Natural Product Research最新文献

Iphiona grantioides (Boiss) Anderb. is a medicinal plant featuring several traditional uses. Nevertheless, this plant has not been widely investigated by modern medicinal chemistry yet, as also the properties of its extracts.In this study, we report the extraction of the essential oil by hydrodistillation from the leaves of I. grantioides. This was characterised by GC-MS analysis and ten chemical constituents were identified.Our findings demonstrate that the essential oil is effective in inhibiting the growth of bacterial strains, and of Klebsiela pneumonia and Staphylococcus aureus in particular. Additionally, its antioxidant properties were evaluated, and it showed radical scavenging activity in vitro.

Medicinal plants such as Leutea avicennae Mozaff. (Apiaceae) have been shown some biological potential for preventing and treating diseases. Fractions and isolated compounds were tested on colon carcinoma (HT-29), cervical carcinoma (HeLa), breast carcinoma (MCF-7), and mouse embryonic fibroblast (NIH/3T3) cell lines. The BSLT method was used for the assessment of the general toxicity of the petroleum ether (PET), chloroform (CHCl₃), ethyl acetate (EtOAc), and methanol (MeOH) fractions obtained from the aerial parts of L. avicennae. 1H-NMR and 13 C-NMR spectroscopy were used for structure elucidation. Five compounds, including two coumarins, osthole and umbelliferone, a diterpene phytol, β-sitosterol, and lauric acid, were isolated for the first time from L. avicennae. Osthole showed potent cytotoxic activity against MCF-7 and HT-29 cell lines with IC₅₀ values of 4.23 ± 0.26 and 12.11 ± 0.13 µg/mL, respectively. Phytol demonstrated potent cytotoxic activity towards MCF-7 and HeLa cell lines with IC₅₀ values of 6.80 ± 0.08 and 12.27 ± 0.18 µg/mL, respectively.

Centaurium erythraea Rafn is employed in Algerian traditional medicine for treating pain. The analgesic activity of the ethanolic extract (EE) from the flowering aerial parts of this plant was examined, and molecular docking of the main bioactive compound was performed. The EE, characterised by the iridoid swertiamarin, was administered to Wistar albino rats in pain models. Peripheral analgesic activity was evaluated using the acetic acid-induced writhing test, and a hot plate test was performed for central antinociceptive activity evaluation. Treatment with EE significantly decreased rats' writhing induced by acetic acid suggesting peripheral analgesic activity. Furthermore, the elevation of mean basal reaction time in the hot plate method indicated central analgesic activity. Molecular docking studies showed good docking energy with acceptable binding interactions of swertiamarin with cyclooxygenase-2 protein. This supports the analgesic activity of C. erythraea EE, justifying the traditional use of the plant as an analgesic herbal remedy.

This study is aimed to investigate the effects of Hypericum perforatum olive oil extract on the cytotoxic and metastatic properties of human colorectal cancer cells and human bone marrow-derived mesenchymal stem cells. In addition, ALDH3A1 and Vimentin expressions were evaluated by qRT-PCR and western blot analysis. Total phenolic and flavonoid contents and antioxidant activity of methanol extracts prepared with oil enrichment were measured using spectrophotometry-based methods. The cytotoxic effects of the extracts on SW-480 and bone marrow-derived mesenchymal stem cells were evaluated by MTT assay, resulting in IC₅₀ values of 4.8 mg/ml and 4.9 mg/ml, respectively. It was determined that cell migration and colony formation were significantly reduced at the IC₅₀ values determined for SW-480 and human bone marrow-derived mesenchymal stem cells.

Three new acylphloroglucinols were isolated from the branches and leaves of Hypericum perforatum L., named as hyperipersions A-C (1-3), together with three known compounds which were identified as elegaphenone (4), 2,6-dihydroxy-3,4-dimethylbenzoic acid methyl ester (5) and 2,3-methylenedioxyxanthone (6), respectively. The structures of isolated compounds were determined by UV, IR, HR-ESI-MS, NMR analysis. Their antiangiogenic activities were studied against HUVECs. The IC₅₀ value of compound 3 was 2.39 ± 0.21 μM against HUVECs, which was stronger than vatalanib, and other compounds had moderate antiangiogenic activity.

