Search Results (216)

Herein, we disclose a highly efficient pathway toward 3-selenylated chromone derivatives via electrosynthesis domino C(sp²)-H bond selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, a wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amenable to scaling up the reaction. Additionally, the preliminary experiments revealed that this reaction probably proceeded via a cation pathway instead of a radical pathway. Full article

Alzheimer’s disease (AD) is a prevalent neurodegenerative condition that progressively impairs cognitive processes, particularly learning and memory. A key pathological feature of AD involves senile plaques mainly composed of β-amyloid (Aβ) peptides, generated via the amyloidogenic pathway from amyloid precursor protein (APP) through sequential β-secretase (BACE1) and γ-secretase cleavage, positioning BACE1 inhibition as a prime therapeutic target. In this study, we applied bioassay-guided fractionation of the butanol-soluble fraction from Dryopteris crassirhizoma rhizomes, previously reported to inhibit Aβ production, to isolate and characterize Aβ-lowering constituents. Through successive chromatographic steps, nine compounds were isolated and structurally classified into flavonoids, chromones, and phloroglucinols, including epicatechin (1), β-carboxymethyl-(-)-epicatechin (2), 7-methoxy-isobiflorin (3), biflorin (4), eriodictyol (5), noreugenin (6), phloroglucinols (butyrylphloroglucinol (7), 2-propionyl-4-methylphloroglucinol (8), and 2-butyryl-4-methylphloroglucinol (9) by comprehensive spectroscopic analysis (NMR, MS, UV, IR). These compounds were assessed for effects on sAPPβ and BACE1 (β-secretase) levels by Western blot, with Aβ production quantified via ELISA in a cellular AD model (APP-CHO cells). Compounds 5–9 significantly reduced sAPPβ and BACE1 expression while potently suppressing Aβ generation. These results demonstrate that diverse constituents from D. crassirhizoma rhizomes inhibited Aβ production through BACE1 suppression, highlighting their potential as natural lead compounds for AD prevention or therapy. Full article

Senna petersiana (Bolle) Lock is a chemically diverse plant widely recognized for its ethnomedicinal applications across various traditional medical systems. It is native to and widely distributed in African countries, including Ethiopia, Cameroon, and South Africa. This review integrates the phytochemical composition, biological activities, and toxicological effects of S. petersiana. Phytochemical analyses reveal the presence of numerous classes of compounds, including alkaloids, flavonoids, phenolics, anthraquinones, chromones, and sterol glycosides, with variations in concentration across different plant parts. Quantitative studies highlight particularly high levels of phenolics and flavonoids in ethanol, methanol, and acetone extracts, correlating these with enhanced biological activities. Pharmacological investigations demonstrate a spectrum of activities, including antibacterial, antioxidant, anti-inflammatory, antiviral, anthelmintic, and anticancer effects, supporting many of the plant’s traditional uses. Toxicological assessments suggest relative safety at moderate doses, though further evaluation is necessary for specific cell types and high-dose exposures. Despite the promising bioactivities, the mechanisms of action and in vivo efficacy of isolated compounds remain underexplored. Future research should focus on bioassay-guided isolation, detailed pharmacodynamic studies, and comprehensive toxicological profiling to validate and harness the therapeutic potential of S. petersiana. This review highlights the plant’s biochemical complexity and paves the way for its development as a valuable phytopharmaceutical agent. Full article

In this work, biscoumarin molecules were obtained by a multicomponent reaction, without catalysts, under thermal heating or microwave irradiation. First, optimization tests were performed using benzaldehyde and 4-hydroxycoumarin as starting substrates. The optimal temperature (100 °C), solvent (1-propanol), and reaction time (4 h for conventional heating and 1 h for microwave irradiation) were then employed for the reaction between 4-hydroxycoumarin and different 3-formylchromones to obtain biscoumarins. Good yields and selectivity, which in most cases were greater than 65%, both with conventional thermal heating and microwave radiation, were achieved. Full article

1,5-disubstituted tetrazoles (1,5-Ds-T) are heterocyclic bioisosteres of the cis-amide bond, commonly found in bioactive compounds, pharmaceuticals, and functional materials. Chromones are privileged scaffolds widely present in natural products that are well known for their diverse biological activities, including anticancer, antimicrobial, antidiabetic, anti-inflammatory, and antioxidant properties. Isocyanide-based multicomponent reactions, such as the Ugi-Azide (UA-4CR), provide a versatile strategy for synthesizing 1,5-Ds-T, which can be incorporated into other privileged heterocyclic or commercially available drugs. Herein, we describe a sonochemical one-pot synthesis of 1,5-Ds-T connected to chromone under mild conditions, highlighting their potential relevance in medicinal chemistry. Full article

Two new chromone derivatives, cnidimols I and J (1 and 2), together with ten known aromatic derivatives (3–12), were isolated from the Beibu Gulf algicolous fungus Aspergillus versicolor GXIMD 02518. Their structures were determined by comprehensive physicochemical and spectroscopic data interpretation. The absolute configurations of 1 and 2 were accomplished by ECD calculations and X-ray diffraction analysis. Compound 1 was obtained as a pair of enantiomers, which were separated by chiral-phase HPLC analysis. Notably, 3,7-dihydroxy-1,9-dimethyldibenzofuran (6) displayed significant inhibition in LPS-induced NF-κB luciferase activity in RAW 264.7 macrophages, which further inhibited RANKL-induced osteoclast differentiation without cytotoxicity in bone marrow macrophage cells. Full article

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