Search Results (52)

Ionic liquid-assisted extraction can improve the recovery of monoterpene glycosides from Radix Paeoniae Alba, whereas post-extraction purification and ionic-liquid-associated marker-level quality control remain necessary before further bioactivity evaluation. In this study, a macroporous resin-based purification process was developed for monoterpene glycoside-enriched extracts obtained by conventional reflux extraction and ionic liquid-assisted microwave–ultrasound extraction. Among the five tested resins, AB-8 resin showed the best adsorption performance and was selected for further process optimization. The optimized purification conditions were a loading concentration of 13 mg/mL, loading pH of 7, elution with 70% ethanol, loading volume of 6 BV and elution volume of 9 BV. After purification, the total quantified monoterpene glycoside content increased from 6.59% to 51.68% in the conventional extract and from 15.30% to 75.30% in the ionic liquid-assisted extract. The ionic-liquid-associated elemental marker content in the ionic liquid-assisted extract decreased from 5.593% to 0.072% after purification, corresponding to an approximately 98.7% reduction at the elemental-marker level. Stability evaluation indicated that Na₂SO₃, Fe³⁺, ascorbic acid, sucrose and light exposure affected the detected monoterpene glycoside content to different extents, whereas short-term heating within 20–80 °C caused only slight fluctuations. The purified extracts showed stronger DPPH and ABTS radical scavenging activities and reducing power than the crude extracts. In LPS-stimulated RAW264.7 cells, the purified extracts reduced NO production and downregulated the mRNA expression of IL-6, IL-1β, TNF-α, iNOS and COX-2, suggesting anti-inflammatory potential at the NO and gene-expression levels. AB-8 resin purification enriched the monitored monoterpene glycosides, reduced the selected ionic-liquid-associated elemental marker, and generated purified fractions suitable for subsequent stability and bioactivity evaluation. Full article

Background: Dragon’s blood (dried resin of Dracaena cochinchinensis (Lour.) S.C.Chen) is a classic traditional medicine for treating ischemic stroke, yet its bioactive components capable of penetrating the blood–brain barrier (BBB) remain ill-defined. This study aims to elucidate its material basis and the synergistic mechanism of Borneol as a “guide drug.” Methods: A systematic strategy integrating UHPLC-Q-TOF-MS/MS and metabolomics was employed to map the chemical profile of dragon’s blood and identify its migrating constituents in rats. Results: A total of 96 compounds were characterized in vitro. In vivo analysis of the cerebrospinal fluid (CSF) revealed a brain-penetrating profile that was significantly enriched by Borneol, with the number of detected constituents increasing from 11 in the DB group to 16 in the DB + B group. The results demonstrated that demethylation, glycoside hydrolysis, and oxidation are primary metabolic pathways, validating a “pro-drug” mechanism where aglycones and hydroxylated derivatives act as the central effectors. Notably, Borneol not only enhanced the BBB permeability of lipophilic flavonoids but also facilitated unique metabolic transformations, such as the cyclization of berberrubine to coptisine. Conclusions: This study elucidates the brain-penetrating material basis of dragon’s blood and reveals the dual synergistic mechanism of Borneol involving both physical permeation enhancement and metabolic modulation, offering scientific evidence for its clinical application in central nervous system diseases. Full article

Honeysuckle berries (Lonicera caerulea) represent a valuable source of bioactive compounds, primarily flavonoids, and iridoids. This study compared the chemical composition and in vitro antioxidant and antidiabetic properties of resin-purified extracts from ripe, unripe, and unripe lactofermented honeysuckle berries. Polyphenols and iridoids were identified using UPLC-ESI-qTOF-MS/MS and quantified using HPLC-PDA. A total of 6 anthocyanins, 7 phenolic acids, 9 flavan-3-ols, 8 iridoids, 8 flavonols, 3 flavones, and 1 flavanonol were identified in the extracts. The extract from ripe fruits was characterized by a high cyanidin glycoside content (273.59 mg/g) and high iridoid content (138.30 mg/g). The amount of individual iridoids varied among the extracts, with the highest level of loganic acid detected in the unripe fruit extract (39.42 mg/g) and the highest level of sweroside in the ripe fruit extract (55.59 mg/g). Phenolic acid content was approximately twofold higher in extracts from unripe and fermented fruits compared with ripe fruit extracts, suggesting a decrease during ripening, while fermentation did not significantly affect phenolic acid content. Among flavonols, quercetin and isorhamnetin derivatives were identified, with quercetin 3-O-rutinoside being the predominant compound in all extracts. The ripe fruit extract exhibited the strongest radical scavenging activity (in ABTS and DPPH assays), ferric ion-reducing power (FRAP), and α-amylase inhibition, while all extracts exhibited comparable α-glucosidase inhibition. These findings indicate that L. caerulea extracts, especially from ripe fruits, are a rich source of biologically active compounds with potential relevance for managing oxidative stress and hyperglycemia. Full article

