Search Results (720)

Coniferyl alcohol and coniferyl aldehyde are precursors of lignin and are used in spices and the pharmaceutical industry. In this work, antioxidant, anticholinergic, antidiabetic, and antiglaucoma effects of coniferyl alcohol and aldehyde were evaluated and compared against the standards. To determine the antioxidant capacities of coniferyl alcohol and aldehyde, ABTS^•+, DMPD^•+ and DPPH^• scavenging abilities as well as cupric ion (Cu²⁺) reduction, ferrous ions (Fe²⁺) reduction and Fe³⁺-TPTZ reduction activities were studied. Butylated hydroxytoluene (BHT), ascorbic acid, α-Tocopherol, Trolox, and butylated hydroxyanisole (BHA) were used as the standard antioxidants. When the antioxidant effects of coniferyl alcohol and coniferyl aldehyde are compared to the standards, they exhibit significant antioxidant effects. In addition, it was determined that coniferyl alcohol and coniferyl aldehyde had a high degree of inhibition effect towards carbonic anhydrase (hCA) I and II isoforms purified from human erythrocytes, α-glycosidase, butyrylcholinesterase (BChE), acetylcholinesterase (AChE), and α-amylase as in vitro and in silico. Molecular docking studies revealed favorable binding affinities of coniferyl alcohol and coniferyl aldehyde toward all investigated enzymes, with key hydrogen bonding and π–π interactions identified at the active sites. The docking findings were found to be compatible with the in vitro enzyme inhibition results, supporting the proposed multi-target biological potential of both compounds. Molecular docking studies revealed favorable binding affinities of coniferyl alcohol and coniferyl aldehyde toward all investigated enzymes. Key hydrogen bonding and π–π interactions were identified within the active sites, particularly for AChE and hCA II. The docking results were consistent with the in vitro enzyme inhibition data, supporting their multi-target biological potential. Docking demonstrated that both compounds can effectively interact with the catalytic regions of the target enzymes. The identified binding modes and interaction patterns support the observed inhibitory activities and provide a molecular basis for their multi-target biological effects. Full article

Lysimachia foenum-graecum Hance (LFG), renowned for its potent aroma, is widely utilized as a culinary spice in the food industry. This study employed GC-IMS and GC-MS to analyze samples from four distinct regions: Guangxi (GX), Guizhou (GZ), Sichuan (SC), and Yunnan (YN). The profiling effort led to the identification of 51 and 47 volatile compounds, respectively, with alcohols, aldehydes, esters, and ketones constituting the predominant organic compounds (74%). The GX samples exhibited the highest overall compound content, while SC samples were characterized by the highest ester content. Significant variations in compound concentrations were observed across different sources. PLS-DA identified 15 distinctive volatile markers that differentiate the four regions. Odor activity value (OAV) analysis revealed five key volatile compounds linalool, borneol, estragole, undecanal, and β-Ionone. In addition, cellular-level assays demonstrated the pharmacological activity of LFG. These findings provide valuable insights for the application of LFG in the food industry. Full article

Chinese lacquerware is a multi-layered natural polymer composite whose characterization is complicated by burial degradation, organic–inorganic mixing, and the overlap of signals from lacquer, drying oils, proteins, polysaccharides, waxes, and pigments. This review evaluates analytical strategies for Chinese lacquerware by distinguishing three complementary levels of evidence: morphological and elemental observation, chemically specific molecular fingerprinting, and biomolecular source recognition. Microscopy, Fourier transform infrared spectroscopy (FTIR), Raman spectroscopy, and scanning electron microscopy–energy dispersive spectroscopy (SEM-EDS) are useful for identifying stratigraphy, pigments, fillers, and functional groups, but they are often insufficient for assigning degraded organic matrices and trace additives independently. Pyrolysis–gas chromatography/mass spectrometry provides more specific molecular evidence through diagnostic marker classes, including alkyl catechols, alkyl phenols, nitrogen-containing pyrolysis products, anhydrosugars, long-chain aliphatics, aldehydes, and ketones. Immunological assays based on lacquer glycoproteins further complement chemical analysis by supporting biological source differentiation, although their reliability depends on protein preservation, extraction efficiency, and antibody specificity. Representative case studies, including a seventeenth-century Swedish lacquered pipe, the Nanyue Kingdom lacquered ear cup, and a Tang Dynasty lacquered leather artifact, show that robust interpretation requires cross-validation among stratigraphic, elemental, spectroscopic, chromatographic, immunological, and archaeological evidence. The review concludes that integrated analytical workflows can improve material identification, clarify manufacturing sequences, assess degradation uncertainty, and provide more reliable evidence for conservation decision-making and the reconstruction of historical lacquer craftsmanship. Full article

