Search Results (232)

The environmental heterogeneity caused by altitude can lead to trade-offs in nutrient utilization and allocation strategies among plant organs; however, there is still a lack of research on the nutrient variation in the “flower–leaf–branch–fine root–soil” systems of native shrubs along altitude gradients in China’s unique karst regions. Therefore, we analyzed the carbon (C), nitrogen (N), and phosphorus (P) contents and their ratios in flowers, leaves, branches, fine roots, and surface soil of Hypericum kouytchense shrubs across 2200–2700 m altitudinal range in southwestern China’s karst areas, where this species is widely distributed and grows well. The results show that H. kouytchense organs had higher N content than both global and Chinese plant averages. The order of C:N:P value across plant organs was branches > fine roots > flowers > leaves. Altitude significantly affected the nutrient dynamics in plant organs and soil. With increasing altitude, P content in plant organs exhibited a significant concave pattern, leading to unimodal trends in the C:P of plant organs, as well as the N:P of leaves and fine roots. Meanwhile, plant organs except branches displayed significant homeostasis coefficients in C:P and fine root P, indicating a shift in H. kouytchense’s P utilization strategy from acquisitive-type to conservative-type. Strong positive relationships between plant organs and soil P and available P revealed that P was the key driver of nutrient cycling in H. kouytchense shrubs, enhancing plant organ–soil coupling relationships. In conclusion, H. kouytchense demonstrates flexible adaptability, suggesting that future vegetation restoration and conservation management projects in karst ecosystems should consider the nutrient adaptation strategies of different species, paying particular attention to P utilization. Full article

Efficient and sustainable extraction of bioactive benzopyrans from Hypericum polyanthemum Klotzsch ex Reichardt (Hypericaceae) remains underexplored, despite their potential applications. The current study aimed to optimize this process by integrating computational simulation and experimental extraction with suitable solvents. The COSMO-RS model was employed to screen deep eutectic solvents (DESs), indicating lactic acid/glycine/water 3:1:3 (DES 1) as a highly promising candidate based on activity coefficients at infinite dilution for target benzopyrans (HP1, HP2, HP3). Ultrasound-assisted extraction (UAE) was then conducted using the proposed DES as well as hexane, and the extracts were analyzed via high-performance liquid chromatography (HPLC) and spectrophotometry for total phenolic content (TPC). The results for DES 1 showed yields for benzopyrans HP1 (1.43 ± 0.09 mg/g plant) and HP2 (0.55 ± 0.04 mg/g plant) close to those obtained in the hexane extract (1.65 and 0.78 mg/g plant, respectively), corroborating the use of COSMO-RS for solvent screening. Kinetic analysis using an adapted Crank diffusion model successfully described the mass transfer process for DES 1 (R² > 0.98, mean average percent error < 9%), indicating diffusion control and allowing estimation of effective diffusion coefficients. This work confirms COSMO-RS as a valuable tool for solvent selection and demonstrates that UAE with the identified DES provides an efficient, greener approach for extracting valuable benzopyrans, offering a foundation for further process optimization. Full article

Carotenoid, chlorophyll and tocochromanol biosynthesis and accumulation are interrelated and age-dependent in plants. Model plants produce tocopherols, but do not produce significant amounts of tocotrienols; consequently, the regulation of tocotrienol biosynthesis in plants has been scarcely studied. The Hypericum genus produces a variety of prenyllipids naturally in all parts of the plant, allowing for a glimpse into the relationship between them without genetic or other interference. Consequently, five Hypericum species’ leaves of different ages were investigated—H. androsaemum, H. pseudohenryi, H. hookerianum, H. patulum and one hybrid H. × inodorum (H. androsaemum × H. hircinum). The leaves contained predominantly α-tocopherol, γ-tocotrienol and δ-tocotrienol (30.9–212.8, 8.13–22.43 and 1.87–20.8 mg 100 g⁻¹, respectively). Higher quantities of tocochromanols, a lower chlorophyll content and a higher a/b ratio were observed in the bottom (older) leaves. The predominant carotenoids were lutein (semi-quantitative) and β-carotene (7.60–28.63 and 2.33–12.43 mg 100 g⁻¹, respectively). Carotenoid contents were lower in bottom leaves than in middle or top leaves, and the highest carotenoid content was observed in H. hookerianum and H. patulum. Leaf tocopherol, tocotrienol, chlorophyll and carotenoid accumulation were section and leaf age-dependent, and distinct relationships can be observed between the accumulation of some prenyl lipids, but not others. Full article

