Chemistry & Biodiversity最新文献

In order to explore the effect of amino introduction of Tanshinone IIA on the antitumor activity, 18 novel N-substituted tanshinone IIA derivatives were synthesized and investigated for their anti-proliferative activity in a panel of cancer cell lines. The biological evaluation of antiproliferative assay led to the discovery of compound TA-16 with a highly potent cytotoxic effect using cervical, colon, liver and breast cancer cells, with IC₅₀ = 1.25 µM against MCF-7 cell. The mechanistic studies indicated the ability of TA-16 in inducing apoptosis of MCF-7 cells through mitochondrial pathway and arresting the cell cycle at the G0/G1 phase. It exhibited significant anti-metastasis properties by inhibiting the expression of MMP-9 and MMP-2. Moreover, the cytotoxic study of compound TA-16 on the MCF-10A, a normal human breast epithelial cell line, further highlighted the potential of compound TA-16 as an anticancer agent for breast cancer with a selectivity index of 4.95. Molecular docking analyses confirmed the binding interaction between compound TA-16 and its target proteins, validating its mechanism of action and potential as a therapeutic agent for breast cancer.

This study presents a comprehensive phytochemical investigation of the stems of Syringa oblata Lindl., leading to the isolation and structural characterization of fourteen previously undescribed compounds, including ten sesquiterpenoids (oblatiosides H-M and syringanoids A-D) and four lignans (syringalignans A-D). Their structures and absolute configurations were rigorously established through extensive spectroscopic analyses (HR-ESI-MS and 1D/2D NMR) and comparative electronic circular dichroism (ECD) calculations. In bioactivity evaluations, most compounds demonstrated significant inhibition of nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with syringalignan D (14), oblatioside K (4), and oblatioside I (2) exhibiting the strongest anti-inflammatory effects (IC₅₀ = 12.5 ± 0.79, 15.2 ± 0.98, and 21.1 ± 0.86 µM, respectively), comparable to dexamethasone (IC₅₀ = 35.4 ± 0.39 µM). Additionally, syringalignan B (12) and syringalignan D (14) displayed potent antioxidant activity in the DPPH assay (IC₅₀ = 13.0 ± 0.48 and 22.6 ± 1.12 µM), outperforming several sesquiterpenoids and approaching the activity of ascorbic acid (IC₅₀ = 23.5 ± 0.46 µM). Notably, compound 14 dose-dependently (5-20 µM) suppressed LPS-stimulated ROS generation and lowered IL-6, TNF-α, and IL-1β mRNA levels in RAW264.7 cells, while also markedly reducing phosphorylated P65, JNK, and Erk proteins, indicating potent anti-oxidant and anti-inflammatory activity. These findings significantly expand the known chemical diversity of S. oblata Lindl., and highlight sesquiterpenes and lignans from this source as promising scaffolds for developing novel anti-inflammatory and antioxidant agents.

This study investigated the neuropharmacological effects of arjunolic acid, with a particular focus on its anxiolytic and anticonvulsant properties. To this end, in vivo tests were performed on adult zebrafish (Danio rerio) and in silico molecular docking analyses were conducted. Acute toxicity (96 h) was evaluated with doses of 4, 20, and 40 mg/kg (i.p.). Motor activity and anxiety levels induced by the different doses were evaluated using open field and light/dark tests, while the anticonvulsant potential was tested by induction with pentylenetetrazol (PTZ). The GABAergic neuromodulation was also investigated using the antagonist flumazenil and the molecular interaction with the GABA_A receptor and carbonic anhydrase II (CAII). The results demonstrated that arjunolic acid is not toxic at the tested doses, but it does cause significant motor alterations, like those caused by diazepam. The compound exhibited an anxiolytic effect and increased the latency to the onset of convulsive seizures. These effects were reversed by flumazenil, confirming mediation by the GABAergic system. These results corroborate the in silico study, which demonstrated a possible allosteric effect of arjunolic acid on the diazepam binding region of the GABA_A receptor and on the active site of CAII. However, arjunolic acid is pharmacologically relevant to the central nervous system and may serve as a basis for the development of new therapeutic agents.