This investigation evaluated temporal variations in metabolic fingerprints, sensory properties, and functional traits of Aronia melanocarpa syrup throughout the fermentation stage followed by an additional 90-day preservation interval. Findings indicated that microbial transformation notably increased the cumulative polyphenolic levels, overall flavonoid concentrations, and DPPH free radical quenching efficiencies of the preparation, which stayed consistent over this duration. Non-targeted metabolomics screening recognized a combined 1918 chemical signatures, whereby phenylpropanoids, fatty acids, and terpenes represented critical components. A total of 1591 distinct metabolites were identified, demonstrating substantial accumulation inside the flavonoid synthesis and pyruvate catabolic pathways. Furthermore, 355 volatile substances were characterized, with aldehydes and esters acting as vital elements providing honey-scented and fragrant tastes. The cooperative impacts of brewing and aging improved the nutritive and gustatory merits of Aronia melanocarpa syrup, providing a theoretical framework for developing superior fermented commodities. Full article

Flavone–thiazole–aryl hybrid molecules based on 6-aminoflavone and 5-arylidene-4-aminothiazol-2(5H)-ones were synthesized and subjected to physicochemical and biological studies. Microwave-assisted synthesis was performed in two steps. First, an aminolysis reaction of isorhodanine with 6-aminoflavone was carried out to achieve the corresponding hybrid flavone-thiazole 3, which was later subjected to a Knoevenagel condensation with selected aromatic aldehydes, yielding 5-arylidene derivatives 5a–5i. The resulting hybrids were purified and characterized by UV–Vis, NMR, and HR-MS (ESI). In the UV–Vis spectra of all compounds, two characteristic bands were noted. The UV–Vis spectra in DMF of the studied flavone–thiazole–aryl hybrids consist of two major bands with maxima appearing at 280–288 nm, corresponding to band II and 383–399 nm, corresponding to band I, which clearly distinguish them from the large group of modified flavonoids. Among the compounds tested on human bladder cancer 5637 cells, (5Z)-5-[(4-hydroxyphenyl)methylene]-4-[(4-oxo-2-phenyl-chromen-6-yl)amino]thiazol-2-one (5b) exhibited interesting micromolar activity (IC₅₀ 2.37 µM). In addition, four of the tested compounds (3, 5f, 5d, and 5b) presented noteworthy antiplasmodial activity against P. falciparum in the low micromolar range (IC₅₀ 1.90–4.90 µM). The obtained group of flavone–thiazole–aryl hybrid molecules constitutes valuable starting points for further structural optimisation, which could usher in future novel active pharmaceutical ingredients and pave the way for novel therapeutic strategies. Full article

Background/Objectives: Chronic myeloid leukemia (CML) is primarily associated with the BCR:ABL1 fusion protein. Although tyrosine kinase inhibitors (TKIs) have markedly enhanced treatment outcomes, the development of agents with improved therapeutic characteristics remains necessary. The present work focused on the synthesis of a new series of thiazolone derivatives (F1-11) and the assessment of their anti-CML activity through inhibition of ABL tyrosine kinase (TK). Methods: The designed compounds were prepared through a multistep synthetic pathway involving the formation of a new chalcone intermediate (A), synthesis of a new pyrazoline carbothioamide intermediate (B), and cyclization with different aldehydes to produce the target new thiazolone derivatives (F1-11). Cytotoxic effects were investigated against K562 CML cells using the MTT assay. The lead compound was additionally evaluated in HL-60 AML cells and normal PBMCs. Apoptotic induction was analyzed using Annexin V/ethidium homodimer staining, whereas ABL TK inhibitory activity was measured through the ADP-Glo assay. Molecular docking studies were conducted to explore ligand interactions within the ATP-binding domain of ABL TK. Results: Among the synthesized molecules, F-4 demonstrated the strongest activity against K562 cells with an IC₅₀ value of 6.85 µM, close to that observed for imatinib (IC₅₀ = 5.20 µM). The compound showed reduced cytotoxicity toward HL-60 cells (IC₅₀ = 33.44 µM) and exhibited favorable selectivity toward PBMCs (SI = 13). Apoptosis studies revealed 51% early apoptotic cells and 43% late apoptotic cells following treatment. In the kinase assay, F-4 inhibited ABL TK activity by 39% at 10 µM and by 70% at 100 µM. Docking simulations suggested interactions with residues His361 and Asp381 in addition to nearby hydrophobic amino acids, although the interaction network was less extensive than that of imatinib. Conclusions: The findings identify F-4 as a promising new thiazolone-derived scaffold with selective anti-CML activity and notable ABL TK inhibitory potential. Additional structural optimization may further enhance its binding characteristics and therapeutic efficacy. Full article

