Phytochemical on-line screening and in silico study of Helianthemum confertum: antioxidant activity, DFT, MD simulation, ADME/T analysis, and xanthine oxidase binding.

Seven components from the methanol extract of the aerial part of the endemic species Helianthemum confertum were isolated and identified for the first time. Investigating this species and its separated components chemical make-up and radical scavenging capacity, was the main goal. Using an online HPLC-ABTS˙+ test, ORAC, and TEAC assays, the free radical scavenging capacity of the ethyl acetate extract was assessed. The fractionation of these extracts by CC, TLC, and reverse-phase HPLC was guided by the collected data, which was corroborated by TEAC and ORAC assays. Molecular docking studies, DFT at the B3LYP level, and an examination of the ADME/T predictions of all compounds helped to further clarify the phytochemicals' antioxidant potential. Isolation and identification of all components were confirmed through spectroscopy, which revealed a mixture (50-50%) of para-hydroxybenzoic acid 1 and methyl gallate 2, protocatechuic acid 3, astragalin 4, trans-tiliroside 5, cis-tiliroside 6, contaminated by trans-tiliroside and 3-oxo-α-ionol-ß-d-glucopyranoside 7, as well as two new compounds for the genus Helianthemum (2 and 7). With a focus on compounds 1, 2, 3, and 4, the results clearly showed that the extract and the compounds tested from this species had a high antioxidant capacity. Within the xanthine oxidase enzyme's pocket, all of the components tested showed strong and stable binding. In light of these findings, the xanthine oxidase/methyl gallate 2 complex was simulated using the Desmond module of the Schrodinger suite molecular dynamics (MD) for 100 ns. Substantially stable receptor-ligand complexes were observed following 1 ns of MD simulation.

In silico ADMET and anti-inflammatory profiles of the stigmast-4-en-3-one and isolation of isovanillin as the antioxidant principle of Imperata cylindrica (L.) P. Beauv.

Imperata cylindrica (L.) P. Beauv. is an invasive species widely used in treatment of several diseases associated with pain and inflammation in different countries including Madagascar. This work aims to report the isolation of the antioxidant, analgesic and anti-nflammatory compounds from the methanol extract of I. cylindrica. The bio-guided method was used to isolate its bioactive compounds by combining chromatographic methods, writhing test in mice and antioxidant assays. Stigmast-4-en-3-one was isolated as one among the compounds responsible for the analgesic and anti-inflammatory properties and isovanillin as one among the antioxidant compounds from the extract. Stigmast-4-en-3-one showed a good oral pharmacokinetic profile and good binding affinities with some pro-inflammatory targets. It did not show any mutagenic effect, nor a carcinogenic one and had a low risk to be a cardiotoxic agent. All of our results provide scientific justification for its traditional medicinal use in the management of pain and inflammatory related diseases.

Revealing the dynamic changes of lipids in coffee beans during roasting based on UHPLC-QE-HR-AM/MS/MS.

Coffee is popular worldwide and its consumption is increasing in recent years. Although mass spectrometry-based lipidomics approaches have been prevalent, their application in studies related to detailed information and dynamic changes in lipid composition during coffee bean roasting is still limited. The aim of this study was to investigate the dynamic changes in coffee bean lipids during the roasting process. The lipid classes and lipid molecular species in coffee beans were characterized by lipidomic analysis combined with chemometrics. A total of 12 lipid classes and 105 lipid molecular species were identified and quantified. Triacylglycerols (TAG) was the most abundant lipid class in both green beans and roasted beans. The content of phosphatidylethanolamine (PE) and lysophosphatidylethanolamine (LPE) in green beans was obviously higher than that in roasted beans. Other phospholipids, such as phosphatidylinositol (PI), lysophosphatidylinositol (LPI), phosphatidylcholine (PC), lysophophatidylcholine (LPC) and phosphatidic acid (PA), showed a tendency to increase at the beginning of roasting, then decreased gradually. Several differential lipid molecule species, for instance, PE (16:0_18:2), PC (18:2_18:2) were significantly down-regulated, and PI (18:1_18:2) was significantly up-regulated. This study provided a scientific basis for the change of coffee bean lipids during the roasting process.

Unraveling the potential of breath and sweat VOC capture devices for human disease detection: a systematic-like review of canine olfaction and GC-MS analysis.

