tools in mitigating metabolic dysfunctions and reducing the burden of cardiometabolic diseases. Full article

Garlic consumption is a well-known cause of unpleasant breath and body odour, with volatile organosulfur compounds, such as diallyl disulfide (DADS) and allyl methyl sulfide (AMS) responsible for the characteristic odour. Certain foods that are rich in polyphenols (PPs) and polyphenol oxidase (PPO) are known to deodorise garlic breath. However, no study into garlic body odour has been reported owing to the very low amounts of emitted volatile organosulfur compounds. Herein, we aimed to demonstrate the effects of ingesting natural food additives rich in both PPs and PPO on the emissions of skin-derived DADS and AMS using a passive flux sampler in conjunction with gas chromatography–mass spectrometry. Three healthy male subjects were subjected to garlic-consumption testing, with all subjects commonly observed to exhibit remarkably higher dermal DADS- and AMS-emission fluxes after consuming 45 g of cooked garlic, which then gradually decreased toward their initial baseline levels. In comparison, remarkably lower emission fluxes of both organosulfur compounds were observed after consuming a natural food additive following garlic consumption in a dose-dependent manner. The optimal amount of ingested natural food additive required to reduce garlic body odour was found to be 1–2 g. Considering the metabolic pathway associated with garlic-derived sulfur compounds and elimination reactions involving PPs and PPO, allyl mercaptan is likely to be a key substance involved in reducing garlic body odour through the ingestion of natural food additives. Full article

S-allyl-L-cysteine (SAC) is a sulfur compound present in fresh garlic. The reference literature describes its anticancer, antioxidant and neuroprotective effects. Breast cancer is infamously known as one of the most commonly diagnosed malignancies among women worldwide. Its morbidity and mortality make it reasonable to complete and expand knowledge on this cancer’s characteristics. Hydrogen sulfide (H₂S) and its naturally occurring donors are well-known investigation subjects for diverse therapeutic purposes. This study was conducted to investigate the SAC antiproliferative potential and effect on three enzymes involved in H₂S metabolism: 3-mercaptopyruvate sulfurtransferase (MPST), cystathionine γ-lyase (CTH), and cystathionine β-synthase (CBS). We chose the in vitro cellular model of human breast adenocarcinomas: MCF-7 and MDA-MB-231. The expression of enzymes after 2, 4, 6, 8, and 24 h incubation with 2.24 mM, 3.37 mM, and 4.50 mM SAC concentrations was examined. The number of living cells was determined by the MTS assay. Changes in cellular plasma membrane integrity were measured by the LDH test. Expression changes at the protein level were analyzed using Western blot. A significant decrease in viable cells was registered for MCF-7 cells after all incubation times upon 4.50 mM SAC exposure, and after 6 and 24 h only in MDA-MB-231 upon 4.50 mM SAC. In both cell lines, the MPST gene expression significantly increased after the 24 h incubation with 4.50 mM SAC. S-allyl-L-cysteine had opposite effects on changes in CTH and CBS expression in both cell lines. In our research model, we confirmed the antiproliferative potential of SAC and concluded that our studies provided current information about the increase in MPST gene expression mediated by S-allyl-L-cysteine in the adenocarcinoma in vitro cellular model for the MCF-7 and MDA-MB-231 cell lines. Further investigation of this in vitro model can bring useful information regarding sulfur enzyme metabolism of breast adenocarcinoma and regulating its activity and expression (gene silencing) in anticancer therapy. Full article