We report the development of a procedure for ultrasound-assisted microscale extraction of metabolites from the flowers of Saint John’s wort (Hypericum perforatum L.), designed for comparative metabolite analysis of plants from genetic resource collections and natural and segregating populations. The procedure involves high-throughput methanol extraction of metabolites from ground-frozen flowers at a selected stage of flower development, which is carried out in a standard 2 mL Eppendorf tube. A total of 18 compounds, including chlorogenic acid, catechins, glycosylated flavonoids, hypericins, and hyperforin, were identified based on LC/DAD/QTOF analysis, of which 16 could be detected in the UV-Vis spectrum. Two alternative versions of the procedure were evaluated: the “single-flower” procedure, including repeated collection and analysis of single flowers from the tested plant, and the “bulk-flower” procedure, employing the collection of a bulk flower sample from the tested plant and analysis of a portion of the ground sample. The results showed excellent technical reproducibility of the “single-flower” procedure when used with the suggested combination of the peak areas for the proto- and stable forms of pseudohypericin and hypericin. Application of the developed “single-flower” procedure for comparison of the plants derived from seed progeny of the apomictic line Hp93 revealed significantly lower metabolite variation among the apomictic progeny plants compared to the variation observed among plants belonging to different genotypes. Full article

Porcine epidemic diarrhea (PED) remains a persistent threat to global swine production, necessitating urgent development of targeted interventions. Our previous research established that Hypericum japonicum Thunb. ex Murray (HJT) extract exhibited significant anti-porcine epidemic diarrhea virus (PEDV) activity both in vivo and in vitro. Nevertheless, the principal bioactive constituents mediating this antiviral activity remained uncharacterized. In this study, it was demonstrated that ethanol eluates with 20% (v/v) and 60% (v/v) ethanol exhibited activity against PEDV. Phytochemical characterization revealed 66 distinct compounds, including 36 flavonoids and 13 organic acids identified as possible antiviral constituents. Among these, taxifolin-7-O-rhamnoside and quercetin-7-rhamnoside were identified as the most potent anti-PEDV components. Notably, neither compound exhibited significant antiviral efficacy as monotherapy. However, co-administration produced a reduction in PEDV-G2 titers. This study mechanistically links taxifolin-7-O-rhamnoside and quercetin-7-rhamnoside as core anti-PEDV phytochemicals in HJT extract. These findings support the further development of HJT as a potential therapeutic for PED. Full article

Chemical analysis of the hydroethanolic Hypericum repens L. extracts was performed using the LC/Q-TοF/HRMS technique. The majority of compounds identified belonged to phenolics, particularly flavonoids. The extract was also studied for its possible bioactivities, demonstrating high antioxidant properties compared to the control (IC₅₀ values ranging from 4.6 to 9.42 μg/mL). Significant antibacterial activity was also detected against Escherichia coli, Staphylococcus aureus, Enterococcus faecalis, and Salmonella enteritidis, with MIC values from 125 to 625 μg/mL. S. aureus presented the highest susceptibility among all bacteria tested. Additionally, the extract showed very mild anticholinesterase activity in the AChE and BChE inhibition assays. These findings provide the first insights into the phytochemical composition, as well as the antioxidant, antimicrobial, and anticholinesterase activities of H. repens extract, suggesting that the endemic Cyprus H. repens is a valuable natural rich source of bioactive compounds with a potentially broad range of bioactivities. Full article

In this study, we combined automated annotation tools with targeted dereplication based on MS/MS fragmentation pathway studies to identify polycyclic polyprenylated acylphloroglucinols (PPAPs) in Hypericum species, using H. patulum and H. hookeranium as a case study. These species, extensively used in traditional medicine, exhibit morphological similarities that often result in misidentification. Following UHPLC-HRMS/MS analysis of plant extracts, a molecular network approach facilitated a comprehensive comparison of their chemical composition, assigning specific clusters to O-glycosylated flavonoids and PPAPs. Eight peaks, including quercitrin, isoquercitrin, procyanidins, chlorogenic acid, quercetin, and glycosylated derivatives, were annotated from the GNPS database. For PPAPs, despite the structural complexity posing challenges for automated annotation using public databases, our targeted-dereplication strategy, relying on in-house spectral data, led to the putative identification of 22 peaks for H. patulum and H. hookeranium. Key compounds such as hyperforin, hyperscabrone K, and garcinialliptone M were detected in both species, underscoring their chemical similarity. MS/MS fragmentation pathways, particularly the successive losses of isobutene and isoprenyl units, emerged as a consistent signature for PPAP detection and may be useful for selecting PPAP-enriched extracts or fractions for further phytochemical investigations. Full article