The lack of treatments and vaccines effective against SARS-CoV-2 has forced us to explore natural compounds that could potentially inhibit this virus. Additionally, Morocco is renowned for its rich plant diversity and traditional medicinal uses, which inspires us to leverage our cultural heritage and the abundance of natural resources in our country for therapeutic purposes. In this study, an extensive investigation was conducted to gather a collection of phytoconstituents extracted from Moroccan plants, aiming to evaluate their ability to inhibit the proliferation of the SARS-CoV-2 virus. Molecular docking of the studied compounds was performed at the active sites of the main protease (6lu7) and spike (6m0j) proteins to assess their binding affinity to these target proteins. Compounds exhibiting high affinity to the proteins underwent further evaluation based on Lipinski's rule and ADME-Tox analysis to gain insights into their oral bioavailability and safety. The results revealed that the two compounds demonstrated strong binding affinity to the target proteins, making them potential candidates for oral antiviral drugs against SARS-CoV-2. The molecular dynamics results from this computational analysis supported the overall stability of the resulting complex.

The methanolic extract of the leaves of Macaranga hurifolia Beille showed arginase inhibitory activity (40% at 100 µg/mL) and was then fractionated to obtain nine polyphenolic compounds. Their structures were elucidated on the basis of NMR spectroscopic data, and by comparison with data previously reported in the literature, as gallic acid (1), 3,4-dihydroxybenzoic acid (2), chlorogenic acid, (3), corilagin (4), cynaroside (5), cosmosiin (6), hyperoside (7) isoquercitrin (8) and guajaverin (9). These compounds have been evaluated as arginase inhibitors. Compounds 4, 7, 8 and 9 showed varying arginase inhibitory activities with IC₅₀ values ranging from 102 to 302 μM. All the isolated compounds were previously identified in this species but their activities on arginase are reported here for the first time.

The chemical composition of the essential oil of Lindera subumbelliflora (Lauraceae) was investigated for the first time. The essential oil was obtained by hydrodistillation and fully characterised by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The antifungal activity of L. subumbelliflora essential oil was tested against Candida albicans and Streptococcus mutans using the broth microdilution assay, whereas the microbial biofilms were determined using a semi-quantitative static biofilm. A total of 28 components (99.6%) were successfully identified, which were characterised by β-eudesmol (14.6%), cis-α-bergamotene (11.0%), α-copaene (8.5%), dodecen-1-ol (8.5%), and (E)-nerolidol (8.3%). The essential oil exhibited activity against Candida albicans and Streptococcus mutans with MIC values of 250 and 500 µg/mL, respectively. The essential oil increased the biofilm of Candida albicans by 38.25%, however, decreased the biofilm of Streptococcus mutans by 47.89% when treated with 500 µg/mL. Thus, the essential oil has a promising application in dentistry via inhibition of the growth of Candida albicans and Streptococcus mutans. However, the antibiofilm activity of the essential oil is only applicable for cariogenic Streptococcus mutans.

Cullen corylifolium is well known for diverse phytoconstituents that possess multifaceted pharmacology, and one such less explored class is coumestans, which have not been well explored for their anticancer activities. One of the popular cancer targets is the Epidermal Growth Factor Receptor, a tyrosine kinase involved in various cancers, especially breast and lung cancer hence, a crucial cancer target. This work is focussed on molecular docking and molecular simulation studies on coumestans against EGFR. The rigorous docking studies resulted in two coumestans (1 and 5) with binding energy less than Gefitinib and Erlotinib. Compounds 1 and 5 were subjected to molecular simulation, binding free energy calculation, per-residue energy decomposition, and in silico ADMET prediction. The best hit, compound 1 was evaluated for its cytotoxicity against MDA-MB-231 and A549 cells via in vitro assay. The ligand-protein complex exhibited good stability, binding free energies, better in silico pharmacokinetics, low toxicity, and good cytotoxicity.

A rapid untargeted UHPLC-Q-TOF-ESI-MS/MS-Based metabolomic profiling of the medicinal plant Entada abyssinica was performed. A total of 18 metabolites were detected, of which 10 could not be identified. Based on this result, an extensive chemical investigation of the CH₂Cl₂-MeOH (1:1) extract of this plant was carried out, leading to the isolation of a new ceramide, named entadamide (1), together with nine known compounds: monomethyl kolavate (2), 24-hydroxytormentic acid (3) chondrillasterol (4), 3-O-β-D glucopyranosylstigmasterol (5), 3-O-β-D glucopyranosylsitosterol (6), quercetin 3'-methylether (7), 2,3-dihydroxypropyl icosanoate (8), 2,3-dihydroxy-propyl 23-hydroxytricosanoate (9) and 2,3-dihydroxy-propyl 24-hydroxytetracosanoate (10). Their structures were elucidated by the analyses of their spectroscopic and spectrometric data (1D and 2D NMR, and HRESI-MS) in comparison with those reported in the literature. Furthermore, the crude extract and some isolated compounds were tested against non-ciprofloxacin resistant strains viz, Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 25922), Samonella thyphi (ATCC 19430) and Samonella enterica (NR4294). The tested samples demonstrated significant activity against all the tested bacteria (MIC values: 3.12-12.5 μg/mL).