Search Results (9,513)

Argemone ochroleuca and Argemone mexicana are widespread weed species known for being rich in various secondary metabolites. However, a comprehensive understanding of their chemical diversity remains limited. Insufficient information exists on metabolite variation between plant parts and the influence of solvent polarity on metabolite recovery. Therefore, this study aimed to characterize the metabolomic profiles of the shoots and root extracts of both species using solvents of varying polarity to evaluate plant part-specific metabolite distribution and solvent effects on metabolome coverage. Untargeted ultra-high-performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS)-based metabolomics and molecular networking were employed for metabolite analysis. Principal component analysis (PCA) did not reveal clear clustering of A. ochroleuca and A. mexicana, suggesting similarities in their metabolomic profiles. A total of 15 and 13 metabolite classes, yielding 59 and 54 metabolites, were identified in A. ochroleuca and A. mexicana, respectively, including flavonoids, terpenoids, phenolic compounds, fatty acids, and monoterpenoids. Argemone ochroleuca exhibited higher metabolite abundance, particularly in methanol and acetone extracts, and with shoots showing higher abundance than roots, with flavonoids being the dominant class. The findings show that LC-MS metabolomics, molecular networking, and careful solvent selection are effective for identifying key metabolites with potential applications in crop protection. Full article

Global agricultural productivity is increasingly threatened by climate change, soil salinization, and freshwater scarcity. In response, edible halophytes such as Crambe maritima L. (sea kale) are emerging as resilient, promising alternative crops for biosaline agriculture. This review comprehensively evaluates the agronomic, phytochemical, and commercial potential of C. maritima and related Crambe species. We examine current propagation protocols and highlight the application of controlled-environment agriculture (CEA) to leverage “saline eustress,” strategically enhancing secondary metabolite biosynthesis without penalizing harvestable biomass. Nutritionally, Crambe species exhibit a highly favorable profile, selectively accumulating essential macro- and micro-minerals alongside potent bioactive compounds, particularly characteristic glucosinolates, including sinigrin, together with diverse phenolic acids. These specific secondary metabolites confer antioxidant defense system and antimicrobial properties, positioning the genus as an unexploited resource for functional foods, nutraceuticals, and cosmeceuticals. However, successfully transitioning C. maritima from a wild coastal halophyte into a reliable horticultural crop necessitates overcoming critical domestication bottlenecks, including mechanical seed dormancy, polygenic salinity tolerance, and a scarcity of long-term field data. By addressing these multidisciplinary challenges through targeted breeding and advanced agronomy, C. maritima represents a highly promising candidate for dietary diversification and the advancement of climate-resilient agricultural systems. Full article

Trigonelline is a bioactive pyridine alkaloid in Trigonella foenum-graecum, which is a legume species, and is known for its hypoglycemic and hypolipidemic activities. Phytosulfokine-δ (PSK-δ), a recently identified legume-specific phytosulfokine peptide, has been implicated in the regulation of nodulation and root development. However, whether PSK-δ participates in the regulation of secondary metabolite biosynthesis remains unclear. In this study, exogenous PSK-δ treatment significantly promoted trigonelline accumulation in T. foenum-graecum seedlings, leading to a 93% increase in trigonelline content after 5 days relative to the scrambled-pentapeptide-treated control, whereas a slight downward trend was observed at 15 days. Comparative transcriptomic analyses between PSK-δ-treated seedlings and the corresponding controls at 5 and 15 days identified 15 candidate genes associated with trigonelline biosynthesis and PSK signaling, whose expression patterns were consistent with trigonelline accumulation dynamics. Co-expression network analysis between these 15 candidate genes and 831 transcription factor-encoding genes identified candidate transcription factors potentially involved in the coordinated regulation of trigonelline biosynthesis and PSK signaling. These findings suggest that PSK-δ may serve as a potential peptide-based biostimulant for regulating alkaloid accumulation in medicinal legume cultivation and provide insights into peptide hormone-mediated regulation of plant metabolism. Full article