The development of disease screening methods using biomedical detection dogs relies on the collection and analysis of body odors, particularly volatile organic compounds (VOCs) present in body fluids. To capture and analyze odors produced by the human body, numerous protocols and materials are used in forensics or medical studies. This paper provides an overview of sampling devices used to collect VOCs from sweat and exhaled air, for medical diagnostic purposes using canine olfaction and/or Gas Chromatography-Mass spectrometry (GC-MS). Canine olfaction and GC-MS are regarded as complementary tools, holding immense promise for detecting cancers and infectious diseases. However, existing literature lacks guidelines for selecting materials suitable for both canine olfaction and GC-MS. Hence, this review aims to address this gap and pave the way for efficient body odor sampling materials. The first section of the paper describes the materials utilized in training sniffing dogs, while the second section delves into the details of sampling devices and extraction techniques employed for exhaled air and sweat analysis using GC-MS. Finally, the paper proposes the development of an ideal sampling device tailored for detection purposes in the field of odorology. By bridging the knowledge gap, this study seeks to advance disease detection methodologies, harnessing the unique abilities of both dogs and GC-MS analysis in biomedical research.

Untargeted Metabolomic Analysis Combined with Chemometrics Revealed the Effects of Different Cooking Methods on Lentinus edodes.

Cooking methods affect the compositions of Lentinus edodes metabolites. Nevertheless, little information is available on the specific impact of different cooking methods on Lentinus edodes via metabolomic analysis. This study determined the influence of boiling, steaming, air-frying, and roasting on the metabolomic profiles of Lentinus edodes based on UHPLC-Q-Exactive Orbitrap MS/MS in combination with chemometrics. A total of 990 metabolites were detected and classified into 11 super-classes. Subsequently, the metabolites of the four cooking methods were distinguished using multivariate statistical analysis. The results showed that boiling caused a massive loss of metabolites while roasting and air-frying led to an evident upregulation. The upregulation of metabolites in the steaming groups was not as significant as in roasting and air-frying. This study provided reference data for a comprehensive understanding of the metabolites associated with domestic cooking methods and valuable guidance for the development of Lentinus edodes and its products in the future.

Construction of whey protein gels prepared by three methods to stabilize high internal phase Pickering emulsions loaded with CoQ10 under different pH.

The aim of this study was to investigate the effect of whey protein gel particles (WPGPs) prepared by heat-induced method, enzyme cross-linking method and calcium ion cross-linking method on the structural properties and intrinsic linkage of their stable high internal phase Pickering emulsions (HIPPEs) under different pH conditions. The effects of different pH and preparation methods on the internal interaction forces, particle size, ζ-potential, wettability and secondary structure of gels was investigated. The results indicated that the construction of HIPPEs system was successfully constructed at pH 3, 5 or 7. The WPGPs stabilized HIPPEs can maintain stable state at 4 °C for 28 days. Coenzyme Q10 (CoQ10) loaded with HIPPEs increased the bioavailability from 13.2% to 79.4%, which was demonstrated in in vitro digestion experiments.

Untargeted Lipidomics Method for the Discrimination of Five Crab Species by Ultra-High-Performance Liquid Chromatography High-Resolution Mass Spectrometry Combined with Chemometrics.

In this study, ultra-high-performance liquid chromatography high-resolution accurate mass-mass spectrometry (UHPLC-HRAM/MS) was applied to characterize the lipid profiles of five crab species. A total of 203 lipid molecular species in muscle tissue and 176 in edible viscera were quantified. The results indicate that Cancer pagurus contained high levels of lipids with a docosahexaenoic acid (DHA) and eicosapntemacnioc acid (EPA) structure in the muscle tissue and edible viscera. A partial least squares discriminant analysis (PLS-DA) showed that PE 16:0/22:6, PE P-18:0/20:5, PA 16:0/22:6 and PC 16:0/16:1 could be used as potential biomarkers to discriminate the five kinds of crabs. In addition, some lipids, such as PE 18:0/20:5, PC 16:0/16:1, PE P-18:0/22:6 and SM 12:1;2O/20:0, could be used as characteristic molecules to distinguish between Cancer magister and Cancer pagurus, which are similar in appearance. This study provides a new perspective on discriminating crab species from MS-based lipidomics.

