Search Results (912)

Gnetol (trans-2,3′,5′,6-tetrahydroxystilbene), a naturally occurring stilbene structurally related to resveratrol (trans-3,5,4′-trihydroxystilbene; RES), has been reported to possess multiple health-promoting activities. In order to support its potential nutraceutical application, a reliable chromatography–tandem mass spectrometry (LC–MS/MS) assay was developed and validated for the quantitative determination of gnetol in mouse plasma and tissue samples, using isotopically labeled RES-¹³C₆ serving as the internal standard (IS). Electrospray ionization (ESI) was performed in negative mode, with multiple reaction monitoring (MRM) transitions m/z 243.2 → 175.0 for gnetol and m/z 233.1 → 191.0 for the IS. Chromatographic separation was achieved on a reversed-phase HPLC column using a 5-min gradient delivery of acetonitrile and 2 mM ammonium acetate at 0.5 mL/min and 40 °C. The linear calibration curve covered the concentration range of 5.0–1500 ng/mL, and the method validation confirmed its selectivity, accuracy, precision, stability, and dilution integrity. The developed method was subsequently applied to a biodistribution study in mice after oral administration of gnetol at 400 µmol/kg (equivalent to 97.7 mg/kg). Gnetol was rapidly absorbed and extensively distributed in key pharmacologically relevant organs. Despite its poor aqueous solubility, oral uptake was not significantly hindered. Collectively, these findings demonstrate that gnetol exhibits favorable absorption and tissue distribution profiles, supporting its promise as a candidate for nutraceutical development. Full article

The Jurubatiba Sandbank National Park (PARNA Jurubatiba) is an ecological reserve characterized by harsh environmental conditions, including low rainfall, high sun exposure, and sandy soil. Among its native vegetation, Eremanthus crotonoides stands out for its richness in flavonoids, phenolic compounds, and sesquiterpene lactones. The objective of this study was to isolate and quantify sesquiterpene lactones from this species using ¹H NMR and to investigate their anti-SARS-CoV-2 potential and cytotoxicity against cancer cells. UPLC-(ESI)-MS/MS analyses enabled metabolite annotation, and semi-preparative HPLC-DAD allowed the isolation of centratherin and goyazensolide, which were identified by 1D and 2D NMR. In vitro assays showed that centratherin at 10 µM concentration reduced the viability of PC-3 and HCT-116 cancer cells by 100%, while goyazensolide had no noteworthy effects. Furthermore, enzymatic inhibition assays on SARS-CoV2 targets revealed that centratherin exhibited a lower apparent IC₅₀ of 12 µM against PL^pro, while goyazensolide was more active against 3CL^pro, with an IC₅₀ of 71 µM. Notably, the dichloromethane fraction demonstrated promising activity against both enzymes, with IC₅₀ values of 30 µM for PL^pro and 11 µM for 3CL^pro. This study reports, for the first time, the isolation of goyazensolide from E. crotonoides and highlights the potential of both sesquiterpene lactones as SARS-CoV-2 enzyme inhibitors. In contrast to centratherin, goyazensolide fortunately had almost no cytotoxic effects at inhibition concentration on the cells tested. This shows that anticancer and anti-SARS effects can be separated and should have different SARs, an important prerequisite for further development. Full article

Background: Pomegranate peel (Punica granatum L.) is a rich source of phenols, particularly ellagitannins, highlighting punicalagin, a bioactive compound with recognized antioxidant potential. However, efficient recovery and purification methods are required to enable its application in food and health-related products. This study aimed to obtain a partially purified fraction of punicalagin from pomegranate peel using optimized extraction and purification strategies. Methods: A Taguchi L9 (3)³ experimental design was employed to optimize ultrasound-assisted extraction, evaluating extraction time (10, 20, 30 min), ethanol concentration (20, 40, 80%), and solid-to-solvent ratio (1:12, 1:14, 1:16). Total polyphenol content was quantified using the Folin–Ciocalteu method. Extracts obtained under optimized conditions were concentrated by rotary evaporation and subjected to semipurification using flash chromatography with Amberlite XAD-16 resin. Subsequently, the fractions were lyophilized and analyzed by HPLC/ESI/MS. Results: The Statistica software determined the optimal conditions for polyphenol extraction (20 min, 40% ethanol, 1:12), with the signal-to-noise (S/N) ratio reaching 88.43 ± 0.66, surpassing the predicted value of 77.42. Flash chromatography yielded four fractions, and HPLC/ESI/MS analysis revealed the presence of ellagitannins in all of them, with fraction number 2 showing the highest relative abundance of punicalagin (89.25%). Conclusions: The combination of ultrasound-assisted extraction and flash chromatography proved effective for obtaining punicalagin-rich fractions from pomegranate peel, supporting its potential for nutraceutical applications. Full article