PBU (N-phenyl-N′-thiazolylurea) promotes callus induction and adventitious bud differentiation in eucalyptus, but the miRNA-mediated regulatory mechanisms underlying these effects remain unclear. In this study, calli of Eucalyptus urophylla × E. grandis clone DH32-29 with distinct phenotypes were cultured at four PBU concentrations (0, 0.1, 1 and 5 mg L⁻¹) and analyzed by small-RNA sequencing, targeted metabolomics, and qRT-PCR validation. A total of 114 common differentially expressed miRNAs were identified, targeting 610 mRNAs. Functional enrichment analysis revealed that these targets were predominantly associated with lignin metabolism, phenylpropanoid metabolism, biotin metabolism, tryptophan metabolism, protein processing in the endoplasmic reticulum, and galactose metabolism. Metabolomic profiling detected 3029 metabolites, with differential metabolites enriched in the ABC transporter pathway, galloyl sugar biosynthesis, and cofactor biosynthesis. Key miRNA families, including miR164, miR165/166, and miR396, exhibited PBU concentration-dependent expression patterns and were predicted, based on in silico target prediction and qRT-PCR co-expression, to be potentially associated with target genes involved in lignin biosynthesis, ROS-related metabolism, and cytokinin homeostasis; these regulatory relationships remain to be experimentally validated. Among the tested concentrations, 1 mg L⁻¹ PBU was the dosage associated with the strongest reprogramming of secondary metabolism and with metabolic signatures suggestive of better preserved redox homeostasis; future work will build on this reference dataset with quantitative regeneration phenotyping and direct redox measurements to confirm this candidate optimum. These findings provide new insights into PBU-mediated in vitro regeneration in eucalyptus and offer a molecular basis for optimizing regeneration systems in E. urophylla × E. grandis. These findings provide new insights into the miRNA-metabolite regulatory network underlying phenylurea-mediated callus differentiation in woody plants. Full article

Rumen biohydrogenation is a microbial process that converts dietary unsaturated fatty acids into more saturated products and produces a range of intermediates that can affect animal products and rumen fermentation. This review summarizes current knowledge on the main biohydrogenation pathways, the microbial groups involved, and the nutritional and breeding strategies used to regulate this process. Particular attention is given to the transformation of C18 fatty acids, the formation of vaccenic acid and conjugated linoleic acid, the trans-10 shift, and the links between lipid metabolism, hydrogen use, and methane formation. Evidence indicates that diet composition, lipid source, plant secondary metabolites, rumen-protected fat technologies, microbial interventions, and host-related factors can all influence biohydrogenation outcomes. These strategies can improve the fatty acid profile of meat and milk, but their effects are context-dependent and vary with animal species, diet, and rumen microbial structure. Important gaps remain, including the identification of active microbial populations, the functions of many transient intermediates, and the extent to which changes in biohydrogenation directly contribute to methane mitigation. Clarifying these mechanisms is essential for improving the nutritional quality of ruminant products and the sustainability of production systems. Full article

Wild plant biodiversity represents a largely untapped source of chemically diverse metabolites. However, many wild edible species remain poorly characterized despite their potential as sources of antioxidant and anti-inflammatory phytochemicals. Daucus carota L. subsp. carota, commonly known as wild carrot, has attracted interest due to its long history of medicinal use. In this study, seed extracts collected from populations growing in two Italian regions (Lazio and Molise) were investigated to evaluate their phytochemical composition, mineral content, antioxidant activity, and anti-inflammatory potential. The metabolite profiles were characterized by qualitative Liquid Chromatography-Mass Spectrometry analysis, allowing the identification of several phenolic compounds and other secondary metabolites. Antioxidant activity was assessed using in vitro assays, while anti-inflammatory activity was evaluated through the inhibition of cyclooxygenase and soluble epoxide hydrolase, two key enzymes involved in the arachidonic acid cascade. To gain further insight into the possible mechanisms underlying these activities, molecular docking analyses were performed on selected metabolites identified in the extracts, exploring their interactions with the target enzymes. The extracts displayed promising antioxidant and anti-inflammatory properties, while docking results supported the potential role of specific metabolites in enzyme modulation. These findings highlight the value of underexplored wild D. carota seeds as a source of natural compounds with potential applications in the development of nutraceutical and cosmeceutical products. Full article

