Chemical Compositions of Scutellaria baicalensis Georgi. (Huangqin) Extracts and Their Effects on ACE2 Binding of SARS-CoV-2 Spike Protein, ACE2 Activity, and Free Radicals.

The water and ethanol extracts of huangqin, the roots of Scutellaria baicalensis Georgi. with potential antiviral properties and antioxidant activities, were investigated for their chemical profiles and their abilities to interfere with the interaction between SARS-CoV-2 spike protein and ACE2, inhibiting ACE2 activity and scavenging free radicals. A total of 76 compounds were tentatively identified from the extracts. The water extract showed a greater inhibition on the interaction between SARS-CoV-2 spike protein and ACE2, but less inhibition on ACE2 activity than that of the ethanol extract on a per botanical weight concentration basis. The total phenolic content was 65.27 mg gallic acid equivalent (GAE)/g dry botanical and the scavenging capacities against HO●, DPPH●, and ABTS●+ were 1369.39, 334.37, and 533.66 µmol trolox equivalent (TE)/g dry botanical for the water extract, respectively. These values were greater than those of the ethanol extract, with a TPC of 20.34 mg GAE/g, and 217.17, 10.93, and 50.21 µmol TE/g against HO●, DPPH●, and ABTS●+, respectively. The results suggested the potential use of huangqin as a functional food ingredient in preventing COVID-19.

Bioactive Compositions of Cinnamon (Cinnamomum verum J. Presl) Extracts and Their Capacities in Suppressing SARS-CoV-2 Spike Protein Binding to ACE2, Inhibiting ACE2, and Scavenging Free Radicals.

Cinnamon (Cinnamomum verum J. Presl) bark and its extracts are popular ingredients added to food and supplement products. It has various health effects, including potentially reducing the risk of coronavirus disease-2019 (COVID-19). In our study, the bioactives in cinnamon water and ethanol extracts were chemically identified, and their potential in suppressing SARS-CoV-2 spike protein-angiotensin-converting enzyme 2 (ACE2) binding, reducing ACE2 availability, and scavenging free radicals was investigated. Twenty-seven and twenty-three compounds were tentatively identified in cinnamon water and ethanol extracts, respectively. Seven compounds, including saccharumoside C, two emodin-glucuronide isomers, two physcion-glucuronide isomers, and two type-A proanthocyanidin hexamers, were first reported in cinnamon. Cinnamon water and ethanol extracts suppressed the binding of SARS-CoV-2 spike protein to ACE2 and inhibited ACE2 activity in a dose-dependent manner. Cinnamon ethanol extract had total phenolic content of 36.67 mg gallic acid equivalents (GAE)/g and free radical scavenging activities against HO• and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS•+) of 1688.85 and 882.88 µmol Trolox equivalents (TE)/g, which were significantly higher than those of the water extract at 24.12 mg GAE/g and 583.12 and 210.36 µmol TE/g. The free radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) of cinnamon ethanol extract was lower than that of the water extract. The present study provides new evidence that cinnamon reduces the risk of SARS-CoV-2 infection and COVID-19 development.

Soluble Free, Soluble Conjugated, and Insoluble Bound Phenolics in Tomato Seeds and Their Radical Scavenging and Antiproliferative Activities.

The soluble free, soluble conjugated, and insoluble bound phenolic compounds in tomato seeds were extracted and analyzed using ultra-high-performance liquid chromatography-high-resolution mass spectrometry. Total phenolic content (TPC) and free radical scavenging activities along with the antiproliferative effects against the human colorectal cancer cell line (HCT-116) were also examined for the soluble free, soluble conjugated, and insoluble bound phenolic fractions. 13, 7, and 10 compounds were tentatively identified in the soluble free, soluble conjugated, and insoluble bound phenolic fractions, respectively, including indole-3-acetic acid derivatives, flavonoids, phenolic acid, and tyramine-derived hydroxycinnamic acid amines. The insoluble bound phenolic fraction was observed to have a greater TPC value and stronger free radical scavenging activities against ABTS•+, DPPH•, and peroxyl radicals and a stronger inhibitory effect against HCT-116 cells compared with the soluble free and the soluble conjugated fractions. Soluble free and insoluble bound fractions significantly inhibited the proliferation of the HCT-116 cell line, and no antiproliferative effects were observed with the soluble conjugated fraction under the experimental conditions. The results may provide a foundation for future application of tomato seeds as nutraceuticals in dietary supplements and functional foods.

