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Electrochemically induced, decarboxylative functionalization of chromone‐3‐carboxylic acids by N‐hydroxyphthalimide esters as alkyl radical precursors was studied. Electrochemical protocol offers a sustainable and green approach, obviating the need for catalysts, relying on the direct reduction of NHPI esters using electric current. Developed protocol provides a straightforward route to the synthesis of diverse molecules with potential biological activity. [ABSTRACT FROM AUTHOR]

A highly convenient and straightforward strategy for the synthesis of difluoromethyl substituted tricyclic fused chromono[3,2- c ]pyrazolines/pyrazoles is developed via [3+2]-cycloaddition of difluoroacetohydrazonoyl bromides to chromene derivatives bearing an electron-withdrawing group at the 3-position. The reaction has the advantages of mild conditions, good tolerance of functional groups, and simple operation. [ABSTRACT FROM AUTHOR]

The n-butanol extract of Stachys arvensis (L.) L. aerial parts (BESA) was analysed by LC-HRMS/MS. 43 Polyphenols, including flavonoids, cinnamic acid derivatives, phenylethaoids, chromones, gallotannins, coumarins and chalcones with hyperoside (13.85%), panasenoside (10.31%), myricitrin (7.89%) and sayaendoside (7.16%), as the major compounds, were identified. High total phenolics (470.21 ± 1.22 mg GAE/g extract) and total flavonoids (189.05 ± 0.72 mg QE/g extract) contents were measured. In addition, the BESA exhibited a higher antioxidant effect in CUPRAC (A0.5:0.45 ± 0.03 μg/mL), DPPH (IC50:4.51 ± 0.16 μg/mL) and ABTS (IC50:7.10 ± 0.18 μg/mL) assays than the standards BHA and α-Tocopherol. Moreover the extract showed a good inhibitory effect against BChE (IC50: 145.02 ± 0.03 μg/mL) and α-amylase (IC50:2.66 ± 0.0024 mg/mL). The BESA exhibited an excellent anti-inflammatory activity (IC50:416 ± 0,056 μg/mL) which was close to that of acetylsalicylic acid, used as a control. The BESA was toxic towards T. molitor larvae and it possessed a good antibacterial activity against gram (+) and gram (-) tested strains. [ABSTRACT FROM AUTHOR]

The chemical reactivity of 3-formylchromones toward several carbon and nitrogen nucleophiles is collected in this review. Certain annulated chromones and 3-heteroaryl chromones were synthesized. A diversity of three component reactions including 3-formylchromones was also summarized. [ABSTRACT FROM AUTHOR]

The process of formation of aromatic components for agarwood in Aquilaria sinensis is closely related to endophytic fungi and the result of complex multiple long-term joint interactions with them. However, the interactions between the aromatic components and endophytic fungi remain unclear during the formation of agarwood. In this study, precise mixed solution of hormones, inorganic salts, and fungi was used to induce its formation in A. sinensis, and sample blocks of wood were collected at different times after inoculation. This study showed that the aromatic compounds found in the three treatments of A. sinensis were primarily chromones (31.70-33.65%), terpenes (16.68-27.10%), alkanes (15.99-23.83%), and aromatics (3.13-5.07%). Chromones and terpenes were the primary components that characterized the aroma. The different sampling times had a more pronounced impact on the richness and diversity of endophytic fungal communities in the A. sinensis xylem than the induction treatments. The species annotation of the operational taxonomic units (OTUs) demonstrated that the endophytic fungi were primarily composed of 18 dominant families and 20 dominant genera. A linear regression analysis of the network topology properties with induction time showed that the interactions among the fungal species continued to strengthen, and the network structure tended to become more complex. The terpenes significantly negatively correlated with the Pielou evenness index (p < 0.05), while the chromones significantly positively correlated with the OTUs and Shannon indices. [ABSTRACT FROM AUTHOR]

In the context of designing innovative anticancer agents, the synthesis of a series of chalcones bearing a 3,4,5-trimethoxylated A ring and a variety of B rings, including phenols and original heterocycles such as chromones, was conducted. For this end, Claisen–Schmidt condensation was performed in basic or acidic conditions between the common starting material 3,4,5-trimethoxyacetophenone and appropriate aldehydes; this allowed the recovery of fifteen chalcones in moderate–good yields. The synthesized compounds were screened for their antiproliferative activity against colorectal and prostatic cancer cells, using a colorimetric MTT assay. Among the new chromonyl series, chalcone 13 demonstrates an interesting antiproliferative effect, with IC50 values in the range of 2.6–5.1 µM at 48 h. Then, our study evidenced that indolyl chalcone 10 exhibits excellent activity towards the selected cell lines (with IC50 less than 50 nM). This compound has already been described and has been shown to be a potent anticancer agent against other cancer cell lines. Our investigations highlighted apoptosis induction, through several pro-apoptotic markers, of these two heterocyclic chalcones. Considering phenolic chalcones, compounds 2 and 8 were found to be the most active against cell proliferation, exerting their effect by inducing the depolymerization of cell microtubules. The most promising compounds in this series will be selected for application in a strategy of vectorization by either active or passive targeting. [ABSTRACT FROM AUTHOR]

Natural products have always served as an important source of drugs for treating various diseases. Among various privileged natural product scaffolds, the benzopyrone class of compounds has a substantial presence among biologically active compounds. One of the pioneering anticoagulant drugs, warfarin approved in 1954 bears a benzo‐α‐pyrone (coumarin) nucleus. The widely investigated psoriasis drugs, methoxsalen, and trioxsalen, also contain a benzo‐α‐pyrone nucleus. Benzo‐γ‐pyrone (chromone) containing drugs, cromoglic acid, and pranlukast were approved as treatments for asthma in 1982 and 2007, respectively. Numerous other small molecules with a benzopyrone core are under clinical investigation. The present review discusses the discovery, absorption, distribution, metabolism, excretion properties, and synthetic approaches for the Food and Drug Administration‐approved and clinical‐stage benzopyrone class of compounds. The role of the pyrone core in biological activity has also been discussed. The present review unravels the potential of benzopyrone core in medicinal chemistry and drug development. [ABSTRACT FROM AUTHOR]