Australian plants of the family Haemodoraceae have been a reliable source of new secondary metabolites, particularly those of the ‘phenylphenalenone’ class, and related chromenes and xanthones. Some of these compounds demonstrate anti-microbial properties against both Gram-negative and Gram-positive bacteria. Chemical profiling of thirty individual ethanolic extracts from six separate species of Australian plants belonging to the family Haemodoraceae was conducted using an HPLC-MS approach reinforced by HRLC(ESI)-MS. Six of the extracts were further explored by employing HRLC(ESI)-MS and the compounds present were characterised and confirmed based on a comparison to the original data. All thirty extracts were assessed for biological activity against the parasitic nematode Haemonchus contortus in vitro. The chemical profiling methodology adopted resulted in the identification of thirty-four previously reported compounds, identifying on average 64% of the previously reported secondary metabolites across the species Haemodorum simulans, Haemodorum spicatum, Haemodorum brevisepalum and Macropidia fuliginosa. Furthermore, compounds from the phenylbenzoisoquinolindone class were detected in the bulbs of Haemodorum simulans and Haemodorum coccineum, representing the first report of the structure class in extracts of the genus Haemodorum. Extracts of the H. simulans stems, M. fuliginosa bulbs and H. distichophyllum roots and bulbs exhibited anthelmintic activity in vitro. The chemical profiling HPLC-MS methodology adopted was successful in the rapid identification of most of the previously reported secondary metabolites across the Haemodoracae species, indicating that the analytical approach was robust. This study demonstrates the effectiveness of dereplication via HPLC-MS-based chemical profiling across six Australian Haemodoraceae species, identifying numerous known and putatively novel secondary metabolites. It also reports, for the first time, anthelmintic activity in selected species and marks the first detailed phytochemical investigation of H. distichophyllum since its initial pigment analysis over 50 years ago. Full article

Geum aleppicum Jacq. (yellow avens), a species traditionally used in folk medicine, remains understudied in the ethnopharmacological aspects. In this study, we comprehensively evaluated the phytochemical composition and biological activity of a hydroethanolic (50:50, v/v) extract from the aerial parts of G. aleppicum collected in Kazakhstan. Using the high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (HPLC-ESI-QTOF-MS/MS), we identified 24 compounds, predominantly phenolic acids, flavonoids, tannins, and triterpenoids. The major compound was ellagic acid (2.28 mg/g dry extract) as revealed by the reverse phase high-performance liquid chromatography–diode array detector (RP-HPLC-DAD). The extract exhibited a high polyphenol content (131.45 mg GAE/g) and strong antioxidant activity in Ferric Reducing Antioxidant Power (FRAP) assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay (3.82 ± 0.07 mmol Fe²⁺/g and 106.61 ± 0.89 mg GAE/g, respectively). Antimicrobial assay of the extract revealed notable antifungal activity against Candida spp., especially against C. glabrata and C. tropicalis with minimum inhibitory concentration (MIC) of as low as 0.125 mg/mL, showing fungistatic effect. Although the extract inhibited the cytopathic effect induced by Human Herpesvirus 1 (HHV-1) in VERO cells, it did not significantly reduce viral replication. Moreover, among human cancer cell lines studied, the extract exerted moderate and selective cytotoxicity against A549 lung cancer cells (CC₅₀ = 75.51 µg/mL, SI = 9). These findings highlight G. aleppicum as a rich source of bioactive compounds, especially phenolics, supporting its potential for development of pharmaceutical and cosmetic applications. Full article

This study investigated the extraction, enrichment, characterization, and antioxidant activities of Sargassum fusiforme polyphenols (SFPs). The optimal extraction process conditions of SFPs are as follows: an ethanol volume fraction of 28%, a liquid–solid ratio of 29 mL/g, an extraction temperature of 80 °C, and an extraction time of 3.2 h. After enrichment by D101 macroporous resin, the purity of SFPs increased from 1.20 ± 0.08% to 10.78 ± 0.25%, increasing by approximately 8 times. SFPs were mainly composed of polyphenols, flavonoids, and polysaccharides. Furthermore, after identification by HPLC-QQK-ESI-MS/MS, they were found to contain 11 phlorotannins (mainly of the fuhalol type), 2 flavonoids, etc. In three antioxidant evaluation systems (DPPH free radical scavenging ability, reducing power, and total antioxidant capacity), the enriched SFPs all exhibited superior activities compared to tea polyphenols. The research results provide a theoretical basis and experimental evidence for the development of a new type of food preservative based on SFPs. Full article

