Ethyl Linoleate Research Articles

LC-ESI-MS and GC-MS Profiling, Chemical Composition, and Cytotoxic Activity of Endophytic Fungus Pleosporales sp. Derived from Artemisia annua

The chemical profiling of ethyl acetate extract of the endophytic fungus Pleosporales sp. using liquid chromatography–electrospray ionization–mass spectrometry (LC-ESI-MS) revealed the presence of 12 metabolites of different chemical classes such as steroids, α-pyrones, asterric acid derivatives, and quinones. Additionally, the gas chromatography–mass spectrometry (GC-MS) profiling of the ethyl acetate (EtOAc) and methanol extracts exhibited the presence of fatty acids and their esters, in which methyl palmitate (18.72%, and 25.48%, respectively) and methyl linoleate (11.92% and 23.39%, respectively) were found in both extracts. On the other hand, palmitic acid (12.60%), methyl oleate (26.90%), oleic acid (4.01%) and linoleic acid (3.25%) were present only in methanol extract. Furthermore, ethyl palmitate (12.60%), 13-octadecenoic acid (19.36%), and ethyl linoleate (3.25%) occurred in EtOAc extract. A phytochemical investigation of both extracts led to the isolation of fatty acids such as palmitic acid (18), oleic acid (20), and linoleic acid (21) and their esters including methyl palmitate (13), methyl stearate (22), methyl linoleate (16), methyl 3-hydroxy-5-methylhexanoate (23), and monomethyl azelate (27), in addition to monoacyl derivatives of glycerol such as 3,3-dihydroxypropyl hexadecanoate (24), 2,3-dihydroxypropyl elaidate (25), and 1-linoleoyl-sn-glycerol (26). The structures of the isolated compounds were identified by different spectroscopic analyses including 1H- and 13C-NMR and GC-MS. The EtOAc extract exhibited a cytotoxic effect against MCF-7 and HepG-2 cell lines, with IC50 values of 4.12 ± 0.10 and 10.05 ± 0.05 μg/mL, respectively.

Prediction of storage years of Wuyi rock tea Shuixian by metabolites analysis.

Wuyi rock teas of different storage duration have different flavor, bioactivity, and market value, Shuixian is a main variety of Wuyi rock tea. In this study, metabolites composition of Shuixian with different storage years were analyzed using Ultrahigh Performance Liquid Chromatography-Quadrupole-Time of Flight-Mass Spectrometry (UPLC-Q-TOF-MS). A total of 1201 compounds were identified, and 104 differential compounds (VIP > 1.5) were determined. Furthermore, the results showed that five compounds exhibited a positive correlation with storage time, such as alpha-terpineol formate, carnosol, 2-phenethyl-D-glucopyranoside, Ellagic acid, and D-ribosyl nicotinic acid, while 24 compounds showed a negative correlation, such as Ethyl linoleate, leucocyanidin, cis-3-hexenyl acetate. In total, 29 signature compounds significantly correlated with storage time. These findings shed light on the patterns and mechanisms of changes in the composition of Wuyi rock tea during storage and provide a theoretical foundation for distinguishing the storage years.

Spectral characterization, analgesic, and anti-inflammatory effects of ethanolic extract of Calotropis procera leaf and dry latex from Jazan, Kingdom of Saudi Arabia

Traditional healers have used the shrub Calotropis procera (CP) for many years for various therapies. The present study investigated the bioactive constituents of ethanolic extract of CP leaf and dried latex using gas chromatography-mass spectrometry and Fourier transforms infrared spectroscopy. The identification and characterization of the compounds were confirmed by examining the constituents' mass spectrum fragmentations and FT-IR spectra and comparing the results with those in the literature. The tail-flick method was used to investigate the analgesic properties of the extract and its anti-inflammatory activities using a rat model of formalin-induced oedema. Acute oral toxicity in rats was studied per OECD recommendations. Twenty male rats were divided into four groups and received an ethanolic extract of the leaves and dried milky sap of CP (200 mg/Kg) in groups 1, 2, and 3. Group 4 rats were administered aspirin 50 mg/kg as a positive control. The CP dried latex extract has the highest content of lupeol and its acetate derivative compared to its leaf extract. The CP dried latex extract inhibited inflammation more significantly than the ethanolic leaf extract and the drug indomethacin at a higher dosage (200 mg/kg). The ethanolic extracts showed analgesia comparable to aspirin. It suggests that fatty acids and their esters, particularly ethyl linoleate (8.96%), ethyl palmitate (7.99%), ethyl linoleate (6.98%), and palmitic acid (5.18%), may be valuable biomarkers for characterizing leaf and latex samples and describing the medicinal potential of CP.

