Chitosan-coated soybean protein isolate/lecithin nanoparticles for enhancing the stability and bioaccessibility of phytosterol.

BACKGROUND: Phytosterols (PS) have various beneficial effects on human health, especially the property of reducing blood cholesterol. However, the low solubility and bioaccessibility of PS have greatly limited their application in functional food ingredients. RESULTS: To improve the bioaccessibility and stability of PS, chitosan-coated PS nanoparticles (CS-PNP) were successfully prepared by self-assembly. The properties of CS-PNP, including size, zeta potential, encapsulation efficiency (EE) and loading amount (LA) were characterised. The optimisation of CS concentration (0.4 mg mL-1) and pH (3.5) resulted in the formation of CS-PNP with an EE of over 90% and a particle size of 187.7 nm. Due to the special properties of CS chitosan, the interaction between CS and soybean protein isolate (SPI)/lecithin (SL) led to the formation of a soluble complex. CS-PNP exhibited good stability to temperature variations but was more sensitive to salt ions. During in vitro digestion, CS efficiently maintained the stability of nanoparticles against the hydrolysis of SPI by pepsin under acidic conditions. However, these nanoparticles tended to aggregate in a neutral intestinal environment. After 3 h of in vitro digestion, the bioaccessibility of PS increased from 18.2% of free PS to 63.5% of CS-PNP. CONCLUSION: Overall, these results highlight the potential of chitosan-coated nanoparticles as effective carriers for the oral administration of PS. This multilayer construction may serve as a promising for applications in food products as delivery vehicles for nutraceuticals. © 2024 Society of Chemical Industry.

In Situ Rapid Analysis of Squalene, Tocopherols, and Sterols in Walnut Oils Based on Supercritical Fluid Chromatography-Quadrupole Time-of-Flight Mass Spectrometry.

Quantification of liposoluble micronutrients in large-scale vegetable oil samples is urgently needed, because their health benefits are increasingly emphasized. However, current analytical methods are limited to either labor-intensive preparation processes or time-consuming chromatography separation. In this work, an online oil matrix separation strategy for direct, rapid, and simultaneous determination of squalene, tocopherols, and phytosterols in walnut oil (WO) was developed on the basis of the lipid class separation mode of supercritical fluid chromatography. A single run was completed in 13 min containing 6 min of column cleaning and balancing. Satisfactory limit of detections (0.05-0.20 ng/mL), limit of quantifications (0.15-0.45 ng/mL), recoveries (70.61-101.44%), and matrix effects (78.43-91.62%) were achieved, indicating the reliability of this method. In addition, eight sterol esters were identified in WO, which have not previously been reported. The proposed method was applied to characterize the liposoluble micronutrient profile of WO samples obtained from different walnut cultivars, geographical origins, and processes.

Effects of food formulation on bioavailability of phytosterols: phytosterol structures, delivery carriers, and food matrices.

Daily intake of phytosterols (PSs) as a diet supplement can lower blood-cholesterol levels and reduce the risks of cardiovascular diseases. However, the high crystallinity, low water solubility, easy oxidizability, and other characteristics of PSs restrict their application and bioavailability in food products. The formulation parameters including the structures of PSs, delivery carriers, and food matrices may play an important role in the release, dissolution, transport, and absorption of PSs in functional foods. In this paper, the effects of formulation parameters, including phytosterol structures, delivery carriers, and food matrices, on the bioavailability of phytosterols are summarized and suggestions are provided for the formulation design of functional foods. The side chain and hydroxyl esterification group of PSs may significantly affect their lipid or water solubilities and micellization capacities, which in turn affect the bioavailability of PSs. Selecting suitable delivery carriers based on the characteristics of the food system can reduce the crystallinity and oxidation of PSs and control the release of PSs, thereby improving the PS stability and delivery efficiency. Moreover, the ingredients of the carriers or food products would also influence the release, solubility, transport, and absorption of PSs in the gastrointestinal tract (GIT).

A novel method based on saponification coupled to micelle-extraction for recovering valuable bioactive compounds from soybean oil deodorizer distillate.

