Multiscale structure changes and mechanism of polyphenol-amylose complexes modulated by polyphenolic structures.

This study was designed to investigate the effect of polyphenolic structure on the interaction strength and process between polyphenols (gallic acid (GA), epigallocatechin gallate (EGCG) and tannic acid (TA)) and amylose (AM). The results of Fourier transform infrared spectroscopy, isothermal titration calorimetry, X-ray photoelectron spectroscopy and molecular dynamic simulation (MD) suggested that the interactions between the three polyphenols and AM were noncovalent, spontaneous, low-energy and driven by enthalpy, which would be enhanced with increasing amounts of pyrogallol groups in the polyphenols. The results of turbidity, particle size and appearance of the complex solution showed that the interaction process between polyphenols and AM could be divided into three steps and would be advanced by increasing the number of pyrogallol groups in the polyphenols. At the same time, MD was intuitively employed to exhibit the interaction process between amylose and polyphenols, and it revealed that the interaction induced the aggregation of amylose and that the agglomeration degree of amylose increased with increasing number of pyrogallol groups at polyphenols. Last, the SEM and TGA results showed that TA/AM complexes had the tightest structure and the highest thermal stability (TA/AM˃EGCG/AM˃GA/AM), which could be attributed to TA having five pyrogallol groups.

Dietary sinensetin and polymethoxyflavonoids: Bioavailability and potential metabolic syndrome-related bioactivity.

Sinensetin is among the most ubiquitous polyphenols in citrus fruit and recently has been extensively studied for its ability to prevent or treat diseases. The current literature on the bioavailability of sinensetin and its derivatives was reviewed and the potential ameliorative effects of metabolic syndrome in humans were evaluated. Sinensetin and its derivatives mainly aggregated in the large intestine and extensively metabolized through gut microbiota (GM) and the liver. So intestinal microorganisms had a significant influence on the absorption and metabolism of sinensetin. Interestingly, not only GM acted on sinensetin to metabolize them, but sinensetin also regulated the composition of GM. Thus, sinensetin was metabolized as methyl, glucuronide and sulfate metabolites in the blood and urine. Furthermore, sinensetin was reported to have the beneficial effect of ameliorating metabolic syndromes, including disorders of lipid metabolism (obesity, NAFLD, atherosclerosis), glucose metabolism disorder (insulin resistant) and inflammation, in terms of improving the composition of intestinal flora and modulating metabolic pathway factors in relevant tissues. The present work strongly elucidated the potential mechanism of sinensetin in improving metabolic disorders and supported the contribution of sinensetin to health benefits, thus offering a better perspective in understanding the role played by sinensetin in human health.

Biological Activities and Solubilization Methodologies of Naringin.

Naringin (NG), a natural flavanone glycoside, possesses a multitude of pharmacological properties, encompassing anti-inflammatory, sedative, antioxidant, anticancer, anti-osteoporosis, and lipid-lowering functions, and serves as a facilitator for the absorption of other drugs. Despite these powerful qualities, NG's limited solubility and bioavailability primarily undermine its therapeutic potential. Consequently, innovative solubilization methodologies have received considerable attention, propelling a surge of scholarly investigation in this arena. Among the most promising solutions is the enhancement of NG's solubility and physiological activity without compromising its inherent active structure, therefore enabling the formulation of non-toxic and benign human body preparations. This article delivers a comprehensive overview of NG and its physiological activities, particularly emphasizing the impacts of structural modification, solid dispersions (SDs), inclusion compound, polymeric micelle, liposomes, and nanoparticles on NG solubilization. By synthesizing current research, this research elucidates the bioavailability of NG, broadens its clinical applicability, and paves the way for further exploration and expansion of its application spectrum.

Novel Umami-, Salty-, and Kokumi-Enhancing γ-Glutamyl Tripeptides Synthesized with the Bitter Dipeptides from Defatted Peanut Meal Protein Hydrolysate.

