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Purpose The objective was to investigate the metabolic fate of phytosteryl/-stanyl fatty acid and ferulic acid esters upon consumption by healthy humans. Methods A capillary gas chromatographic methodology was employed to follow a randomized, single-blind three group crossover clinical trial and to quantify simultaneously individual intact esters, liberated phytosterols/-stanols and their metabolites in feces. Skimmed milk drinking yogurts enriched with complex mixtures of phytosteryl/-stanyl fatty acid esters and ferulates, respectively, were employed as food carriers. Results On average, 73 % of total plant stanyl fatty acid esters and 80 % of total plant steryl fatty acid esters were hydrolyzed. Among the individuals, the hydrolysis rates ranged from 40 to 96 %. In addition, there were subject-dependent discrepancies between the amounts of phytosterols/-stanols actually determined in the feces and the calculated hydrolysis rates. On average, 69 % of the amounts of sterols/stanols expected from the amounts of remaining intact esters were found. Conclusions The study revealed large interindividual variability regarding the recoveries of dietary phytosteryl/-stanyl esters upon gastrointestinal passage in healthy humans. Nevertheless, there was a significant impact of the acid moiety (oleate = linoleate = linolenate > eicosanoate > palmitate > ferulate) on the hydrolysis rates; the influence of the phytosterol/-stanol moiety was less pronounced.

Phytosterols constitute a class of natural products that are an important component of diet and have vast applications in foods, cosmetics, and herbal medicines. With many and diverse isolated structures in nature, they exhibit a broad range of biological and pharmacological activities. Among over 200 types of phytosterols, stigmasterol and β-sitosterol were ubiquitous in many plant species, exhibiting important aspects of activities related to neurodegenerative diseases. Hence, this mini-review presented an overview of the reported studies on selected phytosterols related to neurodegenerative diseases. It covered the major phytosterols based on biosynthetic considerations, including other phytosterols with significant in vitro and in vivo biological activities.

Indigofera zollingeriana Miq (I. zollingeriana) is a widely grown tree in Vietnam. It is used to cure various illnesses. The purpose of this study was to investigate the chemical constituents of an I. zollingeriana extract and test its anticancer activity on hepatocellular cells (Huh7 and HepG2). The experimental results of the analysis of the bioactive compounds revealed that β-sitosterol (β-S) and β-sitosterol-glucoside (β-SG) were the main ingredients of the I. zollingeriana extract. Regarding anticancer activity, the β-S and β-SG of I. zollingeriana were found to exhibit cytotoxic effects against HepG2 and Huh7 cells, but not against normal human primary fibroblasts. The β-S was able to inhibit the proliferation of HepG2 and Huh7 cells in a dose-dependent manner with half-maximal inhibitory concentration (IC50) values of 6.85 ± 0.61 µg/mL and 8.71 ± 0.21 µg/mL, respectively (p < 0.01), whereas the β-SG IC50 values were 4.64 ± 0.48 µg/mL for HepG2 and 5.25 ± 0.14 µg/mL for Huh7 cells (p < 0.01). Remarkably, our study also indicated that β-S and β-SG exhibited cytotoxic activities via inducing apoptosis and activating caspase-3 and -9 in these cells. These findings demonstrated that β-S and β-SG from I. zollingeriana could potentially be developed into promising therapeutic agents to treat liver cancer.

Background The hypolipidemic effect of phytosterols has been wildely recognized, but its application is limited due to its insolubility in water and low solubility in oil. In this study, β-sitosterol ester with linoleic acids and β-sitosterol self-microemulsions were prepared and their hypolipidemic effects on hyperlipidemia mice were studied. Methods Firstly, the mice were randomly divided into normal group and model group,they were fed with basic diet and high-fat diet for 70 days respectively. After high-fat model mice was successfully established, the model group was further divided into eight groups: HFD (high-fat diet feeding), SELA-TSO(8 ml/kg, SELA:700 mg/kg), TSO (8 ml/kg), SSSM (8 ml/kg,SS:700 mg/kg), NLSM (8 ml/kg), SSHT-TSO (8 ml/kg, SS: 700 mg/kg) and SS-TSO (8 ml/kg, SS: 700 mg/kg) groups, and treated with β-sitosterol ester with linoleic acid, β-sitosterol self-microemulsion, commercial β-sitosterol health tablets and β-sitosterol powder for 35 days, respectively, and blank control groups were established. At the end of the treatment period, the blood lipid level, tissues, cholesterol and lipids in feces of mice in each group were investigated. Statistical and analytical data with SPSS 17.0 Software,statistical significance was set at p * < 0.05 and p ** < 0.01 levels . Results The order of lowering blood lipid effect is listed as: SSSM> SELA-TSO > SSHT-TSO > SS-TSO, which shows that β-sitosterolself-microemulsion have the highest treatment effect among the experimental groups. Conclusions In this study, a new formulation of β-sitosterol was developed, and its hypolipidemic effect was investigated. The results showed that β-sitosterol self-microemulsion has a good blood lipid lowering effect.