The feasibility of using saponification coupled to extraction with mixed micellar systems to recover bioactive compounds from soybean oil deodorizer distillate, was evaluated for the first time. Under the selected conditions, saponification with KOH 0.6 M and aqueous micellar system prepared with Tergitol 15-S-7 9% w/w, rhamnolipids 0.25 %w/w and sodium citrate 100 mM pH 5.00, at 65 °C, allow the recovery of almost 100% of α- and δ- tocopherols, and 90% of γ-tocopherols. LC-MS measurements demonstrated that the final extract also contained phytosterols and squalene. Additionally, the obtained extract preserved about 100% of the total antioxidant activity. This result was attributable to the fact that 93% of the tocopherols recovered in the micellar phases resulted to be associated with surfactant micelles, environment that is known to improve their antioxidant capacity. These results open perspectives to the use of this methodology to extract these valuable compounds from complex oily sources.

Production, Characterization, Delivery, and Cholesterol-Lowering Mechanism of Phytosterols: A Review.

Phytosterols are natural plant-based bioactive compounds that can lower blood cholesterol levels and help prevent cardiovascular diseases. Consequently, they are being utilized in functional foods, supplements, and pharmaceutical products designed to improve human health. This paper summarizes different approaches to isolate, purify, and characterize phytosterols. It also discusses the hypolipidemic mechanisms of phytosterols and their impact on cholesterol transportation. Phytosterols have a low water-solubility, poor chemical stability, and limited bioavailability, which limits their utilization and efficacy in functional foods. Strategies are therefore being developed to overcome these shortcomings. Colloidal delivery systems, such as emulsions, oleogels, liposomes, and nanoparticles, have been shown to be effective at improving the water-dispersibility, stability, and bioavailability of phytosterols. These delivery systems can be used to incorporate phytosterols into a broader range of cholesterol-lowering functional foods and beverages. We also discuses several issues that need to be addressed before these phytosterol delivery systems can find widespread commercial utilization.

Phytosterol oxidation products from coffee silverskin.

Coffee silverskin is a byproduct of the coffee roasting process contributing to organic waste burdens in urban areas. Silverskin is a potential source of dietary fiber, protein, carbohydrates, caffeine as well as vitamins and minerals. However, phytosterols present in the plant are susceptible to thermal oxidation resulting in the formation of phytosterol oxidation products (POPs) in the silverskin during roasting. In collaboration with a small roastery, the formation of POPs in three coffee varieties with roasting time was monitored by GC-MS. The objective was to evaluate the safety and potential benefits of incorporating coffee silverskin into value-added products. The qualitative profile of POPs in the silverskin from the three varieties was similar. Average total POPs were 0.32 g POPs/kg silverskin. POPs from the dominant plant sterol, sitosterol, were present at the highest concentrations. Caffeine, total antioxidant capacity, and total flavonoids were measured in the silverskin of the three coffees. Average values were 1.3 g caffeine/100 g silverskin, TEAC of 11 mmol Trolox/kg silverskin, and 1.94 to 8.60 mg catechin equivalent (CE)/g silverskin, respectively. An analysis of the impact of consuming teas and baked goods containing silverskin was also performed. Using published formulations, a tea or cookie containing silverskin would contribute approximately 1 and 0.3 mg POP per day, respectively. Consumption of these products would not substantially increase dietary exposure to POPs, while increasing fiber and antioxidants while reducing organic waste. PRACTICAL APPLICATION: Coffee silverskin has been studied as a possible source of fiber, antioxidants, and caffeine when incorporated in snack foods and used to make teas. To assess possible concerns about increasing dietary oxidized phytosterols, the formation of phytosterol oxidation products (POPs) was investigated in the silverskin fraction during the roasting process in three coffee varieties. In addition, caffeine, antioxidant capacity, and total flavonoids were determined. We found that silverskin can be safely used for value-added products including caffeinated teas, cookies, and bars with minimal impact on dietary POP exposures.

First report of compounds from an Ancistrocarpus species: Triterpenoids from A. densispinosus Oliv. (Malvaceae).