Defatted peanut meal protein hydrolysates (DPMHs) usually have a bitter taste. γ-Glutamylation by Bacillus amyloliquefaciens l-glutaminase was introduced to DPMH to reduce its bitterness and generated a γ-glutamylated product (DPMH-G). Extra l-glutamine (l-Gln) (5% w/w) was added to DPMH, and the mixture was then γ-glutamylated (DPMH-G-Q). Results showed that γ-glutamylation decreased the bitterness of the products and also enhanced their kokumi, umami, and salty taste, especially for DPMH-G-Q. Bitter amino acids and bitter peptides were found to be substrates (acceptors) of the synthesized γ-[Glu](1,2)-AAs and γ-Glu-AA-AAs, respectively. The production yield of γ-[Glu](1,2)-AAs was only 0.69/100 g for DPMH-G and 2.30/100 g for DPMH-G-Q, which was much lower than that of γ-Glu-AA-AAs (5.73/100 g for DPMH-G and 18.72/100 g for DPMH-G-Q). The improvement in taste attributes of DPMH might mainly be due to the consumption of bitter dipeptides and the production of γ-Glu-AA-AAs. In DPMH-G-Q, eight γ-Glu-AA-AAs were identified, including γ-Glu-Ile-Lys, γ-Glu-Ala-Ile, γ-Glu-Leu-Leu, γ-Glu-Phe-Leu, γ-Glu-Thr-Leu, γ-Glu-Ile-Met, γ-Glu-Val-Leu, and γ-Glu-Ser-Tyr, which were first time reported. They all can enhance umami, salty, and kokumi taste with a threshold value between 1.61 ± 0.21-2.16 ± 0.19, 1.65 ± 0.19-2.23 ± 0.20, and 0.67 ± 0.21-1.00 ± 0.22 mM, respectively. Insufficient l-Gln restricted the formation of γ-glutamyl peptides, and this was why DPMH-G had a lower yield and variety than DPMH-G-Q. This also suggested that l-glutaminase is selective to different substrates. Overall, this study provides a new method to reduce the bitterness of protein hydrolysates and also improve the taste by synthesizing γ-glutamyl tripeptides.

Composition, functional properties and safety of honey: a review.

Honey has been used not only as a food source but also for medicinal purposes. Recent studies have indicated that honey exhibits antioxidant, hepatoprotective, hypolipidemic, hypoglycemic and anti-obesity properties, as well as anticancer, anti-atherosclerotic, hypotensive, neuroprotective and immunomodulatory activities. These health benefits of honey could be attributed to its wide range of nutritional components, including polysaccharides and polyphenols, which have been proven to possess various beneficial properties. It is notable that the composition of honey can also be affected by nectar, season, geography and storage condition. Moreover, the safety of honey requires caution to avoid any potential safety incidents. Therefore, this review aims to provide recent research regarding the chemical composition, biological activities and safety of honey, which might be attributed to comprehensive utilization of honey. © 2023 Society of Chemical Industry.

Effect of polyphenolic structure and mass ratio on the emulsifying performance and stability of emulsions stabilized by polyphenol-corn amylose complexes.

O/W emulsions stabilized by polyphenol/amylose (AM) complexes with several polyphenol/AM mass ratios and different polyphenols (gallic acid (GA), epigallocatechin gallate (EGCG) and tannic acid (TA)) were prepared by a high-intensity ultrasound emulsification technique. The effect of the pyrogallol group number of polyphenols and the mass ratio of polyphenols/AM on polyphenol/AM complexes and emulsions was studied. The soluble and/or insoluble complexes gradually formed upon adding polyphenols into the AM system. However, insoluble complexes were not formed in the GA/AM systems because GA has only one pyrogallol group. In addition, the hydrophobicity of AM could also be improved by forming polyphenol/AM complexes. The emulsion size decreased with increasing pyrogallol group number on the polyphenol molecules at a fixed ratio, and the size could also be controlled by the polyphenol/AM ratio. Moreover, all emulsions presented various degrees of creaming, which was restrained by decreasing emulsion size or the formation of a thick complex network. The complex network was enhanced by increasing the ratio or pyrogallol group number on the polyphenol molecules, which was because the increasing number of complexes was adsorbed onto the interface. Altogether, compared to GA/AM and EGCG/AM, the TA/AM complex emulsifier had the best hydrophobicity and emulsifying properties, and the TA/AM emulsion had the best emulsion stability.

Synergistic Effect of Kokumi-Active γ-Glutamyl Peptides and l-Glutamate on Enhancing Umami Sensation and Stimulating Cholecystokinin Secretion via T1R1/T1R3 Activation in STC-1 Cells.

