Molecules最新文献

Copper(II) complexes have great potential as antitumor and antimicrobial agents, and their coumarin derivatives bearing histamine substituents possess versatile structural and biological properties. The present article describes the synthesis of novel copper(II)-coumarin-histamine complexes and ligands and their characterization by IR, NMR, X-ray diffraction, and elemental analysis. Their antimicrobial activity (MIC, MBC/MFC) was tested against 11 reference strains. Cytotoxicity was evaluated using the MTT assay against 15 selected cancer cell lines and normal HMEC-1 cells. It presents three new ligands and three new complexes with copper(II) ions and selected histamine-containing coumarin derivatives. The new copper(II) complexes demonstrated markedly higher anticancer activity than their corresponding ligands across all evaluated cancer cell lines. The highest anticancer activity against the Hep3B liver cancer cell line was demonstrated by the copper(II) complex (3b), which also showed the strongest inhibition of S. epidermidis ATCC 12228 and S. aureus ATCC 6538. The copper(II) ions play a crucial role in the antitumor activity of these derivatives. Despite limited antimicrobial effects, the tested complexes, particularly 3a and 3b, demonstrate promising anticancer potential, especially against the Hep3B cancer cell line. Only 3b demonstrated antimicrobial activity against S. epidermidis ATCC 12228 and S. aureus ATCC 6538.

In order to achieve high-quality yields, it is essential to provide plants with the necessary nutrients, including selenium (Se) and sulphur (S), to meet their nutritional requirements. This study aimed to determine the effect of selenium (0, 10 and 20 g Se ha^-1) and the date of its application (in the tillering phase and in the stem elongation phase) and sulphur application (0, 15 and 30 kg S ha^-1) on the content of selenium and various forms of sulphur (total sulphur, sulphate sulphur and organic sulphur) and the N:S ratio in winter spelt wheat and winter common wheat. The research hypothesis assumed that different doses of selenium and sulphur and the timing of their application would have a beneficial effect on the Se and S content in the grain and straw of spelt wheat and common wheat. Selenium fertilisation significantly increased the content of this element in the grain of spelt wheat and common wheat. The concentration of selenium was also influenced by the timing of its application in the plant growth environment. However, the dose of selenium and the timing of its application were not associated with significant changes in the content of both forms of sulphur in the tested plants. The experimental factors used did not contribute to the achievement of selenium levels toxic to humans and animals. The presence of sulphur in the growth environment of spelt wheat and common wheat was associated with an increase in the content of both total sulphur, sulphate sulphur and organic sulphur in their grain and straw, especially in spelt wheat straw by an average of 17%, 29% and 23%, respectively, and in common wheat straw by 26%, 18% and 57%, respectively. The sulphur content in the plant growth environment was not associated with a change in the selenium content in the grain of the tested plants. The results of our study suggest that the optimal dose of selenium for biofortification of humans and animals is 20 mg Se ha^-1 on clay soil, applied during the stem elongation phase of spelt and common wheat. Biofortification of wheat with selenium and sulphur is a good method of supplementing deficiencies of this element in the human diet.

The challenges of glioblastoma multiforme treatment are related to limitations in tumor removal surgery, its high heterogeneity and aggressiveness, development of resistance to standard therapy, the blood-brain barrier, and the side and toxic effects of the conventional antitumor agents used in clinical practice. Although new treatment strategies continue to emerge, progress remains slow and has not resulted in substantial improvements in patient survival. The main goal of research in recent years has been aimed at developing ways to deal with all these challenges. One of the ways to improve the control of glioblastomas is the introduction of effective new antitumor agents. Metal complexes represent a particularly promising class of compounds in this context. This is why the aim of this study was to assess the effects of six homo- and heterometallic coordination compounds bearing Schiff base ligands-[Zn₂(Ampy)(µ-OH)(H₂O)₂](ClO₄)₂ (ZnAmpy), [Zn₂(Dmen)(µ-OH)(H₂O)₂](ClO₄)₂ (ZnDmen), ¹_∞[{Zn₂(Ampy)(μ₃-OH)}₂(H₂O){μ-[Au(CN)₂]}](ClO₄)₃·THF·H₂O (ZnAmpyAu), [{Zn₂(Dmen)(μ-OH)}₂{μ-[Au(CN)₂]}{[Au(CN)₂]₂}](ClO₄)·H₂O (ZnDmenAu), ¹_∞[Zn(Salampy){μ-Au(CN)₂}] (ZnSalampyAu), and ¹_∞[Zn(Saldmen)(μ-Au(CN)₂}] (ZnSaldmenAu)-on the viability and proliferation of 8MGBA and U251MG human glioblastoma multiforme cells (HDmen and HAmpy are bicompartmental Schiff base ligands resulting from the condensation of 2,6-diformyl-p-cresol with N,N-dimethylethylenediamine and 2-(aminomethyl)pyridine, respectively, while HSaldmen and HSalampy are tridentate Schiff base ligands obtained via condensation of salicylaldehyde with N,N-dimethylethylenediamine and 2-(aminomethyl)pyridine, respectively). Among these compounds, ZnSaldmenAu is a new compound and is reported here for the first time. Cytotoxicity of the compounds was evaluated through analysis of cell viability, 2D/3D growth, cytopathological alterations, and induction of cell death. The results obtained by methods with different targets in cells and the associated mechanisms of action revealed that the compounds investigated show promising cytotoxic/potential antitumor activity in treated cells.

