Characterization, Stability and Antioxidant Activity of Vanilla Nano-Emulsion and Its Complex Essential Oil.

As a natural flavoring agent, vanilla essential oil has a special aroma and flavor, but its volatility and instability limit its value. Therefore, in this study, vanilla essential oil was compounded with cinnamon essential oil to prepare nano-emulsions (composite nano-emulsions called C/VT and C/VM), and the stability of the composite essential oil emulsions was investigated. Transmission electron microscopy (TEM) images showed that the nano-emulsions were spherical in shape and some flocs were observed in C/VM and C/VT. The results showed that the average droplet sizes of C/VM and C/VT increased only by 14.99% and 15.01% after heating at 100 °C for 20 min, and the average droplet sizes were less than 120 nm after 24 days of storage at 25 °C. Possibly due to the presence of reticulated flocs, which have a hindering effect on the movement of individual droplets, the instability indices of C/VM and C/VT were reduced by 34.9% and 39.08%, respectively, in comparison to the instability indices of C/VM and C/VT. In addition, the results of antioxidant experimental studies showed that the presence of composite essential oil flocs had no significant effect on the antioxidant capacity. These results indicate that the improved stability of the composite essential oil nano-emulsions is conducive to broadening the application of vanilla essential oil emulsions.

Encapsulation of rutin in protein nanoparticles by pH-driven method: impact of rutin solubility and mechanisms.

BACKGROUND: The use of rutin in the food industry is limited by its poor solubility. Encapsulation can be used as an effective way to improve polyphenol solubility. Proteins with high safety, biocompatibility and multiple binding sites are known as the most promising encapsulating carriers. Therefore, the improvement of rutin solubility by pH-driven encapsulation of rutin in soy protein isolate (SPI) nanoparticles, as well as the form of rutin after encapsulation and rutin-protein binding index were investigated. RESULTS: SPI had a high encapsulation efficiency (87.5%) and loading amount (10.6%) for rutin. When the mass ratio of protein to rutin was 5:1, the highest concentration of rutin in solution was 3.27 g L-1 , which was a 51.57-fold increase compared to the original rutin. At this situation, rutin transformed from crystalline to amorphous form. During the formation of nanoparticles, SPI was in a dynamic change of unfolding and refolding. Rutin deprotonated in alkaline conditions increasing its solubility and bound to protein to form nanoparticles during the process of returning to neutral. Hydrophobic interactions and hydrogen bonding promoted the formation of the nanoparticles and there were at least 1-2 binding sites between rutin and each SPI molecule. CONCLUSION: The results suggested that encapsulation of rutin in protein nanoparticles can effectively increase the solubility of rutin. This study may provide important information for the effective utilization of polyphenol functional foods. © 2023 Society of Chemical Industry.

Complex bio-nanoparticles assembled by a pH-driven method: environmental stress stability and oil-water interfacial behavior.

BACKGROUND: Protein-based nanoparticles have gained considerable interest in recent years due to their biodegradability, biocompatibility, and functional properties. However, nanoparticles formed from hydrophobic proteins are prone to instability under environmental stress, which restricts their potential applications. It is therefore of great importance to develop green approaches for the fabrication of hydrophobic protein-based nanoparticles and to improve their physicochemical performance. RESULTS: Gliadin/shellac complex nanoparticles (168.87 ~ 403.67 nm) with various gliadin/shellac mass ratios (10:0 ~ 5:5) were prepared using a pH-driven approach. In comparison with gliadin nanoparticles, complex nanoparticles have shown enhanced stability against neutral pH, ions, and boiling. They remained stable under neutral conditions at NaCl concentrations ranging from 0 to 100 mmol L-1 and even when boiled at 100 °C for 90 min. These nanoparticles were capable of effectively reducing oil-water interfacial tension (5 ~ 11 mNm-1 ) but a higher amount of shellac in the nanoparticles compromised their ability to lower interfacial tension. Moreover, the wettability of the nanoparticles changed as the gliadin/shellac mass ratio changed, leading to a range of three-phase contact angles from 52.41° to 84.85°. Notably, complex nanoparticles with a gliadin/shellac mass ratio of 8:2 (G/S 8:2) showed a contact angle of 84.85°, which is considered suitable for the Pickering stabilization mechanism. Moreover, these nanoparticles exhibited the highest emulsifying activity of 52.42 m2 g-1 and emulsifying stability of 65.33%. CONCLUSIONS: The findings of the study revealed that gliadin/shellac complex nanoparticles exhibited excellent resistance to environmental stress and demonstrated superior oil-water interfacial behavior. They have strong potential for further development as food emulsifiers or as nano-delivery systems for nutraceuticals. © 2023 Society of Chemical Industry.