Orchid seeds are dust-like and lack endosperm, which limits their capacity to support germination using endogenous nutrient reserves. Successful germination therefore depends on the establishment of a compatible symbiotic association with germination-promoting orchid mycorrhizal fungi (OMF). In plant-root symbioses, host-derived small molecules, such as strigolactones and flavonoids, function as early chemical signals that recruit microbial partners and stimulate their growth. However, the chemical constituents that may facilitate fungal recognition, growth, or colonization during orchid seed germination remain poorly understood. In this report, we combined metabolomics, UPLC-Q-TOF-MS/MS, molecular networking, phytochemical isolation, and bioactivity assays to characterize bioactive metabolites from the seeds of the medicinal orchid Cremastra appendiculata. Metabolomic profiling revealed abundant primary metabolites, including lipids, amino acids, organic acids, saccharides, and nucleosides. And then, nineteen secondary metabolites were isolated and identified, including two new structures. Functional assays showed that selected organic acids, saccharides, and lignanamides promoted the growth of Coprinellus disseminatus, a fungus required for seed germination, whereas lignanamides inhibited the plant pathogen Fusarium oxysporum. These findings provide the first systematic chemical and functional characterization of metabolites from C. appendiculata seeds and offer new insight into the molecular basis of symbiosis between orchids and fungi. Full article

Plant secondary metabolites play important roles in plant defense, environmental adaptation, and ecosystem functioning, yet large-scale monitoring of foliar phenolics remains limited because of the high cost and restricted spatial coverage of airborne imaging spectroscopy and the limited spectral resolution of multispectral satellites. This study explored a cross-scale remote sensing framework to map foliar phenolics through the synergy of airborne imaging spectroscopy and Sentinel-2 multispectral imagery. Foliar samples were collected from 634 plots across seven National Ecological Observatory Network (NEON) ecological domains in the United States, representing six plant functional types. Community-weighted mean foliar phenolic concentrations were linked with NEON Airborne Observation Platform (AOP) imaging spectroscopy to develop phenolic retrieval models using partial least squares regression (PLSR) and Gaussian process regression (GPR). The optimized airborne-derived phenolics were subsequently aggregated across multiple spatial windows and used as reference data to train Sentinel-2 models using PLSR, random forest regression (RFR), and GPR. Both airborne hyperspectral models achieved strong predictive performance, with comparable accuracy between PLSR (R² = 0.770, RMSE = 16.11 mg·g⁻¹) and GPR (R² = 0.771, RMSE = 16.16 mg·g⁻¹). However, PLSR showed substantially lower predictive uncertainty (4.62 mg·g⁻¹) than GPR (12.58 mg·g⁻¹), indicating more stable predictions across NEON samples. Spectral importance analysis identified consistent phenolic-sensitive wavelength regions in the visible and shortwave infrared domains, particularly near previously reported absorption features. For Sentinel-2 upscaling, prediction accuracy increased consistently with larger spatial aggregation windows, indicating improved agreement between Sentinel-2 observations and airborne-derived phenolics through reduced spatial scale mismatch and geolocation misalignment. Among the evaluated approaches, RFR achieved the best performance, improving from R² = 0.479 at the 10-pixel window to R² = 0.776 (NRMSE = 7.0%) at the 100-pixel window. Feature importance analysis showed increasing contributions of red-edge and shortwave infrared information at larger aggregation scales. Spatial comparisons demonstrated that Sentinel-2 successfully reproduced major phenolic distribution patterns observed by airborne imaging spectroscopy. These results demonstrate that airborne imaging spectroscopy can effectively bridge field observations and satellite multispectral imagery for foliar phenolics estimation and highlight the potential of Sentinel-2 as a scalable approach for monitoring vegetation chemical traits across heterogeneous ecosystems. Full article