The new natural products reported in 2023 in peer-reviewed articles in journals with good reputations were reviewed and analyzed. The advances made by Asian research groups in the field of natural products chemistry in 2023 were summarized. Compounds with unique structural features and/or promising bioactivities originating from Asian natural sources were discussed based on their structural classification. [ABSTRACT FROM AUTHOR]

It is well known that chromones possess numerous of biological activities. Due to their significant applications, there are increasing for synthesizing of several chromones but few pyranochromene have been synthesized. So, simple and convenient routes for the synthesizing of new pyrano[3,2‐g]chromenone derivatives in high yields were illustrated using visnagin as starting naturally occurring. Ring opening of visnagin afforded 6‐formyl‐7‐hydroxychromone derivative which was subjected to react with variety of active methlyene derivatives to afford pyrano[3,2‐g]chromenone derivatives. Thus, heating of 6‐formylchromone with aroylacetate gave the 3‐(aroyl)‐pyranochromene‐2,6‐dione. The desired pyranochromene‐3‐carboxamide derivatives were obtained when the precursor 6‐formylchromone was condensed with ethyl 3‐oxo‐3‐(arylamino)propanoates. When 6‐formylchromone was condensed with hippuric acid gave oxazolone derivative rather than pyranochromene derivative. Condensation of 6‐formylchromone with cyanothioacetamide led to the formation of thioamide derivative. 2‐Iminopyranochromene derivatives were synthesized through reaction of 6‐formylchromone with diverse cyanoacetamide derivatives. Finally, reaction of 6‐formylchromone with 3‐(dimethylpyrazolyl)‐3‐oxopropanenitrile gave 3‐cyano‐pyranochromenedione rather than pyrazole derivative. Antimicrobial activity of the synthesized pyranochromenone derivatives was evaluated. Nearly all compounds showed weak effects towards B. subtilis and P. vulgaris. All compounds showed no effects towards S. aureus and E. coli. All compounds showed no effects towards all tested fungi except thioamide derivative 6 showed moderate activity. [ABSTRACT FROM AUTHOR]

Obtained from Aquilaria Lam. and Gyrinops Gaertn., agarwood is a prestigious perfume and medicinal material in the world. Its primary chemical constituents and indicators of agarwood's development are 2-(2-phenylethyl)chromones (PECs). However, how PECs affect its quality, accumulation, and transformation pattern is still unclear. The present study investigated this issue by monitoring resin filling in agarwood generated by the whole-tree agarwood-inducing technique over a span of a year, observing the ethanol extract concentration at different sampling times, and statistically examining PECs in agarwood from each sampling period. In agarwood, the resin accumulated over time, except during the 4th-6th month due to the creation of a barrier layer. The relative content of total PECs demonstrated an overall increase throughout the year but a decrease from the 4th month to the 6th month, and the relative content of 19 PECs that persisted throughout the year was positively correlated with the content of ethanol extracts. In addition, the process of chromone accumulation was accompanied by the production and transformation of different types of chromones, with flindersia type 2-(2-phenylethyl)chromones, epoxy-2-(2-phenylethyl)chromones, and diepoxy-2-(2-phenylethyl)chromones being the major chromone components; in addition, the content of 5,6,7,8-tetrahydro- 2-(2-phenylethyl)chromones kept increasing after 6 months of agarwood formation. Three main trends were identified from 58 analogs of PECs, each with notable variation. The first type had the highest content at the beginning of resin formation. The second type had the highest content at 6 months and then started to decrease, and the third type had a slowly increasing content. As a whole, this study systematically investigated the accumulation of PECs during injury-induced agarwood production in A. sinensis, which is of scientific significance in resolving the transformation of PECs and revealing the secret of agarwood formation. [ABSTRACT FROM AUTHOR]

An electrochemical decarboxylative addition of N‐substituted glycines to enaminones has been developed and conducted under oxidant‐, catalyst‐, and light‐free conditions in acetonitrile at room temperature by using electron as the traceless oxidant, which provided a green approach to access C3‐aminomethyl chromones. The resulting products were formed through radical addition/oxidation/cyclization or electrophilic addition/cyclization pathway and could act as valuable building blocks to construct polysubstituted pyrimidine derivatives. [ABSTRACT FROM AUTHOR]

Molecular dynamics (MD) simulation is an in silico method used in the biomolecular level of research to study how the protein interacts with the target with time. It provides a detailed information of the protein dynamics and ligand structure with the crucial amino acid interactions. Monoamine oxidase B (MAO−B) is a crucial isoenzyme responsible for the catalyses of oxidative deamination of various biogenic amines in the brain and peripheral tissues. The selective inhibitors of MAO−B are considered as the management of symptoms of neurodegenerative disorders like Alzheimer's disease(AD) and Parkinson disease(PD). Recently the structural scaffolds containing chalcones, coumarins and chromones derived candidates shown potent, selective, competitive and reversible type of MAO−B inhibitors. The structural similarities between the above scaffolds can produce almost similar type of interactions in the inhibitor binding cavity of MAO−B. Numerous molecular simulation reports were supported by the above mentioned fact. The current review focus on the last ten year molecular dynamics report of chalcones, coumarins and chromones towards MAO−B inhibition. The review also focuses on the software details used in the MD dynamics simulation and the structural requirement from each class of compound for the recognition of MAO−B inhibitory activity. [ABSTRACT FROM AUTHOR]

AbstractZhachong-13 pills (ZC-13), as a traditional prescription of Mongolian medicine, are often used in the clinical practice of Mongolian hospitals for the treatment of stroke and rheumatic arthritis. In this experiment, UHPLC-Q-Exactive Orbitrap MS was used to explore the chemical composition of ZC-13. The results showed that 315 compounds were identified or inferred, including 56 alkaloids, 77 2-(2-phenylethyl)chromones, 61 flavonoids, 31 tannins, 8 coumarins, 16 lignans, 21 terpenoids, 5 amino acids, 19 organic acids, and 21 other components. In addition, the pharmacological activities related to anti-cerebral ischemia of these components were summarized. This result laid a foundation for further study on the pharmacodynamic material basis of ZC-13 and provided a scientific basis for the formulation of ZC-13 quality specifications. [ABSTRACT FROM AUTHOR]

