Search Results (209)

Thiochromen-4-ones are known to possess useful optical properties and rich bioactivities, including antioxidant, antimicrobial, and anticancer properties. They are known to inhibit tumor cell growth, induce apoptosis, and have antiplatelet aggregation effects. Thiochromen-4-ones are also used as synthons and precursors in organic synthesis for bioactive agents. Although many synthetic approaches to oxygen-containing counterparts, chromones, have been reported, research on the synthesis of thiochromen-4-ones is scarce. The synthesis of thiochromen-4-ones can be challenging due to the inherent nature of sulfur, including its multiple oxidation states and tendency to form diverse bonding patterns. Here, we report the one-pot synthesis of thiochromen-4-ones, where two transformations of the starting material, 3-(arylthio)propanoic acid, are performed within a single reaction vessel, eliminating the need for an intermediate purification step. This one-pot reaction worked well with a variety of substrates with both electron-withdrawing and donating groups on the aromatic ring of 3-(arylthio)propanoic acids to give thiochromen-4-ones with good yields (up to 81%). This approach offers advantages like time and cost savings, increased efficiency, and reduced waste. This synthetic approach will allow access to a broader scope of thiochromen-4-ones due to the readily available thiophenols. Full article

A new copper(II) complex was synthesized using chromone-2-carboxylic acid as the main ligand, and coordinated pyridine molecules. The complex was successfully crystallized and structurally characterized by single crystal X-ray diffraction. This revealed a mononuclear structure with a distorted square pyramidal geometry around the central Cu(II) ion. The coordination sphere comprises oxygen atoms from the chromone moiety and nitrogen atoms from pyridine, resulting in a five-coordinate complex. A comprehensive physicochemical characterization was performed using Fourier transform infrared spectroscopy (FT-IR), UV–Vis spectroscopy, elemental (C, H, N), electrochemical (CV) and thermal analysis (TGA/DSC) to confirm the coordination environment and thermal stability of the compound. The complex exhibits distinct spectroscopic features indicative of ligand–metal charge transfer and d–d transitions typical of Cu(II) species. In addition, the synthesized complex was subjected to antimicrobial screening against Gram-positive and Gram-negative bacteria. The compound showed promising antibacterial activity, particularly against Escherichia coli, indicating its potential as a bioactive coordination compound. These results contribute to the growing body of research on metal-based chromone derivatives and emphasize the importance of copper complexes for the development of new antibacterial agents with defined crystal structures. Full article

Cicerbita alpina (L.) Wallroth and Peucedanum ostruthium W.D.J. Koch occur in megaphorb communities in alpine and subalpine areas; both species often share the same habitats. P. ostruthium is used as a spice for spirits, while young shoots of C. alpina are collected in the northeastern regions of Italy as a local delicacy. In the present study, we isolated eleven known coumarins and one chromone from subaerial parts of P. ostruthium; two furanocoumarins were found for the first time in this species. Using UHPLC-HRMS, we analyzed the furanocoumarin content of two P. ostruthium accessions, one commercially purchased and one collected in the wild. These samples were compared to six rootstock samples of Cicerbita alpina collected in the wild. Though the furanocoumarins imperatorin, isoimperatorin, oxypeucedanin, and ostruthol had been reported from C. alpina before, we were not able to detect any of these compounds in our samples of C. alpina. Therefore, and due to the occurrence of both taxa in the same habitat, we assume that the original report of furanocoumarins in C. alpina was based on a mixed collection of C. alpina and P. ostruthium. This hypothesis seems plausible, because furanocoumarins have not been reported from any other taxon of the Cichorieae tribe of the Asteraceae family. Full article

Agarwood, valued for its resin, has long been used in perfumery, incense, and traditional medicine. Its resin is primarily derived from species of Aquilaria and is produced through a still-unknown process in response to biotic or abiotic stress. Concerns regarding agarwood’s sustainability and conservation have emerged because of the substantial loss of natural resources due to overharvesting and illegal trade. To address these concerns, artificial techniques are being used to produce agarwood. The mechanism underlying agarwood production must be elucidated to enhance yield. The authentication of agarwood species is challenging because of morphological similarities between pure and hybrid Aquilaria species. Techniques such as DNA barcoding, molecular marker assessment, and metabolomics can ensure accurate identification, facilitating conservation. Artificial intelligence and machine learning can support this process by enabling rapid, automated identification on the basis of genetic and phytochemical data. Advances in resin induction methods (e.g., fungal inoculation) and chemical induction treatments are improving yield and quality. Endophytic fungi and bacteria promote resin production at minimal harm to the tree. Agarwood’s pharmacological potential—antimicrobial, anti-inflammatory, and anticancer effects—has driven research into bioactive compounds such as sesquiterpenes and flavonoids for the development of novel drugs. This systematic review synthesized current evidence on species authentication, induction techniques, and pharmacological properties. The findings may guide future research aimed at ensuring sustainable use and enhancing the medicinal value of agarwood. Full article