Hypericum perforatum L. (H.P.), a plant renowned for its wound-healing properties, was investigated for antioxidant/antimicrobial efficacy, toxicological safety, and in vivo wound-healing effects in this research to develop and characterize novel nanoemulsion hydrogel (NG) formulations. NG were prepared via emulsion diffusion–solvent evaporation and polymer hydration using Cremophor RH40 and Ultrez 21/30. A D-optimal design optimized oil/surfactant ratios, considering particle size, PDI, and drug loading. Antioxidant activity was tested via DPPH, ABTS⁺, and FRAP. Toxicological assessment followed HET-CAM (ICH-endorsed) and ICCVAM guidelines. The optimized NG-2 (NE-HPM-10 + U30 0.5%) demonstrated stable and pseudoplastic flow, with a particle size of 174.8 nm, PDI of 0.274, zeta potential of −23.3 mV, and 99.83% drug loading. Release followed the Korsmeyer–Peppas model. H.P. macerates/NEs showed potent antioxidant activity (DPPH IC₅₀: 28.4 µg/mL; FRAP: 1.8 mmol, Fe²⁺/g: 0.3703 ± 0.041 mM TE/g). Antimicrobial effects against methicillin-resistant S. aureus (MIC: 12.5 µg/mL) and E. coli (MIC: 25 µg/mL) were significant. Stability studies showed no degradation. HET-CAM tests confirmed biocompatibility. Histopathology revealed accelerated re-epithelialization/collagen synthesis, with upregulated TGF-β1. The NG-2 formulation demonstrated robust antioxidant, antimicrobial, and wound-healing efficacy. Enhanced antibacterial activity and biocompatibility highlight its therapeutic potential. Clinical/pathological evaluations validated tissue regeneration without adverse effects, positioning H.P.-based nanoemulsions as promising for advanced wound care. Full article

Food components and herbal substances can inhibit or enhance the therapeutic effects of drugs, thus influencing their efficacy and safety. As relatively little in known of these interactions, the aim of this review is to shed further light on the potentially dangerous influences that food and herbs may have on cytochrome P450 enzyme (CYP) and monoamine oxidase (MAO) activity in the first stage of drug biotransformation. The review includes documented cases in which such interactions have led to health complications in patients. For example, fruit juices, such as grapefruit juice, cranberry juice, and pomegranate juice, have been found to interact with drugs, and to particularly inhibit CYP450 activity, and commonly used herbs are known to inhibit (e.g., Astragalus membranous) or induce (e.g., Hypericum perforatum) CYP enzymes involved in drug metabolism. CYP is also induced by polycyclic aromatic hydrocarbons (PAHs), found in grilled meat and tobacco smoke. The paper also discusses the toxic effects of tyramine, present in inter alia blue cheese, resulting from interactions with MAO-metabolised drugs. Most importantly, while the quantity of food and herbs consumed plays a significant role in the described drug interactions, it is possible for toxic effects to be observed even after the consumption of relatively small amounts. Patients are encouraged to consult a healthcare provider about any potential drug interactions that may occur when starting a new medication. Full article

Hypericum hircinum L., commonly known as goat St. John’s wort or stinking tutsan, is a medicinal plant native to the Mediterranean basin and widespread across Europe and parts of the Middle East. It has a long history of traditional uses in folk medicine to treat respiratory diseases, wounds, and burns and to relieve migraine, rheumatism, and muscular pains. Despite numerous scientific studies shading light on the phytochemical profile and on the beneficial properties of the plant extracts, a comprehensive overview of the current knowledge is missing. In this paper, we summarized the available information on botany, traditional uses, phytochemistry, and pharmacological properties of Hypericum hircinum from peer-reviewed articles published till March 2025 in PubMed, ScienceDirect, Wiley, Springer, ACS, Scielo, and Web of Science databases. The presence of numerous valuable compounds, including terpenes, phenolic acids, flavonoids, and phloroglucinols, is reported as well as the wide range of pharmacological properties, such as antimicrobial, antifungal, antiviral, antidepressant, anti-collagenase, anti-α-glucosidase, and antioxidant activities, together with non-pharmacological properties. The data reported in this review contribute to a deeper understanding of the biological properties of the species and pave the way for further investigation of its potential applications. Full article

