Search Results (57)

Flavonoids from Pinus koraiensis needle (PN) litterfall were efficiently recovered using an enzyme-assisted ultrasonic extraction (EAU) method optimized via response surface methodology (RSM). The optimal conditions (enzyme dosage 1.7%, ethanol concentration 70%, ultrasonic time 21 min, cellulase–pectinase ratio 1:3, liquid–solid ratio 40:1, enzymatic hydrolysis at 42.5 °C for 1 h, ultrasonic extraction at 50 °C and 150 W) yielded a total flavonoid content (TFC) of 17.08 mg rutin/g, which was significantly higher than that obtained via conventional extraction (CE). Scanning electron microscopy (SEM) confirmed that the treatment disrupted the cell wall, promoting flavonoid release. Ultra-performance liquid chromatography coupled with triple-quadrupole time-of-flight mass spectrometry (UPLC-Triple-TOF/MS) identified 60 flavonoids in the purified extract obtained under the optimal EAU conditions (OT group), including quercitrin, tiliroside, taxifolin, and procyanidin B2. Fourier-transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC) showed higher crystallinity but slightly reduced thermal stability for OT flavonoids. Notably, compared with the purified flavonoids obtained by CE (CK1 group), the OT group achieved a higher TFC and exhibited significantly better in vitro antioxidant activity (DPPH IC₅₀ = 71.82 μg/mL; ABTS IC₅₀ = 28.93 μg/mL) and in vitro carbohydrate-digesting-enzyme-inhibitory activity (α-glucosidase (α-GLU) IC₅₀ = 79.52 μg/mL; α-amylase (α-AMY) IC₅₀ = 793.9 μg/mL), with α-AMY inhibition being approximately 8.2-fold higher. These findings suggest that enzyme-assisted ultrasonic extraction is an efficient and reliable method for recovering flavonoids from PN and may provide a theoretical reference for the development and utilization of these flavonoids. Full article

Background/Objectives: Atopic dermatitis (AD)-related skin inflammation involves the release of cytokines and chemokines from keratinocytes; therefore, keratinocyte-based models are widely used to evaluate the anti-inflammatory potential of botanical extracts. This study examined the relationship between phytochemical profiles and anti-inflammatory potential of baobab fruit 30% and 70% ethanol extracts (BE-30 and BE-70, respectively) in a TNF-α/IFN-γ (TI)-stimulated HaCaT keratinocyte model. Methods: The anti-inflammatory effects of both extracts were evaluated by measuring cytokine and chemokine secretion in TI-stimulated HaCaT cells. Phytochemical characterization was performed using liquid chromatography–tandem mass spectrometry (LC–MS/MS) and targeted high-performance liquid chromatography (HPLC). Results: Both extracts were non-cytotoxic. TI-stimulation markedly increased interleukin (IL)-6, IL-8 and monocyte chemotactic protein (MCP)-1 secretion, while BE-30 and BE-70 significantly reduced all three mediators in a dose-dependent manner. At comparable doses, BE-70 exhibited greater inhibition than BE-30. BE-30 showed a non-monotonic IL-8 response at low concentrations, whereas BE-70 consistently reduced IL-8 in a dose-dependent manner. LC–MS/MS profiling revealed a polyphenol-rich composition, including flavonol glycosides and related phenolic compounds. HPLC confirmed the presence of four marker analytes (procyanidin B2, epicatechin, rutin and tiliroside), which were enriched in BE-70. The content of these four polyphenols was 1.94-fold higher in BE-70. Conclusions: Baobab fruit extracts exhibit anti-inflammatory activity associated with polyphenols. These findings suggest that they could be used as analytical standards and in dermatological applications. Full article

Tiliroside (kaempferol-3-O-(6′′-p-coumaroyl)-glucoside), a flavonoid glycoside found in rose hips and berries, has been reported to possess various bioactivities. This study aimed to evaluate its antihyperuricemic potential by assessing direct xanthine oxidase (XO) inhibitory activity, suppression of uric acid (UA) production in AML12 hepatocytes, and efficacy in male ICR mice with purine nucleotide-induced hyperuricemia. XO inhibition was evaluated using a UV absorbance-based assay, and UA production was measured in hepatocytes stimulated with UA precursors. Mice were orally administered tiliroside for three days prior to purine nucleotide injection. Although tiliroside exhibited weak XO inhibition (IC₅₀ > 100 µM), it significantly suppressed UA production in hepatocytes in a concentration-dependent manner. In hyperuricemic mice, tiliroside (300 mg/kg) lowered plasma and hepatic UA levels by approximately 30% and 55%, respectively (p < 0.05). Hepatic XO activity was significantly decreased, while XO protein expression remained unchanged. Furthermore, mRNA levels of urate transporter 1 (URAT1) were significantly decreased in the kidney of tiliroside-treated hyperuricemic mice. These findings suggest that tiliroside exerts antihyperuricemic effects by suppressing UA production in the liver and modulating renal UA reabsorption. Tiliroside may serve as a beneficial dietary compound with bioactivity for the prevention and management of hyperuricemia and gout. Full article