Tannic acid delaying metabolism of resistant starch by gut microbiota during in vitro human fecal fermentation.

This work investigated the effect of tannic acid on the fermentation rate of resistant starch. It was found that 1.0 and 1.5 µmol/L tannic acid decreased the rate of producing gas and short-chain fatty acids (SCFAs) from fermentation of resistant starch, and 1.5 µmol/mL tannic acid had a more profound effect, which confirmed that tannic acid delayed the metabolism of resistant starch. Moreover, tannic acid significantly inhibited the α-amylase activity during fermentation. On the other hand, tannic acid delayed the enrichment of some starch-degrading bacteria. Besides, fermentation of the resistant starch/tannic acid mixtures resulted in more SCFAs, particularly butyrate, and higher abundance of beneficial bacteria, including Bifidobacterium, Faecalibacterium, Blautia and Dorea, than fermentation of resistant starch after 48 h. Thus, it was inferred that tannic acid could delay the metabolism of resistant starch, which was due to its inhibitory effect on the α-amylase activity and regulatory effect on gut microbiota.

The interaction and physicochemical properties of the starch-polyphenol complex: Polymeric proanthocyanidins and maize starch with different amylose/amylopectin ratios.

This study investigated the impact of polymeric proanthocyanidins (PPC) on the physicochemical characteristics of maize starch with varying amylose content, and their potential interaction mechanism. PPC with a lower content (1 %) reduced the viscoelasticity of the high amylose maize starch (HAM) system, inhibited amylose rearrangement, and enhanced its fluidity. However, excessive PPC restrained the interaction between PPC and amylose. In contrast to HAM, PPC improved the gelation ability of waxy maize starch (WAM) as PPC concentration was raised. PPC suppressed the recrystallization of starch during storage, and PPC had a superior inhibition influence on the retrogradation of WAM in comparison to HAM. This indicated that amylopectin was more likely to interact with PPC than amylose. Hydrogen bonds were the main driving force between PPC and starch chains, which was clarified by Fourier transform-infrared, nuclear magnetic resonance, X-ray diffraction, iodine bonding reaction, and dynamic light scattering data. Additionally, the mechanism of interaction between PPC and the two starch components may be similar, and variance in physicochemical attributes can be primarily credited to the percentage of amylose to amylopectin in starch.

Fermentation of resistant starch from the starch-ferulic acid inclusion complex compared with high-amylose corn starch.

Fermentation of resistant starch from the starch-ferulic acid inclusion complex, one representative of the starch-polyphenol inclusion complex, was investigated in this study. It was found that this complex-based resistant starch, high-amylose corn starch and the mixture of ferulic acid and high-amylose corn starch were mainly utilized at the initial 6 h as indicated by the gas production and pH. Besides, the supplement of high-amylose corn starch, the mixture and the complex promoted production of short-chain fatty acids (SCFAs), reduced the ratio of Firmicutes/Bacteroidetes (F/B) and selectively stimulated the proliferation of some beneficial bacteria. Specifically, the production of SCFAs in the control and high-amylose starch, mixture and complex groups was 29.33 mM, 140.82 mM, 144.12 mM, and 167.4 mM after fermentation for 48 h, respectively. Moreover, the F/B ratio of those groups was 1.78, 0.78, 0.8 and 0.69, respectively. These results suggested that the supplement of the complex-based resistant starch led to the most SCFAs and the lowest F/B ratio (P < 0.05). Moreover, the complex group had the largest abundance of beneficial bacteria, including Bacteroides, Bifidobacterium and Lachnospiraceae_UCG-001 (P < 0.05). In summary, the resistant starch from the starch-ferulic acid inclusion complex exhibited stronger prebiotic activity than high-amylose corn starch and the mixture.