Chemical Composition Profiling and Biological Activities of Phenolic Compounds in Eleven Red Sorghums.

The profiles of soluble and insoluble phenolic compounds in 11 commercial red sorghums (B11, B12, B13, B14, J124, J127, J138, J140, J142, J152, and J158) were investigated using ultraperformance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS) analysis. A total of 48 phenolic compounds including 35 phenolic acids and their derivatives, 12 flavonoids, and 1 proanthocyanidin were identified, and 8 phenolic compounds were reported for the first time in sorghums. Four major 3-deoxyanthocyanidins were also quantified, with their soluble forms accounting for 99.75-99.87% of the total contents. Pearson's correlation analyses indicated that 3-deoxyanthocyanidins significantly contributed to the antioxidant capacities of the red sorghums and that 5-methoxy-luteolinidin showed the strongest correlation. Besides, the soluble phenolic fraction of B13 dose-dependently inhibited the proliferation of Caco-2 cells and the secretion of IL-1ß and NO in RAW264.7 macrophages, which might be attributed to its relatively high total phenolic (TPC), flavonoid (TFC), and proanthocyanidin content (TPAC) values and radical scavenging capacities.

Chemical Composition of Tomato Seed Flours, and Their Radical Scavenging, Anti-Inflammatory and Gut Microbiota Modulating Properties.

In the current study, the chemical composition and total phenolic content of tomato seed flours, along with potential health beneficial properties, including free radical scavenging capacities, anti-inflammatory capacities, and gut microbiota profile modulation, were examined using two different batches. Eight compounds were identified in the tomato seed flour, including malic acid, 2-hydroxyadipic acid, salicylic acid, naringin, N-acetyl-tryptophan, quercetin-di-O-hexoside, kaempferol-di-O-hexoside, and azelaic acid. The total phenolic contents of tomato seed flour were 1.97-2.00 mg gallic acid equivalents/g. Oxygen radical absorbing capacities (ORAC), 2,2-diphenyl-1-picrylhydrazyl radical scavenging capacities (DPPH), and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical scavenging capacities (ABTS) were 86.32-88.57, 3.57-3.81, and 3.39-3.58 µmoles Trolox equivalents/g, respectively, on a per flour dry weight basis. The mRNA expression of the pro-inflammatory markers, interleukin-1 beta (IL-1ß), interleukin-6 (IL-6), and tumor necrosis factor alpha (TNF-α), were dose-dependently suppressed by tomato seed flour extracts. The extracts altered five of the eight bacterial phyla and genera evaluated. The results may provide some scientific support for the use of tomato seed flour as value-added food ingredients.

Non-targeted detection of butter adulteration using pointwise UHPLC-ELSD and UHPLC-UV fingerprints with chemometrics.

A non-targeted chemometric method was devised to detect possible butter adulteration without prior knowledge of the adulterant and marker compounds. Nine common edible oils including vegetable oils, animal fats and margarines were selected as potential adulterants to build a unified classification model. The samples were analyzed using the high-performance liquid chromatography hyphenated with an evaporative light scattering detector (UHPLC-ELSD) and an ultraviolet detector (UHPLC-UV), with the pointwise chromatograms instead of individual peaks for modelling. Both models achieved over 95% correct classification in external validation at the adulteration levels as low as 5% (w/w). The root mean squared errors of prediction (RMSEP) of the regression model were 0.9865 and 1.9080 for UHPLC-ELSD and UHPLC-UV, respectively. Non-targeted chemometrics analyses based on pointwise chromatographic profiles could be valuable for detecting adulterated butter.

Triacylglycerols compositions, soluble and bound phenolics of red sorghums, and their radical scavenging and anti-inflammatory activities.

Six commercial red sorghum varieties (Tong Za 117, 141, 142 and 143, Chi Za 109 and 101) were investigated for their triacylglycerol (TAG) profiles, soluble and bound phenolics, and radical scavenging and anti-inflammatory activities. A total of 21 TAGs were identified in red sorghum oils for the first time. Total phenolic (TPC) and flavonoid contents (TFC) in the soluble or bound phenolic fractions differed among red sorghums. Significant correlation among TPC, TFC and DPPH radical scavenging activities was observed in both fractions. Except for caffeic acid, most of phenolic acids in red sorghums are in the bound form. Soluble 3-deoxyanthocyanidins contents (2.12-57.14 µg/g) were significantly higher than those of bound forms (0.01-0.18 µg/g) regardless of sorghum varieties and types of 3-deoxyanthocyanidins. Moreover, the stronger anti-inflammatory capacity of soluble phenolic fraction in Tong Za 117 correlated with its higher TPC, TFC and radical scavenging activity than those of its bound counterpart.