This study aimed to determine the influence of using black garlic (BG) at different levels on organic volatile compounds in heat-treated sucuk (HTS), a semi dry fermented sausage. Three independent batches of sausages were prepared: control: 1% white garlic (WG): WG-1%; BG-1%: 1% BG; BG-2%: 2% BG; and BG-3%: 3% BG. After stuffing, the sausages were subjected to fermentation, heat treatment (internal temperature of 64 °C), and drying, respectively. After production, the final products were analyzed for volatile compounds. A solid-phase microextraction technique was used for the extraction of volatile compounds, and identification was carried out by a gas chromatograph/mass spectrometer. A total of 47 volatile compounds, including sulfur compounds, alcohols, esters, ketones, aliphatic hydrocarbons, acids, aromatic hydrocarbons, aldehydes, and terpenes, were identified from the sausages. The use of BG in HTS had no significant effect on aliphatic hydrocarbons, acids, ketones, aromatic hydrocarbons, and esters. BG increased the abundances of 2-propen-1-ol, allyl methyl sulfide, methyl 2-propenyl-disulfide, sabinene, β-pinene, and β-phellandrene regardless of the increase in the addition rate. BG-3% increased the level of hexanal. According to the PCA results, BG-containing groups showed positive correlation with esters, sulfur compounds, aldehydes, aromatic hydrocarbons, and alcohols, but these chemical groups were more closely correlated with BG-3%. In addition, diallyl disulfide, which is one of the main factors that causes the pungent and spicy smell of garlic, showed a close correlation with WG-1%. Full article

To identify the volatile flavor components in mustard paste (MP), the volatile compounds in seven MPs available on the market were isolated and analyzed by headspace solid-phase microextraction combined with gas chromatography–mass spectrometry. A total of 27 volatile constituents were found by mass spectra and retention index compared to the data obtained from reference compounds or the related literature and databases; these compounds included nine esters, three sulfur-containing compounds, two nitriles, three ketones, three alkenes, and seven other compounds. Of the 27 compounds, 6 compounds came from the turmeric added to MPs. Among the components detected, some compounds derived from AITC were allyl thiocyanate, carbon disulfide, allyl mercaptan, diallyl sulfide, and diallyl disulfide. The results obtained provide a better and comprehensive recognition of the volatile flavor compounds in MPs, and have some reference values for developing and applying isothiocyanate compounds. Full article

The regiospecific S-benzylation/allylation of two 4-aryl-5-indolyl-1,2,4-triazole-3-thione precursors was carried out using Et₃N as a base. Allyl group migration from exocyclic sulfur to the triazole nitrogen (N3) was successfully achieved in a short time via thermal fusion without the need for any catalyst. The allylation of indole nitrogen, along with exocyclic sulfur or triazole nitrogen (N3), was carried out using K₂CO₃ as stronger base. S,N-Diallylated products were converted to N,N-diallylated analogues using a simple fusion approach. Structural analyses of the two newly synthesized hybrids 2b and 5b investigated via the X-ray diffraction of a single crystal combined with Hirshfeld calculations. The compound 5b was crystallized in a monoclinic crystal system and the P2₁/c space group, whereas in compound 2b, the crystal system comprises the less symmetric triclinic and P − 1 space group. The asymmetric unit contains one and two molecules of 5b and 2b, respectively, while the unit cell contains four molecules in both cases. Hirshfeld analysis was performed in both systems to analyze the non-covalent interactions that control molecular packing. For 5b, C…H, N…H, S…H, Cl…N and H…H interactions are the most significant. Their percentages are 23.7, 8.8, 4.5, 1.2 and 48.2, respectively. In the case of 2b, the Cl…C, S…N, C…H, H…H and N…H interactions have the upper hand in molecular packing. In one unit, the percentages of these contacts are 2.3, 0.9, 26.8, 38.7 and 9.3%, while in the other unit, the corresponding values are 4.4, 1.3, 22.1, 43.6 and 9.0%, respectively. Full article

