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ACS Organic & Inorganic Au Aug 2023Monodentate phosphine-ligated nickel compounds, , [Ni(PPh)] are relevant as active catalysts across a broad range of reactions. This report expands upon the coordination...
Monodentate phosphine-ligated nickel compounds, , [Ni(PPh)] are relevant as active catalysts across a broad range of reactions. This report expands upon the coordination chemistry of this family, offering the reactivity of allyl- and vinyl-substituted diphenylphosphine (PPhR) with [Ni(COD)] (COD = 1,5-cyclooctadiene). These reactions provide three-coordinate dinickelacycles that are intermolecularly tethered through adjacent {Ni}-olefin interactions. The ring conformation of such cycles has been studied in the solid-state and using theoretical calculations. Here, a difference in reaction outcome is linked to the presence of an allyl vs vinyl group, where the former is observed to undergo rearrangement, bringing about challenges in clean product isolation.
PubMed: 37545661
DOI: 10.1021/acsorginorgau.3c00010 -
Marine Drugs Oct 2023Natural products are a very rich source for obtaining new compounds with therapeutic potential. In the search for new antiparasitic and antimicrobial agents, molecular...
Natural products are a very rich source for obtaining new compounds with therapeutic potential. In the search for new antiparasitic and antimicrobial agents, molecular hybrids were designed based on the structures of antimicrobial marine quinazolinones and eugenol, a natural phenolic compound. Following reports of the therapeutic potential of quinazolinones and eugenol derivatives, it was expected that the union of these pharmacophores could generate biologically relevant substances. The designed compounds were obtained by classical synthetic procedures and were characterized by routine spectrometric techniques. Nine intermediates and final products were then evaluated in vitro against and . Antifungal and antibacterial activity were also evaluated. Six compounds (, , , , , and ) showed mild activity against with IC in the range of 11.17-31.68 μM. Additionally, intermediate showed anti- activity (IC 7.54 μM) and was six times less cytotoxic against THP-1 cells. In conclusion, novel derivatives with a simple quinazolinone scaffold showing selectivity against parasites without antibacterial and antifungal activities were disclosed, paving the way for new antitrypanosomal agents.
Topics: Antifungal Agents; Eugenol; Antiprotozoal Agents; Anti-Infective Agents; Trypanosoma brucei brucei; Anti-Bacterial Agents; Leishmania infantum; Quinazolinones; Structure-Activity Relationship
PubMed: 37999375
DOI: 10.3390/md21110551 -
Molecules (Basel, Switzerland) Jul 2023To 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...
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.
PubMed: 37513353
DOI: 10.3390/molecules28145482 -
Evidence-based Complementary and... 2024This study was conducted to isolate and identify the chemical compounds from the roots of (L.) and evaluate their antioxidant and antibacterial activities. From the...
This study was conducted to isolate and identify the chemical compounds from the roots of (L.) and evaluate their antioxidant and antibacterial activities. From the acetone (99.5%) extract of the roots of this plant, four anthraquinones, such as chrysophanol (), asphodeline (), aloesaponarin I (), and laccaic acid D-methyl ester (), and a new catechol derivative, 5-allyl-3-methoxybenzene-1,2-diol (), were isolated and elucidated by different chromatographic and spectroscopic methods together with linoleic acid (), respectively. Compounds , and were reported here for the first time from this plant and compound from the genus . The compounds were evaluated for their antioxidant activity using HO and DPPH assays and bactericidal activity against and . Compounds and showed highest antioxidant activities with IC values of 19.38 ± 0.64 and 32.81 ± 0.78 g/mL in DPPH, and 28.52 ± 1.08 and 27.31 ± 1.46 g/mL in HO, respectively. The isolated compounds also demonstrated considerable activity towards . Among these compounds, compound exhibited the highest activity (91.20 ± 0.12% and 9.14 ± 0.93 mm at 1.0 mg/mL) against this bacterium. The overall results suggest that the isolated compounds may be considered as potential sources of the bioactive agents to be used in the pharmacological, food, and other industries. Moreover, their high sensitivity against may also support the use of plant in the traditional medicine to treat wounds. Therefore, the isolated compounds are responsible for medicinal properties of this plant.