Dendrobium moschatum neutral polysaccharide (DMP-NP) was isolated using a water extraction–ethanol precipitation method, followed by purification with DEAE-cellulose anion-exchange resin and a dextran gel column. The resulting DMP-NP1 exhibited a weight-average molecular weight of 16.23 kDa. The molar ratio of monosaccharides was as follows: glucose–mannose–galactose–fucose–rhamnose = 78.54:19.11:1.59:0.53:0.23, with a glucose-to-mannose ratio of 4.1:1. Infrared spectroscopic analysis revealed characteristic carbohydrate absorption peaks and confirmed the presence of pyranosidic linkages. NMR analysis revealed that DMP-NP1 possesses a backbone mainly formed by 1→4 glycosidic linkages, a small number of 1→6 branches, and O-acetyl substitutions at the C2 and C3 positions of mannose residues. In vitro experiments demonstrated that treatment with 0–20 μg/mL (0–1.23 μM) DMP-NP significantly enhanced the activities of catalase (CAT) and superoxide dismutase (SOD) in IPEC-J2 cells, along with upregulation of the corresponding antioxidant genes. Concurrently, DMP-NP reduced the secretion of key pro-inflammatory cytokines, including TNF-α, IL-1β, and IL-6, and downregulated the expression of genes associated with both antioxidant and inflammatory signaling pathways. Collectively, these findings indicate that DMP-NP not only prevents but also ameliorates LPS-induced inflammatory injury in intestinal epithelial cells, thereby providing a basis for the application of DMP-NP in intestinal inflammation mitigation. Full article

In the present study, seven previously undescribed resin glycosides, designated cusponins I-VII (1–7), together with one known analog (8), were isolated from the seeds of Cuscuta japonica, a traditional medicine used in China. Structural elucidation revealed them to be glycosidic acid methyl esters, generated through on-column methyl esterification of naturally occurring resin glycosides catalyzed by NH₂-functionalized silica gel. All isolates were characterized as either pentasaccharides or tetrasaccharides, incorporating D-glucose, L-rhamnose, or D-fucose units as the sugar residues. Notably, compounds 1 and 3–7 contained the uncommon aglycone, 11S-hydroxypentadecanoic acid. Bioactivity assessments demonstrated that compounds 1–4, 6 and 8 suppressed α-glucosidase activity, with IC₅₀ values between 8.02 and 71.39 μM. In addition, compounds 3 and 5 exhibited inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), with IC₅₀ values of 14.19 ± 1.29 μM and 62.31 ± 8.61 μM, respectively, marking the first report of PTP1B inhibitory activity among resin glycosides. Enzyme kinetic analyses indicated that compound 2 acted as an uncompetitive α-glucosidase inhibitor (K_is = 3.02 μM), whereas compound 3 inhibited PTP1B via a mixed-type mechanism (Kᵢ = 24.82 μM; K_is = 64.24 μM). Molecular docking combined with molecular dynamics simulations suggested that compounds 2 and 3 interacted with α-glucosidase-pNPG and PTP1B, respectively, forming stable complexes with favorable binding free energies. Collectively, this study reported eight resin glycosides from C. japonica, seven of them newly identified, with compounds 2 and 3 highlighted as promising scaffolds for antidiabetic drug discovery. Full article

