Search Results (67)

A naturally sourced phenolic compound, umbelliferone, has been used to synthesize four monofunctional benzoxazines, two of which have been previously synthesized from aniline and furfurylamine. This study contributes two more—using benzylamine and phenethylamine—to provide insight into how the amine’s aromatic group and aliphatic chain length influence resulting properties. The proposed chemical structures of the novel monomers are confirmed by ¹H nuclear magnetic resonance (¹H-NMR) and ¹H-¹H nuclear Overhauser effect spectroscopy (NOESY). The polymerization behavior of each resin is determined by differential scanning calorimetry (DSC). The thermal degradation pattern and the flammability of each polymer are assessed by thermogravimetric analysis (TGA) and microscale combustion calorimetry (MCC), respectively. Char yields between 49% and 63% suggest the thermoset materials to be thermally stable and competitive for thermally demanding applications. All four polybenzoxazines demonstrate non-ignitable behavior, with heat release capacities below 100 J/g·K. Structure–property analyses on the two newly synthesized compounds have been provided to deepen our existing understanding of umbelliferone-benzoxazine systems, particularly regarding the effect of the aminic moiety on thermal properties. Full article

Background: Sarcopenic obesity (SO) and diabetic sarcopenia (DS) represent overlapping metabolic–musculoskeletal disorders characterized by the coexistence of excessive adiposity, insulin resistance, and progressive muscle wasting. The Planetary Health Diet (PHD), proposed by the EAT–Lancet Commission, emphasizes plant-forward, nutrient-dense, and environmentally sustainable food patterns that may concurrently address metabolic and muscle health. This review aimed to systematically evaluate dietary and bioactive nutritional interventions aligned with the PHD and their effects on muscle mass, strength, metabolism, and underlying mechanisms in SO and DS. Methods: Following PRISMA guidelines, studies published between 2015 and 2025 were identified across PubMed, Scopus, and Google Scholar. Eligible studies included dietary, nutritional, or supplement-based interventions reporting muscle-related outcomes in obesity- or diabetes-associated conditions. Results: Ninety-one eligible studies were categorized into plant-derived, animal/marine-based, microorganism/fermented, synthetic/pharmaceutical, and environmental interventions. Across diverse models, bioactive compounds such as D-pinitol, umbelliferone, resveratrol, GABA, ginseng, whey peptides, probiotics, and omega-3 fatty acids consistently improved muscle mass, strength, and mitochondrial function via AMPK–SIRT1–PGC-1α and Akt–mTOR signaling. These mechanisms promoted mitochondrial biogenesis, suppressed proteolysis (MuRF1, Atrogin-1), and enhanced insulin sensitivity, antioxidant capacity, and gut–muscle communication. Conclusions: PHD-aligned foods combining plant proteins, polyphenols, and fermented products strengthen nutrient sensing, mitochondrial efficiency, and cellular resilience, representing a sustainable nutritional framework for preventing and managing SO and DS. Full article

Medicinal agroforestry system contributes to enhancing agricultural productivity. In this process, allelochemicals play a crucial role, and certain allelochemicals can even promote the growth of intercropped plants significantly. Previous studies by our group have shown that fig tree (Ficus carica L.) extract promotes woad (Isatis indigotica Fort.) growth significantly. However, the specific mechanism by which fig tree influences the growth of woad remains unclear. In this study, we demonstrated the growth-promoting effects of fig tree extract on woad through sterile seedling cultivation experiments and identified three allelochemicals—psoralen, bergapten, and umbelliferone. To further validate the growth-promoting activity of these compounds, a pot experiment was conducted by exogenously applying the three allelochemicals. The results revealed that all three allelochemicals derived from fig tree exhibited a property of concentration dependence on the growth of woad seedlings. Specifically, it shows an obvious promoting effect at the low concentration, while exhibiting inhibiting effects at high concentrations. Among them, the magnitude of the promoting effect, from strongest to weakest, was as follows: bergapten, psoralen, and umbelliferon. This study primarily aimed to elucidate the growth-promoting effect of woad induced by allelochemicals present in fig tree extracts and to clarify how these allelochemicals regulate woad growth. Full article