The stem bark of Ancistrocarpus densispinosus Oliv. exhibited triterpenoids, including the rare fernane-type, fern-9(11)-ene-2α,3ß-diol (1) a possible chemotaxonomically distinct biomolecule for the genus. Other triterpenoids that were isolated from this plant include the ursane-type ursolic acid (2) and corosolic acid (3), friedelane-type friedelin (4) and canophyllol (5), lupane-type lupeol (6), betulin (7), betulinic acid (8) and hennadiol (9), oleanoic acid (10), maslinic acid (11) and taraxerol (12) and three sterols. This is the first report of the chemistry of a plant of the Ancistrocarpus. The structures of the compounds were elucidated based on their NMR, IR and MS techniques and by comparisons of their experimental data with those reported. The twelve triterpenoids 1-12 were found to be inactive against five bacterial strains Escherichia coli, Bacillus subtilis, Pseudomonas agarici, Micrococcus luteus and Staphylococcus warneri; inactive against KB-3-1 cervix carcinoma cancer cell line and inactive as antioxidants in the DPPH assay.

Bioactive Molecules of Mandarin Seed Oils Diminish Mycotoxin and the Existence of Fungi.

Mandarin is a favorite fruit of the citrus family. Mandarin seeds are considered a source of nontraditional oil obtained from byproduct materials. This investigation aimed to assess the biomolecules of mandarin seeds and evaluated their antimycotic and antimycotoxigenic impact on fungi. Moreover, it evaluated the protective role of mandarin oil against aflatoxin toxicity in cell lines. The two types of extracted oil (fixed and volatile) were ecofriendly. The fatty acid composition, tocopherol, sterols, and carotenoids were determined in the fixed oil, whereas volatiles and phenolics were estimated in the essential oil. A mixture of the two oils was prepared and evaluated for its antimicrobial impact. The reduction effect of this mixture was also investigated to reduce mycotoxin secretion using a simulated experiment. The protective effect of the oil was evaluated using healthy strains of cell lines. Fixed oil was distinguished by the omega fatty acid content (76.24%), lutein was the major carotenoid (504.3 mg/100 g) and it had a high ß-sitosterol content (294.6 mg/100 g). Essential oil contained limonene (66.05%), α-pinene (6.82%), ß-pinene (4.32%), and γ-terpinene (12.31%) in significant amounts, while gallic acid and catechol were recorded as the dominant phenolics. Evaluation of the oil mix for antimicrobial potency reflected a considerable impact against pathogenic bacteria and toxigenic fungi. By its application to the fungal media, this oil mix possessed a capacity for reducing mycotoxin secretion. The oil mix was also shown to have a low cytotoxic effect against healthy strains of cell lines and had potency in reducing the mortality impact of aflatoxin B1 applied to cell lines. These results recommend further study to involve this oil in food safety applications.

Advances in Research on Food Bioactive Molecules and Health.

Fresh and processed food products are rich in bioactive molecules, including polysaccharides, vitamins, carotenoids, peptides, antioxidants, phenolics, phytosterols, and novel lipids. Bioactive molecules in food could prevent several diseases (i.e., metabolic syndrome, cardiovascular diseases, cancer, etc.). Thus, consumer awareness is growing about the health-promoting impact of food bioactive molecules. Health claims are essential added-value features, wherein health-enhancing potential of bioactives depend on their chemical structure. On the other hand, the investigation of the structure-function relationship of food bioactive molecules is of importance. In this regard, Molecules is delighted to highlight the importance of food bioactive molecules and their effect on health. In this Special Issue of Molecules, researchers are invited to contribute original research and up-to-date reviews.

Phytosterols: Potential Metabolic Modulators in Neurodegenerative Diseases.

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 ß-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.

New Steroidal Saponins Isolated from the Rhizomes of Paris mairei.