In silico pharmacokinetic and therapeutic evaluation of Musa acuminata peels against aluminium chloride-induced hepatotoxicity in adult BALB/c mice.

East Africa (Musa spp.), notably Musa acuminata, "Matooke" a staple and economically important food in the region. Here, 12 selected M. acuminata peels extract (MAPE) bioactive compounds were studied for hepatoprotective potentials in aluminium chloride-induced hepatoxicity in adult BALB/c mice. GC-MS analysis was used to identify active components of MAPE. In silico estimation of the pharmacokinetic, the GCMS-identified compounds' toxicity profile and molecular docking were compared with the standard (Simvastatin) drug. Hepatotoxicity was induced using aluminium-chloride treated with MAPE, followed by biochemical and histopathological examination. Twelve bioactive compounds 2,2-Dichloroacetophenone (72870), Cyclooctasiloxane 18993663), 7-Hydroxy-6,9a-dimethyl-3-methylene-decahydro-azuleno[4,5-b]furan-2,9-dione (534579), all-trans-alpha-Carotene (4369188), Cyclononasiloxane (53438479), 3-Chloro-5-(4-methoxyphenyl)-6,7a-dimethyl-5,6,7,7a-tetrahydro-4H-furo[2,3-c]pyridin-2-one (536708), Pivalic acid (6417), 10,13-Octadecadienoic acid (54284936), Ethyl Linoleate (5282184), Oleic acid (5363269), Tirucallol (101257), Obtusifoliol (65252) were identified by GC-MS. Of these, seven were successfully docked with the target proteins. The compounds possess drug likeness potentials that do not inhibits CYP450 isoforms biotransformation. All the docked compounds were chemoprotective to AMES toxicity, hERGI, hERGII and hepatotoxicity. The animal model reveals MAPE protective effect on liver marker's function while the histological studies show regeneration of the disoriented layers of bile ducts and ameliorate the cellular/histoarchitecture of the hepatic cells induced by AlCl3. The findings indicate that MAPE improved liver functions and ameliorated the hepatic cells' cellular or histoarchitecture induced by AlCl3. Further studies are necessary to elucidate the mechanism action and toxicological evaluation of MAPE's chronic or intermittent use to ascertain its safety in whole organism systems.

Effects of Walnut Septum on The Enzyme Pathways Associated with Plasma Cholesterol Level

Objective: Cholesterol is crucial compound that plays pivotal role in cellular function in living organisms. Its excess or deficiency in plasma can lead to destruction and disintegration of cell membrane structure. Maintaining balanced intake of cholesterol in diet and seeking medical treatment, if necessary, can help prevent these negative effects. Furthermore, people often resort to natural and herbal remedies, such as walnut septum. Due to dearth of scientific data regarding effects of walnut septum on cholesterol metabolism, this research was undertaken to explore its potential effects. Method: Analysis was begun by extracting septum using various solvents. Resulting extracts were then analyzed using GC-MS, and compounds were identified by using an integrated library database. To detect effects of extracts on cholesterol esterase and HMG-CoA reductase, a colorimetric method was employed. Result: Monophenol, 2,4-Di-tert-butylphenol, 2,6-Di-tert-butylphenol, ethyl linoleate, and butyl linoleate were some of compounds detected by GC-MS scanning. The highest inhibitions were observed in the enzymatic analysis, with a rate of 3.2% (acetone) in the HMG-CoA reductase analysis and 13.6% (water) in the cholesterol esterase analysis. Conclusion: Although the walnut septum extract contains various chemical compounds, our in vitro analysis data suggest that there is no inhibitory effect at therapeutic level on enzyme pathways that regulate plasma cholesterol levels, namely HMG-CoA reductase and cholesterol esterase. We believe that further research is necessary to comprehensively evaluate its effects on other pathways.