Chamaecrista rotundifolia (C. rotundifolia) is a perennial herb of leguminosae, which increasingly being grown as a forage in China. In our search for original bioactive metabolites from Cassia plants, the phytochemical reinvestigation of the C. rotundifolia was carried out, which led to the isolation of three new (1–3) and six known (4–9) chromones. Their structures were confirmed by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1–9 were evaluated for their anti-rotavirus activities, and the results revealed that compounds 1–9 exhibited potential anti-rotavirus activities with therapeutic index (TI) valves in the range of 12.0 ∼ 20.2, respectively. [ABSTRACT FROM AUTHOR]

An efficient RuPHOX−Ru catalyzed asymmetric cascade hydrogenation of 3‐substituted chromones has been achieved under mild reaction conditions, affording the corresponding chiral 3‐substituted chromanols in high yields with excellent enantio‐ and diastereoselectivities (up to 99 % yield, >99 % ee and >20 : 1 dr). Control reactions and deuterium labelling experiments revealed that a dynamic kinetic resolution process occurs during the subsequent hydrogenation of the C=O double bond, which is responsible for the high performance of the asymmetric cascade hydrogenation. The resulting products allow for several transformations and it was shown that the protocol provides a practical and alternative strategy for the synthesis of chiral 3‐substituted chromanols and their derivatives. [ABSTRACT FROM AUTHOR]

Simple Summary: This study is an analytic review of the data on the two most used ALK TKIs, alectinib and lorlatinib, used as the first treatment for ALK-positive NSCLC. These drugs have shown promise in separate studies, but there has not been a direct comparison until now. We analyzed data from two major clinical trials that compared these drugs to crizotinib. We found that lorlatinib may be more effective in delaying the progression of the disease compared to alectinib, especially in controlling brain metastases. Although both drugs have side effects, and an alert has been created for the peculiar toxicities of lorlatinib, more people had to stop taking alectinib due to side effects compared to lorlatinib. Overall, the data suggest that lorlatinib might be a better option for patients with this type of lung cancer, but more research is needed to confirm these findings. This information could help clinicians make better treatment decisions for patients with ALK-positive NSCLC. Various next-generation ALK TKIs are available as first-line options for ALK-positive NSCLC, with alectinib and lorlatinib being commonly preferred. However, no direct comparison between them has been conducted, making it impossible to pick a winner. We performed an analytic, 'non-comparative' assessment of the two phase 3 pivotal clinical trials showing superiority of alectinib (ALEX) and lorlatinib (CROWN) in comparison to crizotinib. Overall, the two studies were very similar in the study design and patient characteristics, with the exception of the selection and evaluation of brain metastases. PFS hazard ratios numerically favored lorlatinib, both according to the investigator and to BICR. Notably, the 3-year PFS rate was numerically higher with lorlatinib (64%) than with alectinib (46.4%). Despite similar response rates and overall intracranial response, the rate of complete intracranial response was higher with lorlatinib, with a cumulative incidence risk of CNS disease progression at 12 months of 9.4% with alectinib and 2.8% with lorlatinib. The peculiar toxicities of lorlatinib were related to lipidic profile alterations, peripheral oedema and cognitive effects, with no impact on cardiovascular risk nor impairment in quality of life versus crizotinib. Furthermore, the rate of permanent treatment discontinuation due to adverse events was numerically higher with alectinib (26%) than with lorlatinib (7%). In conclusion, despite the immature OS data for both drugs, the efficacy of lorlatinib appears higher than alectinib while maintaining a manageable toxicity profile. [ABSTRACT FROM AUTHOR]

In Search of new antibacterial, antifungal agents with improved potency, herein we report the synthesis of a series of new substituted 2-(4-fluorophenyl)-3-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)-4H-chromen-4-one derivatives (6a‐q), starting from acetophenone. All the synthesized compounds have been screened for in vitro antibacterial and antifungal activity by using the agar well diffusion method. Among fifteen synthesized compounds, four chromone derivatives i.e. (6a-b), (6h), and (6i) have shown proficient antimicrobial activities. Compound (6a) showed powerful inhibitory activity against all bacterial pathogens but it was not that effective against fungal pathogens on the other hand compound (6b) showed satisfactory activity against fungal pathogens as well. The activity of compounds (6h) and (6i) against S. aureus was remarkable. Other compounds were found active against a few pathogens but activity was good. The compound (6b) was found very effective in inhibiting the growth of S. aureus ATCC 6538 at a low concentration with MIC 190 µg/ml. [ABSTRACT FROM AUTHOR]

The 2-(2-phenethyl)chromones (PECs) are the signature constituents responsible for the fragrance and pharmacological properties of agarwood. O -Methyltransferases (OMTs) are necessary for the biosynthesis of methylated PECs, but there is little known about OMTs in Aquilaria sinensis. In this study, we identified 29 OMT genes from the A. sinensis genome. Expression analysis showed they were differentially expressed in different tissues and responded to drill wounding. Comprehensive analysis of the gene expression and methylated PEC content revealed that AsOMT2 , AsOMT8 , AsOMT11 , AsOMT16 , and AsOMT28 could potentially be involved in methylated PECs biosynthesis. In vitro enzyme assays and functional analysis in Nicotiana benthamiana demonstrated that AsOMT11 and AsOMT16 could methylate 6-hydroxy-2-(2-phenylethyl)chromone to form 6-methoxy-2-(2-phenylethyl)chromone. A transient overexpression experiment in the variety 'Qi-Nan' revealed that AsOMT11 and AsOMT16 could significantly promote the accumulation of three major methylated PECs. Our results provide candidate genes for the mass production of methylated PECs using synthetic biology. [ABSTRACT FROM AUTHOR]

Candida species are frequently implicated in the development of both superficial and invasive fungal infections, which can impact vital organs. In the quest for novel strategies to combat fungal infections, there has been growing interest in exploring synthetic and semi-synthetic products, particularly chromone derivatives, renowned for their antimicrobial properties. In the analysis of the antifungal activity of the compound (E)-benzylidene-chroman-4-one against Candida, in silico and laboratory tests were performed to predict possible mechanisms of action pathways, and in vitro tests were performed to determine antifungal activity (MIC and MFC), to verify potential modes of action on the fungal cell membrane and wall, and to assess cytotoxicity in human keratinocytes. The tested compound exhibited predicted affinity for all fungal targets, with the highest predicted affinity observed for thymidylate synthase (−102.589 kJ/mol). MIC and CFM values ranged from 264.52 μM (62.5 μg/mL) to 4232.44 μM (1000 μg/mL). The antifungal effect likely occurs due to the action of the compound on the plasma membrane. Therefore, (E)-benzylidene-chroman-4-one showed fungicidal-like activity against Candida spp., possibly targeting the plasma membrane. [ABSTRACT FROM AUTHOR]