Aquilaria sinensis (Lour.) Gilg, the exclusive botanical source of Chinese agarwood, holds significant medicinal value. This study investigated the agarwood-inducing potential of a Fusarium strain obtained through prior isolation work. Through integrated morphological characterization and molecular phylogenetic analysis, the strain was conclusively identified as Fusarium equiseti. GC-MS analysis revealed that fungal inoculation induced the synthesis of characteristic sesquiterpenes and aromatic compounds consistent with natural agarwood profiles. Quantitative determination demonstrated progressive accumulation of agarotetrol, a key quality marker, reaching 0.034%, 0.039%, and 0.038% at 2, 4, and 6 months post-inoculation, respectively—significantly exceeding levels from physical wounding (p < 0.05) and PDA control treatments. Histological examination showed characteristic yellow-brown oleoresin deposits concentrated in the inner phloem, mirroring the anatomical features of wild-type agarwood. Critical quality parameters measured in December-harvested samples included ethanol extractives (17.69%), chromone derivatives 2-[2-(4-methoxyphenyl) ethyl] chromone, and 2-(2-phenylethyl) chromone (2.13%), all meeting or surpassing the specifications outlined in the National Standard for Agarwood Classification (LY/T 3223-2020). These comprehensive findings establish F. equiseti as a promising microbial agent for sustainable agarwood production in A. sinensis plantations. Full article

This study aims to explore the anti-inflammatory pharmacological components and anti-inflammatory mechanisms of the alcohol extract of Saposhnikoviae Radix (SR). The components of the alcohol extract of SR were analyzed using the UPLC-MS/MS system. The anti-inflammatory efficacy of the alcohol extract and core components of SR was evaluated using the LPS-induced inflammation model of RAW264.7 cells. The anti-inflammatory mechanism of SR in a mouse model of rheumatoid arthritis was expounded by means of serum metabolomics, network pharmacology, and molecular docking. A total of 12 chromones and 13 coumarins were identified in the alcohol extract of SR. The alcohol extract of SR and its components all had good anti-inflammatory activities. In the mouse model of rheumatoid arthritis, the glycoside compounds of SR were transformed into aglycones, thereby exerting anti-inflammatory effects. Moreover, the alcohol extract of SR alleviated the inflammatory response by up-regulating the expression levels of metabolites such as phenylalanine and tyrosine. Network pharmacology and molecular docking results show that SR could exert an anti-inflammatory effect by regulating AGE-RAGE, PI3K-Akt, TNF, MAPK, and Toll-like signaling pathways. In this study, the anti-inflammatory efficacy and mechanisms of the alcohol extract of SR are explored, with the aim of providing a reference for subsequent research. Full article

Alzheimer’s disease (AD) is a multi-factorial neurodegenerative disease with a complex pathomechanism that can be best treated with multi-target medications. Among the possible molecular targets involved in AD, acetylcholinesterase (AChE) and monoamine oxidase B (MAO-B) are well recognized because they control the neurotransmitters responsible for memory processes. This review discusses the current understanding of AD pathology, recent advances in AD treatment, and recent reports in the field of dual AChE/MAO-B inhibitors for treating AD. We provide a classification of dual inhibitors based on their chemical structure and describe active compounds belonging to, i.a., chalcones, coumarins, chromones, imines, and hydrazones. Special emphasis is given to the computer-aided strategies of dual inhibitors design, their structure–activity relationships, and their interactions with the molecular targets at the molecular level. Full article

Fungal infections are recognized as a global health issue, in particular considering the spread of different forms of resistance to the commonly used antifungal drugs and their involvement in the occurrence of co-infections in hospitalized and immunocompromised patients. In this paper, a small series of hybrid compounds were designed and synthesized by linking the privileged chromone and xanthone scaffolds, endowed with recognized antimicrobial potential, to the tert-butylbenzylamino portion of the antifungal drug butenafine, through selected linkers. The results showed for the xanthone-based compound 3 a promising activity towards C. auris, C. tropicalis, and C. neoformans, for which a high degree of resistance is commonly observed, together with a significant antibacterial potency towards Gram-positive bacteria, such as S. aureus. Considering that compound 3 displayed favorable selectivity and therapeutic indexes (9.1 and >16, respectively), it appeared as a valuable prototype, deserving further hit-to-lead optimization. Full article