This study aimed to investigate the synergistic effect of γ-glutamyl peptides (γEL, γEV, and γEγEV) and l-glutamate (MSG) on the activation of the umami receptor (T1R1/T1R3) in relation to enhanced umami taste and promoted cholecystokinin (CCK) secretion. The synergy of γ-glutamyl peptides and MSG (1-15 mM, 1:1) caused a significant increase in both the umami taste score by 0.218 ± 0.015-1.216 ± 0.031 times and the CCK secretion by 41.41 ± 6.46-201.16 ± 12.91% when compared to the group treated with individual MSG. The increase in CCK secretion promoted by γ-glutamyl peptides was only reduced by 11.54 ± 0.01-45.65 ± 3.58% after adding yjr CaSR inhibitor (NPS 2143), implying that there were other receptors besides CaSR involved in the stimulation of CCK secretion. The mixture of γEγEV and MSG synergistically increased the intracellular calcium release by 111.26 ± 11.94-135.28 ± 16.60% in STC-1 and 108.47 ± 7.89-152.33 ± 26.26% in HEK 293 compared to MSG. The protein expression for T1R1/T1R3 was increased, indicating that the mixture can activate T1R1/T1R3. The amino acids V277, S147, and D190 of T1R3 can be critical for the binding of γEγEV to T1R3. This is the first report on the synergistic effect of taste-active substances on taste sensation and hormone release via taste receptor activation.

Identification of EGFR-Related LINC00460/mir-338-3p/MCM4 Regulatory Axis as Diagnostic and Prognostic Biomarker of Lung Adenocarcinoma Based on Comprehensive Bioinformatics Analysis and Experimental Validation.

Background: Lung adenocarcinoma (LUAD) is one of the most aggressive and lethal tumor types and requires effective diagnostic and therapeutic targets. Though the epidermal growth factor receptor (EGFR) is an important target for LUAD therapy, acquired resistance is still inevitable. In recent years, the regulation of the EGFR by competing endogenous RNAs (ceRNAs) has been extensively studied and significant progress has been made. Therefore, we aim to find new targets for the diagnosis and treatment of LUAD by analyzing the EGFR-related ceRNA network in LUAD and expect to address the problem of EGFR resistance. Methods: We identified differentially expressed lncRNAs, miRNAs and mRNAs closely associated with the EGFR by analyzing transcriptome data from LUAD samples. Comprehensive bioinformatics analysis strongly suggests that the LINC00460-mir-338-3p-MCM4 ceRNA network plays an important role in the diagnosis and prognosis of LUAD. The effects of different patterns of the LINC00460/MCM4 axis on the overall survival of patients with LUAD were analyzed by a polygene regulation model. We also verified the expression of these genes in LUAD cell lines and tumor tissues by RT-PCR and immunohistochemistry. The functional enrichment analysis and targeted drug prediction of the MCM4 gene were performed. Results: Survival analysis indicated that high expressions of LINC00460 and MCM4 predict a shorter survival period for patients. Univariate and multivariate regression analyses demonstrated that higher expressions of LINC00460 and MCM4 were significantly associated with tumor size, lymph node metastasis, distant metastasis and TNM stage. A multi-gene regulation model analysis revealed that the LINC00460 (downregulation)-mir-338-3p (upregulation)-MCM4 (downregulation) pattern significantly improved the overall survival of LUAD patients (p = 0.0093). RT-PCR and immunohistochemical experiments confirmed our analytical results. In addition, the functional enrichment analysis indicated that MCM4-related genes were mainly enriched in the cell cycle and cell division. A functional association network analysis showed that MCM4 was closely related to the EGFR. Finally, the possible targeted drugs of MCM4 were queried through the drug database platform, hoping to solve its drug resistance problem by targeting EGFR-related genes. Conclusions: In summary, the LINC00460/MCM4 axis can be used as a potential new perspective for targeting EGFR genes in precision medicine and is expected to serve as a diagnostic, prognostic and drug target for LUAD.

Identification and comparison of umami-peptides in commercially available dry-cured Spanish mackerels (Scomberomorus niphonius).

Dry-cured Spanish mackerel (DSM; Scomberomorus niphonius) is a popularity worldwide dry-cured marine fish product due to its salty and umami flavor. Umami peptides from eight commercial DSMs were identified and compared, and their molecular mechanisms were evaluated via molecular simulation. The results showed that the sequence of peptides varied in different DSMs, wherein only ten sequences were repeated across multiple samples and the remaining 19 were detected in only one sample. The sensory characteristics of eight repeated peptides were evaluated, and four were found to exhibit umami taste and umami-enhancing effects, including Arg-Asp, Asp-Gly-Val, Asp-Arg, and Asp-Lys. They all had a strong affinity for umami receptors, and several amino acid residues of the receptors were mobilized as binding sites to form hydrogen bonds and hydrophobic bonds in ligand-receptor interactions. These results indicated that DSM was rich in umami and umami-enhancing peptides, but their sequence were different in different DSMs.

