Search Results (143)

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

Background/Objectives: Vinegar–egg is a traditional health-promoting beverage prepared by soaking eggs in vinegar. While both eggs and vinegar are common dietary components with well-documented nutritional and pharmacological activities, eggs treated with vinegar have been rarely studied. This study aims to identify and characterize bioactive compounds in vinegar–egg and investigate their potential wound-healing activities. Methods: The vinegar–egg extract was analyzed using liquid chromatography–mass spectrometry (LC–MS) and column chromatography, including HPLC purification, which led to the isolation of four phenolic compounds. Results: These compounds were identified as 4-hydroxybenzoic acid (1), vanillic acid (2), methyl syringate (3), and leptosperin (4) using ESI-MS, UV, and NMR spectroscopic data. Among the isolates, 4-hydroxybenzoic acid (1) and vanillic acid (2) demonstrated wound-healing properties in mouse embryonic fibroblast (MEF) cells. None of the compounds, 4-hydroxybenzoic acid (1), vanillic acid (2), methyl syringate (3), or leptosperin (4), exhibited cytotoxicity in PC12, AGS, MEF, or MDA-MB-231 cells. Notably, 4-hydroxybenzoic acid (1) enhanced cell motility by 2.59-fold and cell invasion by 1.20-fold, while vanillic acid (2) increased cell motility by 2.69-fold and cell invasion by 1.23-fold. Western blot analysis revealed that treatment with 4-hydroxybenzoic acid (1) and vanillic acid (2) increased the phosphorylation of focal adhesion kinase (p-FAK) and matrix metalloproteinase 2 (MMP-2). Furthermore, both compounds elevated the phosphorylation of p38, a key regulator in wound-healing pathways. Conclusions: These findings demonstrate that 4-hydroxybenzoic acid (1) and vanillic acid (2) accelerate wound healing through the activation of focal adhesion and mitogen-activated protein kinase (MAPK) signaling pathways. These results highlight vinegar–egg as a promising therapeutic candidate for wound healing. Full article

Recently, vegetable oil-derived monounsaturated fatty acids (MUFAs) have predominantly been utilized in producing bio-based surfactants, resulting in low bioresource utilization and high separation costs. Although polyunsaturated fatty acids (PUFAs) are abundant and often co-exist with MUFAs, bio-based surfactants synthesized from PUFA-rich feedstocks have been less researched due to concerns regarding their interfacial performance. In this study, a novel series of PUFA-based zwitterionic surfactants with strong interfacial activity was synthesized from waste vegetable oils via an eco-friendly three-step process, optimized through an orthogonal experimental design. The structures and conversion rates of the surfactants were confirmed using GC-MS, LC-MS, and ESI-MS. At 0.5 g/L and 3.0 g/L (typical concentrations often used in most oil fields), the bio-based surfactants derived from waste soybean oil (PUFA-to-MUFA ratio ≈ 2.11, C18:2, and C18:1 in large contents) could reduce the interfacial tension between Daqing crude oil and simulated formation groundwater to an ultra-low level of ~10⁻³ mN/m. These results confirm our hypothesis that bio-based zwitterionic surfactants derived from PUFA-rich feedstocks possess excellent interfacial activity, providing a potential sustainable option to be considered for chemically enhanced oil recovery. Full article

Marine organism-associated microbes are an important source of structurally diverse and biologically active secondary metabolites exhibiting antimicrobial, anticancer, and anti-inflammatory activities. In this study, we investigated Penicillium brevicompactum MSW10-1, isolated from Hydractinia echinata, a marine invertebrate adapted to extreme intertidal and subtidal environments with variable temperature, salinity, and oxygen conditions. Through a combination of LC/MS-guided chemical analysis and chromatographic purification, eight secondary metabolites were isolated, including brevicolactones A (1) and B (2). The absolute chemical structures of 1 and 2 were determined based on NMR spectroscopic experiments, HR-ESIMS data, and quantum chemical ECD calculations. The isolated compounds (1–8) were evaluated for their ability to inhibit hepatic lipogenesis, a key process in lipid metabolism that is dysregulated in metabolic-dysfunction-associated steatotic liver disease. Furthermore, the inhibitory effects of the isolated compounds on lipid accumulation were further evaluated in primary mouse hepatocytes, using Oil Red O staining. These findings suggested that the isolated compounds may serve as promising candidates for the treatment of metabolic liver diseases associated with lipid dysregulation. Full article