Combining Untargeted Lipidomics Analysis and Chemometrics to Identify the Edible and Poisonous Mushrooms (Pleurotus cornucopiae vs Omphalotus japonicus).

The global phenomenon of eating poisonous mushrooms by mistake occurs every year. Untargeted lipidomics analysis combined with chemometrics was used to identify mushroom varieties. Two kinds of mushrooms with similar appearance, namely, Pleurotus cornucopiae (P. cornucopiae) and Omphalotus japonicus (O. japonicus) were selected as models, where O. japonicus was a poisonous mushroom and P. cornucopiae was an edible mushroom. First, the lipid extraction efficiency of eight solvents was compared. The methyl tert-butyl ether/methanol (2:1, v/v) had higher lipid extraction efficiency of extracting mushroom lipids than other solvents, in terms of the lipid coverage, response intensity, and solvent safety. Afterward, the comprehensive lipidomics analysis of the two mushrooms was conducted. A total of 21 lipid classes and 267 molecular species were identified in O. japonicus, whereas 22 lipid classes and 266 molecular species in P. cornucopiae. The principal component analysis demonstrated that 37 characteristic metabolites, including TAG 18:1_18:2_18:0;1O, TAG 18:1_18:1_18:2, TAG 16:2_18:2_18:2, etc., could be used to distinguish the two mushrooms. These differential lipids were able to identify P. cornucopiae blended with 5% (w/w) O. japonicus. This study explored a novel method for identifying poisonous mushrooms from edible mushrooms and provided a reference for food safety of consumers.

Protein-Based High Internal Phase Pickering Emulsions: A Review of Their Fabrication, Composition and Future Perspectives in the Food Industry.

Protein-based high internal phase Pickering emulsions (HIPEs) are emulsions using protein particles as a stabilizer in which the volume fraction of the dispersed phase exceeds 74%. Stabilizers are irreversibly adsorbed at the interface of the oil phase and water phase to maintain the droplet structure. Protein-based HIPEs have shown great potential for a variety of fields, including foods, due to the wide range of materials, simple preparation, and good biocompatibility. This review introduces the preparation routes of protein-based HIPEs and summarizes and classifies the preparation methods of protein stabilizers according to their formation mechanism. Further outlined are the types and properties of protein stabilizers used in the present studies, the composition of the oil phase, the encapsulating substances, and the properties of the constituted protein-based HIPEs. Finally, future development of protein-based HIPEs was explored, such as the development of protein-based stabilizers, the improvement of emulsification technology, and the quality control of stabilizers and protein-based HIPEs.

Characterization and discrimination of volatile organic compounds and lipid profiles of truffles under different treatments by UHPLC-QE Orbitrap/MS/MS and P&T-GC-MS.

The lipid profiles of the truffles with different treatments were determined by ultra-high-performance liquid chromatography-Quadrupole-Exactive Orbitrap mass spectrometry (UHPLC-QE Orbitrap/MS/MS) and the volatile organic compounds (VOCs) were identified by purge-and-trap-gas chromatography-mass spectrometry (P&T-GC-MS). A total of 37 lipid molecular species and 28 VOCs were tentatively identified. Lysophophatidylcholine (LPC), triacylglycerol (TG) and sphingomyelin (SM) in heat-drying truffles, phosphatidic acid (PA) in freeze-drying and fresh truffles might be the key lipids that bound VOCs. Furthermore, the correlation between lipids and VOCs were analyzed by 19 differential lipids and 7 VOCs. The findings indicated that TG 18:2/18:2/18:2 and Cardiolipin (CL) 16:0/16:0/18:2/18:2 might be the key lipid molecule species for the formation of 2-methoxyphenol. The study helps to understand the effect of different treatments on the lipid profiles and provides the mechanistic insights to the relationship between the lipids and VOCs of truffles.

Discrimination of chrysanthemum varieties using lipidomics based on UHPLC-HR-AM/MS/MS.