Eugenin (5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one) is a bioactive phytoalexin mainly found as a bitter component in carrots (Daucus carota L.; Apiaceae) and cloves [ Syzygium aromaticum (L.) Merr. & L. M. Perry; Myrtaceae]. An extensive literature search was performed involving various established databases like Web of Science, PubMed, Science Direct, Dictionary of Natural Products and Google Scholar, using the keyword 'eugenin'. The literature reports that describe various aspects of naturally occurring eugenin, e.g., isolation, structure elucidation, biosynthesis, bioactivity studies and therapeutic potential, have been included in this review, while the papers that present total synthesis or structural modifications of eugenin have been excluded. Eugenin, biosynthesized from the acetate-malonate pathway, has been reported from at least 22 plant species from 13 families. It has also been found in two fungal species, Aschersonia confluens and Chaetomium minutum. Dacaus carota and Syzygium aromaticum are two major sources of this chromone. Antimalarial, antimicrobial, antioxidant, antiplatelet aggregation, antiviral, cytotoxic, immunosuppressive/immunomodulatory, osteogenesis-inducing, pyrolyl endopeptidase (PEP)-inhibitory and blue-green algae growth inhibitory activities of eugenin have been reported in the literature. Among these bioactivities, antioxidant, antiplatelet aggregation, immunosuppressive/immunomodulatory activities of eugenin and its in silico prediction of antiviral property against severe-acute-respiratory-syndrome-related coronavirus-2 (SARS-CoV-2) activity may have some therapeutic potential. The distribution of eugenin is rather limited to a few plant species and only a couple of fungal species. Based on the reported bioactivities, it could be concluded that this chromone might have some potential as a template for new drug development. [Display omitted] • Eugenin, a chromone, has been reported from at least 22 different plant species from 13 families.. • Carrots and cloves are two major sources of eugenin. • Eugenin has also been isolated from two fungal species, Aschersonia confluens and Chaetomium minutum. • The biosynthesis of this compound follows the acetate-malonate pathway. • Some bioactivities of eugenin and in silico prediction of activity against SARS-CoV-2 may have some therapeutic potential. [ABSTRACT FROM AUTHOR]

Abstract A series of novel chromone derivatives of (N-(4-oxo-2-(trifluoromethyl)-4H-chromen-6-yl) benzamides) were synthesized by treating 7-amino-2-(trifluoromethyl)-4H-chromen-4-one with K2CO3 and/or NaH, suitable alkyl halides and acetonitrile and/or 1,4-dioxane. The obtained products are in high yields (87 to 96%) with various substituents in short reaction times with no more by-products and confirmed by FT-IR, 1H, and 13C-NMR Spectral data. The in vitro cytotoxic activity was examined against two human cancer cell lines, namely the human lung adenocarcinoma (A-549) and the human breast (MCF-7) cancer cell line. Compound 4h showed promising cytotoxicity against both cell lines with IC50 values of 22.09 and 6.40 ± 0.26 µg/mL respectively, compared to that of the standard drug. We also performed the in vitro antioxidant activity by DPPH radical, hydrogen peroxide, NO scavenging, and total antioxidant capacity (TAC) assay methods, and they showed significant activities. The possible binding interactions of all the synthesized chromone derivatives are also investigated against selective pharmacological targets of human beings, such as HERA protein for cytotoxic activity and Peroxiredoxins (3MNG) for antioxidant activity which showed closer binding free energies than the standard drugs and evidencing the above two types of activities.

A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope and good functional group tolerance. Furthermore, the 3‐furylmethyl chromone skeleton shows the potential synthetic application value through further gram‐scale synthesis and derivatization. [ABSTRACT FROM AUTHOR]

Introduction: Agarwood is a traditional aromatic southern medicine. It has a long history of being used in traditional Chinese aromatherapy to treat insomnia, anxiety and depression. Due to the scarcity of wild resources, people have planted trees successfully and begun to explore various agarwood-inducing techniques. This study comparative analysis of volatile metabolites in agarwood produced by various inducing techniques and its potential sleep-promoting, anti-anxiety and anti-depressant network pharmacological activities. Methods: A total of 23 batches of two types of agarwood were collected, one of which was produced by artificial techniques, including 6 batches of TongTi (TT) agarwood produced by "Agar-Wit" and 6 batches of HuoLao (HL) agarwood produced by "burning, chisel and drilling", while the other was collected from the wild, including 6 batches of BanTou (BT) agarwood with trunks broken due to natural or man-made factors and 5 batches of ChongLou (CL) agarwood with trunks damaged by moth worms. The study employed metabolomics combined with network analysis to compare the differences in volatile metabolites of agarwood produced by four commonly used inducing techniques, and explored their potential roles and possible action targets in promoting sleep, reducing anxiety, and alleviating depression. Results: A total of 147 volatile metabolites were detected in agarwood samples, mainly including small aromatic hydrocarbons, sesquiterpenes and 2-(2- phenylethyl) chromone and their pyrolysis products. The results showed composition of metabolites was minimally influenced by the agarwood induction method. However, their concentrations exhibited significant variations, with 17 metabolites showing major differences. The two most distinct metaboliteswere 6-methoxy-2-(2-phenylethyl) chromone and 6,7-dimethoxy- 2-(2-phenylethyl) chromone. Among the volatile metabolites, 142 showed promising potential in treating insomnia, anxiety, and depression, implicating various biological and signaling pathways, predominantly ALB and TNF targets. The top three active metabolites identified were 2-(2-phenylethyl) chromone, 1,5-diphenylpent-1-en-3- one, and 6-methoxy-2-[2-(4'-methoxyphenyl) ethyl] chromone, with their relative content in the four types of agarwood being TT>HL>CL>BT. Conclusion: The differences in the content of 2-(2-phenylethyl) chromones suggest that they may be responsible for the varying therapeutic activities observed in different types of agarwood aromatherapy. This study offers theoretical support for the selection of agarwood in aromatherapy practices. [ABSTRACT FROM AUTHOR]