Comprehensive analysis of spatial heterogeneity reveals the important role of the upper-layer fermented grains in the fermentation and flavor formation of Qingxiangxing baijiu

Different spatial positions lead to inconsistent fermentation effects and flavors, however, the spatial heterogeneity of Qingxiangxing (QXX) Baijiu remains unknown. We investigated the microbes, flavors, and physicochemical properties of different layers in fermented grains of QXX Baijiu using Illumina HiSeq sequencing, two-dimensional gas chromatography–mass spectrometry (GC × GC–MS) and ultra-high performance liquid chromatography-mass (UHPLC-MS). A total of 79 volatiles, 1596 metabolites, 50 bacterial genera, and 52 fungal genera were identified. The contents distribution followed the order: upper layer > bottom layer > middle layer. Organic acids and derivatives were the main differential metabolites across the three layers. Starch, pH, and reducing sugar levels increased from the upper to bottom layer. Saccharomyces and Lactobacillus were dominant microbes. Pediococcus, the biomarker of upper layer, showed positive correlations with formic acid, ethyl lactate, acetic acid, ethyl linoleate, and ethyl oleate. These findings deepen our understanding of the fermentation and flavor formation mechanisms of QXX Baijiu.

Bio profiling of brackish water alga Gracilaria tenuistipitata C.F.Chang & B.-M.Xia – an indigenous species from Andhra Pradesh, East Coast, India

ABSTRACT Gracilaria is one of the commercially important genera for the superior quality of phycocolloids, and high nutritional and therapeutic values. The present study is subjected to the bio-profile of the brackish water species Gracilaria tenuistipitata from the shoreline of Andhra Pradesh, East Coast, India. Proximate analysis of this species contains a high amount of carbohydrate (58.19 ± 3.52%), ash (32.64 ± 3.21%), moisture (5.84 ± 3.88%) and fiber (10.35 ± 0.595). The preliminary analysis of the algal extract confirmed the presence of alkaloids, saponins, tannins, flavonoids, steroids, glycosides, terpenoids, phenols, quinones and anthraquinones. The existence of important bioactive compounds such as ethyl oleate (18.45%), ethyl palmitate ((17%), ethyl linolenate (16.34%), phytol (12.46%) and clionasterol (8.56%) were also been confirmed in G. tenuistipitata by GCMS technique. The antibacterial potentiality of this species recorded the maximum zone of inhibition against E. coli (18.83 ± 0.6 mm), P. syringae (18 ± 1 mm) and S. aureus (17.33 ± 0.66 mm) at the concentration of 50 µg/ml. Further, this species exhibited a significant effect of antioxidant (IC50 = 24.08 ± 1.32) and anti-cancerous (IC50 = 39.90 ± 1.60 µg/ ml) activities against human lung cancer cells A459. Thus, G. tenuistipitata could be a promising element and alternative source for the potential activities.

Volatile organic composition of five Rubiaceae species: Insights into their phytochemical diversity

Natural volatile organic compounds (VOCs) obtained from five Rubiaceae plants native to south China, namely Damnacanthus indicus, Hamelia patens, Exallage chrysotricha, Psychotria serpens, and Spermacoce pusilla, were isolated and characterized in this study. The analysis revealed that each plant contained 71, 57, 80, 73, and 70 volatile organic chemical compounds, respectively. The main VOCs shared by five plants was palmitate (10.20%–36.26%). Methyl salicylate, caryophyllene oxide, tetradecanoic acid, 6,10,14-trimethyl-2-pentadecanone, pentadecanoic acid, pentacosane, pentadecanal, nonanal, hexadecanoic acid methyl ester, phytol, linalool, and (E)-β-ionone were shared by at least 4 Rubiaceae plants in this study. Besides, each of the five plants has its main components as follows: 12.81% ethyl linoleate and 6.13% (E)-13-octadecenoic acid for D. indicus; 35.17% methyl salicylate for H. patens; 9.50% (Z, Z)-9,12-octadecadienoic acid and 7.56% endo-borneol for E. chrysotricha; 13.93% methyl salicylate for P. serpens; 6.19% humulene and 6.08% humulene oxide II for S. pusilla. This research provides insights into the phytochemical diversity and classification of Rubiaceae plants, laying a solid foundation for future natural product development in the Rubiaceae family.