BACKGROUND: Chrysanthemum is one of the most important and popular ornamentals over the world. Chrysanthemum drink is a type of traditional healthy drink like Chinese tea. Owing to the differences in the chemical compositions, different chrysanthemum varieties have different medicinal effects on human health. Thus, the identification of different chrysanthemum varieties is very important and necessary. This study aims to distinguish seven chrysanthemum varieties that are widely used in China. First, total lipids were obtained from chrysanthemums. After that, lipid profiles were characterized using ultra-high-performance liquid chromatography hyphenated with a Q Exactive™ high resolution-accurate-mass mass spectrometer. RESULTS: A total of 163 lipid molecular species from 17 types of lipid classes in seven varieties of chrysanthemums were determined. Principal component analysis indicated that three lipid molecules, lysophosphatidylethanolamine(18:2) (LPE(18:2)), LPE(16:0), and phosphatidic acid(18:2/18:3) (variable importance in projection >3, P < 0.001), can be used as potential biomarkers to distinguish seven chrysanthemum varieties. Hierarchical cluster analysis showed that the lipid molecular profiles of 'Gongju' were most similar to 'Jinzijianju', followed by 'Huaibaiju', 'Boju', 'Hangbaiju', 'Chuju', and 'Fubaiju'. CONCLUSION: This comprehensive analysis provided a new method to identify chrysanthemum varieties through the perspective of lipidomics combined with chemometrics. © 2022 Society of Chemical Industry.

Cytotoxic and Pro-Apoptotic Effects of Leaves Extract of Antiaris africana Engler (Moraceae).

Antiaris africana Engler leaves have been used in Senegalese folk medicine to treat breast cancer. The present study aimed to investigate the anticancer potential of Antiaris africana Engler leaves using several human cancer cell lines. The leaves of Antiaris africana Engler were extracted in parallel with water or 70% ethanol and each extract divided into three parts by successive liquid-liquid extraction with ethyl acetate and butanol. The phytochemical components of the active extract were investigated using ultra-performance liquid chromatography-diode array detector-quadrupole time-of-flight tandem mass spectrometry (UPLC-DAD-QTOF-MS/MS). The cytotoxic and cytostatic effects of each extract, as well as their fractions, were evaluated in vitro via flow and image cytometry on different human cancer phenotypes, such as breast (MCF-7), pancreas (AsPC-1), colon (SW-620) and acute monocytic leukemia (THP-1). Both hydro-alcoholic and aqueous extracts induced strong apoptosis in MCF-7 cells. The water fraction of the hydro-alcoholic extract was found to be the most active, suppressing the cell growth of MCF-7 in a dose-dependent manner. The half maximum effective concentration (EC50) of this fraction was 64.6 ± 13.7 µg/mL for MCF-7, with equivalent values for all tested phenotypes. In parallel, the apoptotic induction by this fraction resulted in a EC50 of 63.5 ± 1.8 µg/mL for MCF-7, with again equivalent values for all other cellular tested phenotypes. Analysis of this fraction by UPLC-DAD-QTOF-MS/MS led to the identification of hydroxycinnamates as major components, one rutin isomer, and three cardiac glycosides previously isolated from seeds and bark of Antiaris africana Engler and described as cytotoxic in human cancer models. These results provide supportive data for the use of Antiaris africana Engler leaves in Senegal.

Physicochemical degradation of phycocyanin and means to improve its stability: A short review.

The cyanobacterium Arthrospira platensis, spirulina, is a source of pigments such as phycobiliprotein and phycocyanin. Phycocyanin is used in the food, cosmetics, and pharmaceutical industries because of its antioxidant, anti-inflammatory, and anticancer properties. The different steps involved in extraction and purification of this protein can alter the final properties. In this review, the stability of phycocyanin (pH, temperature, and light) is discussed, considering the physicochemical parameters of kinetic modeling. The optimal working pH range for phycocyanin is between 5.5 and 6.0 and it remains stable up to 45 °C; however, exposure to relatively high temperatures or acidic pH decreases its half-life and increases the degradation kinetic constant. Phycobiliproteins are sensitive to light; preservatives such as mono- and di-saccharides, citric acid, or sodium chloride appear to be effective stabilizing agents. Encapsulation within nano- or micro-structured materials such as nanofibers, microparticles, or nanoparticles, can also preserve or enhance its stability.

Gold nanostructured membranes to concentrate low molecular weight thiols, a proof of concept study.