The post-column reaction method enables the evaluation of the antiradical capacity of individual components in a mixture by separating the components using HPLC and measuring stable free radical (e.g., DPPH●) scavenging that occurs after the chromatography column. The equipment typically consists of two detectors. The first records signals of the analytes leaving the column. The second records radical scavenging by the analytes, which appears as a negative band. The recorded signals are found on two separate chromatograms, which must be combined to interpret the results. In this study, a single DAD detector was used behind the post-column reactor, enabling the simultaneous recording of the analyte bands and negative signals, indicating radical scavenging. The objective of this study was to evaluate the antiradical capacity of key compounds found in two herbal raw materials used in traditional Chinese medicine. Saposhnikovia divaricata roots contain phenolic acids, chromones, and furanocoumarins. Chlorogenic acid, rosmarinic acid, and imperatorin demonstrated strong radical scavenging, while prim-O-glucoslocimifugin showed a weaker response, both in standards and in root extracts. However, scavenging was not observed for cimifugin and 4′-O-β-D-glucosyl-5-O-methylvisamminol. Astragalus mongholicus roots contain astragalosides I-IV (triterpene saponins). None of these showed DPPH● scavenging. Furthermore, additional signals were observed, indicating the presence of unidentified radical scavenging compounds. [ABSTRACT FROM AUTHOR]

An unprecedented solvent-tuned electrochemical method for selective C(sp³)--H bond activation towards the synthesis of C3 functionalized chromone derivatives has been developed. This electrosynthesis protocol provides an efficient and green way to access various C3-functionalized chromones by avoiding traditionally employed transition metals and high temperatures. The swappable chemoselectivity was controlled mainly by altering the solvent and the current. A plausible reaction mechanism has been proposed with the help of radical capture and cyclic voltammetry experiments. [ABSTRACT FROM AUTHOR]

Cimicifugae Rhizoma, generally known as "Sheng Ma" in China, has great medicinal and dietary values. Cimicifugae Rhizoma is the dried rhizome of Cimicifuga foetida L., Cimicifuga dahurica (Turcz.) Maxim. and Cimicifuga heracleifolia Kom., which has been used to treat wind-heat headache, tooth pain, aphtha, sore throat, prolapse of anus and uterine prolapse in traditional Chinese medicine. This review systematically presents the traditional uses, phytochemistry, pharmacology, clinical studies, quality control and toxicity of Cimicifugae Rhizoma in order to propose scientific evidence for its rational utilization and product development. Herein, 348 compounds isolated or identified from the herb are summarized in this review, mainly including triterpenoid saponins, phenylpropanoids, chromones, alkaloids, terpenoids and flavonoids. The crude extracts and its constituents had various pharmacological properties such as anti-inflammatory, antitumor, antiviral, antioxidant, neuroprotective, anti-osteoporosis and relieving menopausal symptoms. The recent research progress of Cimicifugae Rhizoma in ethnopharmacology, phytochemistry and pharmacological effects demonstrates the effectiveness of its utilization and supplies valuable guidance for further research. This review will provide a basis for the future development and utilization of Cimicifugae Rhizoma. [ABSTRACT FROM AUTHOR]

Copper nanoparticles (Cu2O NPs) supported on graphitic carbon nitride (g‐C3N4) have been introduced as an effective heterogenous catalyst for the synthesis of 3‐indolmethyl chromones (3 a–q) under visible light conditions via the cyclization of o‐hydroxyaryl enaminones with 3‐indoleacetic acids. The catalyst was thoroughly characterized using various techniques such as FT‐IR, PXRD, XPS, FE‐SEM, EDX, TEM, and HR‐TEM analysis. The optimized reaction conditions enabled the high yield production of a wide range of 3‐indolmethyl chromones in a short timespan at room temperature under visible light and method was successfully applied to the gram‐scale synthesis. Importantly, the catalyst could be reused for up to five cycles without significant decrease in its activity. This approach aligns with eco‐friendly principles, demonstrating favorable green chemistry metrics for compound 3 a, including process mass intensity (7.83), environmental impact factor (6.83), atom economy (67.56 %), reaction mass efficiency (60.76 %), chemical yield (92.37 %), mass intensity (1.64), mass productivity (60.97 %), carbon efficiency (69.15 %) and optimum efficiency (89.93 %). [ABSTRACT FROM AUTHOR]

A series of novel chromone derivatives of (N-(4-oxo-2-(trifluoromethyl)-4H-chromen-6-yl) benzamides) were synthesized by treating 7-amino-2-(trifluoromethyl)-4H-chromen-4-one with K2CO3 and/or NaH, suitable alkyl halides and acetonitrile and/or 1,4-dioxane. The obtained products are in high yields (87 to 96%) with various substituents in short reaction times with no more by-products and confirmed by FT-IR, 1H, and 13C-NMR Spectral data. The in vitro cytotoxic activity was examined against two human cancer cell lines, namely the human lung adenocarcinoma (A-549) and the human breast (MCF-7) cancer cell line. Compound 4h showed promising cytotoxicity against both cell lines with IC50 values of 22.09 and 6.40 ± 0.26 µg/mL respectively, compared to that of the standard drug. We also performed the in vitro antioxidant activity by DPPH radical, hydrogen peroxide, NO scavenging, and total antioxidant capacity (TAC) assay methods, and they showed significant activities. The possible binding interactions of all the synthesized chromone derivatives are also investigated against selective pharmacological targets of human beings, such as HERA protein for cytotoxic activity and Peroxiredoxins (3MNG) for antioxidant activity which showed closer binding free energies than the standard drugs and evidencing the above two types of activities. [ABSTRACT FROM AUTHOR]