Grape pomace (GP), a significant by-product of winemaking, is gaining increasing recognition for its potential as a source of bioactive compounds with antioxidant and cardioprotective properties. This study aimed to characterize the polyphenolic profile, fatty acid composition, and antioxidant activity of 17 GP samples from Transylvanian cultivars. Polyphenolic content was determined using the Folin–Ciocalteu method and high-performance liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry (HPLC–DAD–ESI MS) analysis. Fatty acid composition was analyzed using gas chromatography with flame ionization detection (GC–FID). Antioxidant capacity was assessed using five methods, which included the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, 2,2′-azino-bis (3-ethylbenzothialzoline-6-sulfonic acid) (ABTS) radical scavenging, ferric-reducing antioxidant power (FRAP), cupric ion reducing antioxidant capacity (CUPRAC), and reducing power (RP) assays. Additionally, all extracts were analyzed by Fourier transform infrared (FTIR) spectroscopy to identify the presence of functional groups and chemical bonds associated with bioactive compounds. The results showed that Neuburger (NE), Radames (RA), and Regent (RE) cultivars had the highest phenolic concentrations, particularly of catechin, epicatechin, and procyanidin dimers. NE and Feteascǎ Regalǎ (FR) exhibited the greatest radical scavenging and electron transfer activities across multiple antioxidant assays. Rose Blaj (RB) and Astra (AS) displayed the most favorable fatty acid profiles, with high unsaturated-to-saturated fatty acid (UFA/SFA) and hypocholesterolemic-to-hypercholesterolemic fatty acid (H/H) ratios, as well as low atherogenicity (AI) and thrombogenicity (TI) indices, suggesting cardioprotective potential. Additionally, RB and NE cultivars also demonstrated a strong chelation of Cu²⁺ and Fe²⁺ ions, enhancing their antioxidant efficacy by mitigating metal-catalyzed oxidative stress. These findings underscore the potential of GP, particularly from NE, RB, RA, and AS cultivars, the last three of which were homologated in Transylvania at SCDVV Blaj, as valuable sources of health-promoting compounds for use in food, nutraceuticals, and other health-related applications. Full article

Blue honeysuckle (Lonicera caerulea) is widespread across the Eurasian continent, mainly in northern latitudes. Its berries are a rich source of biologically active compounds. In this study, plant samples collected in four regions of Russia separated by more than 10,000 km were examined in detail: St. Petersburg, Kamchatka, Magadan and the Far East (Vladivostok). The study was unique in that it covered almost the entire Eurasian continent in northern latitude, which had not been previously presented in other scientific studies. The study revealed the presence of 110 polyphenols and 34 compounds belonging to other chemical groups. In particular, honeysuckle berries were rich in polyphenols, including flavonoids, flavanones, flavanols, flavan-3-ols, anthocyanins, stilbenes, and lignans. The method of tandem mass spectrometry was used to identify biologically active substances from the extracts, which allows obtaining fairly accurate results. The metabolomic composition of L. caerulea berries originating from Kamchatka and Magadan showed the greatest diversity of polyphenols, which is associated with special northern climatic conditions and associated stress factors for plants. The results we obtained provide new data on the composition of the honeysuckle berry metabolome. The wealth of biologically active substances in blue honeysuckle berries can be very interestingly used in the development of both biologically active additives for pharmaceutical use and for the development of functional and specialized nutrition products for various population groups. Full article