Lemon essential oil/vermiculite encapsulated in electrospun konjac glucomannan-grafted-poly (acrylic acid)/polyvinyl alcohol bacteriostatic pad: Sustained control release and its application in food preservation.

Lemon essential oils (LEO), as natural bacteriostatic agents, show significant loss in the preparation processes of food packaging materials, therefore, an effective encapsulation of LEO is urgent for realizing the protection. In this study, LEO was absorbed by thermally stable and porous vermiculite (VML) to form LEO/VML complex, which is further coupled with konjac glucomannan-grafted-poly (acrylic acid)/polyvinyl alcohol (KGM-g-PAA/PVA) composite. KGM-g-PAA/PVA bacteriostatic water-absorbing pad was prepared via electrospinning technique, which can minimize the loss of LEO. The VML (1 g) can significantly reduce LEO loss and achieve sustained control LEO release from the pad, which follows the predominant mechanism of Fick diffusion law. The sustained control LEO release from the pad can effectively inhibit the growth of E. coli during storage, thus prolonging shelf life of chilled pork for 3 day. This study suggests that KGM-g-PAA/PVA pad may have a great potential in the field of intelligent packaging.

Potential carcinogenic heterocyclic aromatic amines (HAAs) in foodstuffs: Formation, extraction, analytical methods, and mitigation strategies.

During the heat treatment of proteinaceous food, heterocyclic aromatic amines (HAAs), a kind of strong mutagens/carcinogens are formed. HAAs can be classified into two major groups based on the heating temperature, which are thermic HAAs generally formed in 150 to 300 °C and pyrolytic HAAs produced above 300 °C. This review focuses on the formation mechanisms of HAAs and identifies different mechanisms of the formation of HAAs in foodstuffs. Moreover, an overview of the available extraction, purification methods, and instrumental analytical methods in the last two decades is shown to determine the HAAs in various foodstuffs. Finally, based on the factors that affect the formation of HAAs in heat-processed foodstuffs, such as the cooking method, food type, the recipe, and the content of substances with enhancing or inhibiting effects on the formation of HAAs, this review also highlights the most promising strategies for mitigating HAAs, which include adjusting cooking methods or process conditions, adding natural product extracts, antioxidants or other compounds, or reasonable selection of types of foodstuff. The review intends to provide a broad but comprehensive understanding of the formation, extraction, purification, analytical methods, and possible mitigation strategies for isolated and identified HAAs.

γ-[Glu](n=1,2)-Phe/-Met/-Val stimulates gastrointestinal hormone (CCK and GLP-1) secretion by activating the calcium-sensing receptor.

This study was conducted to discover the effectiveness of dietary peptides (γ-[Glu](n=1,2)-Phe/-Met/-Val) as stimulators of cholecystokinin (CCK) and glucagon-like peptide 1 (GLP-1) secretion. The kokumi-active γ-[Glu](n=1,2)-Phe/-Met/-Val at concentrations of 2.5-10 mM would trigger the release of CCK and GLP-1 by activating the calcium-sensing receptor (CaSR). The CaSR-mediated Ca2+/CaM/CaMK pathway was proposed in γ-[Glu](n=1,2)-Phe/-Met/-Val-induced CCK and GLP-1 secretion based on the following results: the exposure to γ-Glu-Phe increased the protein expression level (western blot analysis), the intracellular calcium ([Ca2+]i) mobilization in response to γ-[Glu](n=1,2)-Phe/-Met/-Val was strongly enhanced, and the inhibitors of signaling pathway proteins (NPS-2143, BAPTA-AM, and KN62) abolished partially γ-[Glu](n=1,2)-Phe/-Met/-Val-induced CCK and GLP-1 secretion.

Modified QuEChERS purification and Fe3O4 nanoparticle decoloration for robust analysis of 14 heterocyclic aromatic amines and acrylamide in coffee products using UHPLC-MS/MS.

Based on QuEChERS dispersed purification, Fe3O4 nanoparticle decoloration and UHPLC-MS/MS, a robust and sensitive method was established for simultaneous analysis of 14 heterocyclic aromatic amines (HAAs) and acrylamide (AA) in coffee products. Sample was extracted by 90% acetonitrile water (v/v), dispersed with primary secondary amine (PSA) and further purified with Fe3O4 nanoparticle. Then, 15 analytes were detected using ESI positive ion under MRM mode. Good linearity was observed for all analytes in the range of 0.2-100 µg/L with the determination coefficients being above 0.996. Limits of detection (S/N ≥ 3) and limits of quantification (S/N ≥ 10) were in the range of 0.02-0.15 µg/L and 0.2-0.7 µg/L, respectively. The intra-day average recoveries were between 81.6% and 100%, and the intra-day precisions ranged from 4.3% to 9.0%. The inter-day average recoveries were in the range of 81.0-101% with precisions ranging from 5.0% to 7.8%. Results indicated that the combination of PSA and Fe3O4 exhibited superior purification and adsorption effects for removing pigments and acid compounds. Real samples analysis indicated that coffee products were widely contaminated with AA, harman and norharman.