Electrospray mass spectrometry off-line profiling monitored the recovery of targeted indole alkaloids from a fortified crude extract of Catharanthus roseus (790 mg) using semi-preparative high-performance countercurrent chromatography (HPCCC) fractionation. Visualization of selected single-ion traces projected the HPCCC molecular weight elution profile. Experimental partition-ratio values K_D and peak widths for detected metabolites were determined. Structural characterization of metabolites and co-elution effects were monitored in the scan range m/z 100–2000. In this study, the biphasic solvent system containing n-hexane–n-butanol–water with 0.5% ion-pair reagent trifluoro-acetic acid [1:1:2, v/v/v] was used based on partition ratio K_D-value liquid chromatography–electrospray ionization–mass spectrometry (LC-ESI-MS) analysis prediction. The monitoring of target ions resulted in the isolation of six major concentrated indole alkaloids (akuammicine, catharanthine, perivine, vindoline, vindorosine, and 19R-vindolinine), which were fully elucidated by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. Full article

The depolymerization of chitosan using chitinolytic enzymes is one of the most promising approaches for the production of bioactive soluble chitooligosaccharides (COS) due to its high specificity, environmental safety, mild reaction conditions, and potential for development. However, the comparative efficacy of bacterial chitinases and chitosanases in terms of yield, solubility, and antimicrobial activity of produced COS remains understudied. In this work, chitinase (73 kDa) and chitosanase (40 kDa) from the strain Bacillus thuringiensis B-387 (Bt-387) were purified using various chromatographic techniques and compared by their action on chitosan (DD 85%). The molecular mass and structure of generated COS was determined using TLC, LC-ESI-MS, HP-SEC, and C¹³-NMR techniques. Chitosanase converted the polymer more rapidly to short COS (GlcN₂-GlcN₄), than chitinase, and was more specific in its action on mixed bonds between GlcN and GlcNAc. Chitosanase needed a noticeably shorter incubation time and enzyme–substrate ratio than chitinase for production of larger oligomeric molecules (Mw 2.4–66.5 and 15.4–77.7 kDa, respectively) during controlled depolymerization of chitosan. Moreover, chitosanase-generated oligomers demonstrate better solubility and a higher antifungal activity in vitro against the tested plant pathogenic fungi. These features, as well as the high enzyme production and its simplified purification protocol, make chitosanase B-387 more suitable for the production of antifungal chitooligomers than chitinase. Full article

Platycladus orientalis, an evergreen tree belonging to the Cupressaceae family, has been traditionally used to treat various ailments, including fever, cough, diarrhea, diuresis, cold symptoms, and gastrointestinal disorders in folk medicine. As part of our ongoing investigation aimed at discovering bioactive natural products and elucidating their mechanisms of action from various natural sources, we investigated a methanol (MeOH) extract of P. orientalis leaves. This investigation led to the isolation and identification of a labdane-type diterpene, lambertianic acid (LA), via column chromatography and HPLC purification. The structure of LA was elucidated using LC/MS and NMR spectroscopic analyses, including HR-ESIMS, while its absolute configuration was confirmed through electronic circular dichroism (ECD) calculations. Recent studies have reported that labdane-type diterpenes exhibit diverse pharmacological activities, such as anticancer, anti-inflammatory, anti-obesity, and hypolipidemic effects. Notably, LA has been shown to modulate adipocyte metabolism via AMPK signaling; however, its role in skeletal muscle atrophy remains unexplored. Therefore, in this study, we investigated the effects of LA on dexamethasone (Dex)-induced muscle atrophy in C2C12 myotubes. Treatment with LA at concentrations of 25 µM and 50 µM significantly rescued myotube diameter and reduced the expression of atrophy-related proteins, including MuRF-1 and atrogin-1/MAFbx, without compromising cell viability at these moderate concentrations. These findings suggest that LA derived from P. orientalis exerts protective effects against skeletal muscle atrophy, highlighting its potential as a promising natural therapeutic candidate for muscle-wasting disorders. Full article