Metabolic enzymes and cancer-driving transcriptions factors are often overexpressed in neoplastic cells, and their exposed cysteine residues are amenable to chemical modification. This review explores cysteine alkylation as a cancer treatment strategy, focusing on Michael acceptors like curcumin and helenalin, which interact with transcription factors NF-κB, STAT3 and HIF-1α. Molecular docking studies using AutoDockFR revealed distinct binding affinities: curcumin showed strong interactions with STAT3 and NF-κB, while helenalin exhibited high affinity for STAT3 and HIF-1α. Synthetic compounds like STAT3-IN-1 and CDDO-Me demonstrated superior binding in most targets, except for CDDO-Me with HIF-1α, suggesting unique structural incompatibilities. Natural products such as zerumbone and umbelliferone displayed moderate activity, while palbociclib highlighted synthetic-drug advantages. These results underscore the importance of ligand−receptor structural complementarity, particularly for HIF-1α’s confined binding site, where helenalin’s terminal Michael acceptor system proved optimal. The findings advocate for integrating computational and experimental approaches to develop cysteine-targeted therapies, balancing synthetic precision with natural product versatility for context-dependent cancer treatment strategies. Full article

This study developed a rapid, non-destructive method combining near-infrared (NIR) spectroscopy with chemometric techniques (OPLS-DA, ANN, and PLS) to accurately identify the geographic origin and quantify six key chemical components of V. thibetica rhizomes. The results demonstrated that the combination of NIR spectroscopy, OPLS-DA, and ANN successfully and accurately distinguished V. thibetica from three distinct origins. Additionally, combining partial least squares (PLS) and NIR spectroscopy, the contents of chlorogenic acid, isochlorogenic acid A, isochlorogenic acid C, umbelliferone (7-hydroxycoumarin), senkyunolide I, and ligustilide measured by HPLC-UV were used as reference values to predict the contents of the six chemical components in V. thibetica, and spectral preprocessing methods optimized the model. The correlation coefficients of the final quantitative model for the contents of the six components in V. thibetica were between 0.7852 and 0.9538, the root mean square error of calibration (RMSEC) was between 0.0027 and 0.2530, and the root mean square error of prediction (RMSEP) was between 0.0031 and 0.4240. The results suggest that NIR spectroscopy combined with OPLS-DA and ANN can be used as a rapid and accurate method to evaluate the quality of V. thibetica herbs. Full article

We established a real-time Förster resonance energy transfer (FRET) based assay to evaluate targeted drug delivery using polymeric micelles. Red fluorescent protein (RFP)-expressing E. coli cells were used as a test system to monitor the delivery of drug-fluorophore such as curcumin and umbelliferones (MUmb and AMC) encapsulated in the polymeric micellar formulations. The efficiency of the drug delivery was quantified using the FRET efficiency, measured as the degree of energy transfer from the drug to the RFP. FRET efficiency directly provides the determination of the delivery efficacy, offering a versatile platform adaptable to various drugs and cell types. We used polymer micelles as a carrier for targeted delivery of fluorescent drugs to bacterial cells expressing RFP. The physicochemical characterization of the interaction between the drugs and the micelles including spectral properties, and the solubility and binding constants, were determined. We revealed a stronger affinity of MUmb for heparin-based micelles (K_d~10⁻⁵ M) compared to chitosan-based micelles (K_d~10⁻⁴ M), underscoring the influence of polymer composition on drug loading efficiency. For micelles containing MUmb, a FRET efficiency significantly exceeds (by three times) the efficiency for non-micellar MUmb, which have minimal penetration into bacterial cells. The most noticeable effect was observed with the use of the micellar curcumin providing pronounced activation of the RPF fluorescence signal, due to the interaction with curcumins (fluorophore-donor). Curcumin delivery using Chit5-OA micelle resulted in a 115% increase in RFP fluorescence intensity, and Hep-LA showed a significant seven-fold increase. These results highlight the significant effect of micellar composition on the effectiveness of drug delivery. In addition, we have developed a visual platform designed to evaluate the effectiveness of a pharmaceutical product through the visualization of the fluorescence of a bacterial culture on a Petri dish. This method allows us to quickly and accurately assess the penetration of a drug into bacteria, or those located inside other cells, such as macrophages, where the intercellular latent forms of the infection are located. Micellar formulations show enhanced antibacterial activity compared to free drugs, and formulations with Hep-OA micelles demonstrate the most significant reduction in E. coli viability. Synergistic effects were observed when combining curcumin and MUmb with moxifloxacin, resulting in a remarkable 40–50% increase in efficacy. The presented approach, based on the FRET test system with RFP expressed in the bacterial cells, establishes a powerful platform for development and optimizing targeted drug delivery systems. Full article