Solid phase extraction with high polarity Carb/PSA as composite fillers prior to UPLC-MS/MS to determine six bisphenols and alkylphenols in trace level hotpot seasoning.

The present study reports an ultra high-performance liquid chromatography tandem mass spectrometry method for the simultaneous determination of six bisphenols (bisphenol A, bisphenol B and bisphenol F) and alkylphenols (4-nonylphenol, 4-n-nonylphenol and octylphenol) in hotpot seasoning. Samples were dispersed in n-hexane after addition of internal standards bisphenol A-d4 and 4-n-nonylphenol-d4. Sample solutions were then centrifuged, and the supernatants purified using solid phase extraction with high polarity Carb/PSA composite fillers. Six target analytes were separated on a Waters ACQUITY BEH C18 column by gradient elution with methanol and 0.05% ammonium hydroxide in water as the mobile phase, and determined under multiple reactions monitoring mode. The limits of detection and quantitation, matrix effect, recovery and precision of the method were investigated. Results were linear in the concentration range 0.1-250 µg/L for all compounds of interest, with R2 > 0.9950. Limits of detection were in the range 0.1-0.4 µg/kg, and limits of quantitation were between 0.5 µg/kg and 1.0 µg/kg. The mean recoveries for negative samples at three spiked concentrations were in the range 87.9%-102.4%, and the intra-day precision and inter-day precision were in the ranges 2.1-8.2% and 4.8-11.2%, respectively. This method is accurate and sensitive, and had good clean-up characteristics, which might apply to screening and quantitation of target bisphenols and alkylphenols in hotpot seasoning.

Development of an indirect ELISA for the determination of ethyl carbamate in Chinese rice wine.

The widespread occurrence of ethyl carbamate (EC, 89.09 Da), a group 2A carcinogen, in fermented foods and alcoholic beverages has raised worldwide public health concern. Immunoassay for EC is unavailable due to the simple and small structure of EC. In this work, an initial attempt to produce antibody specific for EC, by using 4-((ethoxycarbonyl)amino)butanoic acid as hapten, was made but failed. However, since EC can easily react with 9-xanthydrol to form xanthyl ethyl carbamate (XEC), two haptens based on XEC structure were designed and synthesized. Polyclonal antibody against XEC, instead of EC was obtained and then used to develop a competitive indirect ELISA for EC via a pre-analysis derivatization. After optimization, the ciELISA was applied in analyzing Chinese rice wine with detection limit of 166 µg/L, and negligible cross-reactivity with EC analogs. Recoveries of EC in fortified samples were from 84.4% to 100.9%, with coefficients of variation below 10%. Results for analysis of real samples by the ci-ELISA correlated well with that by reference method GC-MS, suggesting the good accuracy and reproducibility of the proposed method. This is the first report of an immunoassay capable of detecting EC, which is suitable for monitoring EC in a large amount of samples.

Determination of oligosaccharides and monosaccharides in Hakka rice wine by precolumn derivation high-performance liquid chromatography.

This article presents a precolumn derivatization procedure with 1-phenyl-3-methyl-5-pyrazolone (PMP) reagent to detect oligosaccharides and monosaccharides in Hakka rice wine. The subsequent separation of the derivatized glucose-PMP also was performed using a mobile phase consisting of the molar ratio of acetonitrile to ammonium acetate buffer (0.1M) of 22:78 at a flow rate of 1.0 mL/min with the column temperature of 35°C, and the pH of ammonium acetate buffer at 5.5. The optimum derivation conditions were as follows: reaction temperature, 70°C; reaction time, 30 minutes; molar ratio of PMP to glucose, 10:1 (v/v); molar ratio of sodium hydroxide to glucose, 3:1 (v/v). The recovery rates were between 93.13% and 102.08% with relative standard deviation of 0.96-2.48%. The established method provides sufficient sensitivity with values of limit of detection of 0.09-0.26 mg/L and limit of quantification of 0.27-0.87 mg/L for determination of oligosaccharides and monosaccharides.