In this paper, the physicochemical, structural properties, antioxidant, and prebiotic activities of polysaccharides obtained from Nitraria sibirica pall fruit with different extraction methods were investigated and compared. Structural features were characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, x-ray diffraction, Congo red staining, thermogravimetric analysis, periodate oxidation, and Smith degradation analysis. Results showed that extraction methods had a remarkable impact on the chemical compositions and structural properties of the polysaccharides. Ultrasound or enzyme-assisted extraction significantly increased the yield and functionality of Nitraria sibirica polysaccharides (NSPs), yielding the highest amount of 14.11% ± 1.23% and exhibiting the strongest DPPH/•OH scavenging ability with IC₅₀ values of 0.209/0.138 mg/mL. At the same time, pectinase released the highest neutral sugar of 61.24% ± 1.39%. All NSPs are rhamnose-rich heteropolysaccharides with distinct Mw and surface morphology, and the extraction method did not alter monosaccharide types, but affected their molar ratio. Crucially, each NSP selectively stimulated probiotic growth (Bifidobacterium adolescentis, Lactobacillus bulgaricus, Enterococcus faecalis), confirming the NSP's prebiotic potential. The biological activity correlates with uronic acid level, molecular weight, and surface porosity, rather than any single factor. These results could provide a theoretical and technical foundation for selecting the appropriate extraction method for Nitraria sibirica polysaccharides, thereby enabling their applications in the pharmaceutical, cosmetic, and food industries.

Two new naphthoquinone-naphthalene hybrid dimers featuring a complex polycyclic fused skeleton, named chimedermycins O (1) and P (2), were isolated from the marine-derived Streptomyces sp. OUCMDZ-4982. Their structures, including the absolute configurations, were established by spectroscopic methods and quantum chemical calculations. These compounds are formed through the coupling of medermycin, a major metabolite produced by the same strain, with naphthalene-1,8-diol derivatives. Both compounds exhibited significant cytotoxicity against two human cancer cell lines (MDA-MB-231 and MGC-803) with IC₅₀ values ranging from 2.30 to 9.78 µM.

Flavonoids, a natural polyphenolic substance, exhibit a wide range of biological activities and outstanding potential for marine antifouling. Inhibition zone tests and analysis of the structure-activity relationship were conducted on 10 flavonoids, after which L-epicatechin, dihydromyricetin, and quercetin were selected as antifoulants to prepare three epoxy resin composite antifouling coatings, and their marine antifouling efficacy was further evaluated. The anti-protein adhesion rates of the three composite coatings are all above 90%, and the anti-algae adhesion rates are also all above 80%. They also exhibited excellent inhibitory adhesion effects on gram-positive bacteria, gram-negative bacteria, and marine bacteria. Especially for S. aureus, the inhibition rate is all higher than 90%. The antifoulants can release continuously for a long period of time, and the results of the sea anchor plate tests show that they still have a certain inhibitory effect on the attachment of marine organisms in seawater, with a duration of up to 105 days. This study aims to evaluate the antifouling potential of commercially available flavonoids in epoxy resin coatings, thereby providing a low-cost and easily industrializable strategy for green marine antifouling.

Magnoliae flos (Shin-i) has been traditionally utilized in Chinese medicine for rhinitis, sinusitis, and headaches. However, the underlying anti-inflammatory mechanisms of Shin-i essential oil (SIEO), especially its effects on the Janus kinase/signal transducer and activator of transcription (JAK-STAT) signaling pathway, remain inadequately elucidated. The chemical composition of SIEO was characterized using gas chromatography-mass spectrometry (GC-MS). Network pharmacology and gene ontology (GO) enrichment analyses predicted that SIEO may target the JAK-STAT signaling pathway. Cellular experiments revealed that the excellent anti-inflammatory effects of SIEO were dose-dependent and attributed to the main component, eucalyptol, which reduced nitric oxide (NO) levels and reactive oxygen species (ROS), respectively. Molecular docking results indicated favorable binding affinities between eucalyptol and both JAK1 and STAT1. Western blot analysis further confirmed that SIEO and eucalyptol inhibited the phosphorylation levels of JAK1 to 68.63% and 84.43%, respectively, STAT1 to 47.61% and 74.90%, respectively, and inducible nitric oxide synthase (iNOS) expression to 38.70% and 74.58%, respectively. Therefore, it is suggested that the component eucalyptol plays a key role in the anti-inflammatory functions of SIEO, acting via the JAK1/STAT1/iNOS axis. This study provided insights for the research on the anti-inflammatory mechanisms of SIEO and suggested its potential application prospects in functional cosmetics and medical care.