Thiols are very important molecules in the biomedical field involved for example in redox homeostasis. Their detection and quantification remain difficult due to their poor stability (oxidation) linked to their strong reactivity towards other thiols (by the formation of S-S bonds) or other interfering molecules in the medium. Cellulose membranes with immobilized gold nanoparticles (AuNP) were developed to capture and quantify thiols in simple and complex matrices. This device was first optimized and characterized in terms of nanostructuration and thiol adsorption. N-Acetylcysteine (NAC) and reduced glutathione (GSH), chosen as model molecules, were filtered through the device demonstrating a maximal adsorption capacity of 270 and 60 nmol respectively. In a second step, the adsorbed species were subjected to ligand exchange using a more reactive thiol, dithiothreitol. The results showed release rates of approximately 90% for NAC and GSH. Finally, the amount of endogenous GSH in rat plasma was determined without any pretreatment. For the first time to our knowledge, a nanostructured device for the capture, selective and sensitive quantification of thiols is proposed. This device is easy to handle and overcomes matrix effects. Moreover, the very large concentration factor induced by this technology will be a valuable asset to decrease the quantification limits of analytical methods.

First report on phytochemical investigation, antioxidant and antidiabetic activities of Helianthemum getulum.

A new flavonoid, 5,7,2',4',5'-pentahydroxyflavone 3-O-ß-D-galactopyranoside (12) and twelve known derivatives: an aryltetralin-lignan (3), seven flavonoids (4-5, 7-10, 13) and four phenolic acids (1-2, 6, 11) have been isolated from the aerial parts of Helianthemum getulum Pomel. (Cistaceae family) an endemic species to the septentrional Sahara that is being studied for the first time. Structure elucidation of the isolated compounds was established by means of spectroscopic methods especially NMR and Mass Spectrometry. In vitro antioxidant (DPPH, ABTS, GOR and CUPRAC assays) and antidiabetic (micro-dilution method) activities of the crude extract, fractions and isolated compounds were performed. The new flavonol (12) and Compounds (2, 3, 7, 9) were found to be the most active, some of them exhibiting better activity than the antioxidant standards. Compounds 7, 9 and 3 showed higher α-glucosidase inhibitory activity compared to standard acarbose (IC50= 2.70 ± 0.03 µM, 3.09 ± 0.03 µM, 37.28 ± 1.20 µM and 275.43 ± 1.59 µM, respectively).

Physicochemical degradation of phycocyanin and means to improve its stability:A short review / 药物分析学报

The cyanobacterium Arthrospira platensis,spirulina,is a source of pigments such as phycobiliprotein and phycocyanin.Phycocyanin is used in the food,cosmetics,and pharmaceutical industries because of its antioxidant,anti-inflammatory,and anticancer properties.The different steps involved in extraction and purification of this protein can alter the final properties.In this review,the stability of phycocyanin(pH,temperature,and light)is discussed,considering the physicochemical parameters of kinetic modeling.The optimal working pH range for phycocyanin is between 5.5 and 6.0 and it remains stable up to 45℃;however,exposure to relatively high temperatures or acidic pH decreases its half-life and increases the degradation kinetic constant.Phycobiliproteins are sensitive to light;preservatives such as mono-and di-saccharides,citric acid,or sodium chloride appear to be effective stabilizing agents.Encapsulation within nano-or micro-structured materials such as nanofibers,microparticles,or nanoparticles,can also pre-serve or enhance its stability.

Anti-Hyperalgesic Properties of Menthol and Pulegone.