Abeliophyllum distichum is rich in polyphenols and flavonoids with various bioactivities; however, studies on enzymatic modifications to enhance its functional properties remain limited. This study investigated the effect of Viscozyme^® L treatment on the secondary metabolite profile of A. distichum leaves. Phytochemical profiling using liquid chromatography–electrospray ionization tandem mass spectrometry revealed a decrease in the total number of detectable compounds, from 26 in the untreated extract to 16 in the enzyme-treated extract. Following Viscozyme^® L treatment, a notable shift in metabolite composition was observed, with significant enrichment of flavonoid glycosides, pyranone derivatives, and amino acid-related metabolites. Quantitative high-performance liquid chromatography analysis showed significant reductions in glycosylated compounds such as rutin (1), acteoside (2), and isoacteoside (3), while the aglycone quercetin (4) content increased more than four-fold compared to the control. These results indicate that Viscozyme^® L facilitates the deglycosylation of flavonoid glycosides into their aglycone forms. This enzymatic transformation suggests a potential strategy to enhance the bioavailability and functional value of A. distichum leaf extracts for nutraceutical and pharmaceutical applications. Full article

Macroalgae are often used to produce sodium alginate, but their by-products have not been fully utilized. This study aimed to optimize the extraction of bound polyphenols (BPs) from Macrocystis pyrifera (L.) residues, analyze the composition of free polyphenols (FPs) and BPs, and evaluate their antioxidant activities and ability to inhibit glycosidase activity. The optimal conditions for extracting BPs achieved by the response surface method were as follows: 50 °C, a solid–liquid ratio of 1:50, an alkaline hydrolysis time of 2.38 h, and a NaOH concentration of 8 mol/L. Polyphenol content determination results indicated that FPs had significantly higher total polyphenols (13.02 ± 0.05 μg GAE/mg) and phlorotannin (3.44 ± 0.04 μg PE/mg) than BPs (6.57 ± 0.07 μg GAE/mg and 1.32 ± 0.20 μg PE/mg). HPLC/ESI-QTOF-MS showed distinct profiles: FPs had one polyhydroxy phenol, nine flavonoids, and four additional compounds, whereas BPs had five flavonoids and four other compounds. Antioxidant activity was found to be higher in FPs than in BPs (DPPH: 3.03 vs. 1.79 μg TE/mg; FRAP: 19.40 vs. 7.43 μg TE/mg). Furthermore, FPs exhibited 4.59- and 11-fold higher inhibition capacity toward α-amylase and α-glucosidase, respectively, compared to BPs. The results provide valuable basic data for the application of macroalgae residues in the marine biological industry and reveal their potential hypoglycemic ability. Full article

Protaetia brevitarsis seulensis (Kolbe, 1886) larvae have traditionally been used in East Asian medicine and have recently attracted attention as functional food ingredients because of their pharmacological potential. However, chemical investigations remain limited, and no marker compounds have been established for quality control. This study aimed to isolate and identify a primary constituent from the 70% ethanol extract of P. brevitarsis (PBE) and to develop an analytical method for its quantification. Among the solvent-partitioned fractions, the n-butanol fraction (PBE-B) exhibited a major peak in HPLC analysis. The compound was purified through a combination of vacuum liquid chromatography (VLC), medium-pressure liquid chromatography (MPLC), and recycling preparative HPLC. Its structure was identified as L-tryptophan based on HR-ESI-MS and NMR spectroscopy. Quantitative analysis was conducted using HPLC-DAD under optimized analytical conditions, employing a Thermo Scientific™ Acclaim™ Polar Advantage II column and an acidified mobile phase (0.1% formic acid in water and methanol) to improve resolution. The method demonstrated excellent linearity (r² > 0.9999), and the L-tryptophan content in PBE was determined to be 1.93 ± 0.05 μg/mg. The analyte was well separated with minimal interference, supporting the reproducibility of the method. These results indicate that L-tryptophan is a promising candidate Q-marker for the quality control of P. brevitarsis extracts. Full article

Cocoa pod husk (CPH), the principal by-product of cocoa processing, represents an abundant and underutilized source of bioactive phenolics with potential applications in the food and nutraceutical sectors. This study optimized the extraction of catechin, epicatechin, procyanidin B2, and clovamide from CPH (CCN-51 variety) using microwave-assisted extraction (MAE) and evaluated the influence of drying temperature on their retention. A Box–Behnken design within a response surface methodology framework was employed to evaluate the effects of ethanol concentration (0–100%), extraction temperature (50–150 °C), and extraction time (15–60 min) on compound recovery. The phenolic profile was characterized by high-performance liquid chromatography with diode-array detection and electrospray ionization ion trap tandem mass spectrometry. Optimal MAE conditions of 51% ethanol, 104 °C, and 38 min yielded maximum concentrations of clovamide, procyanidin B2, and epicatechin of 3440, 908, and 445 mg/kg dry matter of cocoa pod husk, respectively. Drying studies demonstrated that moderate hot-air temperatures (40–50 °C) preserved the highest phenolic levels. These results underscore the importance of optimizing both extraction and drying conditions to enhance the recovery of phenolic compounds from cocoa processing residues, supporting their potential valorization as antioxidant-rich functional ingredients. Full article