Recently, some new Qi-Nan clones of Aquilaria sinensis (Lour.) Spreng which intensively produces high-quality agarwood have been identified and propagated through grafting techniques. Previous studies have primarily focused on ordinary A. sinensis and the differences in composition when compared to Qi-Nan and ordinary A. sinensis. There are few studies on the formation mechanism of Qi- Nan agarwood and the dynamic changes in components and endophytic fungi during the induction process. In this paper, the characteristics, chemical composition, and changes in endophytic fungi of Qi-Nan agarwood induced after 1 year, 2 years, and 3 years were studied, and Qi-Nan white wood was used as the control. The results showed that the yield of Qi-Nan agarwood continued to increase with the induction time over a period of 3 years, while the content of alcohol extract from Qi-Nan agarwood reached its peak at two years. During the formation of agarwood, starch and soluble sugars in xylem rays and interxylary phloem are consumed and reduced. Most of the oily substances in agarwood were filled in xylem ray cells and interxylary phloem, and a small amount was filled in xylem vessels. The main components of Qi-Nan agarwood are also chromones and sesquiterpenes. With an increasing induction time, the content of sesquiterpenes increased, while the content of chromones decreased. The most abundant chromones in Qi-Nan agarwood were 2-(2-Phenethyl) chromone, 2-[2-(3-Methoxy-4-hydroxyphenyl) ethyl] chromone, and2-[2-(4- Methoxyphenyl) ethyl] chromone. Significant differences were observed in the species of the endophytic fungi found in Qi-Nan agarwood at different induction times. A total of 4 phyla, 73 orders, and 448 genera were found in Qi-Nan agarwood dominated by Ascomycota and Basidiomycota. Different induction times had a significant effect on the diversity of the endophytic fungal community in Qi-Nan. After the induction of agarwood formation, the diversity of Qi-Nan endophytic fungi decreased. Correlation analysis showed that there was a significant positive correlation between endophytic fungi and the yield, alcohol extract content, sesquiterpene content, and chromone content of Qi-Nan agarwood, which indicated that endophytic fungi play a role in promoting the formation of Qi-Nan agarwood. Qi-Nan agarwood produced at different induction times exhibited strong antioxidant capacity. DPPH free radical scavenging activity and reactive oxygen species clearance activity were significantly positively correlated with the content of sesquiterpenes and chromones in Qi-Nan agarwood. [ABSTRACT FROM AUTHOR]

The interaction of 7-hydroxyneoflavone-6-enamino ketone with 8-dialkylamino-7-hydroxy-3-hetarylbenzopyran-2- and 4-ones led to the formation of 10-methyl-4-phenyl-2H,6H-pyrano[3,2-g]-chromen-2,6-dione, which incorporated coumarin or chromone fragments at C-7 using a methylene linker. The recyclization of 7-[3-(1,3-benzothiazol-2-yl)-7-hydroxy-2-oxo-2H-8-chromenylmethyl]-10-methyl-4-phenyl-2H,6H-pyrano[3,2-g]chromene-2,6-dione and 7-[6-ethyl-7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-4-oxo-4H-8-chromenylmethyl]-10-methyl-4-phenyl-2H,6H-pyrano[3,2-g]chromene-2,6-dione was investigated under the influence of N,N- and N,O-binucleophiles. [ABSTRACT FROM AUTHOR]

A new chromone, (S)-5-hydroxy-2,8-bis(hydroxymethyl)-2-methyl-2H,6H-pyrano[3,2-g]chromen-6-one [named polymorphachromotriol, (5)], was isolated from the leaves Angelica poylmorpha along with seven known compounds hamaudol (1), isocopoletin (2), nodakenetin (3), 2′,3′ -dehydromarmesin (4), oxypeucedanin hydrate (6), norcimifugin (7), and cimifugin (8). NMR and CD techniques were used to elucidate their structures. [ABSTRACT FROM AUTHOR]

We studied a reaction of chromone‐containing acrylonitriles and cyanoacrylates with acid hydrazides. This reaction turned out to be a method for the synthesis of salicyloyl‐substituted 1,2,4‐triazolo[1,5‐a]pyridines. The synthesis developed is a tandem ring‐opening/double ring‐closing process. This synthetic approach is characterized by low toxic solvents (ethanol, butanol) and mediator (Et3N), 37–84% yields, non‐chromatographic isolation of products, and substrate tolerance (59 examples). [ABSTRACT FROM AUTHOR]

We report the development of a convenient organocatalytic method for the synthesis of 5H‐pyrano[3,2‐c]chromenes from chromone‐containing acrylates and ethyl cyanoacetate. The synthesis is characterized by simple conditions (ethanol, basic catalysis) and good yields (up to 90 %). The synthesized pyrano[3,2‐c]chromenes are a promising new class of fluorescent compounds. They have intense fluorescence in the yellow‐green region of the spectrum (495–554 nm) with high quantum yields (up to 72 %) and exhibit large Stokes shifts (3514–5856 cm−1). We have demonstrated the possible application of the obtained pyrano[3,2‐c]chromenes as selective "turn‐off" sensors for nucleophilic anions, such as cyanide, sulfide and sulfite. [ABSTRACT FROM AUTHOR]

Organophotocatalytic cascade cross-dehydrogenative-coupling/cyclization reaction of o-hydroxyarylenaminones with α-amino acid derivatives for the construction of α-chromone substituted α-amino acid derivatives was developed. Various N-arylglycine esters, amides and dipeptides underwent the cascade cyclization reaction well with o-hydroxyarylenaminones to afford the corresponding 3-aminoalkyl chromones in good to excellent yields. This approach consists of visible-light-promoted oxidation of α-amino acid derivatives, the Mannich reaction, and intramolecular nucleophilic cyclization under acidic conditions, and features a wide reaction scope, a simple operation and mild reaction conditions, which may have the potential to be used for the synthesis of bioactive molecules. [ABSTRACT FROM AUTHOR]