Current Progresses on Monochloropropane Diol Esters in 2018-2019 and Their Future Research Trends.

The fatty acid esters of monochloropropane diol (MCPD) are a group of food source contaminants formed during thermal processing. These components were recognized as potential food source toxicants in the past few decades, and growing evidence has proven their toxic effects, especially to kidneys and testes. Therefore, increasing research articles reported their results about MCPD esters in recent years. In this perspective, a total of 35 research articles/reviews about MCPD esters, including the studies concerning the analytical methods, occurrences, toxicity, formation mechanism, and mitigation strategies of MCPD esters in 2018-2019 have been summarized and discussed. Updating the latest research results about MCPD esters could improve our understandings about these components, especially on the toxic effects and the mitigation approaches in both academia and industry.

Fabrication and Characterization of Zein Composite Particles Coated by Caseinate-Pectin Electrostatic Complexes with Improved Structural Stability in Acidic Aqueous Environments.

Zein composite particles coated with caseinate-pectin electrostatic complexes (zein-caseinate-pectin particles) were fabricated using an electrostatic deposition and liquid-liquid dispersion method without heating treatment. Compared to zein particles coated only with caseinate, the acidic stability of zein-caseinate-pectin particles was greatly improved, and the particle aggregation was suppressed at pH 3-6, especially at pH values near the isoelectric point of caseinate (pH 4-5). Besides, desirable long-term storage stability and re-dispersibility were observed. Under different zein to curcumin (Cur) feeding ratios (10:1, 20:1, 30:1 and 40:1, w/w), the Cur-loaded zein-caseinate-pectin particles had a spherical shape with an average diameter ranging from 358.37 to 369.20 nm, a narrow size distribution (polydispersity index < 0.2) and a negative surface charge ranging from -18.87 to -19.53 mV. The relatively high encapsulation efficiencies of Cur (81.27% to 94.00%) and desirable re-dispersibility were also achieved. Fluorescence spectroscopy indicated that the encapsulated Cur interacted with carrier materials mainly through hydrophobic interactions. The in-vitro release profile showed a sustained release of Cur from zein-caseinate-pectin particles in acidic aqueous environment (pH 4) up to 24 h, without any burst effect. In addition, the encapsulation retained more ABTS•+ radical scavenging capacity of Cur during 4 weeks of storage. These results suggest that zein-caseinate-pectin particles may be used as a potential delivery system for lipophilic nutrients in acidic beverages.

The chemical composition of a cold-pressed milk thistle seed flour extract, and its potential health beneficial properties.

Cold-pressed milk thistle seed flour was extracted with 50% acetone and evaluated for its phytochemical composition, and gut microbiota modulating, free radical scavenging, anti-inflammatory and anti-proliferative capacities. UHPLC-MS analysis detected fifteen compounds in the milk thistle seed flour extract with silychristin as the primary component followed by silybin B and isosilybins A & B. The milk thistle seed flour extract enhanced the total bacteria number and altered the abundance of a specific bacterial phylum or genus under the experimental conditions. The extract had RDSC, ORAC, HOSC, and ABTS˙+ scavenging capacities of 49, 634, 10 420 and 116 µmol Trolox equivalents (TE) per g flour, respectively. In addition, the milk thistle seed flour extract suppressed LPS induced IL-1ß mRNA expression in the cultured J774A.1 mouse macrophages and the proliferation of LNCaP prostate cancer cells. The results suggest milk thistle seed flour's potential health benefits in functional foods.

Triacylglycerol, fatty acid, and phytochemical profiles in a new red sorghum variety (Ji Liang No. 1) and its antioxidant and anti-inflammatory properties.

