Chemistry & Biodiversity最新文献

Phytochemical investigation of the CH₂Cl₂/MeOH (1:1, v/v) extract of the Red Sea coral Lemnalia sp. led to the identification and purification of a previously undescribed ylangene-type sesquiterpenoid, designated as (1S,2S,3S,6R,7R,8R)-6,7-dihydroxy-13-methoxy-3,4-dihydro-α-ylangene (1), together with a known nardosinane-type sesquiterpene, 6,7-seco-13-nornardosinane (2), and three known steroids: 24-methylcholesterol (3), 24-methylenecholesterol (4), and 4α,24-dimethyl-5α-cholest-24(28)-en-3β,8β-diol (5). The structures of all isolated metabolites were elucidated through comprehensive spectroscopic analyses, including one- and two-dimensional nuclear magnetic resonance experiments, high-resolution electrospray ionization mass spectrometry, and electronic circular dichroism calculations. The antitumor activities of the purified sesquiterpenoid compounds were assessed against two cancer cell lines, MCF-7 (breast adenocarcinoma) and HT-29 (colorectal adenocarcinoma), using doxorubicin as the reference drug. Metabolite 1 exhibited cytotoxic effects against MCF-7 (half-maximal inhibitory concentration [IC₅₀] = 15.7 ± 1.21 µM) and HT-29 (IC₅₀ = 12.9 ± 1.22 µM), whereas compound 2 showed cytotoxicity toward MCF-7 (IC₅₀ = 22.5 ± 1.54 µM) and HT-29 (IC₅₀ = 17.8 ± 1.35 µM). Although these compounds display limited potency, their distinctive structural features broaden the chemical diversity of Lemnalia-derived metabolites and may offer promising scaffolds for future chemical or biosynthetic optimization.

Recently, the insecticidal, antifungal, antibacterial, and antioxidant properties of pyrolysis liquid (bio-oil) obtained from agricultural and industrial plants have been investigated in foods. As no previous studies had been conducted on the Capparis sicula subsp. sicula (caper) species, this study was chosen. For the first time, a methanol–chloroform extract, pyrolysis liquid, and green-synthesized silver nanoparticles (AgNPs) were obtained from caper fruit. GC–MS/MS analysis of the extract and pyrolysis revealed linoleic and palmitic acid methyl esters. In contrast, LC–ESI–MS/MS analysis revealed high amounts of hesperidin (7.534 mg/g extract) and caffeine (0.216 mg/g extract), respectively. It was observed that the pyrolysis liquid had higher activity than the extract in terms of antioxidant activity (93.33% for DPPH and 8.01 µmol Trolox/g extract), antibacterial activity (average of 8 mm for all bacteria), and enzyme inhibition (4.72 µg/mL for α-glucosidase and 2.00 µg/mL for α-amylase). A molecular docking study found that caffeine was effective against the enzyme catalase (−6.9 kcal/mol). Therefore, by enabling the release of compounds not detected by conventional methods through pyrolysis, it will be possible to expand the use of these compounds as antioxidant and antibacterial agents in the food industry, pharmacology, and other industries.

Cytotoxic activity-guided fractionation of the ethanolic extract of Verbascum aydogdui, an endemic halophyte plant to Türkiye, resulted in the isolation of 16 secondary metabolites, including eight triterpene saponins, mulleinsaponins III (1), ilwensisaponin A (2), buddlejasaponin I (3), mulleinsaponin IV (4), ilwensisaponins D (5), ilwensisaponin C (6), craniosaponin A (7) and buddlejasaponin Ia (8), six iridoid glycosides, aucubine (9), eurostoside (10), geniposidic acid (11), nigroside III (13), 6-O-β-D-glucopyranosylaucubine (12), 6-O-[3-O-(E-feruloyl)-α-L-rhamnopyranosyl]-aucubine (14), and two phenylethanoid glycosides, verbascoside (15) and alyssonoside (16). Compounds 1–5 displayed significant cytotoxicity against PC3, HEPG2, HGC27, A375, MCF7, and SW480 cancer cell lines with half-maximal inhibitory concentration values of 17.6–85.1 µM, being 2 and 3 the most cytotoxic ones. Thus, 2 and 3 were further assayed for their cell death mechanisms, including apoptosis and necrosis. Compound 2 exerted anti-cancer effects in all cancer cell lines tested, except for MCF7, especially via inducing apoptosis. Its apoptotic activity was predominantly mediated by a significant increase in p53 and p21 expressions in all cancer lines tested, but for SW480. This is the first bioactivity and phytochemical study on V. aydogdui. Our results indicated that 2 could be a potential anticancer natural product that merits further in vitro and in vivo studies.