As wild Aquilaria sinensis resources are exhausted and protected, China has established a huge number of plantations of Aquilaria trees and developed artificial induction techniques. However, the current output and quality of artificial induction technology have not yet met the expected results. It has been found that high-oil-containing agarwood may contain particular fungal stains associated with agarwood production. To enhance the quality of agarwood, we recovered and characterized three highly active fungi from high-oil-containing agarwood and inoculated them onto A. sinensis trees using two traditional physical methods. The results showed that fungi extracted from high-oil-containing agarwood can effectively increase the yield and quality of agarwood. During the agarwood formation process, parenchyma cells, xylem rays, and axial parenchyma cells in the xylem gradually undergo apoptosis, thereby promoting the expansion of the color range of agarwood. Nine months after the treatment, the alcohol-soluble extract content in agarwood reached the standard specified in the Chinese Pharmacopoeia (10%), and the proportions of sesquiterpenes and chromones in each treatment were 55.82%, 58.31%, 62.65%, 70.97%, and 13.71%, respectively. These results indicate that fungal induction has a positive impact on the quality of agarwood. In addition, compared to drilling and fungus combined induction, "burning holes and fungi" combined induction demonstrates better results and can further improve the yield and quality of agarwood. [ABSTRACT FROM AUTHOR]

Herein, we present a new Ag(I)-catalyzed three-component radical cascade reaction for the construction of 3-organoselenyl chromones from 2-methoxyaryl alkynones, Se powder and organic boronic acids. With 20 mol% of AgNO3 as a catalyst, 10 mol% of SDS as an additive and under an O2 atmosphere in 1,4-dioxane, a wide range of multi-functionalized 3-organoselenyl chromones have been achieved in good to excellent yields. This protocol features easy availability of starting materials, simple operation, high step-economy and high structural diversity of products. [ABSTRACT FROM AUTHOR]

An electrochemical synthesis of various 3‐selenylated chromones via selenylation of alkynyl aryl ketones without the employment of catalyst and chemical‐oxidant is described here. This method features mild conditions, high efficiency, and wide substrate scope. Furthermore, the scale‐up reaction runs smoothly which indicates the practicability of this electrosynthesis strategy. [ABSTRACT FROM AUTHOR]

This article discusses the application of the Heck reaction for the synthesis of C-glycosyl phenolic compounds. The authors successfully synthesized C-glycosylated 2-styrylchromones and xanthones with high stereoselectivity. The article also includes detailed experimental procedures and characterization data for the synthesized compounds. The given text appears to be a scientific article or research paper that includes data related to chemical compounds. The text provides information about the chemical structure and properties of different compounds, including their nuclear magnetic resonance (NMR) spectra, mass spectrometry data, and physical characteristics. The compounds mentioned in the text are described in terms of their chemical composition, yield, and various spectroscopic data. [Extracted from the article]

An I2/PPh3‐mediated synthesis of 3‐thiolated chromones starting from 2‐hydroxyphenylenones and sodium sulfinates was reported. This method features one pot manner, metal‐free, easy performance, readily available starting materials and illustrating potential value for some biologically or pharmaceutically active compounds. In addition, a possible mechanism was proposed based on the control experiments. [ABSTRACT FROM AUTHOR]

Background: The successful launch of icaritin, a therapeutic drug for liver cancer derived from Epimedium brevicornu, has provided new impetus for the development of prenylated flavonoids in the field of oncology. Flemingia macrophylla is reported to contain characteristic prenylated flavonoids which can regulate the p53 protein. We aimed to isolate these constituents and conduct activity evaluation, structure–activity relationship, and mechanism studies to provide candidate compounds for antitumor drug development. Methods: In this study, chromatographic techniques combined with spectroscopic methods were used to separate, purify, and identify the constituents of Flemingia macrophylla methanol extract. The cytotoxic activity of the constituents was evaluated using an MTT assay with A549 and H1975 cells as the model. The binding mechanism between the compounds and the p53 protein was investigated with molecular docking and validated with cellular thermal shift assay (CETSA). Western blotting (WB) was employed to detect the expression of p53 protein and apoptosis-related proteins in cells. Results: Chiral HPLC separation of racemates 1 and 7 provided two pairs of undescribed enantiomers (1a/1b and 7a/7b), along with eight known compounds (2 − 9) isolated from Flemingia macrophylla roots. Their structures were elucidated by spectroscopic analysis, and the absolute configurations of the enantiomers were determined from experimental and calculated electronic circular dichroism data. Compounds 1 − 7, and the non-prenyl analogues 10 − 13, were evaluated for cytotoxic activity against the human lung cancer A549 and H1975 cell line. Compounds 5 − 7 displayed better cytotoxicity than the positive control icaritin in A549 and H1975, with IC50 values ranging from 4.50 to 19.83 μmol·L-1 and < 5 μmol·L-1, respectively. The structure–activity relationships of the chromone or flavonoid analogues against A549 cells were discussed. Molecular docking results demonstrated that compound 7a has strong interaction with p53 and WB indicated that 7a induced apoptosis by increasing the p53 protein, decreasing the anti-apoptotic protein Bcl-2, and activating the caspase family in A549 cells. These results suggest that prenylated flavonoids are potential p53 protein activators. Conclusion: This study demonstrates that Flemingia macrophylla is rich in prenylated flavonoid constituents, among which compounds 5 and 7 exhibited significant cytotoxic activity against A549 cells and served as reference candidates for the design and development of prenylated compounds as antitumor therapeutic drugs. Highlights: Two pairs of undescribed enantiomers (1a/1b and 7a/7b) were isolated from Flemingia macrophylla. Prenylated flavonoids 5 − 7 exhibited significant cytotoxicity against A549 cells. Structure-activity relationship study revealed that the presence of B-ring and 2ʹ-OH substitution and the cyclization of 6/8-pentenyl group with 7-OH were beneficial for cytotoxicity. Molecular docking results showed that Cys124 and Cys277 were the key amino acid residues for binding. Compound 7a induced apoptosis of A549 cells by activating the p53 protein. [ABSTRACT FROM AUTHOR]

This review summarizes information about the chemical composition and beneficial properties of species of the genus Eranthis Salisb. from the world's flora. To date, seven out of ~14 species found in Asia and parts of Europe have been studied to various degrees. Here, data are presented on the diversity of sets of chromones, furochromones, triterpene saponins, coumarins, and other classes of secondary metabolites of Eranthis species according to the literature. For new compounds—isolated from Eranthis for the first time—structural formulas are also provided. Among the new compounds, chromones and coumarins predominate, as do triterpene saponins of the olean and cycloartane series and lectin. The results of pharmacological studies are presented showing anti-inflammatory, antioxidant, antiviral, and other types of biological activities found in extracts, in their fractions, and in individual compounds of the aboveground and underground organs and parts of Eranthis species. Despite the limited geographic range of Eranthis plants, it is possible to search for active substances, develop methods for biological and chemical synthesis of the isolated substances, and create a finished therapeutic substance based on them. In addition, it is feasible to obtain the desired standardized pure materials from Eranthis species grown in vitro. [ABSTRACT FROM AUTHOR]