Endosomal sequestration of lipid-based nanoparticles (LNPs) remains a formidable barrier to delivery. Herein, structure-activity analysis of cholesterol analogues reveals that incorporation of C-24 alkyl phytosterols into LNPs (eLNPs) enhances gene transfection and the length of alkyl tail, flexibility of sterol ring and polarity due to -OH group is required to maintain high transfection. Cryo-TEM displays a polyhedral shape for eLNPs compared to spherical LNPs, while x-ray scattering shows little disparity in internal structure. eLNPs exhibit higher cellular uptake and retention, potentially leading to a steady release from the endosomes over time. 3D single-particle tracking shows enhanced intracellular diffusivity of eLNPs relative to LNPs, suggesting eLNP traffic to productive pathways for escape. Our findings show the importance of cholesterol in subcellular transport of LNPs carrying mRNA and emphasize the need for greater insights into surface composition and structural properties of nanoparticles, and their subcellular interactions which enable designs to improve endosomal escape. Endosomal sequestration of lipid-based nanoparticles is a barrier to delivery of nucleic acids. Here the authors test an array of cholesterol variants and perform in-depth investigation of nanoparticle shape, internal structure and intracellular trafficking.

Structures of some bioactive phytochemicals in bran extract of the black rice cv. Riceberry that had demonstrated anti-cancer activity in leukemic cell line were investigated. After saponification with potassium hydroxide, separation of the unsaponified fraction by reversed-phase high performance liquid chromatography (HPLC) resulted in four sub-fractions that had a certain degree of anti-proliferation against a mouse leukemic cell line (WEHI-3 cell), this being IC50 at 24 h ranging between 2.80–467.11 μg/mL. Further purification of the bioactive substances contained in these four sub-fractions was performed by normal-phase HPLC. Structural characterization by gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) resulted in, overall, the structures of seven phytosterols and four triterpenoids. Four phytosterols, 24-methylene-ergosta-5-en-3β-ol, 24-methylene-ergosta-7-en-3β-ol, fucosterol, and gramisterol, along with three triterpenoids, cycloeucalenol, lupenone, and lupeol, were found in the two sub-fractions that showed strong anti-leukemic cell proliferation (IC50 = 2.80 and 32.89 μg/mL). The other sterols and triterpenoids were campesterol, stigmasterol, β-sitosterol and 24-methylenecycloartanol. Together with the data from in vitro biological analysis, we suggest that gramisterol is a significant anti-cancer lead compound in Riceberry bran extract.

Phytosterols, essential components of plant cell membranes, are abundant in fruits, vegetables, nuts, and seeds. Among them, β-sitosterol, campesterol, and stigmasterol have drawn significant interest for their well-documented biological activities. This review highlights recent advancements in extraction and analytical methods aimed at improving phytosterol yield, maintaining chemical stability, and reducing environmental impact. These innovative, eco-friendly techniques offer promising alternatives to traditional extraction approaches and hold potential for industrial-scale use. Phytosterols possess various bioactive properties, including antioxidant, anti-inflammatory, chemopreventive, cholesterol-lowering, and neuroprotective effects. Through these mechanisms, dietary phytosterols may help prevent cardiovascular and neurodegenerative diseases, type 2 diabetes, and certain cancers. Recent studies have focused on the identification, isolation, purification, and characterization of phytosterols from diverse food matrices, along with assessing their health benefits. However, the specific molecular pathways responsible for their pharmacological actions remain poorly understood, highlighting the need for further research, particularly in human clinical trials. This review provides a comprehensive overview of the extraction strategies, biological functions, and mechanisms of action of phytosterols, offering valuable insights for developing phytosterol-enriched functional foods and nutraceuticals.