Phytochemical screening and antibacterial activity testing of n-hexane extract from Barringtonia asiatica seeds

Barringtonia asiatica, a marine plant belonging to the Lecythidaceae family, exhibits bioactivity in all parts of the plant. In the Simeulue region, the seeds of this plant are used for fish trapping. The polar extracts of B. asiatica seeds has shown antibacterial activity, but the non-polar extracts has not been studied yet. Therefore, this study aimed to determine the secondary metabolites of B. asiatica using a non-polar solvent (n-hexane) and evaluate its activity against Gram-positive and Gram-negative bacteria. The extraction method employed using soxhlet extraction, and the antibacterial activity was determined using the Kirby-Bauer method. The presence of secondary metabolites in the B. asiatica seed extract was assessed using phytochemical tests, and its chemical composition was analyzed using Gas Chromatography Mass Spectrophotometry (GC-MS). The yield of n-hexane extract from B. asiatica seeds was 1.7%, and the phytochemical analysis revealed that the B. asiatica seed’s n-hexane extract contains only terpenoids compounds. The B. asistica seed’s n-hexane extract at concentration of 10% (w/v) showed the highest zone of inhibition against Staphylococcus aureus (9.3 mm) followed by Escherichia coli (9,9 mm). The GC-MS analysis showed that B. asiatica seed’s n-hexane extract contains Guaiene, Guaiene, Ledene, 9,12-Octadecadienoic acid, and Ethyl linoleate. Based on these findings, it can be concluded that B. asiatica seed's n-hexane extract exhibited antibacterial activity against S. aureus and E. coli.

Influence of Sucrose and Activated Charcoal on Phytochemistry and Vegetative Growth in Zephyranthes irwiniana (Ravenna) Nic. García (Amaryllidaceae).

Zephyranthes irwiniana (Ravenna) Nic. García is an endemic, red list threatened species from the Brazilian savanna (Cerrado) with pharmacological potential to treat the symptoms of Alzheimer's Disease (AD). This work analyzed the vegetative growth and phytochemistry of its potential compounds, in response to variations in sucrose concentration and activated carbon (AC). Seeds were germinated in vitro and in the greenhouse. The in vitro bulbs were separated in six treatments with different sucrose concentrations (30, 45 and 60 gL-1) and/or AC (1 gL-1). Biomass increases in individuals grown in the greenhouse were higher than those cultivated in vitro. Sucrose concentration significantly increased biomass and root number. AC had a positive influence on leaf and root size, and a negative influence on root number. GC-MS analyses indicated great variation in the abundance of α-terpenyl-acetate, ethyl linoleate, clionasterol and lycorine between treatments, with maximum concentrations of 53.06%, 38.68, 14.34% and 2.57%, respectively. Histolocalization tests indicated the presence of alkaloids in the leaf chlorenchyma and bulb cataphylls. Finally, the present study provided new evidence that the constitution of the culture medium directly influences the vegetative growth and phytochemistry of this species, providing a good medium condition for propagating the species under threat.

Elucidation of the mechanism of Zhenbao pills for the treatment of spinal cord injury by network pharmacology and molecular docking: A review.