ß-Cyclodextrin network crosslinked by novel phosphonium-based tetrakiscarboxylic acid derived from PH3 tail gas: Synthesis and application for rapid removal of organic dyes from wastewater.

Organic dyes, such as methyl orange (MO), Congo red (CR), crystal violet (CV) and methylene blue (MB), are common organic pollutants existing in wastewater. Therefore, the exploration of bio-based adsorbents for the efficient removal of organic dyes from wastewater has gained many attentions. Here, we report a PCl3-free synthetic method for the synthesis of phosphonium-containing polymers, in which the prepared tetrakis(2-carboxyethyl) phosphonium chloride-crosslinked ß-cyclodextrin (TCPC-ß-CD) polymers were applied to the removal of dyes from water. The effects of contact time, pH (1-11), and dye concentration were investigated. The selected dye molecules could be captured by the host-gest inclusion of ß-CD cavities, and the phosphonium and carboxyl groups in the polymer structure would respectively facilitate the removal of cationic dyes (MB and CV) and anionic dyes (MO and CR) via electrostatic interactions. In a mono-component system, over 99 % of MB could be removed from water within the first 10 min. Based on the Langmuir model, the calculated maximum adsorption capacities of MO, CR, MB, and CV were 180.43, 426.34, 306.57, and 470.11 mg/g (or 0.55, 0.61, 0.96 and 1.15 mmol/g), respectively. Additionally, TCPC-ß-CD was easily regenerated using 1 % HCl in ethanol, and the regenerative adsorbent still showed high removal capacities for MO, CR, and MB even after seven treatment cycles.

Investigation of bovine ß-lactoglobulin-procyanidin complexes interactions and its utilization in O/W emulsion.

Procyanidins are bioactive polyphenols that have a strong affinity to proteins. Beta-lactoglobulin (BLG) is widely used as an emulsifier in the food and other industries. This study evaluated the interaction between BLG and A-type procyanidin dimer (PA2) using the spectroscopic, thermodynamic, and molecular simulation. PA2 decreased the transmissivity and quenched the intrinsic fluorescence of BLG, suggesting that the two molecules formed a complex. The binding of PA2 reduced the surface hydrophobicity and altered the conformation of BLG with increasing the random coil regions. Thermodynamic and isothermal titration calorimetry analyses suggested that the main driving force of PA2-BLG interaction was hydrophobic attraction. Molecular docking simulations were used to identify the main interaction sites and forces in the BLG-PA2 complexes, which again indicated that hydrophobic interactions dominated. In addition, the influence of PA2 on the ability of BLG to form and stabilize O/W emulsions was analyzed. Emulsions formulated using BLG-PA2 complexes contained relatively small droplets (D4,3 ≈ 0.7 µm) and high surface potentials (absolute value >50 mV). Compared to BLG alone, BLG-PA2 complexes improved the storage stability of the emulsions. This study provides valuable new insights into the formation, properties, and application of protein-polyphenol complexes as functional ingredients in foods.

Improving shikonin solubility and stability by encapsulation in natural surfactant-coated shikonin nanoparticles.

It is significant to develop a colloidal delivery system to improve the water solubility, stability, and bioavailability of shikonin, which is a hydrophobic plant polyphenol with a variety of physiological activities. In this study, three kinds of natural surfactants (saponin, sophorolipid, and rhamnolipid) were used to prepare shikonin nanoparticles by the pH-driven method. The physicochemical and structural properties of the shikonin nanoparticles were characterized, including particle size, zeta potential, and morphology. The encapsulation efficiencies of shikonin nanoparticles coated with saponin and sophorolipid were 97.6% and 97.3%, respectively, which were much higher than that of rhamnolipid-coated shikonin nanoparticles (19.0%). Shikonin nanoparticles coated with saponin and sophorolipid showed good resistance to heat and light and maintained long-term stability during storage. Moreover, shikonin nanoparticles coated with saponin and sophorolipid improved their in vitro-bioavailability. PRACTICAL APPLICATION: These article results are of great importance for improving the stability and bioavailability of shikonin in functional foods, dietary supplements, or pharmaceutical preparations. Moreover, this study provided theoretical and practical guides for further research of shikonin nanoparticles and may promote the development of natural colloidal delivery systems.

