Search Results (75)

Central nervous system diseases are highly complex in terms of etiology and pathogenesis, making their treatment and interventions for them a major focus and challenge in neuroscience research. Anthocyanins, natural water-soluble pigments widely present in plants, belong to the class of flavonoid compounds. As natural antioxidants, anthocyanins have attracted extensive attention due to their significant functions in scavenging free radicals, antioxidation, anti-inflammation, and anti-apoptosis. The application of anthocyanins in the field of central nervous system injury, particularly in neurodegenerative diseases, neurotoxicity induced by chemical drugs, stress-related nerve damage, and cerebrovascular diseases, has achieved remarkable research outcomes. However, anthocyanins often exhibit low chemical stability, a short half-life, and relatively low bioavailability, which limit their clinical application. Recent studies have found that the stability and bioavailability of anthocyanins can be significantly improved through nanoencapsulation, acylation, and copigmentation, as well as the preparation of nanogels, nanoemulsions, and liposomes. These advancements offer the potential for the development of anthocyanins as a new type of neuroprotective agent. Future research will focus on the innovative design of nano-delivery systems and structural modification based on artificial intelligence. Such research is expected to break through the bottleneck of anthocyanin application and enable it to become a core component of next-generation intelligent neuroprotective agents. Full article

Cyanidin-3-O-glucoside (C3G) was used as a substrate for enzymatic acylation, and different compounds (methyl n-octanoate and methyl salicylate) were selected as acyl donors. Structural analysis (UV–Vis, FTIR, and HPLC) revealed the successful integration of methyl ester compounds into the structural units of C3G. The thermostability and photostability of acylated C3Gs, particularly those with methyl salicylate as the acyl donor, exhibited significant improvements. The molecular geometries of the different anthocyanins were optimized using computational chemistry, and energy level calculations were performed by using Density Functional Theory (DFT) to identify the antioxidant active site. Then, the antioxidant properties of C3G and acylated C3Gs (O-C3G and S-C3G) were studied in both aqueous and lipid systems. In aqueous systems, acylated C3Gs exhibited higher antioxidant properties than C3G in DPPH radical scavenging and hydroxyl radical scavenging assays, with cyanidin-3-O-glucoside salicyl acyl product (S-C3G) demonstrating the highest activity. However, the antioxidant properties varied in lipid systems. In lipid systems, acylated C3Gs displayed better antioxidant properties than C3G in POV and TBARS assays, with cyanidin-3-O-glucoside n-octanoate acid acyl product (O-C3G) showing better antioxidant properties compared to that in aqueous systems. Full article

Traditionally employed as hydrogenation reagents, benzothiazolines have emerged as versatile carbanion and radical transfer reagents, playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress in photochemistry and radical chemistry have prompted the study of visible light-driven radical reactions, bringing benzothiazolines into a vibrant focus. Their chemical processes have been uncovered to encompass a variety of activation mechanisms, with five distinct modes having been identified. This work reviews the innovative applications of benzothiazolines as donors of alkyl or acyl groups, achieving hydroalkylation or hydroacylation and alkyl or acyl substitution. By examining their diverse activation mechanisms, this review highlights the potential of benzothiazolines serving as alkyl and acyl groups for further research and development. Moreover, this review will offer exemplary applications and inspiration to synthetic chemists, contributing to the ongoing evolution of benzothiazolines utility in organic synthesis. Full article

Dietary interventions with food-derived natural products have emerged as a promising strategy to alleviate obesity. This study aims to investigate the anti-obesity effect of Hericium erinaceus protein (HEP) and its underlying mechanism. Our results demonstrated that HEP exhibited excellent radical scavenging activity in vitro. In vivo, HEP intervention reduced pancreatic lipase activity in the intestine and enhanced fat excretion, thereby inhibiting the absorption of dietary fats. Meanwhile, HEP ameliorated the body weight and organ indexes, dyslipidemia, insulin resistance, hepatic steatosis, and liver oxidative stress injuries in obese mice. The results of real-time PCR (qRT-PCR) and Western blot analyses indicated that HEP upregulated the expression of peroxisome proliferator-activated receptor α (PPARα), subsequently upregulated the expression of liver fatty acid oxidation-related genes (lipoprotein lipase (LPL), carnitine palmitoyltransferase 1a (CPT-1a), and acyl-CoA oxidase 1 (ACOX1)) and downregulated the expression of lipogenesis-related genes (sterol regulatory element-binding protein-1c (SREBP-1c), stearoyl-coenzyme A desaturase 1 (SCD-1), and fatty acid synthase (FASN)), thereby ameliorating lipid metabolism disorders. Therefore, these findings demonstrated that HEP exerted protective effects on lipid metabolism disorders by activating the PPARα pathway, indicating its potential as a dietary supplement for the prevention and amelioration of obesity. Full article