This study investigated the anti-inflammatory effects of Rubus parvifolius leaf (RPL) extract, and its phytochemical composition was characterized using LC-MS/MS and HPLC analyses. In an inflammation model using HaCaT keratinocytes, treatment with RPL extract led to a significant reduction in inflammatory markers, indicating strong anti-inflammatory activity. Phytochemical analysis revealed that the extract is rich in flavonoids, with quercetin 3,7-diglucoside (12.73 mg/g DW) as the most abundant compound, followed by hirsutrin (4.74 mg/g DW) and ellagic acid (1.58 mg/g DW). Kaempferol 3-O-glucuronide was detected in lower amounts (0.31 mg/g DW), and tiliroside was present only in trace levels. These compounds are well known for their antioxidant and anti-inflammatory properties, suggesting that RPL extract may exert multiple beneficial effects on skin health. Collectively, these findings support the potential of RPL extract as a natural therapeutic agent for managing skin inflammation, particularly in conditions such as atopic dermatitis, with its efficacy likely attributed to the high levels of quercetin 3,7-diglucoside, hirsutrin, and ellagic acid. However, the present work was confined to in vitro experiments, and the mechanistic pathways were not experimentally validated. Future in vivo studies are needed to confirm these findings. Full article

Rose hips are rich in polyphenols, making them a promising ingredient for the development of functional fruit-based beverages. This study aimed to evaluate the effect of Pulsed Electric Field (PEF) extraction treatment on rose hip (RH) pulp to enhance the extraction of polyphenols, carotenoids, and volatile compounds. Additionally, this study examined the impact of adding rose hip berries during different stages of carbohydrate fermentation on the resulting phenolic and aroma profiles. A control wort and four experimental formulations were prepared. Rose hip pulp—treated or untreated with PEF—was added either during fermentation or beforehand, and the volatiles produced were analyzed using GC-MS (in triplicate). Fermentation was carried out over 10 days at 20 °C using Saccharomyces cerevisiae and Torulaspora delbrueckii. At a 10:1 ratio, all beverage samples were subjected to physicochemical testing and HPLC analysis for polyphenols, organic acids, and carotenoids, as well as GC-MS analysis for aroma compounds. The results demonstrated that the use of PEF-treated rose hips significantly improved phenolic compound extraction. Moreover, the PEF treatment enhanced the aroma profile of the beverage, contributing to a more complex and appealing sensory experience. This research highlights the rich polyphenol content of rose hips and the potential of PEF-treated fruit as a natural ingredient to improve both the functional and sensory qualities of fruit-based beverages. Their application opens new possibilities for the development of innovative, health-promoting drinks in the brewing industry. Full article

Lagopsis supina (Steph. ex. Willd.) Ikonn.-Gal., an ancient Chinese herbal medicine, is traditionally used to treat blood stasis diseases such as myocardial ischemia (MI). However, its pharmacodynamics substances of the anti-MI effect and their potential mechanisms remain unclear. This study aims to elucidate the pharmacodynamics effects of L. supina against MI and reveal their underlying mechanisms in zebrafish. LSD fraction was screened out for anti-MI active fraction from L. supina by isoprenaline hydrochloride (ISO)-induced zebrafish. It could increase the stroke volume, ejection fraction, and ventricular short-axis systolic rate in the zebrafish model. A total of 30 compounds (Nos. 1–30) were isolated and identified from LSD by various chromatographic techniques and nuclear magnetic resonance spectroscopy. Among them, six compounds, including three lignin compounds (Nos. 15, 16, and 18) and three flavonoid glycosides (Nos. 14, 25, and 26), showed noticeable anti-MI activities, and tiliroside (No. 25) was more active. Molecular docking indicated that tiliroside has a strong binding ability with the proteins KDR, PI3K, Akt, Erk, p38, Bcl-2, Bax, and Caspase3. In the end, the results of RT-qPCR manifested that tiliroside markedly upregulated expression levels of genes kdr, pik3cb, akt2, mapk1, mapk11, mapk14, and bcl-2b and prominently downregulated expression levels of genes bax and caspase3. According to the above results, tiliroside activated the kdr-mediated PI3K-Akt and MAPK signaling pathways to exert the anti-MI activity. These discoveries give a scientific basis for applying L. supina in MI treatment and suggest new avenues for developing tiliroside as a candidate for MI therapy. Full article