To explore the mechanism of the Zhenbao pill (ZBP) in treating spinal cord injury (SCI). The TCMSP Database, HERB Database and literature search were used to screen the effective ingredients and targets of ZBP; SCI-related genes were searched in GeneCards, OMIM, PharmGkb, TTD and DrugBank databases; the potential targets of ZBP for treating SCI were predicted and Venn diagrams were drawn, and the "herb-ingredient-target" network was constructed by Cytoscape software. The PPI network was constructed by STRING software, and the core targets were screened by cytoNCA plug-in; GO enrichment and KEGG pathway analysis were performed on the predicted targets using the DAVID Platform, and visualized with the Microbiology Network Platform. The molecular docking between the key ingredients and the core target was carried out by AutoDockVina software. 391 active ingredients and 836 action targets were obtained from ZBP and there are 1557 SCI related genes in 5 disease databases. The top 5 active ingredients were Quercetin, Camptothecin, Kaempferol, Ethyl iso-allocholate, and Ethyl linoleate, and 5 core genes were SRC, CTNNB1, TP53, AKT1, and STAT3. GO enrichment analysis showed that the core targets were involved in 1206 biological processes, 120 cellular components and 160 molecular functions; KEGG enrichment analysis showed that the core targets involved 183 pathways, including PI3K-Akt signaling pathway and other signaling pathways. Molecular docking indicated that CTNNB1, SRC, TP53, AKT1 and STAT3 showed good binding ability with the active ingredients quercetin, kaempferol and ethyl isobutyric acid. ZBP improves SCI through multi-components, multi-targets and multi-pathways.

CHROMATOGRAPHIC AND SPECTRAL STUDY OF ARCTIUM LAPPA AND ARCTIUM TOMENTOSUM FRUCTUS CULTIVATED IN ALTAI

Burdock is an ingredient of official and traditional medicines in different countries, its roots are used for food, biologically active additives, functional nutrition products, fertilizers, etc. A great demand led to the situation when many countries including Russia began the plant’s cultivation. Despite that, the aboveground parts of the plant including its fructus still remain expendable. At the moment, burdock fructus are officially used only in China and Japan. In Russia they are not used and studies of their chemical composition and pharmacological properties are scarce.
 The research showed that fructus of Arctium lappa and A. tomentosum cultivated in Altai using by traditional way of growing, and new of agrotechnics of cultivation contain lignans, hydroxycinamic acid, fatty acids and their derivatives, polysaccharides and anthocyanin’s. The use of a new cultivation technology increased the content of lignans and other BAS by 10–25%. Hydroxycinamic acid is one of the dominant substances in fructus by content, therefore it is possible to standardize raw material according to this parameter. The presence of methyl cis-9, cis-15-octadecadienoate and 11-Eicosenoic acid methyl ester in fructushas been discovered for the first time. Ethyl linoleate and methylfolate or methyl cis-9-octadecenoate are found to be dominant components of fatty acids and their derivatives.
 Additional studies of chemical composition, pharmacological properties, clinical approbation are needed to obtain evidence of the efficiency of burdock fructus utilization for clinical purposes and prevention.

Solvent-free synthesis of hydrophobic and amphiphilic esters using a chemically modified lipase from Thermomyces lanuginosus: a comparative study with native and immobilized forms.

Using lipases to catalyze the synthesis of the most differentiated type of compounds remains one of the major challenges among scientists. Seeking more economic and advantageous catalysts is a current goal of green chemistry. In this work, we demonstrate the potential of a chemically modified form of lipase from Thermomyces lanuginosus (cmLTL) for the synthesis of both hydrophobic (heptyl heptanoate, heptyl octanoate, heptyl decanoate, decyl heptanoate, decyl octanoate and decyl decanoate) and amphiphilic (2-(2-ethoxyethoxy)ethyl oleate and 2-(2-ethoxyethoxy)ethyl linoleate) esters, in bulk. The results were compared with its native (LTL) and immobilized (imLTL) forms. The data revealed that LTL showed poor activity for all reactions performed with n-heptane (η<20 %). ImLTL was able to synthesize all hydrophobic esters (η>60 %), with exception of the short ester, heptyl heptanoate. cmLTL was the only form of LTL capable of producing hydrophobic and amphiphilic esters, without compromising the yield when the reactions were performed under solvent-free conditions (>50 %). Molecular modeling showed that the active pocket of cmLTL is able to deeply internalize transcutol, with stronger interactions, justifying the outstanding results obtained. Furthermore, owing to the possibility of cmLTL filtration, the reusability of the catalyst is ensured for at least 6 cycles, without compromising the reaction yields.

