Natural Product Research最新文献

Ternatusine A has been synthesised in a highly diastereoselective manner starting from a readily available D-allal. It is a novel approach for the Ternatusine A, which is a natural product isolated from the rοοts οf Ranunculus ternatus. An intramolecular 1,3-dipoar cycloaddition of azomethine ylide generated in situ from C2-formyl-D-allal and ethyl N-benzyl glycinate, is a key step to construct the pyrrole core structure of the Ternatusine A. The carboxylic acid directed transition metal-catalysed C-H functionalization of pyrrole at C3 position is another notable feature of this process.

This study aimed to isolate secondary metabolites produced by the endophytic fungus Xylaria sp. derived from Andrographis paniculata and to evaluate their cytotoxic potential using in vitro and in silico methods. The fungus was cultivated on rice medium for three weeks, extracted with ethyl acetate, and purified by chromatographic techniques, yielding two compounds identified as 19,20-epoxycytochalasin C (1) and ergosterol (2) based on NMR and FT-IR analyses. Both compounds exhibited cytotoxicity against MCF-7 breast cancer cells, with IC₅₀ values of 38.4 and 45.7 μM, respectively. Molecular docking against the HER2 protein supported the in vitro results, showing binding free energies of -8.023 and -7.310 kcal/mol for compounds 1 and 2, respectively. These findings suggest that both metabolites possess significant anticancer potential, particularly as candidate anticancer compounds against MCF-7 cancer cells. Notably, this is the first report of the chemical characterisation of Xylaria sp. associated with A. paniculata.

Seventeen molecules, including hydroxycinnamate esters, lignans and flavonoids, were isolated from Larrea divaricata and Larrea cuneifolia. The hydroxycinnamate ester divaricatoate (3) and its 4-deoxy form (4) are reported for the first time, whereas the flavonoid 3-methoxyherbacetin (14) is redescribed here, as it had been previously mischaracterised in the literature. Extracts and most of the 17 compounds were tested against Fusarium graminearum and Salmonella enterica. Nordihydroguaiaretic acid (5) and ent (R-R)-parakmerin A (8) showed the lowest MIC values on S. enterica (1.6 and 12.5 µg, respectively) and F. graminearum (25 µg and 3.1 µg, respectively). Both compounds synergized the antimicrobial activity of chloramphenicol and tebuconazole. Tested on human cell lines, Larrea extracts showed higher EC₅₀ values than tebuconazole, whereas compound 5 exhibited similar values and compound 8 showed similar or lower values. These compounds are promising antimicrobial agents and chemosensitizers, but their cytotoxicities require further investigation for therapeutic or pesticidal use.

Ephedra fragilis is a medicinal plant known for its richness in bioactive compounds and therapeutic potential. This study aimed to evaluate and compare the antioxidant activity and phytochemical content of aqueous extracts obtained by decoction and infusion. Various classes of secondary metabolites, including polyphenols, flavonoids, flavonols, tannins, and hydroxycinnamic acids, were quantified. Antioxidant activity was assessed using multiple complementary assays. The results showed that the decoction method yielded extracts with notably higher antioxidant capacity compared to the infusion. High-performance liquid chromatography analysis confirmed the presence of several major compounds, such as caffeic acid, catechin, and rutin. These findings demonstrate that decoction is a more efficient extraction method for recovering antioxidant constituents from Ephedra fragilis, supporting its potential use in health-related applications and functional products.

This study investigates the bioprospecting potential of marine-derived bacteria from the Lombok Sea, Indonesia, as a source of anti-nontuberculous mycobacteria (anti-NTM) agents. A total of fifty-two isolates were fermented in two different media and extracted, yielding 104 crude extracts. The bioassay-guided screening was evaluated, and the extract derived from the strain SPL22-064 exhibited the most potent activity, with a minimum inhibitory concentration (MIC) of 31.25 µg/ml against Mycobacterium fortuitum ATCC 6841. The strain was identified as Nocardia sp. Untargeted LC-HRMS-based analysis was performed to provide an overview of the chemical profile of the active extract. To our knowledge, this study represents the first report suggesting the potential of a marine-derived Nocardia sp. as a source of antimycobacterial agents.

Cornus mas L. is traditionally used for various medicinal purposes, although systematic data on its pharmacognostic properties are still limited. Considerable variation was observed among plant organs, so phenolic and flavonoid content varied by plant part, with location-related differences among samples, with the highest in leaf and fruit from Bijeljina and the lowest in leaf from Sarajevo. Antioxidant activity was much better in leaf and bark than in fruit. Extracts inhibited ESBL-producing Escherichia coli, with MICs mainly at 125 µg/mL; bark extract (Tuzla) showed 250 µg/mL and reduced biofilm formation. Leaf and bark extracts showed dose-dependent cytotoxicity against PC-9, MCF-7, and MDA-MB-231 cells, while fruit extracts were weaker. In human lymphocytes, bark (Bileća) and leaf (Tuzla) extracts decreased nuclear division and induced micronuclei at 200 µg/mL. Molecular docking indicated strong bacterial target binding for loganin and cornuside, supporting the antibacterial and antitumor potential of C. mas.