Ficus benjamina is a common park tree, with previous reports of some medicinal properties. In this work, we identified and explored phytochemicals from F. benjamina for potential antimicrobial, pro-wound-healing, anti-inflammatory, and effect on cancer cell lines’ proliferation, both experimentally and bioinformatically. Gas chromatography/mass spectrometry (GC/MS) analysis was performed to identify the volatile compounds. The nonvolatile active components of the extract were identified by HPLC and LC-ESI-MS. We found that some drug-resistant microorganisms (Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Serratia marcescens, and Salmonella enteritidis) were inhibited by the extract, the 80% fraction, and all the identified flavonoids except quercetin 3-O-rutinoside. Furthermore, the extract and above-mentioned compound also inhibited the growth of biofilm-producing bacterium. The extract and 80% fraction were very potent (p < 0.001) at inducing death of MCF7 and U87 cancer cell cultures and were more effective in that than the chemotherapeutic agent doxorubicin which served as a positive control. Additionally, the extract of F. benjamina, the 80% fraction, and selected phytochemicals had pronounced pro-wound-healing properties. Finally, the extracts, the 80% fraction, caffeic acid, kaempferol 3-O-rutinoside, and kaempferol 3-O-robinobioside significantly inhibited the secretion of pro-inflammatory cytokines, IL-6 and IL-8 (p < 0.001). In conclusion, this comprehensive research revealed convincing and promising indications of significant therapeutic potential of a F. benjamina extract and its active phytochemicals. Full article

Microbial biosurfactants have become increasingly attractive as promising ingredients for environmentally friendly products. The reasons for this are their generally good performance and biodegradability, low toxicity, production from renewable raw materials, and benefits for the environment perceived by consumers. In this study, we investigated the chemical structure and properties of a novel glycolipid from a new biosurfactant-producing strain, Rouxiella badensis DSM 100043^T. Bioreactor cultivation was performed at 30 °C and pH 7.0 for 28 h using 15 g/L glycerol as a carbon source. The glycolipid was successfully purified from the ethyl acetate extract of the supernatant using medium pressure liquid chromatography (MPLC). The structure of the glycolipid was determined by one- and two-dimensional (¹H and ¹³C) nuclear magnetic resonance (NMR) and confirmed by liquid chromatography electrospray ionization mass spectrometry (LC-ESI/MS). NMR analysis revealed the hydrophilic moiety as a glucose molecule and the hydrophobic moieties as 3-hydroxy-5-dodecenoic acid and 3-hydroxydecanoic acid, which are linked with the glucose by ester bonds at the C2 and C3 positions. Surface tension measurement with tensiometry indicated that the glucose–lipid could reduce the surface tension of water from 72.05 mN/m to 24.59 mN/m at 25 °C with a very low critical micelle concentration (CMC) of 5.69 mg/L. Moreover, the glucose–lipid demonstrated very good stability in maintaining emulsification activity at pH 2–8, a temperature of up to 100 °C, and a NaCl concentration of up to 15%. These results show that R. badensis DSM 100043^T produced a novel glycolipid biosurfactant with excellent surface-active properties, making it promising for further research or industrial applications. Full article

Ralstonia solanacearum is an important pathogen causing bacterial wilt in pepper (Capsicum annuum L.). The concurrent infection of R. solanacearum and root-knot nematodes (Meloidogyne spp.) exacerbates the severity of bacterial wilt in pepper. Utilizing plant endophytic bacteria to control these mixed diseases is a viable strategy. Waltheria indica L. (Sterculiaceae) is a traditional medicine plant. A total of 209 endophytic bacteria were isolated from W. indica, and Pseudomonas aeruginosa W-126 showed an efficient antagonistic effect against R. solanacearum. Based on active compound tracking principles, a compound was isolated through silica gel column chromatography and preparative HPLC combined with TLC analysis. It was identified as phenazine-1-carboxamide (PCN) by spectral techniques (ESI-MS, ¹H-NMR, ¹³C-NMR). PCN displayed excellent inhibitory activity against R. solanacearum, with an EC₅₀ of 64.16 μg/mL in vitro. In addition, it showed certain nematocide activity, with an LC₅₀ value of 118.63 μg/mL at 72 h. PCN also showed certain inhibitory activity against five other phytopathogenic bacteria. The structure−activity relationship indicated that the phenazine skeleton and acylamide groups were the key pharmacophores for the activity of phenazine-related compounds against R. solanacearum. PCN controlled the complex diseases of R. solanacearum and M. incognita in a pot experiment, with respective 51.41 and 39.80% inhibitory rates. The exploration of secondary metabolites of biocontrol bacteria can provide reference for the development of novel and efficient pesticides. Full article