The endophytic fungi from plants are recognized as a valuable source of structurally diverse secondary metabolites with intriguing bioactivities. Three previously undescribed compounds, including two benzophenones, 2-(2,6-dihydroxy-4-methylbenzoyl)benzoic acid (1) and 2-(2,6-dihydroxy-4-(hydroxymethyl)benzoyl)benzoic acid (2), one biphenyl, 4′,5,5′-trihydroxy-3-methoxy-2′-methyl-(1,1′-biphenyl)-2-carbaldehyde (4), along with two known compounds (3 and 5), were isolated from the endophytic fungus Penicillium sp. QM-4 associated with Pteris cretica. Their structures were established by extensive spectroscopic analysis of HRESIMS, UV, IR, and 1D and 2D NMR data. Free radical scavenging activity of compounds 1–5 was assessed, and compound 3 displayed a significant antioxidant effect in the DPPH assay. Structure–activity relationships of compounds 1–3 were also discussed. These findings enrich the structural diversity and bioactivities of benzophenones and biphenyls derived from fungal source. Full article

Breast cancer remains a major global health burden. Dactylospongia species have been explored for their cytotoxic potential. This study aims to evaluate the cytotoxic potential of compounds derived from the marine sponge Dactylospongia elegans. Dactylospongia elegans were collected from the Lembeh Strait, macerated using methanol, then partitioned to an ethyl acetate fraction. The cytotoxic activity of these fractions was assessed using MDA-MB-231 cells while toxicity testing was done using the BSLT. TLC was carried out to determine the groups of compounds, while LC-MS/MS was used to predict active compounds contained in the ethyl acetate fractions. In silico studies were conducted as preliminary studies to determine the antitumor mechanism. The ethyl acetate fraction and F4 subfraction of Dactylospongia elegans exhibited cytotoxicity toward MDA-MB-231 cells with IC₅₀ values of 15.72 and 41.76 µg/mL, respectively. The BSLT indicated the strongest toxicity belongs to the F6 subfraction (LC₅₀ = 32.831 µg/mL). TLC analysis confirmed the presence of major secondary metabolites as terpenoids, steroids, and alkaloids, then confirmed with LC-MS/MS including 5-epi-illimaquinone and calciferol. Molecular docking revealed that calciferol exhibited the strongest binding affinity toward tyrosine kinase and p53–MDM2 receptors, with binding energies of −10.13 and −10.28 kcal/mol, respectively. These findings suggest that Dactylospongia elegans contains bioactive constituents with potential anticancer activity, particularly against TNBC. Full article

Developing sustainable agricultural biostimulants that simultaneously optimize vegetative growth and specialized metabolic pathways is critical for maximizing plant growth, photosynthetic efficiency, and metabolome reprogramming. In this study, for the first time, the effects of the biostimulant 3-acetonyl-3-hydroxyoxindole (AHO) on plant growth, photosynthetic efficiency and metabolomics reprogramming were evaluated. The multifaceted effects of AHO (0, 1, 5, 10, and 20 µg/mL) applied via foliar application were evaluated via comprehensive morpho- physiological, UPLC–MS/MS metabolomic and computational docking approaches. AHO positively affects plant growth performance in a concentration-dependent manner. Foliar application at 20 µg/mL produced the maximum vegetative vigor and biomass accumulation, as well as the highest levels of chlorophyll a, chlorophyll b, carotenoids, total flavonoids, and indole contents, while the maximum value of total phenolics was 1 µg/mL. Substantial metabolic flux modulation was confirmed by UPLC–MS/MS profiling, which revealed that 10 µg/mL selectively accumulated chlorogenic acid and rutin, whereas 5 µg/mL preferentially enriched quercetin, quercitrin, limonin and catechin. These empirical metabolic responses are supported by computational docking models, which predict favorable structural interactions between AHO and key biosynthetic enzymes. Insights gained from these integrated morphological, physiological, metabolomic, and computational analyses indicate that AHO applications can effectively improve plant growth and biomass, increase the concentration of bioactive compounds, and enhance the accumulation of bioactive secondary metabolites within the plant. Full article