Transfer hydroformylation of alkenes with formaldehyde constitutes a green and sustainable route to aldehydes. In this work, the transfer hydroformylation of styrene with formaldehyde was efficiently catalyzed by [Rh(κ²-dppe)₂]⁺ (A), where dppe stands for 1,2-bis(diphenylphosphino)ethane. The reaction was found to be first order with respect to both Rh and substrate concentrations and fractional order with respect to formaldehyde concentration, in line with the behavior previously reported for 1-hexene. DFT was used to investigate the reaction mechanism by using ethene and [Rh(κ²-dpe)₂]⁺ (A), where dpe stands for 1,2-bis(phosphine)ethane, as simplified models of the substrate and catalyst, respectively, and by considering several functionals. The DFT calculations indicate that M06-L provides the most suitable description of the thermodynamic and activation parameters associated with the elementary steps. The combined analysis of kinetic results and the DFT calculations allowed us to propose a detailed catalytic cycle for this reaction, initiated by the reversible oxidative addition of formaldehyde to complex A to afford [Rh(H)(CHO)(κ²-dppe)₂]⁺ (B, ${\mathit{K}}_{\mathbf{1}}$). Coordination of ethene occurs through partial dissociation of one phosphorus atom of the diphosphine ligand, generating [Rh(H)(alkene)(CHO)(κ²-dppe)(κ¹-dppe)]⁺ (I_B, ${\mathit{K}}_{\mathbf{2}}$), followed by the transfer of the hydride to the alkene to give [Rh(alkyl)(CHO)(κ²-dppe)₂]⁺ (C, ${\mathit{k}}_{\mathbf{3}}$), which is considered the rate-determining step of the process. The cycle is completed by reductive elimination of propanal, thereby regenerating A. The overall activation energy calculated by DFT (Ea = 20.0 kcal mol⁻¹) is in good agreement with the experimental values determined for 1-hexene and styrene (20.1 and 22.9 kcal mol⁻¹, respectively). On the basis of these experimental and DFT results, a mathematical kinetic model with the canonical form $r_0={{\mathit{K}}_{\mathbf{1}}{\mathit{K}}_{\mathbf{2}}\mathit{k}}_{\mathbf{3}}{\left[Rh\right]}_o\left[alkene\right]\left[C{H}_{2}O\right]/\left({1+\mathit{K}}_{\mathbf{1}}\left[C{H}_{2}O\right]\right)$ was developed and fitted using a tandem LMFit/Bayesian approach, allowing the values of K₁ and K₂k₃ to be estimated, with comparatively low uncertainty. Overall, this integrated kinetic, computational, and statistical study provides a consistent mechanistic and quantitative framework for understanding the transfer hydroformylation of alkenes with formaldehyde. Full article