One chromone (1), together with four known alkaloids, were isolated from the mangrove endophytic fungus Aspergillus sp. ZJ-68. Their structures were elucidated by a combination of HRESIMS and NMR spectroscopic analyses. Compound 1 showed strong anti-inflammatory activity in vitro by inhibiting nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 cells with an IC50 value of 4.094 ± 0.8 μM, which was better than positive drug indomethacin (IC50=35.8 ± 0.5 μM). [ABSTRACT FROM AUTHOR]

Saposhnikovia divaricata (Turcz.) Schischk (S. divaricata, Fangfeng) is a herb in the Apiaceae family, and its root has been used since the Western Han Dynasty (202 B.C.). Chromones and coumarins are the pharmacologically active substances in S. divaricata. Modern phytochemical and pharmacological studies have demonstrated their antipyretic, analgesic, anti-inflammatory, antioxidant, anti-tumor, and anticoagulant activities. Technological and analytical strategy theory advancements have yielded novel results; however, most investigations have been limited to the main active substances—chromones and coumarins. Hence, we reviewed studies related to the chemical composition and pharmacological activity of S. divaricata, analyzed the developing trends and challenges, and proposed that research should focus on components' synergistic effects. We also suggested that, the structure-effect relationship should be prioritized in advanced research. [ABSTRACT FROM AUTHOR]

An efficient method of synthesizing the various 3-Fluorochromones from enamino ketones by using N-Fluoro benzenesulfonimide (NFSI) is described. The key step in the synthesis involves tandem cyclization and fluorination to form 3-fluorochromones in good yields. The significant features of this method include simple operational procedures, high purity of the product and cost reducing. This reaction achieved good to excellent yields (51–92%) under ambient conditions with significantly faster rate. The products obtained were confirmed by 1H, 13C NMR and mass spectroscopy techniques. [ABSTRACT FROM AUTHOR]

Herein, we have devised a metal‐free stereoselective protocol mediated by selectfluor for the dibromination of sugar enol‐ethers and monobromination of heterocyclic compounds. The dibromination of glycals was achieved within 5 minutes at room temperature with excellent yields. The tolerance of various protecting groups such as acetyl, benzyl, and silyl in sugars was checked. When the same reagent system was applied to substituted indoles and chromones 3‐brominated products were obtained but at elevated temperatures. The synthetic utility of the methodology was demonstrated by using the brominated indoles and chromones to synthesize the 3‐aryl indoles and isoflavones respectively via Suzuki‐Miyura cross‐coupling reactions. [ABSTRACT FROM AUTHOR]

We have developed an electrochemical reaction for the synthesis of 3‐selenylchromones and deutero‐selenylated chalcones of alkynyl aryl ketones. This method is free from metal catalysts and oxidants, and is regulated by solvents. The reaction conditions are mild, and a wide range of substrates can be employed to produce selenylated chromones and deutero‐selenylated chalcones, displaying potential anti‐inflammatory activities. Furthermore, we have demonstrated the applicability of this approach for the late‐stage deutero‐selenylation of the drug molecule, metochalcone. [ABSTRACT FROM AUTHOR]

Monoamine oxidases (MAOs) are a family of flavin adenine dinucleotide-dependent enzymes that catalyze the oxidative deamination of a wide range of endogenous and exogenous amines. Multiple neurological conditions, including Parkinson's disease (PD) and Alzheimer's disease (AD), are closely correlated with altered biogenic amine concentrations in the brain caused by MAO. Toxic byproducts of this oxidative breakdown, including hydrogen peroxide, reactive oxygen species, and ammonia, can cause oxidative damage and mitochondrial dysfunction in brain cells. Certain MAO-B blockers have been recognized as effective treatment options for managing neurological conditions, including AD and PD. There is still a pressing need to find potent therapeutic molecules to fight these disorders. However, the focus of neurodegeneration studies has recently increased, and certain compounds are now in clinical trials. Chromones are promising structures for developing therapeutic compounds, especially in neuronal degeneration. This review focuses on the MAO-B inhibitory potential of several synthesized chromones and their structural activity relationships. Concerning the discovery of a novel class of effective chromone-based selective MAO-B-inhibiting agents, this review offers readers a better understanding of the most recent additions to the literature. [ABSTRACT FROM AUTHOR]

Background: Loss of PTEN function leads to increased PI3Kβ signaling. AZD8186, a selective PI3Kβ/δ inhibitor, has shown anti-tumor activity in PTEN-deficient preclinical models. Although the combination of AZD8186 and paclitaxel was well tolerated, limited clinical efficacy was observed in advanced gastric cancer with PTEN loss. Methods: In the phase Ib dose-escalation, subjects with advanced solid tumors received oral AZD8186 (60 mg or 120 mg; twice daily (BID); 5 days on/2 days off) plus intravenous paclitaxel (70 mg/m2 or 80 mg/m2; days 1, 8, and 15) every 4 weeks. In the phase II part, MRGC patients with PTEN loss or PTEN/PIK3CB gene abnormality were enrolled and received recommended phase II dose (RP2D) of AZD8186 plus paclitaxel. Primary endpoints were to determine maximum tolerated dose (MTD) and RP2D in phase Ib and 4-month progression-free survival (PFS) rate in phase II. Results: In phase Ib, both MTD and RP2D were determined at paclitaxel 80 mg/m2 and AZD8186 120 mg BID. In phase II, 18 patients were enrolled [PTEN loss (n = 18) and PIK3CB mutation (n = 1)]. The 4-month PFS rate was 18.8% (3 of 16 evaluable patients) and further enrollment stopped due to futility. Conclusion: Although the combination of AZD8186 and paclitaxel was well tolerated, limited clinical efficacy was observed. ClinicalTrials.gov Identifier: NCT04001569. This phase Ib/II study was conducted to determine the safety and efficacy of AZD8186 and paclitaxel combination in patients with metastatic or recurrent gastric cancer. [ABSTRACT FROM AUTHOR]