This study aimed to examine wild-growing Hypericum perforatum L. tea (Hyperici herba) collected from Rtanj Mountain (Serbia). This research includes the following approaches: phytochemical and antioxidant characterization of H. perforatum infusion tea to determine its realistic composition (What do we consume when drinking the tea?), as well as a detailed examination of methanol(ic) extracts as the optimal extraction system. Due to the broad spectrum of both polar and nonpolar metabolites, 80% methanolic and pure methanol extracts were prepared for ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC Q-ToF) characterization through untargeted metabolomics analysis. Given the high diversity of compounds identified, the 80% methanolic extract was selected for further antioxidant examination and bioautographic characterization, including an antimicrobial activity assessment. UHPLC Q-ToF analysis identified 35 phenolics in the methanolic extract, compared to 25 metabolites in the infusion tea. The main differences were observed in flavonol/flavan-3-ol aglycones, xantones, and coumestans, which are more nonpolar compounds found only in the methanol(ic) system. Notably, specific H. perforatum metabolites were entirely absent in the infusion tea. Specifically, pseudohypericin, pseudoprotohypricin, and adhyperfirin were detected in the pure methanol extract, whereas hyperfirin was present in both methanol(ic) extracts. Additionally, eight furano-polycyclic polyprenylated acilphloroglucinols (FPPAPs) were identified in the methanol(ic) extracts as possible products of the thermal degradation and/or oxidation of hypericin/hyperforin. Both the infusion tea and methanolic extracts exhibited excellent antioxidant properties, with variations depending on the applied assay. High-performance thin-layer chromatography (HPTLC) analysis also confirmed the presence of a wide spectrum of phytochemical classes. Bioautography confirmed a promising activity of methanolic extracts against both Staphylococcus aureus and Klebsiella pneumoniae. Full article

The continuous emergence of SARS-CoV-2 variants underscores the need for novel antiviral candidates. Hypericin (HY), a compound derived from Hypericum perforatum, exhibited potent in vitro activity against SARS-CoV-2 in Vero E6 cells, with low cytotoxicity (CC₅₀ > 200 nM). HY showed no significant activity against Influenza A (H1N1) or dengue virus serotype 2, supporting its selective action. Antiviral effects were most evident when HY was administered post-infection, in a concentration-dependent manner, while cellular pretreatment or viral pre-incubation produced limited effects. Notably, HY also displayed virucidal activity, significantly reducing viral titers at 4 °C, 22 °C, and 37 °C. Combination treatments with remdesivir or nirmatrelvir enhanced antiviral efficacy by 50–70% relative to monotherapy, depending on compound concentration. Molecular simulations revealed stable interactions with conserved residues in RdRp and 3CLpro, suggesting a low risk of resistance. Together, these findings highlight the potential of HY as a selective antiviral and virucidal agent against SARS-CoV-2, particularly in combination regimens. Full article

α-Tocopherol (α-T) predominates in photosynthetic tissues, while tocotrienols (T3s) are reported very rarely. The genus Hypericum stands out as one of the few exceptions. Given the potential health benefits associated with tocotrienols, sourcing them from natural origins is of interest. The proper selection of plant material and the drying conditions are crucial steps in this process. Therefore, in the present study, we investigated the effects of four different drying techniques (freeze-drying, microwave–vacuum-, infrared oven and air-drying) on the tocochromanol content in leaves of three Hypericum species: H. androsaemum, H. pseudohenryi, and H. hookerianum and one hybrid H. × inodorum. The total tocochromanol content in the freeze-dried leaves harvested in September was 68.1–150.6 mg/100 g dry weight. α-T constituted 66.7–85.9% (w/w), while tocotrienols constituted 13–32% (w/w). H. pseudohenryi was characterized by the lowest tocotrienol content, while H. androsaemum and H. hookerianum had the highest, with δ-T3 and γ-T3, respectively, being predominant. Tocotrienols were more stable during drying than α-T. The greatest decrease in α-T content was observed during air-drying in the presence of sunlight, with a 27% difference compared to the absence of sunlight. The species and harvest time are factors that more strongly affect the tocotrienol content in the Hypericum leaves than the selected drying method. Full article

Hypericum perforatum L. (St John’s wort) has been widely studied and used for antidepressant treatment, as well as, rarely, featuring in studies on its chemical composition for Parkinson’s disease (PD) treatment. Five new nor-prenylated acylphloroglucinols with a cyclohexanone core, norperforatums A–E (1–5), together with four known analogs [(2R,3R,4S,6R)-3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)cyclohexanone (6), hyperscabrin B (7), (2R,3R,4S,6R)-6-methoxycarbonyl-3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)cyclohexanone (8), and hyperscabin K (9)], were isolated from the aerial parts of H. perforatum. The structures and absolute configurations of the new compounds were characterized by multiple spectroscopic means, including nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), ultraviolet visible absorption spectroscopy (UV), infrared spectroscopy (IR), calculated electronic circular dichroism (ECD) data, and X-ray signal crystal diffraction. In addition, the efficacy of these isolations was evaluated against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced PD in zebrafish larvae. Compound 9 had the best therapeutic effect, by significantly increasing the total distance traveled and the mean speed of movement in PD dyskinesia zebrafish larvae. Moreover, it enhanced superoxide dismutase (SOD) activity and inhibited reactive oxygen species (ROS) production in a dose-dependent manner. These results suggest that compound 9 may have ameliorative effects on PD symptoms by inhibiting oxidative stress. This study provides new insights into the treatment of H. perforatum for PD. Full article