In this study, a new red sorghum variety (Ji Liang No. 1) was investigated for its triacylglycerol (TAG) and fatty acid profiles, carotenoid and tocopherol compositions, total phenolic, total flavonoid and phenolic acid contents, and antioxidant and anti-inflammatory properties. A total of 17 TAGs were identified in the red sorghum oil. Linoleic and oleic acids were the primary fatty acids, contributing more than 80% of the total fatty acids. ß-Carotene was the primary carotenoid at a level of 26.14 µg/g. α-, γ-, and δ-tocopherols were at levels of 0.19, 4.08, and 0.10 µg/g, respectively. Moreover, acetone-water (60:40, v/v) extract of the red sorghum exhibited the greatest total phenolic content of 2.77 mg GAE/g and total flavonoid content of 5.44 mg RE/g. The extract had scavenging capacities against DPPH, ABTS +, and peroxyl radicals and suppressed LPS stimulated IL-1ß, IL-6, and COX-2 mRNA expressions in a dose-dependent manner. Ferulic, p-coumaric, isoferulic, and p-hydroxybenzoic acids were found in the red sorghum, with ferulic acid as the predominant phenolic acid and mostly in an insoluble bound form. These data indicated a potential utilization of the red sorghum in health-promoting functional food or supplemental products.

Chemical compositions of chrysanthemum teas and their anti-inflammatory and antioxidant properties.

Seventeen commercial chrysanthemum teas (Chrysanthemum morifolium and Coreopsis tinctoria) were extracted with hot-H2O, and examined and compared to the 75% methanol extracts for their chemical compositions using UPLC/Q-TOF-MS analysis. For the first time, 6, 8-C,C-diglucosylapigenin and eriodicyol-7-O-glucoside were detected in the Snow chrysanthemum, and acetylmarein was detected in HangJu, GongJu and HuaiJu. The extracts were also examined for their radical scavenging and anti-inflammatory activities in vitro. The hot-H2O extract of Kunlunmiju 1 had the greatest total phenolic content, and relative DPPH and oxygen radical absorbance capacity values of 12.72 mg gallic acid equivalents/g, 105.48 and 1222.50 µmol Trolox equivalents/g, respectively. In addition, all the hot-H2O extracts suppressed the lipopolysaccharide-induced interleukin-6, IL-1ß and cyclooxygenase-2 mRNA expressions, and H2O2-induced intracellular reactive oxygen species production in cultured cells. The results from this research may be used to promote the consumption of chrysanthemum as a functional tea.

Chemical Compositions of Cold-Pressed Broccoli, Carrot, and Cucumber Seed Flours and Their in Vitro Gut Microbiota Modulatory, Anti-inflammatory, and Free Radical Scavenging Properties.

Carrot, cucumber, and broccoli seed flours were extracted with 50% acetone and evaluated for their phytochemical compositions along with their potential gut microbiota modulating, free radical scavenging, and anti-inflammatory capacities. Nine and ten compounds were detected in the broccoli and carrot seed flour extracts, with kaempferol-3- O-rutinoside and glucoraphanin as the primary component of each, respectively. All three seed flour extracts enhanced total number of gut bacteria and altered the abundance of specific bacterial phylum or genus in vitro. The broccoli seed flour extract had the greatest relative DPPH radical scavenging capacity, oxygen radical absorbing capacity, and hydroxyl radical (HO•) scavenging capacity values of 85, 634, and 270 µmol trolox equivalent (TE)/g, respectively. Carrot seed flour extract showed the greatest ABTS•+ scavenging capacity of 250 µmol TE/g. Also, three seed flour extracts suppressed LPS induced IL-1ß and COX-2 mRNA expressions in J774A.1 cells. The results might be used to promote the value-added utilization of these vegetable seed flours in improving human health.

Inhibitory Effect of Piceatannol on TNF-α-Mediated Inflammation and Insulin Resistance in 3T3-L1 Adipocytes.