This study aimed to evaluate the feasibility of producing and characterizing Cistus creticus L. powders obtained through spray drying and freeze drying using maltodextrin and inulin as carriers. Quantitative and qualitative analysis of polyphenols by high-performance liquid chromatography with diode-array detection (HPLC-DAD) and high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) identified key bioactive compounds, including punicalagin isomers and their galloyl esters, as well as flavonoids (myricetin-3-galactoside, myricetin-3-rhamnoside, quercetin-3-galactoside, and tiliroside). Phenolics in powders produced by both drying techniques ranged from 73.2 mg to 78.5 mg per g of dry matter. Inulin proved to be as effective as maltodextrin in spray drying, offering a promising alternative for plant-based powder formulation. Antioxidant capacity measured by Trolox equivalent antioxidant capacity assay with 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (TEAC ABTS) and ferric reducing antioxidant power (FRAP) assay indicated that spray-dried powders with inulin exhibited antioxidant properties comparable to those with maltodextrin. The results demonstrated that Cistus creticus L. powders obtained with inulin can serve as valuable sources of bioactive compounds with potential health benefits similar to those obtained with maltodextrin. Moreover, from a technological perspective, inulin proved to be an equally efficient carrier in terms of production-process parameters such as moisture content and water activity, making it a viable alternative to maltodextrin in plant-based powder formulations. Full article

Twelve compounds (1–12), kaempferol (1), luteolin (2), luteolin 4′-O-β-xyloside (3), luteolin 4′-O-β-glucoside (4), quercetin 4′-O-β-xyloside (5), kaempferol-3-O-[6″-O-(E)-p-coumaroyl]-β-D-glucoside (trans-tiliroside) (6), protocatechuic acid (7), gallic acid (8), methyl gallate (9), ethyl gallate (10), shikimic acid-3-O-gallate (11), and 3,3′,4′-tri-O-methyl-ellagic acid 4-sulfate (12), were isolated and identified from the aerial parts of Helianthemum cinereum (Cav.) Pers (synonym: Helianthemum rubellum C. Presl. All compounds were isolated by applying different chromatographic procedures, such as silica gel, RP-18 and Sephadex LH-20 columns. The structures were elucidated by extensive spectroscopic methods, mainly nuclear magnetic resonance NMR 1D and 2D, and mass spectrometry, as well as by comparison with the reported spectroscopic data. The two organic extracts, ethyl acetate (EtOAc) and butanol (BuOH), were evaluated for their potent phenolic and flavonoid contents using the Folin–Ciocalteu and aluminum chloride colorimetric methods. Furthermore, the antioxidant activity of the two extracts was determined using the DPPH, FRAP, and ABTS methods. Pure trans-tiliroside (6), the main isolated compound, and luteolin 4′-O-β-xyloside (3) were evaluated for their antitumor activity against the lung cancer (A549), melanoma (A375) and pancreatic cancer (Mia PaCa-2 and Panc-1) cell lines by MTT assay. Full article

The cloud forest (CF), a hugely biodiverse ecosystem, is a hotspot of unexplored plants with potential for discovering pharmacologically active compounds. Without sufficient ethnopharmacological information, developing strategies for rationally selecting plants for experimental studies is crucial. With this goal, a CF metabolites library was created, and a ligand-based virtual screening was conducted to identify molecules with potential hypoglycemic activity. From the most promising botanical families, plants were collected, methanolic extracts were prepared, and hypoglycemic activity was evaluated through in vitro enzyme inhibition assays on α-amylase, α-glucosidase, and dipeptidyl peptidase IV (DPP-IV). Metabolomic analyses were performed to identify the dominant metabolites in the species with the best inhibitory activity profile, and their affinity for the molecular targets was evaluated using ensemble molecular docking. This strategy led to the identification of twelve plants (in four botanical families) with hypoglycemic activity. Sida rhombifolia (Malvaceae) stood out for its DPP-IV selective inhibition versus S. glabra. A comparison of chemical profiles led to the annotation of twenty-seven metabolites over-accumulated in S. rhombifolia compared to S. glabra, among which acanthoside D and cis-tiliroside were noteworthy for their potential selective inhibition due to their specific intermolecular interactions with relevant amino acids of DPP-IV. The workflow used in this study presents a novel targeting strategy for identifying novel bioactive natural sources, which can complement the conventional selection criteria used in Natural Product Chemistry. Full article