Ptaeroxylon obliquum (Thunb.) Radlk. (Rutaceae) is traditionally used for a range of purposes, including ethnoveterinary medicine and to treat various human ailments such as tuberculosis, inflammatory diseases, and bacterial and fungal infections. This review aims to comprehensively summarize the traditional uses, phytochemistry, toxicology, in silico, and pharmacological activities of P. obliquum and discuss the advances made to date. The phytochemistry of P. obliquum revealed the abundance of secondary metabolites such as coumarins and chromones, essential oils, and several other classes of bioactive compounds. A total of 80 secondary metabolites have been reported from this plant species. In vitro studies on P. obliquum explored its therapeutic potential and reported pharmacological properties such as antifungal, antibacterial, antiparasitic, antimycobacterial, anti-inflammatory, and antiproliferative activities. This review highlights the diversity of the medicinal use of P. obliquum and encourages its preservation. Future research should focus on the efficacy of P. obliquum’s most promising bioactive compounds, and the ADME (absorption, distribution, metabolism, and excretion) pharmacological activities may help determine therapeutic potential in in vivo animal models and validate the wide range of traditional uses of P. obliquum. Full article

The Onocleaceae family, a small group within the Pteridophytes, comprises four genera, but has been phytochemically studied mainly for Pentarhizidium orientale, Pentarhizidium intermedium, and Matteuccia struthiopteris. To date, a total of 91 compounds have been isolated from these three species, including 15 flavonoids, 48 flavonoid glycosides, 6 stilbenes, 4 isocoumarins, 2 phthalides, 3 chromones, 2 lignan glycosides, 8 isoprenoid derivatives, and 3 phenolic compounds. Notably, most flavonoids and flavonoid glycosides possess C-methyl groups at the C-6 and/or C-8 positions, with several conjugated to (S)-3-hydroxy-3-methylglutaryl (HMG) moieties. Although not all isolates have been evaluated for their pharmacological activities, several compounds have demonstrated bioactivities such as antiviral, anti-inflammatory, α-glucosidase inhibitory, aldose reductase inhibitory, and antioxidant effects. Full article

For the first time, hydroethanolic extracts from Actaea cimicifuga and Actaea erythrocarpa were analyzed using LC-HRMS, HPLC, and spectrometry in this study. Extracts from the above-ground parts of Actaea species exhibited higher concentrations of saponins (up to 248 mg/g of DE), coumarins (up to 162 mg/g of DE), flavonols (up to 32 mg/g of DE), and catechins (up to 11 mg/g of DE) compared to extracts from the underground parts. The concentrations of phenolic acids (up to 112 mg/g of DE) and tannins (up to 202 mg/g of DE) in the underground parts were comparable to or even higher than those in the above-ground parts of the two analyzed species. The concentration of the main metabolites detected was higher in the extract of A. erythrocarpa than that of A. cimicifuga. The metabolite profile of the extracts from both species showed 66 compounds, including chromones, coumarins, phenolic and nitrogenous compounds, fatty acids, and triterpenes. The HPLC analysis of the four extracts revealed that the concentration of caffeic acid (0.74 mg/g of the dry extract [DE]) was the highest in the extract from the underground part of A. erythrocarpa, whereas the extract from the above-ground part of this species showed the highest levels of ferulic (1.16 mg/g of DE) and isoferulic acids (1.49 mg/g of DE) and of hyperoside (13.05 mg/g of DE). The study of biological activity showed that A. erythrocarpa is most promising for further research, with the highest antioxidant activity found in the underground parts of this species (IC₅₀ = 79.7 μg/mL) compared to the above-ground parts (IC₅₀ = 85.8 μg/mL). In addition, the extract from the above-ground part of A. erythrocarpa was found to exhibit the greatest cytotoxic activity among the studied specimens against 3T3-L1, HepG2, and MDA-MB-231 cells. Full article