Okra is a flavonoid-rich food known to confer a variety of health benefits and have extensive therapeutic characteristics. In this study, okra seeds at five stages of development (youngest, young, intermediate, mature and fully mature) were assessed for secondary metabolite content using 70% methanol. Extracts from mature seeds were found to contain the highest accumulation of total polyphenol content (TPC) (536.65 ± 80.13 mg GAE/g), total flavonoid content (TFC) (234.73 ± 45.58 mg ISE/g), DPPH scavenging activity (70.11%) and ABTS+ activity (75.19%). High-performance liquid chromatography (HPLC) analysis revealed that in fully mature seed extracts, quercetin (148.14 ± 11.01 mg/kg) is abundant, while isoquercetin and quercertin-3-O-gentibiose are respectively abundant in the youngest (5205.02 ± 48.54 mg/kg) and mature seeds (12,396.48 ± 77.54 mg/kg). Mature seed extracts also exhibited the highest activity against nitric oxide (NO) production and the pro-inflammatory cytokine interleukin-1 beta (IL-1β) in lipopolysaccharide-induced (LPS) RAW 264.7 cells. The findings from this study showed that secondary metabolite accumulation in okra seeds varies at different stages of development. Thus, determining the bioactive compounds at different levels of seed development is considered essential for potential pharmacological advancements in biologically significant plants. Full article

Phenolic compounds are important plant secondary metabolites with broad biological activity and potential applications in pharmaceutical, food, cosmetic, nutraceutical, and veterinary sectors. Conventional production from field-grown plants is limited by environmental variability, seasonality, and difficulties in standardizing metabolite composition. Plant in vitro cultures provide controlled systems for modulating secondary metabolism and producing phenolic compounds under defined conditions. This review summarizes current advances in plant in vitro platforms for phenolic production and discusses regulation through elicitation, metabolic modulation, molecular approaches, and bioreactor cultivation. The distinctive focus of this review is the critical evaluation of how culture type, production stability, metabolite composition, and structural variation affect biological performance and functional equivalence. Current evidence indicates that increased metabolite accumulation alone does not ensure preserved biological properties or translational applicability. Functional equivalence is therefore considered as a framework integrating chemical profiling, batch-to-batch reproducibility, biological validation, bioavailability, and application-oriented evaluation of in vitro-derived phenolics. Future progress will depend not only on increasing yield but also on achieving stable production, predictable composition, reproducible biological performance, and translational reliability. Full article

Levofloxacin is an antibiotic belonging to the fluoroquinolone family. N-Demethyllevofloxacin, a metabolite and an impurity of levofloxacin, features a secondary amine that is susceptible to N-nitrosation, raising concerns about the formation of a potentially toxic nitrosamine. The corresponding N-nitrosamine was synthesized in two steps and characterized using HRMS, NMR spectroscopy, IR spectroscopy, UV absorption and emission spectroscopies and powder X-ray diffraction. This work provides a reliable reference for the quantitation and control of nitrosamine impurities associated with levofloxacin in chemical and pharmaceutical contexts. Full article

Chamaecyparis obtusa is a valuable conifer species, prized for its high-quality timber and bioactive essential oils. However, commercial micropropagation is challenging due to its resistance to vegetative propagation. This study aimed to develop an efficient in vitro plant regeneration system using leaf explants and to profile the metabolic changes during organogenesis. Leaf explants from one-year-old in vitro-grown plantlets were cultured on media with various plant growth regulators (PGRs) to optimize callus induction, shoot multiplication, and rooting. Secondary metabolites were systematically analyzed throughout the developmental stages: explant, callus, regenerated shoot, and rooted plantlet. The most effective shoot regeneration, leading to whole plantlets, was achieved on a medium supplemented with 1.0 mg/L 2,4-dichlorophenoxyacetic acid and 2.0 mg/L thidiazuron. Metabolic profiling revealed significant stage-specific biochemical transitions. High-Performance Liquid Chromatography (HPLC) precisely quantified individual phenolics, resolving cross-reactivity issues seen in total flavonoid colorimetric assays. Gas Chromatography-Mass Spectrometry (GC-MS) also identified substantial shifts in volatile terpenoid biosynthesis during shoot morphogenesis. This integrated protocol provides a reliable platform for mass propagation of C. obtusa and offers fundamental insights into the metabolic dynamics of in vitro development, with significant potential for future horticultural and biotechnological applications. Full article