Two Novel Anti-Inflammatory 21-Nordammarane Saponins from Tetraploid Jiaogulan (Gynostemma pentaphyllum)

Two novel 20-oxo-21-nordammar-22, 24-diene saponins, 21-norgypenosides A (<b>1</b>) and B (<b>2</b>), were characterized from the aerial parts of tetraploid Jiaogulan (Gynostemma pentaphyllum), a popular tea ingredient. Their structures, including the absolute configurations, were comprehensively elucidated by HRESIMS, 1D and 2D NMR data, chemical degradation, and through comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The two compounds suppressed the expression of interleukin (IL)-1β, cyclooxygenase (COX)-2, and tumor necrosis factor (TNF)-α mRNAs in the lipopolysaccharide-induced RAW 264.7 mouse macrophage cells at 10 and 100 μg/mL, suggesting their potential anti-inflammatory effects

Identification and Quantification of Phytochemical Composition and Anti-inflammatory and Radical Scavenging Properties of Methanolic Extracts of Chinese Propolis

Fifteen propolis samples collected from different regions of China were investigated and compared for their phytochemical composition and anti-inflammatory and radical scavenging properties. Eleven compounds including caffeic, <i>p</i>-coumaric, ferulic, isoferulic, and 3,4-dimethylcaffeic acids, pinobanksin, chrysin, pinocembrin, galangin, pinobanksin 3-acetate, and caffeic acid phenylethyl ester were quantified for the 15 propolis samples using a UHPLC method, whereas 38 compounds were identified by UPLC/Q-TOF-MS. The 15 propolis samples significantly differed in their total phenolic and total flavonoid contents, as well as their phytochemical profiles. The methanol extracts of propolis also showed significant anti-inflammatory effects in LPS-stimulated RAW 264.7 mouse macrophage cells at 10 μg propolis extract/mL concentration. Additionally, the propolis samples differed in their DPPH, ABTS cation, hydroxyl, and peroxide radical scavenging capacities and ferric reducing abilities. The results from this study may be used to improve the commercial production and consumption of Chinese propolis products

Differentiating Milk and Non-milk Proteins by UPLC Amino Acid Fingerprints Combined with Chemometric Data Analysis Techniques

Amino acid fingerprinting combined with chemometric data analysis was used to differentiate milk and non-milk proteins in this study. Microwave-assisted hydrolysis and ultraperformance liquid chromatography (UPLC) were used to obtain the amino acid fingerprints. Both univariate and multivariate chemometrics methods were applied for differentiation. The confidence boundary of amino acid concentration, principal component analysis (PCA), and partial least-squares-discriminant analysis (PLS-DA) of the amino acid fingerprints demonstrated that there were significant differences between milk proteins and inexpensive non-milk protein powders from other biological sources including whey, peanut, corn, soy, fish, egg yolk, beef extract, collagen, and cattle bone. The results indicate that the amino acid compositions with the chemometric techniques could be applied for the detection of potential protein adulterants in milk

Partial Least-Squares-Discriminant Analysis Differentiating Chinese Wolfberries by UPLC–MS and Flow Injection Mass Spectrometric (FIMS) Fingerprints

<i>Lycium barbarum</i> L. fruits (Chinese wolfberries) were differentiated for their cultivation locations and the cultivars by ultraperformance liquid chromatography coupled with mass spectrometry (UPLC–MS) and flow injection mass spectrometric (FIMS) fingerprinting techniques combined with chemometrics analyses. The partial least-squares-discriminant analysis (PLS-DA) was applied to the data projection and supervised learning with validation. The samples formed clusters in the projected data. The prediction accuracies by PLS-DA with bootstrapped Latin partition validation were greater than 90% for all models. The chemical profiles of Chinese wolfberries were also obtained. The differentiation techniques might be utilized for Chinese wolfberry authentication

A Novel Alkaline Hemicellulosic Heteroxylan Isolated from Alfalfa (Medicago sativa L.) Stem and Its Thermal and Anti-inflammatory Properties