Context: Menthol, the main monoterpene found in Mentha piperita L. (M. piperita) is known to modulate nociceptive threshold and is present in different curative preparations that reduce sensory hypersensitivities in pain conditions. While for pulegone, a menthol-like monoterpene, only a limited number of studies focus on its putative analgesic effects, pulegone is the most abundant monoterpene present in Calamintha nepeta (L.) Savi (C. nepeta), a plant of the Lamiaceae family used in traditional medicine to alleviate rheumatic disorders, which counts amongst chronic inflammatory diseases. Objectives: Here, we analyzed the monoterpenes composition of C. nepeta and M. piperita. We then compared the putative anti-hyperalgesic effects of the main monoterpenes found, menthol and pulegone, in acute inflammatory pain conditions. Methods: C. nepeta and M. piperita extracts were obtained through pressurized liquid extraction and analyzed by gas chromatography-mass spectrometry. The in vitro anti-inflammatory activity of menthol or pulegone was evaluated by measuring the secretion of the tumour necrosis factor alpha (TNF α) from LPS-stimulated THP-1 cells. The in vivo anti-hyperalgesic effects of menthol and pulegone were tested on a rat inflammatory pain model. Results: Pulegone and menthol are the most abundant monoterpene found in C. nepeta (49.41%) and M. piperita (42.85%) extracts, respectively. In vitro, both pulegone and menthol act as strong anti-inflammatory molecules, with EC50 values of 1.2 ± 0.2 and 1.5 ± 0.1 mM, respectively, and exert cytotoxicity with EC50 values of 6.6 ± 0.3 and 3.5 ± 0.2 mM, respectively. In vivo, 100 mg/kg pulegone exerts a transient anti-hyperalgesic effect on both mechanical (pulegone: 274.25 ± 68.89 g, n = 8; vehicle: 160.88 ± 35.17 g, n = 8, p < 0.0001), thermal heat (pulegone: 4.09 ± 0.62 s, n = 8; vehicle: 2.25 ± 0.34 s, n = 8, p < 0.0001), and cold (pulegone: 2.25 ± 1.28 score, n = 8; vehicle: 4.75 ± 1.04 score, n = 8, p = 0.0003). In a similar way, 100 mg/kg menthol exerts a transient anti-hyperalgesic effect on both mechanical (mechanical: menthol: 281.63 ± 45.52 g, n = 8; vehicle: 166.25 ± 35.4 g, n = 8, p < 0.0001) and thermal heat (menthol: 3.65 ± 0.88 s, n = 8; vehicle: 2.19 ± 0.26 s, n = 8, <0.0001). Conclusion: Here, we show that both pulegone and menthol are anti-inflammatory and anti-hyperalgesic monoterpenes. These results might open the path towards new compound mixes to alleviate the pain sensation.

Identification and Differentiation of Wide Edible Mushrooms Based on Lipidomics Profiling Combined with Principal Component Analysis.

Mushroom, as a kind of higher fungus, is a precious homology resource of medicine and foods. In this study, total lipids were extracted from eight wild edible mushrooms and subsequently characterized by ultra-high-performance liquid chromatography-Quadrupole-Exactive Orbitrap mass spectrometry. 20 lipid classes and 173 molecular species were identified and quantified. Lipid molecules and their concentrations in Boletus speciosus, Boletus bainiugan, and Tricholoma matsutake exhibited significantly different behaviors compared with the remaining mushrooms. Hierarchical cluster analysis revealed that lipid profiles of B. bainiugan were most similar to B. speciosus followed by T. matsutake, Canthar-ellus cibarius, Sarcodon aspratu, Termitomyces eurrhizus, Laccaria laccata, and Thelephora ganbajun. In addition, several differential lipids can be considered as potential biomarkers to distinguish different mushroom species, for instance, lysophosphatidylethanolamine (16:1) and ceramide non-hydroxy fatty acid-dihydrosphingosine (d23:0-10:0). This study provided a new perspective to discriminate the mushroom species from the perspective of lipidomics.

Determination and comparison of phospholipid profiles in eggs from seven different species using UHPLC-ESI-Triple TOF-MS.

Egg yolk phospholipids from seven different species were purified (purity > 96%) using SPE columns, and subsequently the phospholipid profiles were identified and quantified by ultra-high-performance liquid chromatography-electrospray ionization-triple time-of flight mass spectrometry (UHPLC-ESI-Triple TOF-MS). Eight phospholipid classes and 87 molecular species were characterized. Principal component analysis showed that the molecular species and concentration of phospholipids in pigeon and hen egg yolks had a significant difference with other eggs. Hierarchical cluster analysis indicated that the phospholipid profiles of pigeon egg yolks were closest to hen egg yolks, followed by quail, duck, ostrich, emu and goose egg yolks. Different relative quantities of certain molecular species were different among egg yolk types; for instance, phosphatidylcholine (16:0/16:1) in goose egg yolks and phosphatidylethanolamine (16:0/18:3) in ostrich egg yolks. This study provides a basis for a better understanding of the phospholipid profiles of egg yolks, and better evaluation of the nutritional value of eggs.