Applying HS-SPME-GC-MS combined with PTR-TOF-MS to analyze the volatile compounds in coffee husks of Coffea arabica with different primary processing treatments in Yunnan

Primary processing treatments are crucial to the flavor profile of coffee beans, which create the flavor precursors basis in coffee husks and diffuse into the beans, with satisfying outcomes. In this study, eleven coffee husks of Coffea arabica with different primary processing treatments (sun exposure, washing and honey treatment) from three latitudes of Yunnan were investigated by the combination of HS-SPME-GC-MS and PTR-TOF-MS. A total of 114 volatile organic compounds (VOCs) and 77 masses were identified. The characteristic compounds octanoic acid (S1) and methyl linoleate (S11) in sun-exposed, phenethyl alcohol (F4), methyl salicylate (F7), 3,5-dimethylbenzaldehyde (F9) and phytone (T9) in washed and n-hexadecanoic acid (S9) of honey-treated husks were recognized by the ions at m/z 33.032, m/z 68.049, m/z 83.049, m/z 67.054, m/z 57.034, m/z 41.030 and m/z 49.010, respectively. This study demonstrated the feasibility and complementarity of HS-SPME-GC-MS and PTR-TOF-MS in the rapid identification of VOCs in coffee husks. Meanwhile, the antioxidant capacities of the 11 husks were evaluated in vitro, and the sun-exposed samples exhibited most promising potency, in which methyl salicylate (F7), methyl linoleate (S11), methyl linolenate (S13), ethyl linoleate (S14), ethyl linolenate (S16), linalool (T1), citronellol (T2) and caffeine (J3) contributed mainly to the antioxidant capacities.

Characterization and bioactivity of copaiba essential oil carried in a self-nanoemulsifying drug delivery system

Copaiba essential oil (CEO) is the volatile part of copaiba balsam, which has been topically used for various inflammatory conditions. However, there are some concerns about the CEO safety for oral use. The lipophilic character of CEO also limits its application in the pharmaceutical field. This study prepared a self-nanoemulsifying drug delivery system (SNEDDS) containing CEO and evaluated its toxic effects against a primary culture from pig liver (PLP2) and Green monkey kidney cell line (Vero). The inhibition of oxide nitric production was also evaluated on RAW 264.7 macrophage cell line to access the anti-inflammatory effect. The CEO was extracted by hydrodistillation and β-caryophyllene accounted for 51.8% of the oil. The formulation (FSNEDDS) consisting of CEO, Cremophor and ethyl linoleate was characterized in relation to morphology, stability, rheology, simulated digestion and bioaccessibility in vitro. FSNEDDS displayed Newtonian flow behavior with viscosity depending only on temperature and, in an aqueous medium, it formed small spherical particles (<100 nm size diameter). The FSNEDDS showed higher oxidative stability than the non-formulated CEO. In the simulated digestion, FSNEDDS formed nanoemulsifying droplets in gastric phase and tiny micelles in intestinal phase, and a bioaccessibility of 63%. The FSNEDDS showed a superior anti-inflammatory activity (+11%) than non-formulated CEO and this beneficial concentration was achieved with a non-toxic concentration for none of the cell lines tested. In conclusion, FSNEDDS improves the physicochemical stability, bioaccessibility and bioactivity of CEO, and it could be a phytotherapic option for per oral administration to treat inflammatory diseases.