The genus Paris is an excellent source of steroidal saponins that exhibit various bioactivities. Paris mairei is a unique species and has been widely used as folk medicine in Southwest China for a long time. With the help of chemical methods and modern spectra analysis, five new steroidal saponins, pamaiosides A-E (1-5), along with five known steroidal saponins 6-10, were isolated from the rhizomes of Paris mairei. The cytotoxicity of all the new saponins was evaluated against human pancreatic adenocarcinoma PANC-1 and BxPC3 cell lines.

Chemical Composition and in vitro Anti-inflammatory Activity of Wheat Germ Oil Depending on the Extraction Procedure.

This study aimed to examine the chemical composition of wheat germ oil extracted by three different methods, and to evaluate its inhibitory effect on the cyclooxygenase and proteinase activities. The results showed that the contents of policosanols, tocopherols and phytosterols were affected by the extraction procedure. However, the fatty acid composition of the different oil extracts was nearly the same. Among the tested oils samples, cold pressed oil exhibited the strongest inhibitory activity against proteinase (93.4%, IC50 =195.7 µg/mL) and cyclooxygenase 1 (80.5%, IC50 =58.6 µg/mL). Furthermore, the cold pressed oil had the highest content of octacosanol, ß-sitosterol and α-linolenic acid, suggesting that those bioactive compounds could be essential for the potent ani-cyclooxygenase activity. The present data revealed that wheat germ oil contained cyclooxygenase and trypsin inhibitors, which are the promising therapeutic target for the treatment of various inflammatory diseases. Thus, wheat germ oil might be used to develop functional foods and pharmaceutic products for the human health.

Effects of Enzymatic Pretreatment of Seeds on the Physicochemical Properties, Bioactive Compounds, and Antioxidant Activity of Pomegranate Seed Oil.

Enzymatic pretreatment of seeds is a novel approach that enhances the health benefits of the extracted oil. The study investigated the influence of the enzymatic pretreatment of seeds on the quality of oil from different pomegranate cultivars. The quality of the ultrasound-assisted (and ethanol-extracted) oil was studied, with respect to the refractive index (RI), yellowness index (YI), conjugated dienes (K232), peroxide value (PV) ρ-anisidine value (AV), total oxidation value (TOTOX), total carotenoid content (TCC), total phenolic compounds (TPC), fatty acid composition, phytosterol composition, ferric reducing antioxidant power (FRAP), and 2.2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging capacity. The seeds of three different pomegranate cultivars ('Wonderful', 'Herskawitz', and 'Acco') were digested with an equal mixture of Pectinex Ultra SPL, Flavourzyme 100 L, and cellulase crude enzymes, at a concentration, pH, temperature, and time of 1.7%, 4.5, 40 °C, and 5 h, respectively. Enzymatic pretreatment of PS increased oil yield, PV, TPC, TCC, and DPPH radical scavenging capacity, but decreased the YI. The levels of K232, AV and TOTOX, fatty acids, phytosterols, RI, and FRAP, were not significantly affected by enzymatic pretreatment of PS. Principal component analysis (PCA) established that oil extracted from the 'Acco' seed after enzymatic pretreatment had higher yield, TPC, TCC, and DPPH radical scavenging capacity. Therefore, enzyme-pretreated 'Acco' pomegranate fruit seed is a source of quality seed oil with excellent antioxidant properties.

A Commercial Extract of Cyanotis arachnoidea Roots as a Source of Unusual Ecdysteroid Derivatives with Insect Hormone Receptor Binding Activity.

Ecdysteroids act as molting hormones in insects and as nonhormonal anabolic agents and adaptogens in mammals. A wide range of ecdysteroid-containing herbal extracts are available worldwide as food supplements. The aim of this work was to study such an extract as a possible industrial source of new bioactive ecdysteroids. A large-scale chromatographic isolation was performed from an extract of Cyanotis arachnoidea roots. Ten ecdysteroids (1-10) including eight new compounds were isolated and characterized by extensive nuclear magnetic resonance studies. Highly unusual structures were identified, including a H-14ß (1, 2, 4, and 10) moiety, among which a 14ß(H)17ß(H) phytosteroid (1) is reported for the first time. Compounds with an intact side chain (4-10) and 11 other natural or semisynthetic ecdysteroids (11-21) were tested for insect ecdysteroid receptor (EcR) binding activity. Two new compounds, i.e., 14-deoxydacryhainansterone (5) and 22-oxodacryhainansterone (6), showed strong EcR binding activity (IC50 = 41.7 and 380 nM, respectively). Six compounds were identified as EcR agonists and another two as antagonists using a transgenic ecdysteroid reporter gene assay. The present results demonstrate that commercial C. arachnoidea extracts are rich in new, unusual bioactive ecdysteroids. Because of the lack of an authentic plant material, the truly biosynthetic or artifactual nature of these compounds cannot be confirmed.