Glochidion chodoense, a rare and endangered plant endemic to Republic of Korea, is known for containing a wide variety of phytochemicals, including triterpenoid saponins and flavonoids. This study sought to profile the phytochemical composition of the leaves and branches of G. chodoense harvested during three different periods (May, July, and October 2023) using liquid chromatography–electrospray ionization/mass spectrometry (LC-ESI/MS) and high-performance liquid chromatography–photodiode array detection (HPLC/PDA). Plant materials were harvested, authenticated, and subjected to ethanol extraction prior to chemical analysis. LC-ESI/MS and quantitative HPLC/PDA analyses were conducted to identify and quantify nine key phytochemicals: norbergenin (1), bergenin (2), epigallocatechin (3), ethyl gallate (4), orientin (5), epicatechin gallate (6), isovitexin 2″-O-arabinoside (7), ellagic acid (8), and cynaroside (9). Our findings revealed significant seasonal variations in major phytochemicals, with leaves containing higher concentrations than branches. Notably, bergenin (2) showed the highest content in May leaves (43.42 mg/g extract), followed by October (17.60 mg/g extract) and July branches (8.56 mg/g extract). Ethyl gallate (4), which was absent or present in trace amounts in branches, was abundant in leaves, with concentrations of 22.24 mg/g extract in October, 21.75 mg/g extract in May, and 17.48 mg/g extract in July. A similar trend was observed for norbergenin (1). These findings provide valuable insights into the phytochemical composition of G. chodoense, emphasizing its potential applications in pharmaceuticals, cosmetics, and functional foods, while highlighting the critical importance of conserving this endangered species. Full article

The leaves of Ginkgo biloba have been used in treating freckles and effectively reducing cough and sputum in folk medicines. Recently, investigations into the correlation between ginkgo leaves and the proliferative activity of osteogenic differentiation have been conducted. However, bioactive compounds that enhance osteogenesis or exhibit osteoporosis prevention from G. biloba have not been fully identified. Phytochemical investigation of the MeOH extract of G. biloba leaves led to the isolation and identification of a new biflavonoid glycoside, (aS)-glucosciadopitysin (1), along with five flavonoids (2–6), through LC/MS-guided isolation approach. The structure of the new compound 1 was elucidated by the spectroscopic methods, including 1D and 2D NMR analysis, as well as HR-ESIMS. The absolute configuration of sugar moiety was established through acid hydrolysis, followed by chemical derivatization reaction and the axial chirality arising from the biaryl system with substituents was determined by electronic circular dichroism (ECD) calculations. The isolated flavonoids (1–6) were tested for their effects on mesenchymal stem cell (MSC) differentiation at 20 μM using Oil Red O and alkaline phosphatase (ALP) staining. Ginkgetin (2) was further evaluated for osteogenic activity on C3H10T1/2 cells at concentrations of 1, 2.5, 5, and 10 μM for 10 days. ALP staining and RT-PCR assessed the gene expression of osteogenic markers ALP and osteopontin (OPN). Ginkgetin (2) demonstrated the strongest osteogenic activity, significantly increasing the expression of ALP (12.5-fold) and OPN (4.0-fold) at 10 μM, comparable to the positive control, oryzativol A. Ginkgetin (2) shows potential as a therapeutic agent for osteopenia by promoting osteogenesis in MSCs, suggesting its promising role in treating osteoporosis. Full article