This work aimed to evaluate the chemical composition of the essential oils (EOs) of two cultivars of Allium sativum and their antibiofilm activity against the food pathogens Acinetobacter baumannii, Escherichia coli, Listeria monocytogenes, and Staphylococcus aureus. The crystal violet assay ascertained the susceptibility of the bacterial biofilms, while the MTT assay let to evaluations of the metabolic changes occurring in the bacterial cells within biofilms. Their chemical composition indicated some sulfuric compounds (i.e., allicin, diallyl disulfide, and allyl propyl disulfide), and decene as some of the main components of the EOs. The aerial parts and bulbs’ EOs from the two cultivars showed chemical differences, which seemed to affect the antibiofilm activity. The EOs from aerial parts of ‘Bianco del Veneto’ inhibited the biofilm formation of L. monocytogenes and E. coli (60.55% and 40.33%, respectively). In comparison, the ‘Staravec’ EO inhibited the cellular metabolism of E. coli (62.44%) and S. aureus (51.52%) sessile cells. These results indicate their possible use as preserving agents in the food industry and suggest their potential exploitation in the development of new formulations to avoid or limit nosocomial infections. Full article

Reactive Sulfur Species (RSS), such as allicin from garlic or sulforaphane from broccoli, are fre-quently associated with biological activities and possible health benefits in animals and humans. Among these Organic Sulfur Compounds (OSCs) found in many plants and fungi, the Volatile Sulfur Compounds (VSCs) feature prominently, not only because of their often-pungent smell, but also because they are able to access places which solids and solutions cannot reach that easily. Indeed, inorganic RSS such as hydrogen sulfide (H₂S) and sulfur dioxide (SO₂) can be used to lit-erally fumigate entire rooms and areas. Similarly, metabolites of garlic, such as allyl methyl sulfide (AMS), are formed metabolically in humans in lower concentrations and reach the airways from inside the body as part of one’s breath. Curiously, H₂S is also formed in the gastrointestinal tract by gut bacteria, and the question of if and for which purpose this gas then crosses the barriers and enters the body is indeed a delicate matter for equally delicate studies. In any case, nature is surprisingly rich in such VSCs, as fruits (for instance, the infamous durian) demonstrate, and therefore these VSCs represent a promising group of compounds for further studies. Full article

This research examined the changes of black garlic (BG) quality attributes when raw materials of different initial moisture contents (iMC) were used. Fresh garlic bulbs (cv. Thai) were shade-dried for eight weeks at a controlled condition at 29 °C and relative humidity (RH) of 55% to the desired iMC (ranging from ca. 50–70%). BG processing was at 75 °C, RH = 80% for ten days. After processing, physiological characteristics and chemical properties of garlic were determined. Results illustrated that fresh garlic with higher moisture content (ca. 70%) resulted in BG of a dark brown colour, sloppy texture, and lesser acidity (pH = 4.44), while samples with lower iMCs (<50%) gave products that were completely black, elastic in texture, and with higher acidity (pH = 3.79). The analysed bioactive compounds, as well as their antioxidative potentials, suggested that the longer the curing time, the higher the functional properties of the finished products, possessing a total phenolic, total flavonoid content, and antioxidant activity of 15.54 mg/kg dry matter sample, 1.53 mg/kg dry matter sample, and 95.39%, respectively. Principle component analysis (PCA) of active metabolites confirmed that sulfur, S-allyl-L-cysteine, and flavonoid were among the main phytochemicals found in the BG. In summary, higher quality BG can be achieved by using raw materials of lower iMC. Full article

The belowground pest Bradysia odoriphaga (Diptera: Sciaridae) has a sophisticated and sensitive olfactory system to detect semiochemical signals from the surrounding environment. In particular, odorant-binding proteins (OBPs) are crucial in capturing and transporting these semiochemical signals across the sensilla lymph to the corresponding odorant receptors. In this study, we cloned a full-length cDNA sequence of BodoOBP8 from B. odoriphaga. Real-time PCR (qRT-PCR) analysis revealed that BodoOBP8 has the highest expression levels in males, with more pronounced expression in the male antennae than in other tissues. In this study, the recombinant protein BodoOBP8 was successfully expressed by a bacterial system to explore its function. Competitive binding assays with 33 host plant volatiles and one putative sex pheromone (n-heptadecane) revealed that purified BodoOBP8 strongly bound to two sulfur compounds (methyl allyl disulfide and diallyl disulfide) and to n-heptadecane; the corresponding dissolution constants (Ki) were 4.04, 6.73, and 4.04 μM, respectively. Molecular docking indicated that Ile96, Ile103, Ala107, and Leu111, located in the hydrophobic cavity of BodoOBP8, are the key residues mediating the interaction of BodoOBP8 with two sulfur compounds (methyl allyl disulfide and diallyl disulfide) and n-heptadecane. These results show that BodoOBP8 plays a role in the recognition of plant volatiles and sex pheromones, suggesting its application as a molecular target for the screening of B. odoriphaga attractants and repellents and facilitating a new mechanism of B. odoriphaga control. Full article