A novel hemicellulosic polysaccharide (ACAP) was purified from the cold alkali extraction of alfalfa stems and characterized as a heteroxylan with a weight-average molecular weight of 7.94 × 10³ kDa and a radius of 58 nm. Structural analysis indicated that ACAP consisted of a 1,4-linked β-d-Xyl<i>p</i> backbone with 4-<i>O</i>-MeGlc<i>p</i>A and T-l-Ara<i>f</i> substitutions at <i>O</i>-2 and <i>O</i>-3 positions, respectively. Transmission electron microscopy (TEM) examination revealed the entangled chain morphology of ACAP molecules. The evaluation of thermal degradation property revealed a primary decomposition temperature range of 238.8–314.0 °C with an apparent activation energy (<i>E</i>_a) and a pre-exponential factor (<i>A</i>) of 220.0 kJ/mol and 2.81 × 10²⁴/s, respectively. ACAP also showed significant inhibitory activities on IL-1β, IL-6, and COX-2 gene expressions in cultured RAW 264.7 mouse macrophage cells. These results suggested the potential utilization of ACAP in functional foods and dietary supplement products

Formation of 3‑Monochloro-1,2-propanediol (3-MCPD) Di- and Monoesters from Tristearoylglycerol (TSG) and the Potential Catalytic Effect of Fe²⁺ and Fe³⁺

This study investigated whether and how triacylglycerol (TAG) may serve as a precursor for 3-monochloro-1,2-propanediol (3-MCPD) fatty acid ester formation using tristearoylglycerol (TSG). TSG was reacted with inorganic chloride compounds including NaCl, KCl, FeCl₂, CuCl_2, ZnCl₂, FeCl₃ and dry HCl, or organic chlorine compound lindane at different temperatures. Only FeCl₂ and FeCl₃ were able to form 3-MCPD esters from TSG. Further electron spin resonance (ESR) determination of TSG, Fe₂(SO₄)₃ and 5,5-dimethylpyrroline-<i>N</i>-oxide (DMPO) reactions revealed potential of Fe ion in promoting free radical generations under the experimental conditions. To further confirm the effect of Fe ion, chelating agent (EDTA-2Na) was added to the model reactions. The results showed for the first time that EDTA-2Na was able to reduce the generation of 3-MCPD esters. In addition, FT-IR examination indicated a possible involvement of a carbonyl group during the reaction. Taking all the observations together, the possible mechanisms, involving the formation of either a cyclic acyloxonium or a glycidol ester radical intermediate, were proposed for generating 3-MCPD fatty acid di- and mono- esters from TAG under a high temperature and low moisture condition, as well as the coformation of glycidol esters. The results from this study may be useful for reducing the level of 3-MCPD esters and related toxicants in the refined edible oils and food products

Preparation of Novel Cross-Linked and Octylated Caseinates Using a Biphasic Enzymatic Procedure and Their Functional Properties

A novel microbial transglutaminase-catalyzed aqueous–organic biphasic reaction system was successfully developed to prepare caseinate derivatives by cross-linking and incorporating nonpolar octyl tails for the first time. SDS-PAGE and ¹H NMR analysis confirmed that cross-linking and octyl conjugation occurred simultaneously. The octyl substitution degree (SD) was measured by ¹H NMR and used as an index to determine a suitable reaction condition. It was found that at the condition of 0.125% (w/v) protein concentration and 6 h of reaction time, the modified caseinate had the highest SD of 28.96%. The modified caseinate also had an increased surface hydrophobicity, better emulsifying activity, and improved thermal and salt stabilities. However, its emulsion stability or in vitro enzymatic digestibility was slightly lower than that of the native caseinate

Structural, Thermal, and Anti-inflammatory Properties of a Novel Pectic Polysaccharide from Alfalfa (Medicago sativa L.) Stem