Cipadessa baccifera (Roth) Miq. (Family- Meliaceae) has been traditionally used to treat various ailments, including diabetes. The present study aimed to validate the antidiabetic efficacy of C. baccifera using both in vitro and in vivo diabetic models, followed by a mechanistic evaluation. UPLC-Q-ToF/MS analysis, enzyme inhibition assays, and in silico studies were performed. Cytotoxicity and glucose uptake studies were conducted on MIN6 cell line. qRT‒PCR was carried to assess GLUT4 expression in adipocytes. Immunostaining was performed to examine the differential expression of pancreatic cell subtypes. UPLC-Q-ToF/MS analysis identified 93 compounds, of which 18 were further selected for in silico protein‒protein interaction (PPI) network analysis. PPI network and pathway enrichment analyses predicted that the PPARG, AKT1, SIRT1, and FOXO1 genes are key regulators in diabetes. The in vitro enzyme inhibition assay revealed significant inhibition by the 70% hydroethanolic extract. The mechanistic study showed notable upregulation of GLUT4 mRNA expression, which also supports the network analysis algorithm. The in vivo study demonstrated a significant decrease in blood glucose, insulin, and HbA1c levels in the treated model. Immunostaining revealed significant restoration of insulin and myosin expression. These combined results highlight the potential of C. baccifera as a valuable supplement for diabetes management.

Climate change and nutrient limitations increasingly hinder seed germination and early seedling establishment, highlighting the need for sustainable enhancement strategies. This study evaluates a green nanopriming approach using chitosan-stabilized iron oxide nanoparticles synthesized via an aqueous, low-energy co-precipitation process that employs biodegradable chitosan and avoids hazardous reagents, fully aligning with green chemistry principles. Lettuce seeds were primed in a 1 ppm nanoparticle suspension for 2, 6, 8, 16, and 24 h to identify the optimal priming duration. Chitosan markedly improved nanoparticle dispersion and colloidal stability, producing a strongly positive surface charge (+35.5 mV) that enhanced nanoparticle–seed interactions. The 8-h priming treatment yielded the greatest improvements, achieving a germination rate of 96.67% alongside the highest shoot and root elongation and biomass accumulation. Longer exposures (16 and 24 h) reduced performance, suggesting potential overstimulation or early metabolic imbalance. These enhancements likely arise from improved iron bioavailability, nanoparticle stability, and stimulation of early metabolic activation. A pilot-scale cost assessment demonstrated excellent economic feasibility, with production costs of only $4.40 per 10-L batch, supporting scalability for agricultural use. Overall, optimizing nanopriming duration using chitosan-stabilized iron oxide nanoparticles offers a sustainable, economical, and environmentally responsible approach to strengthen crop establishment under stress.

Polygonum pubescens, known as drooping or lax knotweed is a tropical and subtropical annual herb belonging to Polygonaceae. The weedy and herbaceous nature, wide distribution and availability make this herb an attractive target for useful phytochemicals. This study aimed to investigate the volatile metabolites of this herb which remained unexplored. First, a detailed morphological study established its identity and distinguishing features with closely related Polygonum species. The leaves of this herb produced highest yield of essential oil (0.20%–0.35%) among three aerial parts (leaf, stem, and inflorescence) hydrodistilled. The oil composition was grossly similar across the tissues and exclusively dominated by three eudesmane and cadalane-type sesquiterpene hydrocarbons, namely, β-selinene (36.3%–43.7%, 221.8–254.5 mg/g), α-selinene (11.0%–14.4%, 74.2–86.5 mg/g), and δ-cadinene (29.0%–41.6%, 140.6–197.6 mg/g). This oil was practically composed of sesquiterpenoids which collectively contributed 97.9%–100.0% relative abundance. When phytotoxicity was evaluated, the oil dose-dependently (1.0–200.0 µg/mL) inhibited the growth of wheatgrass coleoptile. However, the inhibitory potency (59%–73%, 200.0 µg/mL) was significantly low for its consideration as an herbicidal candidate. The current study identified P. pubescens as a rich natural source of β-selinene and δ-cadinene, bearing significance in plant defense, chemical synthon and bioactive phytochemicals.