Differentiated 4,4-dimethylsterols from vegetable oils reduce fat deposition depending on the NHR-49/SCD pathway in Caenorhabditis elegans.

Consumption of 4-desmethylsterols has been claimed to have many beneficial effects, but the benefits of 4,4-dimethylsterols are less appreciated. We utilized a nematode model, Caenorhabditis elegans (C. elegans), to explore the anti-obesity effects of different classes of 4,4-dimethylsterols purified from rice bran oil (RST) and shea nut butter (SST). Both SST and RST significantly reduced fat deposition in C. elegans with smaller sizes and numbers of lipid droplets. But the food intake was not significantly affected. Metabolomics analysis indicated a significantly altered pathway after treatment with 4,4-dimethylsterols. Finally, it was found that 4,4-dimethylsterols targeted stearoyl-CoA desaturases (SCD) and nuclear hormone receptor-49 (NHR-49), resulting in a reduced desaturation index as proved by a lower ratio of oleic acid (C18:1n-9) to stearic acid (C18:0). Overall, 4,4-dimethylsterols can inhibit fat deposition via regulating the NHR-49/SCD pathway in C. elegans.

Microwave and Ultrasound Pretreatment of Moringa oleifera Lam. Seeds: Effects on Oil Expression, Oil Quality, and Bioactive Component.

This study investigates the application of green technologies (microwave and ultrasound pretreatment) in the extraction of Moringa oleifera Lam. seed oil and its effects on oil expression, oil quality, and bioactive component. Moringa seeds were pretreated with microwave (90 W, 60 s) or ultrasound (50 W, 1 h) before mechanical expression. A separate group received no pretreatment before oil extraction. Oils from these groups were then compared. Results show that oil yield increased with ultrasound pretreatment (1.24%) and significantly increased with microwave pretreatment (3.11%). For oil flow rate, the microwave and ultrasound pretreatment resulted in faster extraction (7.67 and 6.93 kg/h respectively) as compared with the control (6.51 kg/h). For physicochemical parameters, the microwave and ultrasound group had significantly less free fatty acids and significantly greater unsaponifiable matter as compared with the control. For fatty acid composition, results show that moringa seeds procured from Davao Oriental had greater oleic acid content (~77%) as compared with those reported by other literature. For phytosterol content, the predominant phytosterols found were ß-sitosterol, stigmasterol, and campesterol. Microwave and ultrasound pretreatment significantly increased total phytosterol (680.58 and 369.32 mg/kg respectively) as compared with the control (72.69 mg/kg) due to the mass transfer of the phytosterols. Microwave and ultrasound pretreatment also led to stigmastanol formation. For antioxidant activity, a comparison of both DPPH and FRAP assays depicts that the microwave group exhibited the best overall antioxidant activity. Lastly, for oil stability, a lower peroxide value was found in the microwave and ultrasound groups across time intervals, which may be attributed to their antioxidant activity. In summary, ultrasound and microwave pretreatment can improve oil expression, oil quality, and bioactive content of the mechanically expressed moringa oils.

Cloning and Production of Thermostable Enzymes for the Hydrolysis of Steryl Glucosides in Biodiesel.