Piceatannol, a bioactive component in grape and blueberry, was examined for its potential in decreasing the inflammatory activities in adipocytes using a cocultured adipocyte and macrophage system, and suppressing tumor necrosis factor-α (TNF-α)-mediated inflammation and the related insulin resistance using a 3T3-L1 adipocyte model. Piceatannol at 10 µM significantly reduced the release of inflammatory cytokines of TNF-α and monocyte chemoattractant protein-1 (MCP-1) by 19 and 31% in the cocultured system, respectively. Pretreatment with piceatannol also inhibited TNF-α-induced expression of interleukin-6 (IL-6) and MCP-1 at both mRNA and protein levels in the 3T3-L1 adipocytes. Piceatannol also partially improved the malfunction of insulin-stimulated glucose uptake, which was reduced by TNF-α in 3T3-L1 adipocytes. Furthermore, the inhibitions were mediated by significant blocking of IκBα phosphorylation and nuclear factor-κB (NF-κB) activation through suppressing nuclear translocation of NF-κB p65 along with c-Jun N-terminal kinase (JNK)-mitogen activated protein kinase (MAPK) activation. In addition, the Akt-dependent forkhead box O1 (FoxO1) signaling pathway was involved in the restoration of insulin-stimulated glucose uptake through suppressing the down-regulation of phosphorylation of Akt and FoxO1 expressions. These results suggested the potential of piceatannol in improving chronic inflammatory condition and insulin sensitivity in obese adipose tissues.

Triacylglycerol compositions of sunflower, corn and soybean oils examined with supercritical CO2 ultra-performance convergence chromatography combined with quadrupole time-of-flight mass spectrometry.

A supercritical CO2 ultra-performance convergence chromatography (UPC2) system was utilized with a quadrupole time-of-flight mass spectrometry (Q-TOF MS) to examine the triacylglycerol compositions of sunflower, corn and soybean oils. UPC2 provided an excellent resolution and separation for the triacylglycerols, while the high performance Q-TOF MS system was able to provide the molecular weight and fragment ions information for triacylglycerol compound characterization. A total of 33 triacylglycerols were identified based on their elementary compositions and MS2 fragment ion profiles, and their levels in the three oils were estimated. The combination of UPC2 and Q-TOF MS may determine triacylglycerol compositions for oils and fats, and provide sn-position information for fatty acids, which may be important for food nutritional value and stability.

Separating four diastereomeric pairs of dihydroflavonol glycosides from Engelhardia roxburghiana using high performance counter-current chromatography.

Four pairs of diastereomers were successfully isolated and separated from the water extract of Engelhardia roxburghiana by high performance counter-current chromatography (HPCCC) using a two-step procedure. The diastereomers were initially separated by a two-phase solvent system composed of n-hexane-n-butanol-0.1% trifluoroacetic acid (1:2:3, v/v/v) and followed by the same solvent system using hydroxypropyl-ß-cyclodextrin (HP-ß-CD) as an additive. The chromatographic conditions, elution mode, and concentrations of the additive were refined. The two-step HPCCC isolation yielded 43.7mg (2S, 3S)-astilbin, 27.6mg (2R, 3R)-astilbin, 5.9mg (2S, 3R)-astilbin, 4.8mg (2R, 3S)-astilbin, 6.9mg (2S, 3S)-engelitin, 3.1mg (2R, 3R)-engelitin, 8.2mg (2S, 3R)-engelitin, and 6.0mg (2R, 3S)-engelitin from 384mg crude extract in four runs with purities of 99.3%, 96.2%, 99.8%, 99.9%, 97.0%, 96.5%, 96.1%, and 96.8%, respectively. The present study revealed that HP-ß-CD can be used as an additive in HPCCC to effectively improve the resolution of the diastereomers. The established HPCCC method may serve as an approach to obtain high purity diastereomers on a large scale.

Characterisation of organic and conventional sweet basil leaves using chromatographic and flow-injection mass spectrometric (FIMS) fingerprints combined with principal component analysis.

Sweet basil, Ocimum basilicum, is one of the most important and wildly used spices and has been shown to have antioxidant, antibacterial, and anti-diarrheal activities. In this study, high performance liquid chromatographic (HPLC) and flow-injection mass spectrometric (FIMS) fingerprinting techniques were used to differentiate organic and conventional sweet basil leaf samples. Principal component analysis (PCA) of the fingerprints indicated that both HPLC and FIMS fingerprints could effectively detect the chemical differences in the organic and conventional sweet basil leaf samples. This study suggested that the organic basil sample contained greater concentrations of almost all the major compounds than its conventional counterpart on a per same botanical weight basis. The FIMS method was able to rapidly differentiate the organic and conventional sweet basil leaf samples (1min analysis time), whereas the HPLC fingerprints provided more information about the chemical composition of the basil samples with a longer analytical time.

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 Plantago. 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 Plantago samples significantly differed in their phytochemical compositions. The extracts of Plantago seeds also showed inhibitory effects on LPS-induced IL-1ß, 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 Plantago in improving human health.

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-N-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 sn-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.