Comparative Investigation on the Phytochemicals and Biological Activities of Jackfruit (Artocarpus heterophyllus Lam.) pulp from Five Cultivars.

Jackfruit is one of the major tropical fruits, but information on the phytochemicals and biological benefits of its pulp is limited. In this study, the phytochemicals and biological activities including antioxidant, antitumor and anti-inflammatory activities of five jackfruit pulp cultivars (M1, M2, M3, M7 and T5) were comparatively investigated. A total of 11 compounds were identified in all cultivars of jackfruit pulp, among which 4-hydroxybenzoic acid, caffeic acid, ferulic acid and tryptophan N-glucoside were reported for the first time in jackfruit. T5 exhibited the highest total phenolic content (7.69 ± 0.73 mg GAE/g DW), antioxidant capacity (109.8, 96.7 and 207 mg VCE/g DW for DPPH, ABTS and FRAP, respectively), antitumor activity (80.31%) and anti-inflammatory activity (78.44%) among five cultivars. These results can provide a reference for growers to choose jackfruit cultivar and offer an insight into the industrial application of jackfruit pulp derived-products.

Effects of cell wall polysaccharides on the bioaccessibility of carotenoids, polyphenols, and minerals: an overview.

Carotenoids, polyphenols, and minerals (CPMs) are representative bioactive compounds and micronutrients in plant-based foods, showing many potentially positive bioactivities. Bioaccessibility is a prerequisite for bioactivities of CPMs. Cell wall polysaccharides (CWPs) are major structural components of plant cell wall, and they have been proven to affect the bioaccessibility of CPMs in different ways. This review summarizes recent literatures about the effects of CWPs on the bioaccessibility of CPMs and discusses the potential mechanisms. Based on the current findings, CWPs can inhibit the bioaccessibility of CPMs in gastrointestinal tract. The effects of CWPs on the bioaccessibility of polyphenols and minerals mainly attributes to bind between them, while CWPs affect the bioaccessibility of carotenoids by changing the digestive environment. Further, this review overviews the factors (environmental conditions, CWPs properties and CPMs characteristics) affecting the interactions between CWPs and CWPs. This review may help to better design healthy and nutritious foods precisely.

Impact of starch-lipid complexes on oil absorption of starch and its mechanism.

BACKGROUND: Worldwide, fried food has a huge demand and good development prospects. Low oil in foods is the standard that everyone is now pursuing for a healthy diet. RESULTS: The oil absorption behavior of rice starch during frying was investigated in the presence or absence of fatty acids or fatty acid esters with different carbon chain lengths. The complex formed between starch and fatty acids or fatty acid esters was dependent on lipid chain length, which was confirmed by X-ray diffraction and complexing index. The formation of starch-lipid complexes could significantly reduce the oil absorption of starch, and the complexes with higher complexing index had lower oil absorption. The starch-palmitic acid complex showed the lowest oil absorption after frying, which was 14.06 g per 100 g lower than that of gelatinized starch. This was attributed to the ability of the palmitic acid to increase the density of starch crystalline polymorphs as well as their ability to complex with the amylose spiral cavity. CONCLUSION: These results may be useful for development of healthier fried starch-based foods with reduced oil contents. © 2022 Society of Chemical Industry.

Degradation kinetics of rutin encapsulated in oil-in-water emulsions: impact of particle size.