Brevicoryne brassicae is a problematic pest in cabbage and other field crops. Synthetic pesticides are used to control this pest, but they are injurious for human health and the environment. The present study aimed to purify and identify the active compounds from Citrullus colocynthis leaves with an appraisal of their efficacy against B. brassicae. Separation and purification were performed via different chromatographic techniques. Molecular analysis and chemical structures were recognized by mass spectrum (MS) and nuclear magnetic resonance (NMR), respectively. Moreover, in vitro and in vivo aphicidal activity was assessed using various concentrations, i.e., 6.25, 12.5, 25 and 50 µg/mL at 12, 24, 48 and 72 h exposure. The outcome shows that mass spectrum analyses of the purified compounds suggested the molecular formulae are C30H50O and C29H50O, C29H48O. The compounds were characterized as fernenol and a mixture of spinasterol, 22,23-dihydrospinasterol by 1H-NMR and 13C-NMR spectrum analysis. The toxicity results showed that the mixture of spinasterol and 22,23-dihydrospinasterol showed LC50 values of 32.36, 44.49 and 37.50 µg/mL by contact, residual and greenhouse assay at 72 h exposure, respectively. In contrast, fernenol recorded LC50 values as 47.99, 57.46 and 58.67 µg/mL, respectively. On the other hand, spinasterol, 22,23-dihydrospinasterol showed the highest mortality, i.e., 66.67%, 53.33% and 60% while, 30%, 23.33% and 25% mortality was recorded by fernenol after 72 h at 50 µg/mL by contact, residual and greenhouse assay, respectively. This study suggests that spinasterol, 22,23-dihydrospinasterol are more effective against B. brassicae which may be introduced as an effective and suitable substitute of synthetic chemical pesticides.

β-sitosterol β-d-glucoside (BSSG) was extracted from “piña” of the Agave angustifolia Haw plant by microwave-assisted extraction (MAE) with a KOH solution such as a catalyst and a conventional maceration method to determine the best technique in terms of yield, extraction time, and recovery. The quantification and characterization of BSSG were done by high-performance thin layer chromatography (HPTLC), Fourier-transform infrared spectroscopy (FT-IR), and high-performance liquid chromatography−electrospray ionization−mass spectrometry (HPLC-ESI-MS). With an extraction time of 5 s by MAE, a higher amount of BSSG (124.76 mg of β-sitosterol β-d-glucoside/g dry weight of the extract) than those for MAE extraction times of 10 and 15 s (106.19 and 103.97 mg/g dry weight respectively) was shown. The quantification of BSSG in the extract obtained by 48 h of conventional maceration was about 4–5 times less (26.67 mg/g dry weight of the extract) than the yields reached by the MAE treatments. MAE achieved the highest amount of BSSG, in the shortest extraction time while preserving the integrity of the compound’s structure.

This study investigated the wound healing potential of Khaya senegalensis leaves through a comprehensive approach, including phytochemical, antioxidant, cytotoxicity, migration, and molecular docking analyses. Bioassay-guided isolation identified β-sitosterol and stigmasterol, with structures confirmed by NMR and FTIR analyses. Phytochemical screening revealed the presence of flavonoids, saponins, triterpenoids, tannins, and steroids, with solvent polarity significantly influencing composition. The ethyl acetate extract exhibited the strongest DPPH radical scavenging (IC₅₀ = 5.6 mg/mL). The methanol extract had the highest total phenolic content (198.8 mg GAE/g) while the ethyl acetate had the highest flavonoid content (1,228.1 mg QE/g). MTT assays confirmed the cytocompatibility of all extracts, fractions, and isolated compounds in HaCaT and HDF cells (>50% viability at ≤100 µg/mL). Scratch assays demonstrated significant, concentration-dependent wound closure, with optimal effects at 12.5 μg/mL. The most active fraction (1.2H) and subfractions (1.2.1H, 1.2.3H), as well as the isolated compounds, achieved complete wound closure in HDF cells within 24 hours. Molecular docking revealed strong binding of β-sitosterol and stigmasterol with TNF-α and GSK-3β, supporting their role in modulating inflammatory and proliferative pathways. These findings highlight Khaya senegalensis as a promising candidate for promoting wound repair, exerting antioxidant, cytocompatible, and pro-migratory effects.