PubMed: 38746073
DOI: 10.1155/2024/6651648 -
Journal of Chromatography. A Aug 2023In this work, the simultaneous extraction of bioactives (organosulfur compounds, such as S-allyl-L-cysteine (SAC), carbohydrates, such as neokestose and neonystose, and...
In this work, the simultaneous extraction of bioactives (organosulfur compounds, such as S-allyl-L-cysteine (SAC), carbohydrates, such as neokestose and neonystose, and total phenolic compounds) from aged garlic has been optimized for the first time to obtain multifunctional extracts for further application as food ingredients. Analytical methods using liquid chromatography coupled to mass spectrometry (HPLC-MS) and by hydrophilic interaction liquid chromatography with evaporative light scattering detection (HILIC-ELSD) were also previously optimized. High sensitivity (limits of detection between 0.013 and 0.77 µg mL) and appropriate repeatability (< 12%) and accuracy (> 92%) for the analysis of bioactives were achieved. After selecting water as the extraction solvent and microwave-assisted extraction (MAE) as the most efficient technique, operation conditions were optimized using a Box-Behnken experimental design (60 min; 120 °C; 0.05 g mL; 1 cycle) to maximize the content of bioactives from different aged garlic samples. Regarding organosulfur compounds, only SAC (traces-2.32 mg g dry sample) and cycloalliin (1.23-3.01 mg g dry sample) were detected in all samples, while amino acids such as arginine (0.24-3.45 mg g dry sample) and proline (0.43-3.91 mg g dry sample) were, in general, the most abundant. Bioactive carbohydrates (from trisaccharides to nonasaccharides) were only detected in fresh garlic and aged garlic processed under mild conditions, whereas all garlic extracts showed antioxidant activity. The developed MAE methodology is shown as a successful alternative to other procedures for the simultaneous extraction of aged garlic bioactives intended by the food and nutraceutical industries, among others.
Topics: Garlic; Antioxidants; Microwaves; Chromatography, High Pressure Liquid; Carbohydrates; Plant Extracts
PubMed: 37302253
DOI: 10.1016/j.chroma.2023.464128 -
Scientific Reports Jul 2023Several Eurydema species (Hemiptera: Pentatomidae) are considered as pests, however, reports on their chemical ecology are scarce. In the current study we focused on...
Several Eurydema species (Hemiptera: Pentatomidae) are considered as pests, however, reports on their chemical ecology are scarce. In the current study we focused on Eurydema ornata (Linnaeus) a pentatomid pest of several brassicaceous crops. Since the species is known to feed preferably on generative parts of plants, a series of floral and green leaf volatiles were tested by electroantennography and compounds eliciting remarkable responses were also tested in the field. Three compounds elicited the most outstanding responses from antennae of E. ornata: allyl isothiocyanate, phenylacetaldehyde and ± linalool. Field experiments were conducted in Hungary between 2017 and 2021 to test the potential attractive effects of the compounds. Three Eurydema species were caught in the experiments E. ornata, E. oleracea (Linnaeus) and E. ventralis Kolenati. In the experiments combinations containing allyl isothiocyanate attracted both males and females of E. ornata. The compound was also attractive on its own, in a positive, dose-dependent manner. When presented alone, neither phenylacetaldehyde nor ± linalool was attractive to the species, furthermore, addition of these compounds to allyl isothiocyanate did not affect attraction considerably. To our knowledge this is the first demonstration of field attration of an Eurydema species to a semiochemical and one of the few reports on trapping of a pentatomid species with a synthetic plant volatile in the field. Perspectives regarding research and potential practical applications are discussed in the paper.
Topics: Animals; Male; Female; Hemiptera; Heteroptera; Acyclic Monoterpenes; Volatile Organic Compounds
PubMed: 37422493
DOI: 10.1038/s41598-023-37705-w -
Molecules (Basel, Switzerland) Jun 2023The development of the bamboo industry has been hindered by environmental issues caused by the application of bamboo preservatives. Chinese herbal phenolic compounds...