Salix koreensis Anderss (Salicaceae), commonly referred to as Korean willow, is native to East Asia, particularly Korea and China, and it has been used in traditional Korean folk medicine for its potent anti-inflammatory, analgesic, and antioxidant properties. In our ongoing research efforts to discover biologically new natural products, phytochemical analysis on an ethanolic extract of S. koreensis twigs yielded the isolation and identification of ten phenolic compounds (1–10), including a newly discovered phenolic glycoside (1) named isograndidentatin D, isolated via HPLC purification. The structure of compound 1 was determined through extensive 1D and 2D NMR spectral data analysis and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). Its absolute configuration was established using DP4+ probability analysis combined with gauge-including atomic orbital NMR chemical shift calculations and chemical reaction methods. The other known compounds were identified as isograndidentatin B (2), trichocarposide (3), glanduloidin C (4), tremuloidin (5), 3-O-acetylsalicin (6), 2-O-acetylsalicin (7), salicin (8), salireposide (9), and coumaric acid (10), confirmed by comparing their NMR spectra with previously reported data and further verified through liquid chromatography/mass spectrometry (LC/MS) analysis. The isolated compounds 1–10 were tested for their anti-Helicobacter pylori activities. Among these, compounds 4 and 5 demonstrated moderate anti-H. pylori activity at a concentration of 100 μM. Specifically, compound 5 showed an inhibitory activity of 35.9 ± 5.4%, making it slightly more potent than compound 4, with 34.0 ± 1.0% inhibition. These results were comparable to that of quercetin, a known anti-H. pylori agent used as a positive control in this study, which showed 38.4 ± 2.3% inhibition. The remaining compounds exhibited very weak inhibitory effects. This study highlights the potential of S. koreensis twigs as a valuable natural source of bioactive compounds for therapeutic applications against H. pylori. Full article

Despite the growing interest in using natural compounds for disease prevention and treatment, Allium ursinum (wild garlic), known for its therapeutic properties, has not been extensively studied for its chemical composition and biological activities. Therefore, this study aims to explore the in vitro antioxidant, antibacterial, and antitumor activities of A. ursinum extracts according to their functional phytochemical profile, while assessing whether ultrasound-assisted extraction (UAE) enhances bioactive properties in comparison to conventional maceration (CM). Both extracts were characterized by spectrophotometric methods and LC-ESI+-MS. The antioxidant activity was assessed via the CUPRAC and hydrogen peroxide scavenging assays, the antimicrobial properties via the disk-diffusion method against five pathogenic strains, and the antitumor activity via the MTT assay on four cancer cell lines. The major constituents of the methanolic extracts from leaves were kaempferol derivatives and alliin. The quercetin derivative rutin was also found. Maceration assisted using UAE yielded 20% more bioactive compounds in comparison to CM alone. Employing UAE in the extraction significantly increased antioxidant and antimicrobial proprieties, in line with its chemical composition. The antitumor cytotoxic activity was low to moderate, regardless of method, as explained by the absence of highly cytotoxic compounds. Wild garlic extracts possessed strong antioxidant and substantial antibacterial activities. Full article

Triticum aestivum (wheat) is one of the most significant crops worldwide. This study compares the chemical composition and radical-scavenging activities of two cultivars of T. aestivum, Saekeumkang wheat (SW) and Baekkang wheat (BW). Sprouted wheatgrass extracts of SW and BW were analyzed using assessments of total polyphenol and flavonoid contents, liquid chromatography–electrospray ionization/mass spectrometry (LC-ESI/MS), and high-performance liquid chromatography with a photodiode array (HPLC-PDA). Radical-scavenging activities were evaluated using 2,2-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS·⁺) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays. The results indicated that SW had a higher total polyphenol content than BW, while no significant differences were observed regarding total flavonoid content. HPLC-PDA analysis, guided by LC-ESI/MS, identified four compounds—saponarin, schaftoside, isoorientin, and isovitexin—with isoorientin (3.02 mg/g extract) and schaftoside (4.23 mg/g extract) present in higher concentrations in SW compared to BW. In the ABTS·⁺ assay, the two samples did not show noticeable differences, with SW displaying a scavenging ability with an IC₅₀ of 3.36 mg/mL, and BW with an IC₅₀ of 3.19 mg/mL. Contrarily, the DPPH assay results showed an inverse trend, suggesting that the radical-scavenging behavior may be influenced by the synergistic and antagonistic interactions of the compounds in SW and BW extracts. Full article