Vegetable oil-derived biodiesels have a major quality problem due to the presence of precipitates formed by steryl glucosides, which clog filters and injectors of diesel engines. An efficient, scalable, and cost-effective method to hydrolyze steryl glucosides using thermostable enzymes has been developed. Here, methods to discover, express in recombinant microorganisms and manufacture enzymes with SGase activity, as well as methods to treat biodiesel with such enzymes, and to measure the content of steryl glucosides in biodiesel samples are presented.

Evaluation of Antioxidant and Enzyme Inhibition Properties of Croton hirtus L'Hér. Extracts Obtained with Different Solvents.

Croton hirtus L'Hér methanol extract was studied by NMR and two different LC-DAD-MSn using electrospray (ESI) and atmospheric pressure chemical ionization (APCI) sources to obtain a quali-quantitative fingerprint. Forty different phytochemicals were identified, and twenty of them were quantified, whereas the main constituents were dihydro α ionol-O-[arabinosil(1-6) glucoside] (133 mg/g), dihydro ß ionol-O-[arabinosil(1-6) glucoside] (80 mg/g), ß-sitosterol (49 mg/g), and isorhamnetin-3-O-rutinoside (26 mg/g). C. hirtus was extracted with different solvents-namely, water, methanol, dichloromethane, and ethyl acetate-and the extracts were assayed using different in vitro tests. The methanolic extracts presented the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS), and ferric reducing antioxidant power (FRAP) values. All the tested extracts exhibited inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with a higher activity observed for dichloromethane (AChE: 5.03 and BChE: 16.41 mgGALAE/g), while the methanolic extract showed highest impact against tyrosinase (49.83 mgKAE/g). Taken together, these findings suggest C. hirtus as a novel source of bioactive phytochemicals with potential for commercial development.

Anti-inflammatory effects of Ganoderma lucidum sterols via attenuation of the p38 MAPK and NF-κB pathways in LPS-induced RAW 264.7 macrophages.

Ganoderma lucidum exhibits pronounced anti-inflammatory effects, polysaccharides and triterpenoids are regarded as major constituents displaying the anti-inflammatory activities, whether sterols contribute to this activity remains unclear. Herein Ganoderma lucidum sterols (GLS) were innovatively isolated by a single-step procedure, the profile of GLS was characterized by HPLC-ELSD and shown similar to that of sterols separated by a traditional method, but much higher in content. Furthermore, GLS inhibited inflammation in macrophages by significantly attenuating LPS-induced cell polarization as well as releases and mRNA expressions of pro-inflammatory mediators NO, TNF-α, IL-1ß and IL-6. Moreover, the anti-inflammatory activity of GLS was mediated by MAPK and NF-κB pathways, GLS suppressed MAPK pathways by blocking phosphorylation of p38 but not ERK and JNK, which is complementary with inhibitory effects of Ganoderma polysaccharides and triterpenes on JNK and ERK, indicating Ganoderma sterols may exert synergistic anti-inflammatory effect with polysaccharides and triterpenes. GLS also inhibited NF-κB pathways by restraining phosphorylation and degradation of IκB-α and blocking phosphorylation of NF-κB p65. Molecular docking confirmed that sterols of GLS were directly bound to active sites of p38 and p65 to suppress their activation. Therefore, our findings suggest GLS as natural and safe anti-inflammatory agents to prevent and treat inflammatory diseases.

Antioxidant interaction of α-tocopherol, γ-oryzanol and phytosterol in rice bran oil.

In this study, purified rice bran oil (RBO) was used as a lipid matrix model to study the individual and binary antioxidant capacity of the minor constituents (α-tocopherol, γ-oryzanol and phytosterol) added at different concentrations and ratios. The results revealed that concentration influenced on the oxidation stability and scavenging capacity, while ratio mainly affected the type of interaction or the degree of synergism or antagonism. It was important to notice that the antioxidant capacity of α-tocopherol would decrease under high concentration. Besides, the inhibition of phytosterol on α-tocopherol and the formation of hydrogen bond between γ-oryzanol and phytosterol were speculated by the interactions of these minor constituents. This work helps to select efficient combinations for stabilizing the anti-oxidation of nutrient enriched RBO or provide suggestions for moderate retain of minor constituents in RBO.