Coriandrum sativum L. is a widely cultivated aromatic herb exhibiting substantial variation in essential oil quality and yield among different accessions. This study assessed germination performance, essential oil composition, yield, chemotype distribution, and fragrance characteristics in 48 C. sativum accessions collected from 19 countries spanning four Köppen–Geiger climate zones: Tropical/Subtropical, Arid/Semi-arid, Temperate, and Continental/Cold. All accessions were grown under standardized field conditions, and essential oils were extracted from aerial parts using steam distillation followed by direct-GC/MS analysis. Seed germination rates were consistently high (mean: 92.25 ± 5.85%; range: 71–100%) and did not differ significantly by climate zone (Kruskal–Wallis H = 5.500, p = 0.139) or country of origin (H = 21.833, p = 0.240), indicating that post-harvest management, rather than climatic provenance, primarily determines seed viability. Essential oil profiles were dominated by (E)-2-decenal (mean: 44.56%), decanal (11.75%), and 2-dodecenal (13.47%). Principal component analysis (PCA) of 18 compounds detected in at least 19 accessions accounted for 70.16% of total variance across five components, with PC1 reflecting a gradient from long-chain saturated aldehyde accumulation to linalool enrichment. Permutational multivariate analysis of variance (PERMANOVA) demonstrated significant compositional differentiation among climate zones (Pseudo-F = 1.662, p = 0.028), whereas country-level grouping was not significant (p = 0.256). Tropical/subtropical accessions exhibited the highest linalool content (mean: 15.39 ± 8.71%) and essential oil yield (mean: 0.269 ± 0.120% v/w), significantly surpassing arid/semi-arid and temperate zones (p < 0.05). Two chemotypes were identified, (E)-2-decenal (91.7%) and linalool (8.3%), each associated with distinct fragrance profiles (earthy/aldehydic/woody versus herbal/sweet, respectively). These findings demonstrate that climate zone of origin is significantly associated with C. sativum essential oil composition and productivity, with tropical/subtropical accessions providing superior yield and linalool content. Chemotype characterization offers an additional criterion for germplasm selection in targeted industrial applications. Full article

In this work, the activity of vanadium-doped and undoped phosphomolybdic acids with general formulae H_3+nPMo_12−nV_nO₄₀ (n = 0, 1, 2, and 3) was evaluated in the acetalization of furfural with alkyl alcohols. The main focus was to assess how vanadium charge affects the catalytic activity of phosphomolybdic acid and to link these effects to changes in structural properties. The main reaction parameters, such as charge and concentration of the catalyst, temperature, time, type of alcohol and aldehyde, and charges of vanadium and of H⁺ ions, were studied. Various Brønsted acids (sulfuric, p-toluenesulfonic, undoped, and doped phosphomolybdic acids) were evaluated on the condensation reactions of furfural with methyl alcohol. Notably, H₄PMo₁₁VO₄₀ was the most active and selective catalyst for the formation of methyl acetal furfural. Water has a leveling effect on the strength of these acids. Nonetheless, under reaction conditions, the presence of vanadium affected their acidity strength, and it was possible to verify that the vanadium-monosubstituted phosphomolybdic acid was the strongest. The superior performance of H₄PMo₁₁VO₄₀ was attributed to its additional acidity, resulting from the presence of very strong Brønsted acid sites (H⁺) and Lewis acid sites, due to the inclusion of V⁵⁺ ions in its structure. The novelty of this work is the assessment of vanadium-doped phosphomolybdic acids in the homogeneous phase in the condensation reactions of furfural with various alcohols and of methyl alcohol with various aldehydes. Full article

Lubricants contain various types of additives, with corrosion and rust inhibitors being some of the most important. Due to the importance of 2,5-Dimercapto-1,3,4-thiadiazole (DMTD) in the field of corrosion inhibitors, we used it as a key intermediate to synthesize a series of 4-thiazolidinone and 4-imidazolidinone derivatives. This work also includes performing the reaction of DMTD with ethyl chloroacetate, which produced the corresponding ester, followed by the conversion into a hydrazide derivative using hydrazine hydrate. The next step is the condensing of the yielded hydrazide with various aromatic aldehydes yielding Schiff bases, which were subjected to cyclization by means of mercapto acetic acid and ethyl glycinate to produce the target 4-thiazolidinone and 4-imidazolidinone derivatives, respectively. FT IR, ¹H NMR, and ¹³C NMR spectroscopies were involved to confirm the structures of these derivatives. The synthesized derivatives have been evaluated as copper corrosion and rust inhibitors for medium lubricants in accordance with ASTM-D130 and ASTM-D665 standards. Interestingly, some lubricant blends of the synthesized derivatives showed good performance as copper corrosion and rust inhibitors. Full article