Citrus species are widely cultivated across the globe and frequently encounter drought stress during their growth and development phases. Previous research has indicated that citrus species synthesize flavonoids as a response mechanism to drought stress. This study aimed to comprehensively quantify and analyze the presence of 85 distinct flavonoids in the leaf and root tissues of lemon (drought susceptible) and sour orange (drought tolerant). In drought-stressed sour orange roots, flavonoids, such as isosakuranin, mangiferin, trilobatin, liquiritigenin, avicularin, silibinin, and glabridin, were more elevated than control sour orange roots and drought-stressed lemon roots. Additionally, hydroxysafflor yellow A, cynaroside, tiliroside, and apigenin 7-glucoside were increased in drought-stressed sour orange leaves compared to drought-stressed lemon leaves. Under drought stress, flavonoids such as (-)-epigallocatechin, silibinin, benzylideneacetophenone, trilobatin, isorhamnetin, 3,7,4′-trihydroxyflavone, and liquiritigenin were significantly increased, by 3.01-, 3.01-, 2.59-, 2.43-, 2.07-, 2.05-, and 2.01-fold, in sour orange roots compared to control sour orange roots. Moreover, the total flavonoid content and antioxidant capacity were significantly increased in drought-stressed sour orange leaves and root tissues compared to drought-stressed lemon leaves and root tissues. The expression levels of genes involved in flavonoid biosynthesis were highly expressed in sour orange leaves and roots, compared to lemon leaves and root tissues, post-drought stress. These findings indicate that lemons fail to synthesize protective flavonoids under drought conditions, whereas sour orange leaves and root tissues enhance flavonoid synthesis, with higher antioxidant activities to mitigate the adverse effects of reactive oxygen species generated during drought stress. Full article

Helianthemum nummularium (HN) and Helianthemum oelanticum subsp. incanum (HO) are plant species, among Cistaceae, that are highly distributed in the Mediterranean region. In the current study, extracts of the aerial parts from both species have been analyzed phytochemically. The non-polar extract analysis resulted in the identification of 15 compounds in each species, mainly terpene and fatty acid derivatives, through GC–MS. The methanolic extract analysis, conducted through UHPLC–MS/MS, led to the identification of 39 metabolites in HN and 29 in HO, respectively, the majority of which were phenolics. Among the identified compounds, several have also been isolated and structurally determined (from HN: rutin, linoleic acid, gallic acid, and isoquercetin, and from HO: quercetin-3-O-(2″-O-galloyl)-galactopyranoside, methyl gallate, catechin-3-O-glucopyranoside, and astragalin, while hyperoside, and cis- and trans-tiliroside have been determined in both species). Furthermore, the methanolic extracts of HN and HO displayed a high total phenolic content (177.2 mg GA/g extract and 150.6 mg GA/g extract, respectively) and considerable free-radical scavenging activity against the DPPH radical (94.6% and 94.0% DPPH inhibition, respectively). Antimicrobial testing showed stronger inhibition of HN against Gram (+) bacterial strains (MIC values 0.07–0.15 mg/mL), while both extracts exhibited low tyrosinase-inhibitory activity. Considering the lack of studies conducted on the chemistry and biological activities of the genus Helianthemum, the chemical characterization of extracts could contribute to new sources of bioactive metabolites to be explored and exploited for further potential applications such as food and/ or the cosmetic industry. Full article

Tiliroside is a natural polyphenolic compound with a wide range of biological activity, and defatted strawberry seeds are its rich source. The goal of this study was to optimize accelerated solvent extraction (ASE) conditions, including temperature, solvent composition, and the number of extraction cycles, using Box–Behnken design to maximize the yield of tiliroside. UPLC-DAD-MS was applied to investigate the polyphenolic composition of the extracts, and preparative liquid chromatography (pLC) was used for isolation. All obtained mathematical models generally showed an increase in the efficiency of isolating polyphenolic compounds with an increase in temperature, ethanol content, and the number of extraction cycles. The optimal established ASE conditions for tiliroside were as follows: a temperature of 65 °C, 63% ethanol in water, and four extraction cycles. This allowed for the obtainment of a tiliroside-rich fraction, and the recovery of isolated tiliroside from plant material reached 243.2 mg from 100 g. Our study showed that ASE ensures the isolation of a tiliroside-rich fraction with high effectiveness. Furthermore, defatted strawberry seeds proved to be a convenient source of tiliroside because the matrix of accompanying components is relatively poor, which facilitates separation. Full article