This study introduces a novel water-insoluble dispersant for coal water slurry (CWS), namely, a poly(sodium styrene sulfonate)-grafted SiO₂ nanoparticle (SiO₂-g-PSSNa). SiO₂-g-PSSNa was synthesized by combining the surface acylation reaction with surface-initiated atom transfer radical polymerization (SI-ATRP). Fourier transform infrared spectrometry (FTIR), X-ray photoelectron spectroscopy (XPS), energy dispersive spectrometer (EDS), nuclear magnetic resonance spectroscopy (NMR) and thermogravimetric analysis (TGA) verified that SiO₂-g-PSSNa with the desired structure was successfully obtained. Afterwards, the performance of SiO₂-g-PSSNa as a dispersant in CWS preparation was evaluated. The results indicated that the optimal dosage of SiO₂-g-PSSNa was 0.3%. Compared to the famous commercial products, PSSNa and lignosulfonate (LS), SiO₂-g-PSSNa exhibits improved viscosity reduction performance. When SiO₂-g-PSSNa was used as the dispersant, the maximum coal loading of CWS was 64.2%, which was higher than LS (63.4%) and PSSNa (63.9%). All CWSs obtained in this study were pseudoplastic fluids and more consistent with the Herschel–Bulkley rheological model. The turbiscan stability index (TSI) of CWS prepared with SiO₂-g-PSSNa was 0.05, which was significantly lower than CWSs obtained from PSSNa (0.30) and LS (0.36). Therefore, SiO₂-g-PSSNa also exhibits excellent stability performance. This result was confirmed by rod penetration tests. The underlying mechanism was also clarified by various measurements, such as contact angle, zeta potential, EDS and low-field nuclear magnetic resonance spectra (low-field NMR). The results reveal that SiO₂-g-PSSNa can adsorbed onto the coal surface. SiO₂-g-PSSNa possesses a special branched structure, which bears a higher charge density as compared to linear ones with approximate chemical composition. As a result, coal particles adsorbed with SiO₂-g-PSSNa exhibit more electronegativity. With the enhancement of the electrostatic repulsive between coal particles, the apparent viscosity was lowered and the static stability was improved. This study demonstrated that solubility in water is not an essential factor in engineering the dispersant. Densely charged groups are probably more important. Full article

Acyl-quinic acids (AQAs), present in various plants with many health benefits, are regarded as therapeutic agents in the prevention and treatment of chronic and cardiovascular diseases. The molecular network-guided identification of ten AQA compounds, two new (5 and 7) and eight known compounds, were isolated from V. rotundifolia L. f. by using a newly applied extraction method. Their structures were determined through spectroscopic means, reaction mixtures, and modified Mosher and PGME techniques. These compounds were assessed for their anti-inflammatory and antioxidant capabilities. Notably, compounds 1, 3, 4, 6, 8, and 9 exhibited notable DPPH radical scavenging activity. In LPS-induced HT-29 cells, compounds 2–7 significantly inhibited IL-8 production. Furthermore, compounds 3–5 and 7 markedly suppressed NO production, while compounds 1–10 effectively inhibited IL-6 production in LPS-induced RAW264.7 cells. Western blot analyses revealed that compounds 3–5, and 7 reduced iNOS and COX-2 expression, and compounds 2–5, 7, and 8 also diminished the expression levels of p38 MAPK phosphorylation. Docking studies demonstrated the active compounds’ binding affinity with the IL-8, iNOS, COX-2, and p38 MAPK proteins through interactions with essential amino acids within the binding pockets of complexes. The findings suggest that compounds 1, 3, 4, 6, 8, and 9, and compounds 3–5, and 7, hold promise as potential therapeutic agents for treating antioxidative and inflammatory diseases, respectively. Full article