The development of the bamboo industry has been hindered by environmental issues caused by the application of bamboo preservatives. Chinese herbal phenolic compounds have been shown to possess broad-spectrum, potent antimildew properties, making them promising candidates for the development of new bamboo mildew inhibitors. In this study, we investigated the antimildew properties of three phenolic compounds, eugenol, carvacrol, and paeonol, against common mildews in bamboo materials using the Oxford cup method and the double-dilution method. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) were used to analyze the antimildew mechanism and its effects on mildew cell morphology. Our results showed that carvacrol exhibited the strongest antimildew activity, with minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) values of 1.56 mg/mL and 1.76 mg/mL, respectively, followed by eugenol and paeonol. At a concentration of 25 mg/mL, eugenol and carvacrol had an inhibitory rate of over 50% against various mildews. Different concentrations of the three compounds significantly disrupted the morphology and structural integrity of mildew hyphae, with the extent of damage increasing with concentration and treatment duration. In the sliced bamboo mildew prevention experiment, carvacrol at a concentration of 29.25 mg/mL was found to be highly effective against all tested mildews. Our study provides new insights and a theoretical basis for the development of eco-friendly bamboo mildew inhibitors based on plant phenolic compounds.
Topics: Eugenol; Monoterpenes; Cymenes; Phenols; Fungi
PubMed: 37446603
DOI: 10.3390/molecules28134941 -
Foods (Basel, Switzerland) Oct 2023This 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...
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%.
PubMed: 37893769
DOI: 10.3390/foods12203876 -
Scientific Reports Aug 2023Diabetes, characterized by high blood glucose level, is a progressive metabolic disease that leads to serious health complications. One of the major pathological...
Diabetes, characterized by high blood glucose level, is a progressive metabolic disease that leads to serious health complications. One of the major pathological consequences associated with diabetes is the accumulation of highly reactive carbonyl compounds called advanced glycation end products (AGEs). Most of the AGEs are dicarbonyls and have the potential to covalently modify proteins especially at the lysine residues in a non-enzymatic fashion (a process termed as glycation) resulting in the functional impairment and/or toxic gain in function. Therefore, non-toxic small molecules that can inhibit glycation are of interest for the therapeutic intervention of diabetes. In the present communication, we have investigated the effect of organosulfurs (S-allyl cysteine, SAC and N-acetyl cysteine, NAC) that are major principal components of Allium sativa against the glycation of different proteins. We discovered that both SAC and NAC are potent anti-glycating agents. We also found that both SAC and NAC reduce ROS level and inhibit apoptosis caused by protein glycation.
Topics: Acetylcysteine; Cysteine; Glycation End Products, Advanced; Antioxidants; Maillard Reaction
PubMed: 37567958
DOI: 10.1038/s41598-023-40291-6 -
Pharmacological Research Mar 2024In recent years, isothiocyanates (ITCs), bioactive compounds primarily derived from Brassicaceae vegetables and herbs, have gained significant attention within the... (Review)
Review
In recent years, isothiocyanates (ITCs), bioactive compounds primarily derived from Brassicaceae vegetables and herbs, have gained significant attention within the biomedical field due to their versatile biological effects. This comprehensive review provides an in-depth exploration of the therapeutic potential and individual biological mechanisms of the three specific ITCs phenylethyl isothiocyanate (PEITC), allyl isothiocyanate (AITC), and benzyl isothiocyanate (BITC), as well as their collective impact within the formulation of ANGOCIN® Anti-Infekt N (Angocin). Angocin comprises horseradish root (Armoracia rusticanae radix, 80 mg) and nasturtium (Tropaeoli majoris herba, 200 mg) and is authorized for treating inflammatory diseases affecting the respiratory and urinary tract. The antimicrobial efficacy of this substance has been confirmed both in vitro and in various clinical trials, with its primary effectiveness attributed to ITCs. PEITC, AITC, and BITC exhibit a wide array of health benefits, including potent anti-inflammatory, antioxidant, and antimicrobial properties, along with noteworthy anticancer potentials. Moreover, we highlight their ability to modulate critical biochemical pathways, such as the nuclear factor erythroid 2-related factor 2 (Nrf2)/Kelch-like ECH-associated protein 1 (Keap1), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), and signal transducer and activator of transcription (STAT) pathways, shedding light on their involvement in cellular apoptosis and their intricate role to guide immune responses.
Topics: Kelch-Like ECH-Associated Protein 1; NF-E2-Related Factor 2; Isothiocyanates; Anti-Infective Agents
PubMed: 38354869
DOI: 10.1016/j.phrs.2024.107107