Medicinal plant tissue cultures are potential sources of bioactive compounds. In this study, we report the chemical characterization of the callus cultures of three medicinal Tilia spp. (Tilia cordata, Tilia vulgaris and Tilia tomentosa), along with the comparison to bracts and flowers of the same species. Our aim was to show that calli of Tilia spp. are good alternatives to the calli of T. americana for the production of polyphenols and are better sources of a subset of polyphenolic metabolites, compared to the original organs. Calli were initiated from young bracts and grown on woody plant medium containing 1 mg L⁻¹ 2,4-D and 0.1 mg L⁻¹ BAP. For chemical characterization, a quality-controlled untargeted metabolomics approach and the quantification of several bioactive compounds was performed with the use of LC-ESI-MS/MS. While bracts and flowers contained flavonoid glycosides (astragalin, isoquercitrin) as major polyphenols, calli of all species contained catechins, coumarins (fraxin, esculin and scopoletin) and flavane aglyca. T. tomentosa calli contained 5397 µg g DW⁻¹ catechin, 201 µg g DW⁻¹ esculin, 218 µg g DW⁻¹ taxifolin and 273 µg g DW⁻¹ eriodictyol, while calli from other species contained lower amounts. T. cordata and T. tomentosa flowers were rich in isoquercitrin, containing 8134 and 6385 µg g DW⁻¹, respectively. The currently tested species contained many of the bioactive metabolites described from T. americana. The production of catechin was shown to be comparable to the most efficient tissue cultures reported. Flowers and bracts contained flavonoid glycosides, including tiliroside, resembling bioactive fractions of T. americana. In addition, untargeted metabolomics has shown fingerprint-like differences among species, highlighting possible chemotaxonomic and quality control applications, especially for bracts. Full article

Chenopodium quinoa Willd. is rich in phenolic compounds and exhibits diverse biological activities. Few studies have focused on the effect of colored quinoa’s phenolic profile on potential biological activity. This study used a UPLC–MS/MS-based metabolomic approach to examine the quinoa phenolics and their association with in vitro antioxidant and hypoglycemic properties. In total, 430 polyphenols, mainly phenolic acids, flavonoids, and flavonols, were identified. Additionally, 121, 116, and 148 differential polyphenols were found between the white and black, white and red, and black and red comparison groups, respectively; 67 polyphenols were screened as shared key differential metabolites. Phenylalanine, tyrosine, and the biosynthesis of plant secondary metabolites were the main differently regulated pathways. Black quinoa had better total phenolic contents (643.68 mg/100 g DW) and antioxidant capacity, while white quinoa had better total flavonoid contents (90.95 mg/100 g DW) and in vitro α-amylase (IC50 value of 3.97 mg/mL) and α-glucosidase (IC50 value of 1.08 mg/mL) inhibition activities. Thirty-six polyphenols, including epicatechin and linarin, etc., were highly correlated with in vitro antioxidant activity, while six polyphenols, including tiliroside and chrysoeriol, etc., were highly correlated with in vitro hypoglycemic activity. This study may provide important information for colored quinoa resources to develop their healthy food applications. Full article

There has been growing interest in examining the potential of non-bagging patterns due to the decline of fruit inner quality and the increase in labor force cost and ecological pollution. Spraying a non-bagging film agent is an important method for non-bagging cultivation. This paper aims to study the effects of non-bagging film agents on the contents of mineral elements and flavonoid metabolites in apple fruits and determine the feasibility of this method. Fuji apples were used as the sample material and treated individually with two non-bagging film agents, namely, humic acid film (ABM) and Pirrio calcium film (CAM). Also, two control groups, namely, the clear water spraying without bagging group (CK) and the bagging group (TCK), were set in this study to measure the contents of mineral elements and flavonoid metabolites in these apples. Compared with those two control groups, the spraying treatment groups with two kinds of non-bagging film agents present a significant difference between their total contents of mineral elements, with the total content of mineral elements of apples in the ABM treatment group being 1.36 times the content of apples in the CK group. In terms of the flavonoid metabolites, only Astragalin, Tiliroside, Homoplantaginin, Phlorizin, Apigenin, Hesperidin, Oroxin A, and Kaempferol present significant differences in their proportions in apples, and there are no significant differences among the proportions of other compounds. Individual spraying of two kinds of non-bagging film agents can significantly increase the total contents of mineral elements in apples, with slight effects on the contents of flavonoid metabolites in these fruits. Therefore, both film agents can be used for cultivating Fuji apples. Full article