Background: Liraglutide, a long-acting glucagon-like peptide-1 receptor agonist (GLP1RA), is a well-established anti-diabetic drug, has also been approved for the treatment of obesity at a dose of 3 mg. There are a limited number of studies in the literature that have looked at changes in metabolite levels before and after liraglutide treatment in patients with obesity. To this end, in the present study we aimed to explore the changes in the plasma metabolomic profile, using liquid chromatography-high resolution mass spectrometry (LC-HRMS) in patients with obesity. Methods: A single-center prospective study was undertaken to evaluate the effectiveness of 3 mg liraglutide therapy in twenty-three patients (M/F: 8/15) with obesity, mean BMI 40.81 ± 5.04 kg/m², and mean age of 36 ± 10.9 years, in two groups: at baseline (pre-treatment) and after 12 weeks of treatment (post-treatment). An untargeted metabolomic profiling was conducted in plasma from the pre-treatment and post-treatment groups using LC-HRMS, along with bioinformatics analysis using ingenuity pathway analysis (IPA). Results: The metabolomics analysis revealed a significant (FDR p-value ≤ 0.05, FC 1.5) dysregulation of 161 endogenous metabolites (97 upregulated and 64 downregulated) with distinct separation between the two groups. Among the significantly dysregulated metabolites, the majority of them were identified as belonging to the class of oxidized lipids (oxylipins) that includes arachidonic acid and its derivatives, phosphorglycerophosphates, N-acylated amino acids, steroid hormones, and bile acids. The biomarker analysis conducted using MetaboAnalyst showed PGP (a21:0/PG/F1alpha), an oxidized lipid, as the first metabolite among the list of the top 15 biomarkers, followed by cysteine and estrone. The IPA analysis showed that the dysregulated metabolites impacted the pathway related to cell signaling, free radical scavenging, and molecular transport, and were focused around the dysregulation of NF-κB, ERK, MAPK, PKc, VEGF, insulin, and pro-inflammatory cytokine signaling pathways. Conclusions: The findings suggest that liraglutide treatment reduces inflammation and modulates lipid metabolism and oxidative stress. Our study contributes to a better understanding of the drug’s multifaceted impact on overall metabolism in patients with obesity. Full article

Chinese cordyceps (GL) is a traditional medicinal fungus, with Ophiocordyceps sinensis (O. sinensis, BL) and Paecilomyces hepiali (P. hepiali, JSB) being fungi isolated from wild Chinese cordyceps. These three species share similar chemical composition and pharmacological effects. Existing studies have primarily compared the metabolites of Chinese cordyceps and O. sinensis, overlooking the assessment of antioxidant capacity in Chinese cordyceps, P. hepiali, and O. sinensis. In this study, LC-MS/MS was employed to analyze metabolites in GL, JSB, and BL. Utilizing principal component analysis (PCA), supervised orthogonal partial least squares discriminant analysis (OPLS-DA), and hierarchical cluster analysis (HCA), it was observed that the majority of differential metabolites (DMs) primarily accumulated in organic acids and derivatives, lipids and lipid-like molecules, and organoheterocyclic compounds. Antioxidant activity analysis indicated that GL exhibited the higher 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability (DPPH•, scavenging rate is 81.87 ± 0.97%), hydroxyl free radical scavenging capacity (•OH, scavenging rate is 98.10 ± 0.60%), and superoxide anion radical scavenging capacity (O₂^•−, scavenging rate is 69.74 ± 4.36%), while JSB demonstrated the higher FRAP total antioxidant capacity of 8.26 μmol Trolox/g (p < 0.05). Correlation analysis revealed a positive correlation between DMs (fatty acyls and amino acids) and DPPH•, FRAP, •OH, and O₂^•− (p < 0.05). Additionally, glycerophospholipid DMs were found to be positively correlated with FRAP (p < 0.05). Through KEGG pathway analysis, it was determined that the accumulation of DMs in pathways such as cutin, suberine and wax biosynthesis has a higher impact on influencing the antioxidant activity of the samples. These results shed light on the antioxidant capacity and metabolic characteristics of Chinese cordyceps and its substitutes and offer valuable insights into how different DMs impact the strength of antioxidant activity, aiding in the advancement and application of Chinese cordyceps and its substitutes. Full article

The mechanisms of action of pyrimidine nucleoside derivatives on model lipid membranes of various compositions were studied. A systematic analysis of the tested agents’ effects on the membrane physicochemical properties was performed. Differential scanning microcalorimetry data indicated that the ability of nucleoside derivatives to disorder membrane lipids depended on the types of nucleoside bases and membrane-forming lipids. The 5′-norcarbocyclic uracil derivatives were found to be ineffective, while N⁴-alkylcytidines demonstrated the most pronounced effects, significantly decreasing the dipalmitoylphosphocholine melting temperature and cooperativity of phase transition. The elongation of hydrophobic acyl radicals potentiated the disordering action of N⁴-alkylcytidines, while an increase in hydrophilicity due to replacing deoxyribose with ribose inhibited this effect. The ability of compounds to form transmembrane pores was also tested. It was found that 5-alkyluridines produced single, ion-permeable pores in phosphatidylglycerol membranes, and that methoxy-mycolic acid and trehalose monooleate potentiated the pore-forming activity of alkyloxymethyldeoxyuridines. The results obtained open up perspectives for the development of innovative highly selective anti-tuberculosis agents, which may be characterized by a low risk of developing drug resistance due to the direct action on the membranes of the pathogen. Full article