Two new steroid derivatives, 3-oxoergosta-4,6,8(14),22-tetraen-27-oic acid (1) and (14R,24R)-14-methyl-24,25-dihydroxycholesta-4,8-dien-3-one (2), together with one anthraquinone (3), one amino acid derivative (4), five cyclic dipeptides (5-9) and a quinazolinone alkaloid (10), were isolated from a deep-sea-derived Aspergillus versicolor SCSIO 41325. Notably, compound 2 features an unreported cholesta-4,8-dien-3-one steroid scaffold among natural products. The structures were determined by NMR and high-resolution electrospray ionization mass spectroscopy (HR-ESI-MS) spectroscopic methods, single-crystal x-ray diffraction measurements and comparison with literature data. All isolated compounds were subjected to a broad range of biological assays, including tests against pathogenic bacteria and fungi, as well as for inhibition of pancreatic lipase, acetylcholinesterase, neuraminidase, and antioxidant activity evaluations.

Species of the genus Mentha are valued for their aroma and bioactivity. This study presents a comprehensive 3-year (2022-2024) evaluation of two Mentha spicata and three Mentha × piperita genotypes. Methanolic extracts were analyzed for total phenolic content (TPC), total flavonoid content (TFC), and antioxidant activity (AA) using spectrophotometry; individual phenolic compounds were determined by HPLC-DAD, and essential oils (EOs) were characterized by GC-MS. Significant inter- and intra-species variability was observed. M. × piperita showed higher phytochemical levels (TPC: 33.61-55.23 mg GAE/g DW; TFC: 27.56-43.01 mg CE/g DW; and AA: 46.48-103.93 mg TE/g DW) than M. spicata (TPC: 28.92-39.57 mg GAE/g DW; TFC: 23.48-35.11 mg CE/g DW; and AA: 40.09-93.59 mg TE/g DW). Rosmarinic acid predominated in all samples (6227.11 to 29321.70 µg/g DW), with elevated levels observed in M. × piperita. EO yields ranged from 0.55% to 2.31% (v/w), with carvone dominant in M. spicata and menthone, dl-menthol, or piperitenone oxide in M. × piperita. Principal component analysis confirmed distinct chemical differentiation among genotypes. Genotype had a strong, and year a moderate, effect on phytochemical profiles. These results highlight the species-specific potential of Mentha for food, pharmaceutical, and cosmetic applications.

Eggplant (Solanum melongena L.) is a widely cultivated vegetable and preferred by many people in meals due to its taste. Herein, the fruits, stems, leaves, and roots of four varieties of eggplants were analyzed for their phenolic compounds using high-performance liquid chromatography-diode array detector (HPLC-DAD), while antioxidant, anticholinesterase, and α-amylase and α-glucosidase inhibitory activities were assessed spectrophotometrically. Both chromatographic and bioactivity data were further evaluated through principal component and correlation analyses. Hesperidin (21.23-85.72 mg/g), fumaric acid (9.46-72.92 mg/g), vanillin (0.2-3.92 mg/g), pyrocatechol (0.4-9.91 mg/g), p-coumaric acid (0.59-2.90 mg/g), and p-hydroxybenzoic acid (0.07-0.22 mg/g) were quantified in leaves in higher amounts. On the other hand, roots exhibited notable butyrylcholinesterase (IC₅₀:130.44-180.38 µg/mL) and α-glucosidase (IC₅₀:148.45-165 µg/mL) inhibitory activities, comparable to galantamine (52.18 µg/mL) and acarbose (205.08 µg/mL), respectively. Results suggest exciting opportunities to apply this research to the development of functional foods and therapeutic formulations in the food and pharmaceutical industries through further studies.