BACKGROUND: Rutin is a natural bioactive flavonoid that is poor in water solubility and chemical stability. Encapsulation can be used to protect bioactive molecules from chemical or physical decomposition during food processing and storage. Thus, the effect of initial particle size on the ability of oil-in-water emulsions to retain rutin during storage was investigated. RESULTS: Rutin was encapsulated in oil-in-water emulsions with different mean surface-weighted diameters: d3,2  = 0.56 µm (small), 0.73 µm (medium), and 2.32 µm (large). As expected, the resistance of the emulsions to coalescence and creaming during storage increased as the particle size decreased due to weakening of the colloidal and gravitational forces acting on the droplets. The concentration of rutin in the emulsions decreased during storage (28 days), which was mainly attributed to photodegradation of the flavonoid. The loss of rutin from the emulsions during storage was fitted using a second-order equation. The rutin degradation rate constant k decreased and the half-life t1/2 increased with decreasing droplet size, which was attributed to the stronger encapsulation and light scattering by smaller oil droplets reducing the amount of light that can penetrate into the emulsions. CONCLUSION: This study has important implications for the design of more efficacious emulsion-based delivery systems for incorporating health-promoting nutraceuticals into foods. © 2022 Society of Chemical Industry.

Characterization of a novel squalene-rich oil: Pachira macrocarpa seed oil.

Pachira macrocarpa is a woody oil crop with high economic and ornamental value. Although P. macrocarpa seeds are rich in oil, little information has been reported about its characterization. In this study, the fatty acids, minor components (tocopherols, squalene, phytosterols, and total phenols), antioxidant activity, cytotoxicity, thermal, and rheological behavior of the P. macrocarpa seed oil (PSO) were investigated for the first time. The results showed that the seeds contained 43.34% lipid, which was mainly composed of palmitic acid (49.96%), linoleic acid (31.22%), and oleic acid (13.48%). The contents of tocopherols, squalene, phytosterols, and total phenols in PSO were 42.01 mg/100 g, 96.78 mg/100 g, 119.67 mg/100 g, and 3.79 mg GAE/100 g, respectively. PSO showed relatively strong DPPH radical scavenging capacity (93.47 µmol TE/100 g) and high melting point (20.8°C). In addition, the oil exhibited Newtonian flow behavior and was not toxic to normal L929 cells at concentrations of 500-8000 µg/ml. As a whole, PSO may be considered as a valuable source for new multipurpose products for industrial utilization. PRACTICAL APPLICATION: Pachira macrocarpa is a woody oil crop and its seeds are rich in oil. Our study has investigated the physicochemical properties and chemical composition of the P. macrocarpa seed oil (PSO). The present study revealed PSO had potential as an edible oil, and it may be considered as a valuable source for new multipurpose products for food industrial utilization.

Physicochemical, structural, and functional properties of protein fractions and protein isolate from jackfruit seeds.

The physicochemical, structural, and functional properties of albumin, globulin, glutelin, and protein isolate (JSPI) extracted from jackfruit seeds were investigated. Protein fractions and JSPI were rich in amino acids, which can be comparable to soy protein. Other essential amino acids except histidine met the FAO/WHO/UNO-recommended intake for infants and adults. Jackfruit seed proteins were mainly composed of 17-26 kDa polypeptides, ß-sheet, and random coil were the main secondary structures. Glutelin (572.55) and JSPI (246.14) have higher H0 under neutral conditions, consistent with the solubility and emulsification properties results. Albumin and globulin had good solubility and were mostly soluble under neutral or weak alkaline conditions. In general, protein fractions and JSPI exhibited good foaming and emulsification properties. Therefore, jackfruit seed proteins have the potential to be nutritious functional ingredients in the food industry. PRACTICAL APPLICATION: Jackfruit seed proteins had high essential amino acids content and good functional properties. They can be used as a new type of functional ingredients in the food industry, which can not only reduce the environment pollution of discarded seeds but also improve use of plant protein.

Synergistic Anti-Inflammatory Effects of Lipophilic Grape Seed Proanthocyanidin and Camellia Oil Combination in LPS-Stimulated RAW264.7 Cells.

Combination drug therapy has become an effective strategy to control inflammation. Lipophilic grape seed proanthocyanidin (LGSP) and camellia oil (CO) have been independently investigated to show anti-inflammatory effects, but their synergistic anti-inflammatory effects are unknown. The aim of this study was to investigate the synergistic anti-inflammatory effects of LGSP and CO. The anti-inflammatory activity of LGSP and CO individual or in combination on RAW264.7 cells was detected by MTT assay, Griess reagent, RT-PCR, 2',7'-dichlorfluoroescein diacetate and Western blot analysis. The combined treatment of LGSP with CO (20 µg/mL and 1 mg/mL) synergistically suppressed the production of NO, TNF-α, IL-6 and ROS. Further studies showed that the synergistic effect was attributed to their suppression of the activation of NF-κB and MAPK signaling pathways. Overall, our findings demonstrate the potential synergistic effect between LGSP and CO in LPS-induced inflammation.