Ketones are ubiquitous patterns found in various biological molecules and natural products. In recent years, a number of acylation methods have been developed based on the use of α-oxocarboxylic acids as acyl-transfer reagents, with particular emphasis on the photoinduced decarboxylative acylation of α-keto acids. This review focuses on the latest advancements in acylation methodologies through the decarboxylation of α-keto acids over the past several years, highlighting their product diversity, selectivity, and applicability. Where possible, the mechanistic rationale is presented, providing a positive outlook for the promising future of this field. Full article

Acyl-1,4-dihydropyridines have recently emerged as universal acylation reagents. These easy-to-make and bench-stable NADH biomimetics play the dual role of single-electron reductants and sources of acyl radicals. This review article discusses applications of acyl-1,4-dihydropyridines in organic synthesis since their introduction in 2019. Acyl-1,4-dihydropyridines, activated by photochemical, thermal or electrochemical methods, have been successfully applied as radical sources in multiple diverse organic transformations such as acyl radical addition to olefins, alkynes, imines and other acceptors, as well as in the late-stage functionalisation of natural products and APIs. Release of acyl radicals and an electron can be performed under mild conditions—in green solvents, under air and sunlight, and without the use of photocatalysts, photosensitizers or external oxidants—which makes them ideal reagents for organic chemists. Full article

Biodiesel, an alternative to traditional diesel, is essential for the sustainability of long-term energy supplies and often synthesized through a non-alcoholic route called interesterification. The described synthesis method facilitates the modification of oil and fat by exchanging acyl radical groups between triglyceride and alcoholic acid (alcoholysis), fat (acidolysis), or ester (transesterification). Therefore, this research aimed to determine the effect of the reactant ratio between crude palm oil (CPO) and dimethyl carbonate (DMC), along with the use of an eco-enzyme catalyst, on biodiesel characteristics. The CPO:DMC ratio was 1:1.5, 1:2, 1:2.5, and 1:3, while the immobilized eco-enzyme catalyst was 2%, 3%, 4%, 5%, and 6% of CPO mass. The results showed that interesterification with a 1:3 reactant ratio using a 4%wt catalyst was the best procedure, producing biodiesel yield of 73.65%, density of 0.860 g/mL, viscosity of 4.63 mm²/s (cSt), flash point of 113 °C, calorific value of 34.454 MJ/kg, and cetane number of 70.6%. Full article

Monofluoromethyl (CH₂F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH₂F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In this study, we report on visible light-mediated three-component monofluoromethylation/acylation of styrene derivatives employing NHC and organic photocatalyst dual catalysis. A diverse array of α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance and selectivity. The mild and metal-free CH₂F radical generation strategy from NaSO₂CFH₂ holds potential for further applications in fluoroalkyl radical chemistry. Full article

Puerarin is a flavonoid known as a natural antioxidant found in the root of Pueraria robata. Its antioxidant, anticancer, and anti-inflammatory effects have attracted attention as a potential functional ingredient in various bioindustries. However, puerarin has limited bioavailability owing to its low lipid solubility and stability. Acylation is proposed as a synthesis method to overcome this limitation. In this study, lipase-catalyzed acylation of puerarin and various acyl donors was performed, and the enzymatic synthetic condition was optimized. Under the condition (20 g/L of Novozym 435, palmitic anhydride, 1:15, 40 °C, tetrahydrofuran (THF)), the synthesis of puerarin ester achieved a significantly high conversion (98.97%) within a short time (3 h). The molecule of the synthesized puerarin palmitate was identified by various analyses such as liquid chromatography–mass spectrometry (LC–MS), Fourier-transform infrared spectroscopy (FT-IR), and carbon-13 nuclear magnetic resonance (¹³C NMR). The lipid solubility and the radical scavenging activity were also evaluated. Puerarin palmitate showed a slight decrease in antioxidant activity, but lipid solubility was significantly improved, improving bioavailability. The high conversion achieved for puerarin esters in this study will provide the foundation for industrial applications. Full article