Ocimum gratissimum L. subsp., commonly known as African basil, is a native African medicinal plant that has been used for generations to address various health issues. These include colds, flu, diabetes, diarrhoea, pain and swelling, psychological disorders, malaria, inflammation, and infections caused by fungi and bacteria. In addition, African basil is abundant in vitamins and minerals and is mostly used to add flavour to dishes and soups in West African households. Studies have identified multiple bioactive compounds in this plant, such as alkaloids, polyphenols, triterpenes, steroids, fatty acids, esters, alcohols, essential oils, ketones, and aldehydes. Key bioactive constituents, essential oils like thymol and eugenol, are responsible for the pharmacological effects of Ocimum gratissimum. The diverse bioactive compounds give the plant a wide range of therapeutic properties, including antioxidant, cognitive-enhancing, antimicrobial, anti-inflammatory, analgesic, anticancer, antihypertensive, hepatoprotective, and organoleptic effects. Notable mechanisms of action include the PI3K/Akt, NRF-2, and NF-κB signalling pathways, free radical scavenging, and modulation of pro-inflammatory cytokines such as IL-1β, IL-6, and TNF-α. This review paper aimed to compile recent studies on the phytochemistry, medicinal uses, therapeutic activities, and molecular mechanisms of action of Ocimum gratissimum. Further studies are needed to better understand the effects of Ocimum gratissimum at the pathological and molecular levels. Full article

Chromene derivatives are important structural motifs in biologically active compounds and functional materials, and the development of efficient strategies for their synthesis remains of considerable interest. In this work, simple and sustainable methodologies were developed for the synthesis of chromene dimers linked through short amidine/geminal diamine spacers or long, flexible alkyl diamine linkers. The amidine and geminal diamine linkers were obtained from 3-aminochromene derivatives via nucleophilic addition of the amino group to triethyl orthoformate or non-phenolic aldehydes in ethanol, at room temperature or under reflux, affording the corresponding dimers in moderate to very good yields. In a complementary approach, flexible alkyl diamide linkers were prepared from diamines and ethyl cyanoacetate, followed by condensation with salicylaldehydes in aqueous hydrogen carbonate solution and subsequent acidic hydrolysis, leading to new chromene dimers in excellent yields. These mild and operationally simple protocols provide efficient access to structurally diverse chromene dimers with potential applications in medicinal chemistry and materials science. Full article

Background: An original pre-column derivatisation strategy combining liquid chromatography, supported by gas chromatography, was developed for the determination of malondialdehyde (MDA), formaldehyde (FA), and 4-hydroxynonenal (4-HNE) in selected plant oils and model edible animal tissues (i.e., muscle, adipose tissue, liver, and brain). Methods: In oils, direct derivatisation with 2,4-dinitrophenylhydrazine (DNPH) was applied to quantify the target aldehydes (as hydrazones) without prior saponification. In the analysed animal tissue samples, MDA and FA were released by saponification and subsequently derivatised with DNPH, whereas 4-HNE was extracted from these samples and subsequently derivatised with DNPH. Derivatised aldehydes were quantified using C18 ultra-high performance liquid chromatography (C18-UHPLC) with photodiode array detection (DAD) under binary-gradient elution conditions, supported by gas chromatography (GC) with flame ionisation detection (FID). Results: The combination of the original binary gradient elution programme, selective DAD, and a high-performance C18 column (150 mm, 1.6 µm particle size) resulted in excellent baseline stability, good linearity, and satisfactory repeatability and specificity in the determination of MDA, FA, and 4-HNE. C18-UHPLC–DAD enabled satisfactory separation of MDA, FA and 4-HNE hydrazones from endogenous matrix components in solutions of processed oils and animal tissues, while the addition of acetonitrile to these sample solutions further reduced background interference. C18-UPLC-DAD provided satisfactory symmetrical peak shapes, peak purities, and recoveries of MDA, FA, and 4-HNE in analysed plant oils and ovine tissues, compared with GC–FID. Compared with GC–FID, C18-UHPLC-DAD provided superior resolution of derivatised aldehydes in matrices of analysed biological samples. Conclusions: The determination of lipid peroxidation biomarkers in oils and animal tissues using our novel C18-UHPLC-DAD method may contribute to the optimisation of breeding practices, helping to minimise animal stress and enhance the health-promoting properties of food products. Full article