Lipophilic Grape Seed Proanthocyanidin Exerts Anti-Cervical Cancer Effects in HeLa Cells and a HeLa-Derived Xenograft Zebrafish Model.

Lipophilic grape seed proanthocyanidin (LGSP) synthesized from GSP and lauric acid exhibits an excellent antioxidant and anti-inflammatory effect. However, its anti-cervical cancer activity is still unknown. In this study, the in vitro anti-cervical cancer activity of LGSP on HeLa cell lines was investigated by MTT assay, flow cytometry and Western blot analysis, and its effect was explored by a HeLa-derived xenograft zebrafish model. LGSP exhibited an excellent anti-proliferative effect on HeLa cells by increasing the level of reactive oxygen species, which further induced cell apoptosis and blocked cell cycle progression in the G2/M phase. LGSP-treated HeLa cells showed a reduction in mitochondrial membrane potential, upregulation of the Bax/Bcl-2 ratio, release of cytochrome c into the cytoplasm, and activation of cleaved caspase-9/3 and cleavage of PARP, thus indicating that LGSP induced apoptosis through the intrinsic mitochondrial/caspase-mediated pathway. In the zebrafish model, LGSP effectively suppressed the growth of a HeLa xenograft tumor. These data suggest that LGSP may be a good candidate for the prevention or treatment of cervical cancer.

Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus.

Puniceusines A-N (1-14), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of 9 was determined by ECD calculations, and the structures of 6 and 12 were further confirmed by a single-crystal X-ray diffraction analysis. Compounds 3-5 and 8-13 unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds 3 and 4 showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC50 values of 8.4 and 5.6 µM, respectively, 4 also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC50 value of 11.0 µM, and 14, which contained an active center, -C=N+, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of 1-14 revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity.

Improving foam performance using colloidal protein-polyphenol complexes: Lactoferrin and tannic acid.

In this study, colloidal complexes were prepared from bovine lactoferrin (BLF) and tannic acid (TA) and then their ability to form and stabilize foams was characterized. The molecular interactions between BLF and TA were studied using fluorescence and molecular docking analysis, which suggested that hydrophobic forces were primarily involved in holding the complexes together. The production of colloidal BLF-TA complexes was supported by increases in turbidity and mean particle diameter, quenching of intrinsic fluorescence, decrease in surface hydrophobicity, and change in conformation. When used alone, BLF exhibited good foam formation but poor foam stability properties. In contrast, BLF-TA complexes exhibited good foam stability but poor foamability properties. The change in foaming properties of the proteins was closely related to their interactions with the polyphenols. These findings may be useful for the development of novel functional ingredients to construct food foams with good physicochemical and nutritional attributes.

Comparative Study of Chemical Compositions and Antioxidant Capacities of Oils Obtained from 15 Macadamia (Macadamia integrifolia) Cultivars in China.

The planting area of macadamia in China accounted for more than one third of the world's planted area. The lipid compositions, minor components, and antioxidant capacities of fifteen varieties of macadamia oil (MO) in China were comparatively investigated. All varieties of MO were rich in monounsaturated fatty acids, mainly including oleic acid (61.74-66.47%) and palmitoleic acid (13.22-17.63%). The main triacylglycerols of MO were first time reported, including 19.2-26.1% of triolein, 16.4-18.2% of 1-palmitoyl-2,3-dioleoyl-glycerol, and 11.9-13.7% of 1-palmitoleoyl-2-oleoyl-3-stearoyl-glycerol, etc. The polyphenol, α-tocotrienol and squalene content varied among the cultivars, while Fuji (791) contained the highest polyphenols and squalene content. Multiple linear regression analysis indicated the polyphenols and squalene content positively correlated with the antioxidant capacity. This study can provide a crucial directive for the breeding of macadamia and offer an insight into industrial application of MO in China.