Melanin overexpression causes skin hyperpigmentation, which is associated with various skin disorders and cosmetic concerns. Umbelliferone, a natural coumarin found widely in plant species, has been noted for its antioxidant and anti-inflammatory effects but has received little attention for its impact on melanogenesis. Here, the effects of umbelliferone on melanogenesis were investigated in vitro and in clinical studies. The results showed that umbelliferone was non-cytotoxic to human skin and B16F10 melanoma cells. It also exhibited significant anti-melanogenic effects, reducing both melanin production and tyrosinase activity in a dose-dependent manner. This effect was achieved through a decrease in tyrosinase mRNA levels. Furthermore, umbelliferone in a formulation was stable under different temperature conditions, and after four weeks of topical application, it significantly decreased the melanin index and increased skin lightness (L*) values compared to those at the baseline. Overall, these findings demonstrate the potential of umbelliferone as a promising skin-lightening agent in the cosmetics industry. Full article

Anethum graveolens is an aromatic plant traditionally used as an antispasmodic and carminative. The objective of this study is to analyze the chemical composition of the essential oils and extracts obtained from seeds gathered in Errachidia, southern Morocco. Additionally, the antioxidant and antimicrobial properties of these oils and extracts will be evaluated. GC-MS analysis of the EO isolated by hydrodistillation revealed that its main compounds were E-anethole (38.13%), estragole (29.32%), fenchone (17.21%), and α-pinene (7.37%). The phenolic components were extracted using the methods of decoction and Soxhlet. The assay of the phenolic compounds showed that A. graveolens seeds contained considerable amounts of polyphenols, flavonoids, and condensed tannins, with variable levels depending on the extract analyzed. HPLC/UV-ESI-MS analyses performed on the decoction revealed a structural diversity of the molecules present in this extract, the most important of which were umbelliferone (12.35%), 3-hydroxyflavone (11.23%), rosmanol (8.95%), biotin (8.36%), emmotin H (4.91%), and coumarin (4.21%). The antioxidant activity, as determined by three techniques (DPPH•, FRAP, and CAT), demonstrated that the essential oils (EOs) and extracts had a potent capacity to counteract detrimental free radicals, control the generation of reactive oxygen species, and mitigate oxidative damages. The antimicrobial activity of the Eos and extracts was carried out in a liquid medium against five strains (E. cloacae, K. pneumoniae, E. coli, S. aureus, and S. epidermidis) and four candidiasis (C. albicans, C. dubliniensis, C. tropicalis, and C. parapsilosis) and Aspergillus niger. The results showed the effectiveness of the EOs compared to the aqueous, ethanolic, and decoction extracts against most of the microorganisms tested. In addition, the ethanolic extract showed antifungal activity that was distinguished from that of the other extracts. The antimicrobial efficacy of the essential oils under study can primarily be attributed to the synergistic interactions among its three principal constituents (E-anethole, estragole, and fenchone). Furthermore, molecular docking and molecular dynamics simulation results reveal significant interactions and stability between the selected bioactive compounds and different target proteins involved in antimicrobial and antioxidant activities. Compounds like 3-hydroxyflavone, emmotin H, trans-caftaric acid, methyl rosmarinate, 1-caffeoyl-beta-D-glucose, and kaempferol exhibited better binding energies with the explored proteins, indicating their potential as antimicrobial and antioxidant agents. Finally, our findings emphasize the significance of A. graveolens seeds as a promising reservoir of advantageous health compounds that can serve as organic substitutes for the presently employed synthetic preservatives. Full article

Sweet potato (Ipomoea batatas (L.) Lam.) belongs to family Convolvulaceae. The plant is distributed worldwide and consumed, especially for its edible tubers. Many studies have proved that the plant has variable biological activities such as antidiabetic, anti-cancer, antihypertensive, antimicrobial, and immunostimulant activities. The roots of sweet potatoes are rich in valuable phytochemical constituents that vary according to the flesh color. Our investigation focused on the chemical profiling of two Egyptian sweet potato cultivars, Abees and A 195, using UPLC-QTOF and the analysis of their polysaccharide fractions by GC-MS. Furthermore, we assessed the immunostimulant properties of these extracts in immunosuppressed mice. The study revealed that sweet potato roots contain significant concentrations of phenolic acids, including caffeoylquinic, caffeic, caffeoyl-feruloyl quinic, and p-coumaric acids, as well as certain flavonoids, such as diosmin, diosmetin, and jaceosidin, and coumarins, such as scopoletin and umbelliferone. Moreover, polysaccharides prepared from both studied cultivars were analyzed using GC-MS. Further biological analysis demonstrated that all the tested extracts possessed immunostimulant properties by elevating the level of WBCs, IL-2, TNF, and IFN-γ in the immunosuppressed mice relative to the control group with the highest values in polysaccharide fractions of A195 (the ethanolic extract showed a higher effect on TNF and IFN-γ, while its polysaccharide fraction exhibited a promising effect on IL-2 and WBCs). In conclusion, the roots of the Egyptian sweet potato cultivars Abees and A 195 demonstrated significant immunostimulant activities, which warrants further investigation through clinical studies. Full article