Stevioside, a natural high-intensity sweetener, is widely employed across the food, pharmaceutical, and daily chemical industries due to its intense sweetness and health benefits. However, traditional extraction and purification processes for steviol glycosides from Stevia rebaudiana are plagued by low efficiency, high energy consumption, substantial environmental impact, and inconsistent product quality. This study systematically optimized the extraction, decolorization, decontamination, and desalting processes to overcome these challenges. The extraction method was refined using 20% ethanol as the solvent, an optimal temperature of 50 °C, and a 1:10 material-to-liquid ratio, increasing the steviol glycoside yield from 32.0% to 49.1%. Decolorization employing a combination of resins D940 and T5 achieved decolorization rates of 89–92% with minimized steviol glycoside loss, surpassing the non-selective adsorption limitations of activated carbon. For decontamination, calcium hydroxide (Ca(OH)₂) outperformed diatomaceous earth, attaining a 98% protein removal rate while maintaining steviol glycoside loss below 20%. The desalting resin LXP-016 demonstrated superior performance at 40 °C, enhancing the ability of ionic impurity removal. These optimizations collectively improve the efficiency, sustainability, and quality of steviol glycoside production, offering a promising framework for industrial-scale applications. Full article

Olive mill wastewater (OMW), a byproduct of the olive oil industry, is a potential source of natural bioactive phenolic polymers. In this work, a column chromatography technique was used for the isolation of a new complex polymer (named OMW-2000XAD) from OMW via fractionation on Amberlite^® XAD16 resin. The developed procedure was simple and proved to be reproducible using OMW from two different sources. OMW-2000XAD was further characterized by elemental, glycosidic, and amino acid composition analysis, as well as spectroscopic techniques. The polymer’s molecular size, which was estimated via gel filtration chromatography, was 1960 kDa, which is significantly larger than other high-molecular weight fractions previously isolated from OMW or other agro-industrial wastes. OMW-2000XAD was mainly composed of phenolic compounds (89.8%). It also contained polysaccharides (16.1%) and proteins (10.3%), with glucose (12.25%) and cysteine (1.71%) being the most abundant sugar and amino acid, respectively, as well as metals (1.29%, primarily potassium). However, due to its low solubility, complexity, and heterogeneous composition, it was not possible to identify all phenolic compounds or elucidate a definitive structure via MS, FTIR, and NMR. OMW-2000XAD exhibited strong radical scavenging antioxidant capacity (ABTS^•+, DPPH^• and peroxyl radicals), with results up to 7415 µmol Trolox equivalent/mol (ORAC method), but showed no antiproliferative effects, highlighting the need for further research. Full article

Aglycone-type soy isoflavones, recognized for their bioactive phytoestrogen properties, face industrial limitations due to their low natural abundance and inefficient conversion. This study optimized a multi-enzyme synergistic catalysis system using soybean sprout powder, achieving high conversion rates and purity through response surface methodology. The optimal enzyme system comprised β-glucosidase (25 U/mL), cellulase (200 U/mL), hemicellulase (400 U/mL), and β-galactosidase (900 U/mL) at pH 5.0, 50 °C, and 3.2 h. This system yielded an aglycone conversion rate of 92% and glycoside hydrolysis rate of 97%, outperforming single-enzyme approaches. Upon post-purification with AB-8 macroporous resin, the product reached a purity of 58.1 ± 0.54% and exhibited strong antioxidant activity, with DPPH and ABTS radical scavenging rates of 81.01 ± 0.78% and 71.37 ± 1.01%, respectively. In a zebrafish central nervous system injury model induced by mycophenolate mofetil, the 500 μg/mL sample group significantly reduced neural apoptosis fluorescence intensity compared to controls (p < 0.05), achieving a neuroprotective rate of 76.58%, which was similar to the effect of L-reducing glutathione. This study offers an efficient, cost-effective enzymatic strategy for producing aglycone soy isoflavones, highlighting their potential in functional foods and neuroprotective applications. Full article

Background: Kukeya tablets (KYs), a traditional ethnic medicine prescription, are widely used to treat migraines and eye ailments in China. Despite their extensive clinical use, current knowledge on their therapeutic material basis is limited to a few major compounds, whereas certain minor ones have rarely been investigated. This study was conducted to screen and characterize the chemical components of KYs. Methods: A rapid and effective UHPLC-Q-Orbitrap-HRMS method was established. A mass spectrometry qualitative analysis strategy for KYs was developed, including in-house library matching, accurate molecular mass and elemental composition matching, and MS/MS fragmentation rule elucidation. Results: In total, 144 compounds were identified in KYs, including 36 anthrones and anthraquinones, 36 chromones, 25 triterpenes, 12 resin glycosides, 12 phenylpyrones, 10 phenolic acids, 4 flavonoids, 2 lignans, and 7 others. Meanwhile, the identified compounds were effectively classified into nine chemical classes. Among them, 11 compounds were identified for the first time and the identities of 22 compounds were accurately confirmed using reference substances. Conclusions: The results obtained benefit the understanding of the therapeutic basis of KYs, significantly promote the quality control of KYs, and elucidate potential effective components of other traditional medicines. Full article