Trametes and Laetiporus are globally recognized as major wood-decaying fungi. To explore safe and environmentally friendly alternatives, the antifungal activity of 37 plant essential oils (EOs) against Trametes hirsuta and Laetiporus sulphureus was assessed using the mycelial growth rate method. The results revealed that Litsea cubeba EO exhibited the strongest inhibitory effects, with 50% effective concentration values of 72.3 and 40.2 µg/mL. Subsequent mechanistic studies were conducted. Gas chromatograph-mass spectrometry analysis identified geranial (32.12%) and neral (29.43%) as the primary bioactive compounds. Optical microscopy of the treated mycelia revealed morphological abnormalities, including surface wrinkling, and confirmed membrane damage via propidium iodide fluorescence. Further biochemical analysis revealed increased levels of nucleic acids, proteins, soluble sugars, and ergosterol. These findings collectively demonstrate that L. cubeba EO disrupts plasma membrane integrity in both fungi, effectively inhibiting mycelial growth. These results highlight the significant potential of L. cubeba EO as a natural wood preservative.

Overpopulation poses a global challenge, intensifying the need for safe and effective contraceptive agents. Thevetia peruviana (Pers.) K. Schum., traditionally used for various medicinal purposes, contains cardiac glycosides and other bioactive constituents with potential antifertility effects. This study investigated the phytochemical composition, reproductive toxicity, and spermicidal potential of T. peruviana leaf extract (TPLE) using RP-HPLC-MS/MS profiling and in vivo evaluation in male Wistar rats. Metabolomic analysis identified 52 compounds, including cardiac glycosides, flavonoids, hydroxycinnamic acids, and fatty acids. TPLE showed strong antioxidant activity and high phenolic/flavonoid content. Repeated administration (12–24 mg/kg for 60 days) caused a dose-dependent reduction in sperm motility and count, increased oxidative stress (↑MDA, ↓GSH), and dysregulated apoptotic/steroidogenic genes (↑casp-3, ↑bax, ↓bcl-2, ↓star, ↓cyp11a1). Histopathology revealed seminiferous tubule degeneration, Leydig cell necrosis, and caspase-3 overexpression. These results suggest that TPLE induces spermicidal effects through oxidative stress, apoptosis, and hormonal disruption, highlighting its potential as a plant-based contraceptive. However, toxicity at higher doses warrants further investigation into safety, reversibility, and translational potential.

Two new prunasines, 6'-O-p-trans-coumaroyl prunasin (1) and 6'-O-p-cis-coumaroyl prunasin (2), together with six known compounds, afzelin (3), tamarixetin 3-O-rhamnoside (4), mearnsitrin (5), cis-linalool-3,6-oxide β-D-glucopyranoside (6), n-hexyl-O-β-D-glucoside (7), and cucurbitacin F (8), were isolated from the leaves of Elaeocarpus bachmaensis collected in Bach Ma National Park, Vietnam. Their chemical structures were elucidated by one-dimensional nuclear magnetic resonance (1D-NMR), 2D-NMR, and high-resolution mass spectrometry spectra. Bioassays revealed that compound 6 inhibited α-amylase significantly with a half-maximal inhibitory concentration (IC₅₀) value of 137.3 ± 14.4 µM, whereas compounds 1–5 inhibited α-glucosidase significantly with IC₅₀ values ranging from 82.4 ± 10.4 to 160.0 ± 19.9 µM. These findings suggest that E. bachmaensis may serve as a promising natural source for the development of antidiabetic agents. This is the first report on the chemical composition and bioactivity of the E. bachmaensis species.