Aegle marmelos (L.) Correa is an economically and therapeutically valuable tree. It is cultivated as a fruit plant in southeast Asian countries. In this research, we investigated the allelopathy and possible allelochemicals in the leaves of A. marmelos. Aqueous methanol extracts of A. marmelos exhibited significant inhibitory effects against the growth of Lepidium sativum, Lactuca sativa, Medicago sativa, Echinochloa crusgalli, Lolium multiflorum, and Phleum pratense. Bioassay-directed chromatographic purification of the A. marmelos extracts resulted in identifying five active compounds: umbelliferone (1), trans-ferulic acid (2), (E)-4-hydroxycinnamic acid methyl ester (3), trans-cinnamic acid (4), and methyl (E)-3’-hydroxyl-4’-methoxycinnamate (5). The hypocotyl and root growth of L. sativum were considerably suppressed by these compounds. Methyl (E)-3’-hydroxyl-4’-methoxycinnamate also suppressed the coleoptile and root growth of E. crusgalli. The concentrations of these compounds, causing 50% growth reduction (I₅₀) of L. sativum, were in the range of 74.19–785.4 μM. The findings suggest that these isolated compounds might function in the allelopathy of A. marmelos. Full article

Umbelliferone (UMB), known as 7-hydroxycoumarin, hydrangine, or skimmetine, is a naturally occurring coumarin in the plant kingdom, mainly from the Umbelliferae family that possesses a wide variety of pharmacological properties. In addition, the use of nanoparticles containing umbelliferone may improve anti-inflammatory or anticancer therapy. Also, its derivatives are endowed with great potential for therapeutic applications due to their broad spectrum of biological activities such as anti-inflammatory, antioxidant, neuroprotective, antipsychotic, antiepileptic, antidiabetic, antimicrobial, antiviral, and antiproliferative effects. Moreover, 7-hydroxycoumarin ligands have been implemented to develop 7-hydroxycoumarin-based metal complexes with improved pharmacological activity. Besides therapeutic applications, umbelliferone analogues have been designed as fluorescent probes for the detection of biologically important species, such as enzymes, lysosomes, and endosomes, or for monitoring cell processes and protein functions as well various diseases caused by an excess of hydrogen peroxide. Furthermore, 7-hydroxy-based chemosensors may serve as a highly selective tool for Al³⁺ and Hg²⁺ detection in biological systems. This review is devoted to a summary of the research on umbelliferone and its synthetic derivatives in terms of biological and pharmaceutical properties, especially those reported in the literature during the period of 2017–2023. Future potential applications of umbelliferone and its synthetic derivatives are presented. Full article

The present study focuses on the synthesis of the natural product 4-methyl-umbelliferone (4-MU, hymecromone), the preparation, characterization, and biological activity evaluation of 4-MU inclusion complexes with β-cyclodextrin (β-CD), as well as their incorporation into pharmaceutical tablets. The inclusion complexes (ICs) were characterized using DLS, SEM, TGA as well as FT-IR, UV-vis, and NMR spectroscopies. The release profile of 4-MU from the β-CD-4-MU ICs was studied in three different pH: 1.2 (aqueous hydrochloric acid), 7.4, and 6.8 (phosphate-buffered solutions), to simulate the stomach, physiological, and intestine pH, respectively. The ICs were incorporated in pharmaceutical tablets which were prepared by direct compression and were characterized for their mechanical properties. The optimal composition of 4-MU as the active pharmaceutical ingredient (API) and excipients was determined using design of experiment (DoE), and the dissolution studies were performed at pH 1.2 at 37 ± 0.5 °C. The sustained release profile of the pharmaceutical tablets showed a delayed burst release effect at 20 min (20% drug release) compared to that of the ICs at the same time interval (70%). The results indicated that the kinetic model describing the release profile of 4-MU from the ICs and tablets is the Higuchi model, while the release mechanism is swelling and diffusion, as was indicated by the Korsmeyer–Peppas kinetic model. The optimization analysis revealed that the optimum composition contains x₁ = 150.95 mg of β-CD-4-MU ICs, x₂ = 82.65 mg of microcrystalline cellulose, and x₃ = 12.40 mg of calcium phosphate. Full article