The food industry generates the largest number of valuable by-products. The recovery of compounds such as fatty acids and polyphenols with notorious biological properties from biowaste is a new challenge in the circular economy scenario, as they represent value-added starting materials for the preparation of functional foods, food supplements, cosmetics and over-the-counter drugs. Less commonly explored are industrial wastewaters, which return to the nearby water streams without adequate treatment. Distillation wastewater (DWW) from the essential oils or agro-food industries may represent a valuable source of bioactive compounds to be valorized. In this work, DWW from rosemary was treated with different resins through dynamic and static adsorption/desorption approaches, for the recovery of phenolic compounds including rosmarinic acid. The most effective methodology, selected according to total phenolic and rosmarinic acid contents, as well as antioxidant activity evaluation, was applied to sage, thyme and oregano DWWs. The procedure provides several advantages compared with conventional separation processes, as it involves the lower consumption of reagents/solvents, low operational costs, ease of handling, and simplicity of scale-up. The results of this work highlight a fast and sustainable procedure for the recovery of rosmarinic acid and other phenolics (caffeic acid derivatives and flavonoid glycosides) from DWWS, thus affording a fraction with antioxidant and hypoglycemic activities. Full article

Background/Objectives: Plants species of the Epilobium genus are traditionally used to treat prostatitis and other urinary tract disorders and are particularly rich in ellagitannins and flavonol 3-O-glycosides. The aim of this work was to evaluate the inhibitory activity of different extracts from E. angustifolium L. and E. parviflorum Schreb. and their major bioactive compound, oenothein B, against a panel of Gram-positive (Enterococcus faecalis ATCC 29212, Enterococcus faecalis BS, Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 29213, and Staphylococcus aureus ATCC 43300) and Gram-negative (Escherichia coli ATCC 25922, Escherichia coli ATCC 35218, Escherichia coli BS, Klebsiella pneumoniae ATCC 13883, Klebsiella pneumoniae ATCC 70063, Klebsiella pneumoniae BS, Proteus mirabilis BS, and Pseudomonas aeruginosa ATCC 27853) bacteria responsible for prostatitis. Methods: Aqueous and ethanolic raw extracts were prepared, and the latter were further purified using the resin Amberlite^TM XAD7HP. Then, an HPLC-MS/MS method was developed for the quantification of the marker bioactives and their levels were correlated with the antimicrobial activity. Results: Purified extracts were richer in polyphenols (330.80 and 367.66 mg/g of dry extract for E. angustifolium and E. parvifolium, respectively) than the raw extracts. Oenothein B was the predominant compound in all the extracts (119.98 to 327.57 mg/g of dry extract). The minimum inhibitory concentrations (MICs) in the range of µg/mL indicated significant antibacterial activity, which was higher for the purified extracts and oenothein B (MIC values from 4 to 16 and 8 to 1024 µg/mL on Gram-positive and Gram-negative strains, respectively). Conclusions: These results outline the outstanding potential of E. angustifolium and E. parviflorum extracts and oenothein B as therapeutic alternatives or complementary agents to conventional antibiotic treatments of prostatitis and other urinary tract infections. Full article

Prunus mume (Armeniaca mume Sieb. var. mume f. viridicalyx (Makino) T. Y. Chen) is a common landscape plant. It has rich flavonoid content, which shows strong biological activities. In this study, the application potential of flavonoids in Prunus mume in anti-photoaging cosmetics was developed. Firstly, the flavonoids in Prunus mume were extracted by the heating reflux method, and the total flavonoid content reached 192 mg/g under the optimal process conditions determined by orthogonal testing. Then, the crude extract (PMCE) was purified by NKA-II resin column chromatography, and the purity of the flavonoids reached 83.99%. Subsequently, the Prunus mume purified product (PMPP) was analyzed by UHPLC-DAD-QTOF-MS/MS and 45 compounds were identified including flavonoid glycosides, phenolic acids and p-coumaroyl acetylated sucrose. In addition, in vitro biological experiments showed that PMPP had significant repair effects on UVB-induced photoaging of human keratinocytes (HaCaT), lowering reactive oxygen species (ROS) and malondialdehyde (MDA) levels, restoring superoxide dismutase (SOD) activity, and promoting hyaluronic acid (HA) secretion and Aquaporins-3 (AQP-3) levels. The results laid the foundation for the development of the flavonoids in Prunus mume as materials for anti-photoaging cosmetics. Full article