The presented study aimed to fully characterise berry powders derived from raspberry, blackberry and strawberry (RB, BB, SB) as well as raspberry and blackberry seed powders (RBS, BBS) in terms of proximate composition, the individual profile of minerals, sugars, organic and fatty acids, and phenolic and volatile compounds. Additionally, testing of powders’ colour and antioxidant activity, as well as spectroscopic analysis, were also performed. Higher total and individual sugars, organic and phenolic acids, flavonols and anthocyanins content distinguished berry powders from the seed powders. Individually, RB contained significant amounts of citric and chlorogenic acids, BB was superior in cyanidin-3-O-glucoside and quercetin-3-O-rutinoside content, while SB was characterised by high sucrose, fructose, omega-3, and mineral (Ca, Mg, Fe) content. Berry seed powders exhibited remarkable TDF content, beneficial PUFA/SFA ratio, lighter colour, higher individual flavan-3-ols quantity, TPC and DPPH activity compared to berry powders. Mentioned discrepancies between berry and berry seed powders on a compositional level were also visible on ATR-FTIR spectra across all detected regions reflecting bonds attributed to cellulose, lipids, phenols and sugars. Pleasant, predominantly green, fruity and floral aromas were associated with berry powders, whilst additional herbal notes were characteristic of berry seed powders, all derived from the alcohols, aldehydes, esters and ketones as paramount volatile compounds. All examined powders can bear a nutritional claim of “high in” fibre (20.47–65.33%) and Mg (114.52–128.70 mg/100 g), enabling the design of food products packed with nutrients and bioactives while simultaneously reducing fresh fruit and fruit-processing waste. Full article

Pistacia lentiscus L. var. Chia is an endemic tree cultivated in the Southern part of Chios Greek Island. Chios mastiha, the aromatic resin secreted from this tree, has been used as traditional remedy since ancient times to cure many peptic system diseases and as a nutritional agent. Nowadays, Chios mastiha has been widely investigated for its biological activities and its chemical composition. A major part of Chios mastiha’s bioactive compounds are triterpenoids, which are proposed to interfere with glucocorticoid receptor (GR) signaling, acting as selective GR agonists. In this study a specific “neutral fraction” of Chios mastiha resin, a portion devoid of acidic triterpenoids, was investigated regarding its biological potential and chemical composition. The study aimed to determine if the neutral triterpenoids, the non-carboxylic ones, within this fraction drive Chios mastiha’s interference with GR signaling and whether it exhibits anti-inflammatory, apoptotic, and potential antilipidemic activities. The phytochemical characterization of this specific resin portion, applying ¹H NMR and HPLC-QTOF-MS/MS analysis, identified novel unidentified Chios mastiha’s phenolic components (apigenin, astragalin, diosmetin, flavidin, genistein), a complex mixture of fatty acids (palmitic, stearic, oleic), non-carboxylic triterpenoids (lupeol, β-amyrin, keto-oleanolic aldehyde), and a trace of terpenoids. Biological assessment of DEX-induced GR transcriptional activation revealed that neutral triterpenoid fractions only minimally contribute to GR transcriptional activation while positively regulating GR and its target, phosphoenolpyruvate carboxykinase (PEPCK), protein levels. Additionally, negative regulation of the peroxisome proliferator-activated receptor alpha (PPARα) protein levels as well as inhibition of the TNFα-induced NF-κΒ activity and reduction in the p65 subunit of NF-κΒ protein levels, were observed, indicating potential antilipidemic and anti-inflammatory Chios mastiha’s neutral fraction activities, which were attributed to its composition in triterpenoids, fatty acids, and novel phenolic compounds. Moreover, mitochondrial-dependent induction of apoptosis accompanied by reduction in cell viability was observed in lupeol, β-amyrin, and fatty acids-enriched fractions. The plethora of bioactive compounds associated with a variety of Chios mastiha’s neutral fraction render Chios mastiha a valuable food additive and nutritional agent. Full article