Microorganisms wage constant chemical battles against one another as they compete for space and scarce nutrients, particularly within animal-associated habitats. Here, binary assays were used to investigate chemical interactions among Flavobacteriaceae within Neverita delessertiana egg collars, a moon snail common to the Gulf Coast. Analysis of 140 distinct pairings revealed eight that exhibited growth-inhibitory activity. Chemical evaluation of the crude extract from Cellulophaga omnivescoria EM610, which inhibited the growth of three other Flavobacteriaceae, resulted in the isolation of bacillimidazoles A (1) and E (2), two previously characterized metabolites, isolated from a marine Bacillus species. Further work demonstrated that these compounds are readily formed spontaneously by condensation of 2,3-butanedione with phenethylamine and/or tryptamine. Tandem mass spectrometry analysis of the chemical extracts of individual moon snail egg collars revealed the presence of bacillimidazole A in 62% of the egg collars.

Tea's chemical composition is influenced by cultivar, harvest maturity, and growing environment; however, processing remains the dominant factor shaping final quality. Despite the diversity of Taiwanese native teas, systematic comparisons of functional components across multiple manufacturing stages remain limited. In this study, nine representative Taiwanese teas were evaluated at four key processing stages-green tea (G), enzymatic fermentation (oxidative fermentation, F), semi-finished tea prior to roasting (S), and completed tea (C)-to clarify how enzymatic oxidation, rolling, and roasting alter major bioactive constituents. Green-tea-stage samples exhibited clear cultivar-dependent profiles: large-leaf cultivars contained higher catechins and gallic acid, whereas bud-rich small-leaf teas showed elevated caffeine and amino acids, with amino acids further enhanced at higher elevations. Fermentation intensity governed the major chemical transitions, including catechin depletion, gallic acid formation, accumulation of early stage catechin-derived paired oxidative polymerization compounds (POPCs), and pronounced increases in theasinensins in heavily fermented teas. L-theanine decreased most markedly in teas subjected to prolonged withering. Roasting further reduced amino acids but had minimal influence on caffeine, while rolling effects varied by tea type. Overall, this study provides the first stage-resolved chemical map of Taiwanese native teas, offering practical insights for optimizing processing strategies to enhance functional phytochemical profiles.

Chrysanthemums are appreciated not only for their ornamental and medicinal attributes but also as edible plants long incorporated into teas, infusions, and culinary traditions. Yet, hybrid cultivars specifically adapted to European growing conditions remain poorly characterized with respect to their medicinal potential. In this study, we investigated the phytochemical composition, antioxidant properties, and enzyme-inhibitory activities of inflorescences of four field-grown Chrysanthemum × morifolium 'Donna' × C. rubellum 'Clara Curtis' hybrids of European origin (CD 7, DC 19, DC 26, CD 46). Their profiles were compared with those of a Chinese tea cultivar (C. morifolium CHR18) and a commercial herbal product (CH B). Chemical constituents were analyzed using GC-MS and LC-MS, while antioxidant activity was evaluated by FRAP, CUPRAC, DPPH, ABTS, and iron-chelating assays; hyaluronidase (HYAL) and butyrylcholinesterase (BChE) inhibition were also assessed. A total of 61 volatile compounds were identified, with several terpenoids-such as chrysanthenone and verbenone-occurring exclusively in the European hybrids. CHR 18 possessed the highest flavonoid and phenolic acid levels, whereas hybrid CD 46 exhibited the most pronounced overall antioxidant performance. Hyaluronidase inhibition was strongest in DC 26 and CD 46 (60-62%), surpassing both reference samples, while BChE inhibition remained generally low. Overall, the results highlight that C. morifolium × C. rubellum hybrids developed for cultivation in the temperate European climate offer a unique combination of phytochemical richness, robust antioxidant activity, and noteworthy enzyme inhibition. These traits underscore their promise as emerging functional chrysanthemum resources and support future applications in European herbal products, nutraceutical development, and region-specific functional food innovation.