Ferulopsis hystrix is a perennial plant of the Apiaceae family. In Buryat and Mongolian medicine, it is used as a substitute for Costus speciosus roots (ru rta), and in Tibetan medicine, it is used to cure digestive system diseases and used as a wound-healing agent. However, its metabolites and their bioactivities are still poorly understood. High-performance liquid chromatography with photodiode array detection and electrospray ionization triple quadrupole mass-spectrometric detection (HPLC–PDA–ESI–tQ–MS/MS) were used to identify approximately 42 phenolic compounds in F. hystrix, and 30 coumarins were characterized and quantified. The major compounds in F. hystrix roots were skimmin (umbelliferone 7-O-glucoside) and peucenidin (vaginidiol 3′-O-acetyl-4′-O-senecioyl ester), of which, gastroprotective and antioxidant effects were found for the first time. The abovementioned compounds exhibit a gastroprotective effect against indomethacin and steroid gastropathy by reducing the amount of damage (point, large, and strip-like erosions) in the gastric mucosa and lowering the corresponding Paul’s index. The most pronounced gastroprotective effect was exhibited by skimmin at a dose of 1 mg/kg and by peucenidin at doses of 16 and 48 mg/kg; these compounds help to limit the development of pronounced erosive–necrotic processes in the gastric mucosa. In pathological conditions, these compounds reduce malondialdehyde, increase the activity of catalase, and increase the content of reduced glutathione in the blood. Thus, this study demonstrates that F. hystrix roots are a good source of bioactive coumarins with gastroprotective potential, which supports earlier ethnopharmacological studies. Full article

Quorum sensing inhibitors (QSIs) are an attractive alternative to antibiotic growth promoters in farmed animal nutrition. The goal of the study was the diet supplementation of Arbor Acres chickens with quercetin (QC), vanillin (VN), and umbelliferon (UF), which are plant-derived QSIs preliminarily showing cumulative bioactivity. Chick cecal microbiomes were analyzed by 16s rRNA sequencing, inflammation status was assessed by blood sample analyses, and zootechnical data were summarized in the European Production Efficiency Factor (EPEF). When compared to the basal diet control group, a significant increase in the Bacillota:Bacteroidota ratio in the cecal microbiome was found in all experimental subgroups, with the highest expression > 10 at VN + UV supplementation. Bacterial community structure in all experimental subgroups was enriched with Lactobacillaceae genera and also changed in the abundance of some clostridial genera. Indices of richness, alpha diversity, and evenness of the chick microbiomes tended to increase after dietary supplementation. The peripheral blood leukocyte content decreased by 27.9–45.1% in all experimental subgroups, likely due to inflammatory response reduction following beneficial changes in the cecal microbiome. The EPEF calculation showed increased values in VN, QC + UF, and, especially, VN + UF subgroups because of effective feed conversion, low mortality, and broiler weight daily gain. Full article

Alzheimer’s disease (AD) is a neurodegenerative disorder, characterized by memory loss and cognitive decline. Among the suggested pathogenic mechanisms of AD, the cholinergic hypothesis proposes that AD symptoms are a result of reduced synthesis of acetylcholine (ACh). A non-selective antagonist of the muscarinic ACh receptor, scopolamine (SCOP) induced cognitive impairment in rodents. Umbelliferone (UMB) is a Apiaceae-family-derived 7-hydeoxycoumarin known for its antioxidant, anti-tumor, anticancer, anti-inflammatory, antibacterial, antimicrobial, and antidiabetic properties. However, the effects of UMB on the electrophysiological and ultrastructure morphological aspects of learning and memory are still not well-established. Thus, we investigated the effect of UMB treatment on cognitive behaviors and used organotypic hippocampal slice cultures for long-term potentiation (LTP) and the hippocampal synaptic ultrastructure. A hippocampal tissue analysis revealed that UMB attenuated a SCOP-induced blockade of field excitatory post-synaptic potential (fEPSP) activity and ameliorated the impairment of LTP by the NMDA and AMPA receptor antagonists. UMB also enhanced the hippocampal synaptic vesicle density on the synaptic ultrastructure. Furthermore, behavioral tests on male SD rats (7–8 weeks old) using the Y-maze test, passive avoidance test (PA), and Morris water maze test (MWM) showed that UMB recovered learning and memory deficits by SCOP. These cognitive improvements were in association with the enhanced expression of BDNF, TrkB, and the pCREB/CREB ratio and the suppression of acetylcholinesterase activity. The current findings indicate that UMB may be an effective neuroprotective reagent applicable for improving learning and memory against AD. Full article