Alzheimer’s disease (AD) is a devastating neurodegenerative disorder affecting millions worldwide and imposing a significant social and economic burden. Despite extensive research, there is still no effective cure for this disease. AD is multifactorial and involves multiple etiopathogenic mechanisms, one of which is oxidative stress. Consequently, the Nrf2/ARE pathway, which regulates the expression of cellular defense genes, including those for antioxidant enzymes, is considered to be a prospective therapeutic target for AD. Meanwhile, multitarget-directed ligands (MTDLs) are a promising approach for developing effective AD medications. In this regard, we evaluated the antioxidant potential of eight chromone-containing MTDLs in vitro, including Nrf2 transcriptional activation potencies, Nrf2/ARE downstream genes activation, and antioxidant effects in vitro. All tested compounds effectively activated the Nrf2/ARE pathway. Notably, compounds 4b, 4c, 4f, and 4h demonstrated the highest Nrf2 activation potencies, while compounds 4b, 4c, 4d, and 4g significantly induced the expression of Nrf2-target antioxidant genes, specifically NQO1 and HO1. Additionally, compound 4d exhibited a significant antioxidant effect in vitro. These findings encourage further investigation of the studied compounds, with particular emphasis on compound 4d as the most promising candidate. Full article

Aquisinenins G–I (1–3), three new 2-(2-phenylethyl)chromone-sesquiterpene hybrids, were isolated from the ethanol extract of Hainan agarwood derived from Aquilaria sinensis. Spectroscopic techniques, such as ¹D and ²D NMR and HRESIMS, were used to determine their structures. Experimental and computed ECD data were compared to confirm their absolute configurations. Compounds 1–3 are uncommon dimeric derivatives of 2-(2-phenylethyl)chromone-sesquiterpene, characterized by the fusion of 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone with agarofuran or agarospirane-type sesquiterpene units by an ester linkage. Compound 1 inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells, showing an IC₅₀ value of 22.31 ± 0.42 μM. The neuroprotective effects of compounds 1 and 3 against H₂O₂-induced apoptosis were assessed in human neuroblastoma SH-SY5Y cells. Compound 1 demonstrated cytotoxicity with IC₅₀ values of 72.37 ± 0.20 μM against K562 and 61.47 ± 0.22 μM against BEL-7402, while compounds 2 and 3 showed cytotoxicity across all five tested human cancer cell lines. Full article

Three new complexes of copper(II) and chromone-2-carboxylic acid, a ligand from the group of hydroxypyrones, were synthesised according to the principles of green chemistry. The complexes were characterised by FT–IR and NMR spectroscopy, thermal and electrochemical analysis, and their structures are proposed. The results show the formation of mononuclear (1) and dinuclear hydroxo-bridged dinuclear copper(II) complexes (2 and 3). The results of cyclic voltammetry show that the copper in all complexes is in the +2-oxidation state. The antiproliferative activity was determined by MTT assay on 2D cell models in vitro on seven cell lines. The activity spectrum of complexes 1–3 ranged from the highest to the lowest value in the tumour cell lines tested, in the following order: Hep G2 > NCI-H358 > HT-29 > KATO III > MDA-MB 231 > Caco-2. The most effective concentration was 10⁻⁵ mol dm⁻³, which suppressed the growth of Hep G2 cells as follows: 69.5% (1), 64.8% (2) and 64% (3). The calculated selectivity index clearly shows that Hep G2 is the most sensitive cell line to copper complexes (SI = 1.623 (1); 1.557 (2), 1.431 (3). Full article

One pair of novel enantiomers, gigantdioxin A (+)-1 and B (−)-1, with a skeleton of benzo[d][1,3]dioxin; a new acetophenone gigantone A (3); a known 3-chlorogentisyl alcohol (2), which is the bioprecursor of 1; acetophenone (4); and chromone derivative (5) were obtained from the sponge-associated fungus Aspergillus giganteus MA46-5. Their structures were established by extensive and in-depth spectral analysis, such as UV, 1D and 2D NMR, and HRESIMS. The absolute configurations of (±)-1 were deduced by ORD, chiral separation, and experimental and computational ECD. Meanwhile, we proposed a possible biosynthetic pathway of (±)-1. Fortunately, the pathway was proved by biomimetic synthesis through 2, as a bioprecursor, reacted with n-butyraldehyde. Myocardial protection assays showed that 3 and 4 possessed stronger protective effects than a positive control against myocardial cell H9c2 ischemia–reperfusion injury in low concentrations, and the effect of (−)-1 was almost equal to that of the positive control. Further, we explored the possible mechanism of myocardial protection through network pharmacology. Adenosine A2a receptor (ADORA2A) and serum albumin (ALB) represent potential targets for myocardial protection associated with (−)-1 and 4, respectively. Based on the network pharmacology, we docked the predicted proteins with bioactive compounds using Autodock Vina. Full article