A pectic polysaccharide (APPS) was purified from the cold alkali extract of alfalfa stem and characterized to be a rhamnogalacturonan I (RG-I) type pectin with the molecular weight of 2.38 × 10³ kDa and a radius of 123 nm. The primary structural analysis indicated that APPS composed of a →2)-α-l-Rha<i>p</i>-(1→4)-α-d-Gal<i>p</i>A-(1→ backbone with 12% branching point at C-4 of Rha<i>p</i> forming side chains by l-arabinosyl and d-galactosyl oligosaccharide units. Transmission electron microscopy (TEM) analysis revealed a primary linear-shaped structure with a few branches in its assembly microstructures. The thermal decomposition evaluation revealed the stability of APPS with an apparent activation energy (<i>E</i>_a) of 226.5 kJ/mol and a pre-exponential factor (<i>A</i>) of 2.10 × 10²⁵/s, whereas its primary degradation occurred in the temperature range from 215.6 to 328.0 °C. In addition, APPS showed significant anti-inflammatory effect against mRNA expressions of the pro-inflammatory cytokine genes, especially for IL-1β, suggesting its potential utilization in functional foods and dietary supplement products

Free Radical Mediated Formation of 3‑Monochloropropanediol (3-MCPD) Fatty Acid Diesters

The present study was conducted to test the hypothesis that a free radical was formed and mediated the formation of 3-monochloropropanediol (3-MCPD) fatty acid diesters, a group of food contaminants, from diacylglycerols at high temperature under a low-moisture condition for the first time. The presence of free radicals in a vegetable oil kept at 120 °C for 20 min was demonstrated using an electron spin resonance (ESR) spectroscopy examination with 5,5-dimethylpyrroline-<i>N</i>-oxide (DMPO) as the spin trap agent. ESR investigation also showed an association between thermal treatment degree and the concentration of free radicals. A Fourier transform infrared spectroscopy (FT-IR) analysis of <i>sn</i>-1,2-stearoylglycerol (DSG) at 25 and 120 °C suggested the possible involvement of an ester carbonyl group in forming 3-MCPD diesters. On the basis of these results, a novel free radical mediated chemical mechanism was proposed for 3-MCPD diester formation. Furthermore, a quadrupole-time of flight (Q-TOF) MS/MS investigation was performed and detected the DMPO adducts with the cyclic acyloxonium free radical (CAFR) and its product MS ions, proving the presence of CAFR. Furthermore, the free radical mechanism was validated by the formation of 3-MCPD diesters through reacting DSG with a number of organic and inorganic chlorine sources including chlorine gas at 120 and 240 °C. The findings of this study might lead to the improvement of oil and food processing conditions to reduce the level of 3-MCPD diesters in foods and enhance food safety

Identification and Quantification of Phytochemical Composition and Anti-inflammatory, Cellular Antioxidant, and Radical Scavenging Activities of 12 Plantago Species

Twenty-eight seed samples of 12 Plantago species were investigated for their chemical compositions and anti-inflammatory, cellular antioxidant, and radical scavenging properties. A new UPLC-UV procedure was developed and applied to quantify acteoside and geniposidic acid, the characteristic constituents of the genus <i>Plantago</i>. The amounts of acteoside and geniposidic acid ranged from 0.07 to 15.96 mg/g and from 0.05 to 10.04 mg/g in the tested samples, respectively. Furthermore, 26 compounds were tentatively identified by UPLC/Q-TOF-MS analysis. The <i>Plantago</i> samples significantly differed in their phytochemical compositions. The extracts of <i>Plantago</i> seeds also showed inhibitory effects on LPS-induced IL-1β, IL-6, and COX-2 mRNA expression in RAW 264.7 mouse macrophage cells. Additionally, significant variations were observed among different samples on cellular antioxidant activities in HepG2 cells, as well as DPPH and hydroxyl radical scavenging capacities. The results from this study may be used to promote the use of the genus <i>Plantago</i> in improving human health