Rhododendron tomentosum Harmaja is a marsh plant known for its high content of bioactive components, including essential oil, flavonoids, and phenolic acids. In the current work, the effects of cultivation mode (agar, liquid stationary, shake flask, and temporary immersion) and experiment duration (30, 60, and 90 days) on the growth and contents of non-volatile phenolics in Rhododendron tomentosum microshoots were investigated. Agar and liquid stationary cultures provided the highest dry biomass yield per liter, but their dry weight productivities per day were the lowest among the tested systems. Agitated and temporary immersion cultures, on the other hand, were the most productive in terms of fresh and dry biomass yield per day. LC-DAD-ESI-MS analysis of extracts from microshoots and wild-grown plants revealed similarities in phenolic composition: in both cases, the presence of catechin, chlorogenic acid, and flavonoids of flavonol type (mainly glycosides of quercetin and myricetin) was confirmed. The qualitative composition of the phenolic fraction was not affected by experiment duration and cultivation mode. As determined by HPLC analysis, shake flask and temporary immersion cultures were characterized by the highest phenolic contents: up to 37.5 and 26 mg/g dry weight, respectively. The maximum productivities of the above systems were equal to 18 and 13.5 mg/L/d, respectively. Full article

In recent years, numerous studies have emerged on the biological activities of endemic berries from the Valdivian Forest and their potential for therapeutic use. However, some species appear to have been relatively neglected. The objective of this study was to conduct, for the first time, a phytochemical composition analysis of a hydroalcoholic extract of Luzuriaga radicans Ruiz & Pav. and to evaluate its potential as an antioxidant and as an enzyme inhibitor in relation to chronic non-communicable diseases. The berries were collected in the Saval Park in Valdivia and were subsequently extracted via sonication in ethanol/water. UHPLC-DAD, HPLC-APCI (+)-MS, and UHPLC-ESI (+)-TOF-MS analysis allowed for the identification of several carotenoid ester species. According to UHPLC-DAD, the sum of carotenoids yielded was 983.4 ± 26.3 mg/kg DW, while the concentration of the phenolic compounds was 9.33 ± 0.01 mg GAE/g dry fruit. The extract exhibited antioxidant properties by scavenging DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2-azinobis-(3-ethylbenzothioazolin-6-sulfonic acid)) radicals, and ferric reducing antioxidant power (FRAP). It also demonstrated cholinesterase enzyme inhibitor capacities (AChE and BuChE—IC₅₀: 6.904 ± 0.42 and 18.38 ± 0.48 µg/mL, respectively). Docking calculations were additionally performed for a selection of compounds in the berries. The data obtained suggest that the hydroalcoholic extract of L. radicans possesses significant potential as a natural antioxidant and for the inhibition of enzymes, making it a promising candidate for the development of phytotherapeutic and nutraceutical products, especially as a supplement against chronic diseases. Full article

This study aimed to valorize underutilized local ingredients by developing nutritionally enhanced pasta products enriched with sorghum and cork oak flours. The resulting pasta samples were characterized by their chemical composition, color attributes, functional properties, texture, microstructure, and antioxidant capacity. Semolina-based pasta showed higher protein content, while cork oak flour contributed significantly to lipid content, and sorghum flour was notably rich in fiber and minerals. Colorimetric analysis quantified visible differences in appearance, depending on the type of flour used. Functional assessment showed comparable water absorption indices across all samples; however, sorghum-enriched pasta exhibited significantly higher water solubility. Textural analysis indicated that sorghum reduced pasta adhesiveness and cohesiveness, whereas cork oak flour increased hardness, gumminess, and adhesiveness—likely due to its high fiber content, contributing to a stickier mouthfeel. Microstructural observations confirmed a denser and more compact matrix in pasta formulated with cork oak flour. Antioxidant analysis revealed that cork oak flour imparted the highest antioxidant potential, followed by sorghum and semolina. HPLC/ESI-TOF-MS profiling demonstrated a rich and diverse polyphenolic composition in the enriched samples. These formulations not only enhance the functional and nutritional profile of traditional pasta but also align with the increasing consumer demand for low-carbohydrate, fiber-rich foods. Full article