The ethanolic extract of coastal root tubers of Pouzolzia zeylanica was systematically characterised for its phytochemical composition and bioactivities. Analyses revealed positive results for phenolics and flavonoids and strong saponin reactions, with total contents of 74.39 ± 0.68 mg GAE/g (phenolics), 28.96 ± 1.10 mg QE/g (flavonoids), and 176.25 ± 7.50 mg OA-eq/g (saponins). UPLC-QTOF-MS profiling identified 158 metabolites, dominated by triterpenoid and sterol scaffolds. The extract exhibited antioxidant activity (IC₅₀ values: DPPH 1.622 ± 0.074 mg/mL, ABTS 0.609 ± 0.110 mg/mL, FRP 0.320 ± 0.008 mg/mL) and strong anti-inflammatory potential in the BSA denaturation assay (IC₅₀ 0.024 ± 0.008 mg/mL). Enzyme inhibition was modest (IC₅₀ values: α-amylase 301.34 ± 12.61 mg/mL; α-glucosidase 107.15 ± 5.43 mg/mL), consistent with the absence of enrichment for specific glycosidase inhibitors. These findings highlight P. zeylanica tubers as a triterpenoid- and saponin-rich matrix capable of conferring antioxidant and anti-inflammatory protection.

The moderate cytotoxic of isoeleutherol reported, a naphthalene-derived compound, from Eleutherine bulbosa bulbs collected in Simalungun, North Sumatra. The isolated compound, identified as (3S)-4-hydroxy-5-methoxy-3-methyl-3H-benzo[f][2] benzofuran-1-one, was characterised through FTIR, NMR and EIMS analyses, confirming its structural integrity and molecular formula C₁₄H₁₂O₄. Methanolic extraction of the bulb yielded the highest isoeleutherol concentration (17.35 ± 1.72 ppm), indicating that the bulb serves as the primary storage tissue. The cytotoxic evaluation revealed moderate antiproliferative activity against HeLa, A549 and MCF-7 cancer cell lines, with IC₅₀ values of 27.63 ± 2.52, 32.68 ± 1.60 and 50.13 ± 1.49 μM, respectively, showing the highest sensitivity in HeLa cells. The observed activity is attributed to the naphthoquinone-type framework. These findings provide scientific validation of E. bulbosa's ethnomedicinal use and establish isoeleutherol as a potential lead compound for traditional herb medicine development.

In this study, a series of novel dihydroartemisinin-nonsteroidal anti-inflammatory drug conjugates was designed and synthesised. The cytotoxic effects of these compounds against human leukemic K562 and multidrug-resistant K562/ADR cell lines were evaluated using the CCK-8 assay in vitro. Most hybrids exhibited higher anticancer activities than dihydroartemisinin. Among them, compound KL-7 demonstrated the highest potency, with IC₅₀ values of 0.11 ± 0.01 μM and 0.34 ± 0.02 μM against K562 and K562/ADR cells, respectively. Moreover, KL-7 showed selectivity comparable to that of the positive drug etoposide. Further analysis revealed that KL-7 significantly induced apoptosis in K562/ADR cells. The drug-likeness of KL-7 was also predicted.

This study comparatively evaluated the phytochemical and biological profiles of Origanum leptocladum and O. vulgare subsp. hirtum (Lamiaceae). Aqueous extracts yielded more material than methanolic ones, with O. leptocladum showing superior extractability. GC-MS analysis revealed distinct chemotypes: O. leptocladum was rich in cis-sabinene hydrate and p-cymene, whereas O. vulgare was dominated by carvacrol. Methanol extracts of O. leptocladum exhibited the highest α-glucosidase inhibition (90.10%) and antioxidant capacity, correlating with elevated phenolic content. Molecular docking indicated strong binding affinities of carvacrol, cis-sabinene hydrate, and p-cymene to α-glucosidase, α-amylase, AChE, and BChE, implying multitarget inhibitory potential. ADME predictions confirmed favourable pharmacokinetic properties and BBB permeability, especially for carvacrol and cis-sabinene hydrate. This first report on α-glucosidase and α-amylase inhibition by O. leptocladum underscores its promising antidiabetic and neuroprotective potential, supporting its value for pharmaceutical and nutraceutical development.