Ipomoeassin F (Ipom-F) is a plant-derived macrocyclic resin glycoside that potently inhibits cancer cell growth through blockage of Sec61-mediated protein translocation at the endoplasmic reticulum. Recently, detailed structural information on how Ipom-F binds to Sec61α was obtained using Cryo-EM, which discovered that polar interactions between asparagine-300 (N300) in Sec61α and four oxygens in Ipom-F are crucial. One of the four oxygens is from the carbonyl group at C-4 of the fatty acid chain. In contrast, our previous structure–activity relationship (SAR) studies suggest that the carbonyl group is not essential. To resolve this discrepancy, we designed and synthesized two new open-chain analogues (10 and 11); 10 without the C-4 carbonyl had a dramatic activity loss, whereas 11 with an amide functional group was even more potent than Ipom-F. These new SAR data, in conjunction with some previous SAR information, imply two functional roles of the C-4 carbonyl: (1) to form H-bonds with N300; and (2) to regulate interactions of the fatty acid chain with membrane lipids. Impacts of these dual functions on antiproliferation depend on the overall structure of an Ipom-F derivative. Moreover, 11 can serve as a lead compound for developing future amino acid/peptide-modified analogues of Ipom-F with improved therapeutic properties. Full article

Pistacia lentiscus L., commonly known as the mastic tree or lentisk, is a woody Mediterranean plant revered for its ecological relevance as well as for its extensive ethnobotanical heritage. Historically, the fruits and the resin of P. lentiscus have been widely utilized in traditional medicine, underscoring its important role in local healing practices. Given these properties, this study explored an innovative approach to efficiently extract anthocyanins and flavonols from P. lentiscus oilcakes utilizing ultrasound-assisted extraction (UAE) as an alternative to conventional solvent extraction. Liquid chromatography–mass spectrometry (LC-MS) and high-performance liquid chromatography with diode-array detection (HPLC-DAD) were used to identify and quantify the anthocyanins and flavonols, revealing the successful extraction of eight distinct anthocyanins and twenty flavonols. A Fractional Factorial Design (FFD) followed by a Box–Behnken design (BBD) were applied to optimize the yield of anthocyanins and flavonols. The optimal extraction conditions found were to be an extraction time of 15 min with 70% ethanol as the solvent and a liquid-to-solid ratio of 0.012 L g⁻¹, which resulted in a maximum extraction yield of 19.78 mg g⁻¹ dry extract for the Total Flavonol Content and over 25.4 mg g⁻¹ dry extract for the Total Flavonol and Anthocyanin Content. By elucidating the optimal conditions for extracting anthocyanins and flavonol glycosides, this study opens promising avenues for utilizing P. lentiscus oilcake by-products, supporting sustainable practices, and advancing the valorization of Mediterranean bio-resources for health-promoting applications. Full article

Cholestasis refers to a physiological and pathological process caused by bile acid (BA) overaccumulation inside the circulatory system and liver, leading to systemic and hepatocellular damage. Activating the farnesol X receptor (FXR) to restore BA homeostasis is a promising strategy for treating cholestasis. The objective of this research is to reveal solid evidence for the fact that the total iridoid glycosides from Swertia mussotii Franch. (IGSM) alleviate cholestasis. In this research, the whole plant of S. mussotii was extracted with 70% ethanol and separated by macroporous adsorption resin. A rat cholestasis model was established by the injection of α-naphthyl isothiocyanate (ANIT) at a dose of 75 mg/kg. Biochemical and oxidative stress indicators were determined using commercial assay kits. The mRNA abundance of FXR and target proteins was assessed using RT-qPCR. In addition, the effects of main compounds with FXR were evaluated by molecular docking after IGSM analysis using UPLC. The results indicated that IGSM alleviated ANIT-induced cholestasis through reducing serum ALT, AST, AKP, and TBA levels; increasing the mRNA levels of Fxr, Besp, Ntcp, and Mep2; and reducing oxidative stress. The proportion of iridoid compounds in IGSM exceeded 50%, which may be the active substance basis of IGSM. This study provides a theoretical reference for IGSM in the treatment of cholestasis, and future studies may delve more deeply into the FXR regulatory pathway. Full article