A novel family of [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (N-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the α-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli was evaluated. Compounds with high antibacterial activity were found. Full article

The effects of some sulfur-containing compounds on the isomerization and degradation of lycopene, phytofluene, and phytoene under different thermal treatment conditions were studied in detail. Isothiocyanates such as allyl isothiocyanate (AITC) and polysulfides like dimethyl trisulfide (DMTS) had the effect on the configuration of PTF (phytofluene), PT (phytoene), and lycopene. The proportion of their naturally occurring Z-isomers (Z1,2-PTF and 15-Z-PT) decreased and transformed into other isomers including all-trans configuration, while Z-lycopene increased significantly after thermal treatment, especially for 5-Z-lycopene. The results showed that increase in heating temperature, time, and the concentration of DMTS and AITC could promote the isomerization reaction effectively to some extent. In addition, 15-Z-PT and the newly formed Z4-PTF were the predominant isomers in tomato at the equilibrium. Unlike the lycopene, which degraded significantly during heat treatment, the isomers of PTF and PT were stable enough to resist decomposition. Moreover, the isomerization of three carotenoids was enhanced, and the bioaccessibility of lycopene increased significantly with the addition of shii-take mushroom containing sulfur compounds, while there was no positive effect observed in that of PTF and PT. Full article

The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO₃ affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90–92% yield. Similar sulfides were obtained in 70–72% yields by the reaction of sulfur dichloride in chloroform under reflux. Trihalotellanes containing the same organic moieties were synthesized from allyl thymol, allyl carvacrol and tellurium tetrachloride or tetrabromide in quantitative yields. Corresponding functionalized ditellurides were prepared in 91–92% yields by the reduction of the trichlorotellanes with sodium metabisulfite in two-phase solvent system. The comparison of reactivity of sulfur, selenium and tellurium halides in chalcogenocyclofunctionalization and distinguishing features of each reaction were discussed. Full article

The interaction between plant defensive metabolites and different plant-associated fungal species is of high interest to many disciplines. Volatile organic compounds (VOCs) are natural products that are easily evaporated under ambient conditions. They play a very important role in inter-species communication of microbes and their hosts. In this study, the VOCs produced by 43 different fungal isolates of endophytic and soil fungi during growth on horseradish root (Armoracia rusticana) extract or malt extract agar were examined, by using headspace-gas chromatography-mass spectrometry (headspace-GC-MS) and a high relative surface agar film as a medium. The proposed technique enabled sensitive detection of several typical VOCs (acetone, methyl acetate, methyl formate, ethyl acetate, methyl butanol isomers, styrene, beta-phellandrene), along with glucosinolate decomposition products, including allyl cyanide and allyl isothiocyanate and other sulfur-containing compounds—carbon disulfide, dimethyl sulfide. The VOC patterns of fungi belonging to Setophoma, Paraphoma, Plectosphaerella, Pyrenochaeta, Volutella, Cadophora, Notophoma, and Curvularia genera were described for the first time. The VOC pattern was significantly different among the isolates. The pattern was indicative of putative myrosinase activity for many tested isolates. On the other hand, endophytes and soil fungi as groups could not be separated by VOC pattern or intensity. Full article