Gram-positive cocci of the Enterococcus genus, despite their prevalence in the environment and the microbiota of healthy people, have become a serious threat in hospitals as opportunistic pathogens. These bacteria have many virulence factors and intrinsic resistance to existing drugs, which significantly narrows the group of effective antimicrobials. Due to the spread of Multi-Drug-Resistant (MDR) strains, there is a need to search for new substances as potential antibiotics. Our work aimed to evaluate the antimicrobial effect of commercially available products (five oils containing cannabidiol (CBD) and its derivatives and one 99% CBD product in the form of crystals) on 20 clinical strains of E. faecalis and E. faecium. We determined the Minimal Inhibitory Concentration (MIC) of CBD oils using the microdilution method in Mueller-Hinton broth (MHB). The CBD displayed antibacterial properties against all tested Enterococcus spp. strains (MIC ≤ 1 μg/mL). The higher concentration of CBD resulted in a larger antibacterial effect. The obtained MICs of pure CBD and CBD crystals were statistically lower (W = 97, p < 0.001) for E. feacium than E. faecalis. This work confirms the antibacterial activity of CBD on Enterococcus spp., providing a solid basis for further research that can help identify new therapeutic options and gain a deeper understanding of the CBD mechanism of action.

Diseases caused by oxidative stress can present different susceptibilities depending on blood typing according to the ABO system and RhD factor, which turn out to be of great clinical importance. The use of antioxidants such as C-phycocyanin (a phycobiliprotein) could be an alternative to mitigate oxidative stress in the blood. Therefore, the objective of this study is to evaluate the antioxidant and erythroprotective activity of C-phycocyanin (C-PC) from Spirulina sp. against oxidative stress caused by peroxyl radicals, before and after in vitro digestion, comparing susceptibilities between blood groups. C-phycocyanin from Spirulina sp. was obtained commercially. The antioxidant capacity by ABTS+•, DPPH•, and FRAP assays of the bioaccessible fraction of C-PC increased compared to baseline in all assays. Samples appear to have high hydrogen atom transfer. C-PC is not cytotoxic in most blood groups. The AAPH hemolysis assays showed differences between blood groups, yielding results of 27.90, 22.60, 26.94, 27.66, 28.16, 28.34, and 24.91% hemolysis for O+, O-, A+, A-, B+, AB+, and AB-, respectively. Furthermore, in vitro digestion increased the erythroprotective effect in the bioavailable fraction in most blood groups, showing 37.12, 80.13, 5.48, 92.38, 67.93, 80.30, and 76.49% inhibition of hemolysis in O+, O-, A+, A-, B+, AB+, and AB-, respectively. These results demonstrate the biotechnological and biomedical potential of phycobiliproteins as safe candidates for the development of nutraceuticals and functional foods aimed at preventing oxidative damage.

In the present study the stereoselective addition of malononitrile to trifluoromethyl arylketimines promoted by chiral iminophosphoranes was investigated. A panel of structurally diverse enantiopure bifunctional superbases, which include thiourea or squaramide unit and a basic site connected by a chiral scaffold, was tested in the asymmetric organocatalytic reaction, to afford an adduct featuring a quaternary stereocenter, in up to a 87/13 enantiomeric ratio. The product was then converted in a single step transformation into the corresponding enantioenriched α-CF₃ substituted quaternary aminoester, without any loss of stereochemical integrity. The absolute configuration of the final product was established by chemical correlation of the chiral compound with a known molecule. Preliminary computational studies were performed in order to elucidate the reaction mechanism and rationalize the stereochemical outcome of the reaction.

The glioblastoma multiforme (GBM) microenvironment, characterized by hypoxia and inflammation, is a principal driver of therapeutic resistance. Although natural compounds such as Caffeic Acid Phenethyl Ester (CAPE) are investigated for their anti-neoplastic properties, their bioactivity within the distinct metabolic landscape of the tumor core remains to be fully elucidated. Taking advantage of the recognized immunomodulatory properties of CAPE and its ability to cross the blood-brain barrier, we hypothesized that hypoxia is a key factor determining its effect on glioma-associated inflammation. To test this hypothesis, we investigated the immunomodulatory effects of CAPE on the human astrocytoma cell line CCF-STTG1. Cells were cultured under normoxic and hypoxic conditions, stimulated with lipopolysaccharide (LPS) and interferon-alpha (IFN-α) to induce an inflammatory phenotype, and subsequently treated with CAPE. The secretion profiles of key cytokines (IL-8, IL-10, IL-26) and matrix metalloproteinases (MMPs) as well as pentraxin-3 (PTX-3) were then quantified using a multiplex immunoassay. Our results revealed a striking functional dichotomy. Under normoxic conditions, CAPE suppressed the secretion of key pro-inflammatory mediators. Conversely, under hypoxic conditions, CAPE significantly amplified the release of pro-tumorigenic factors, including the mediator facilitating tumor cell migration, invasion, and angiogenesis such as IL-8 and the invasion-associated metalloproteinase MMP-2. These findings suggesting that hypoxia may fundamentally reprograms the immunomodulatory potential of CAPE. However, due to limitations of study requires further validation in a broader panel of glioblastoma models.