Comparison of Ca-Based Commercial and Natural Catalysts Performance on Olive Pomace Pyrolysis Process

Physicochemical treatment was applied with 20 mg/L alum to the marble processing effluents as 5 minutes 200 rpm mixing, 25 minutes 15 rpm mixing and 60 minutes settling and marble sludge (MS) was produced. Catalytic performance of MS in olive pomace (OP) pyrolysis process was evaluated and compared to commercial Ca(OH)2 since it mainly comprises of different AAEMs (especially Ca and its forms such as CaCO3, CaO) functioned as catalyst. Catalytic pyrolysis was conducted at 600°C and 5°C/min heating rate with 5% and 10% catalyst (MS or Ca(OH)2) dosages. Although both catalysts had important effect on pyrolysis product yields, Ca(OH)2 was found as good alternative for higher gas production and MS was introduced as better option for the higher char production comparing to the conventional OP pyrolysis. Pyrolysis biochars produced with MS were in higher thermal strength than the biochars generated with Ca(OH)2. Moreover, biooils of OP+MS include different organic compounds, such as 9 heptadecanol, 1-eicosanol, ethyl linoleate, ethyl oleate, addition to the compounds observed in pyrolysis liquids of OP and OP+ Ca(OH)2. All detected organic components have diverse usage areas. Ca(OH)2 provided more decrement in the percentages of oxygenated compounds as compared to the MS. Consequently, it can be stated that MS can be used successfully as an alternative to Ca-based commercial catalyst in OP pyrolysis.

Study of the Chemical Composition of Rosa beggeriana Schrenk's Fruits and Leaves.

Rosa species are widely used in folk medicine in different countries of Asia and Europe, but not all species are studied in-depth. For instance, Rosa beggeriana Schrenk, a plant which grows in Central Asia, Iran, and some parts of China, is little described in articles. Column and thin-layer chromatography methods were used to isolate biologically active substances. From a study of fruits and leaves of Rosa beggeriana Schrenk, a large number of compounds were identified, seven of which were isolated: 3β,23-dihydroxyurs-12-ene (1), β-sitosterol (2), betulin (3), (+)-catechin (4), lupeol (5), ethyl linoleate (6), and ethyl linolenoate (7). Their structures were elucidated by 1H, DEPT and 13C NMR spectroscopy, mass spectrometry, and GC-MS (gas chromatography-mass spectrometry). The study also identified the structures of organic compounds, including volatile esters and acids. Consequently, comprehensive data were acquired concerning the chemical constitution of said botanical specimen.

Evaluating phytochemical constituents and in-vitro antiplasmodial and antioxidant activities of Fadogiella stigmatoloba, Hygrophylla auriculata, Hylodesmum repandum, and Porphyrostemma chevalieri extracts

IntroductionFadogiella stigmatoloba, Hygrophylla auriculata, Hylodesmum repandum and Porphyrostemma chevalieri are used against malaria in traditional medicine in the Democratic Republic of the Congo (DRC). To evaluate their potential in the treatment of this disease, the in vitro antiplasmodial property of these four plants was evaluated. All experiments were conducted on methanolic extracts performed on selected organ parts of these plants. MethodsThe methanolic extracts, obtained by maceration, were firstly screened in vitro against the chloroquine sensitive (3D7) and resistant (W2) Plasmodium falciparum strains by the measurement of lactate dehydrogenase activity, and on human keratinocytes (HaCat) cells by the MTT assay to determine their selectivity indices (SI). Secondly, the antioxidant activity of the same extracts was evaluated using DPPH and FRAP assays. Finally, the presence of specific phytochemical constituents was evaluated using standard methods and tentatively identified by GC-MS. ResultsAn optimum antiplasmodial activity (IC50 = 3.4 ± 0.7 μg/mL, for 3D7, SI = 58.2; IC50 = 7 ± 1.0 μg/mL, for W2, SI = 28.3) was obtained with the leave extract of P. chevalieri. The leaves (for F. stigmatoloba and H. repandum), and the aerial part (for H. repandum) extracts showed promising and moderate antiplasmodial activities against respectively the 3D7 strain (IC50: <15 μg/mL), and W2 strain (IC50:15–50 μg/mL). All extracts presented a weak cytotoxic effect (IC50: >100 μg/mL) on HaCat cells. For the antioxidant test, the most interesting activity was obtained with the leaf extract of P. chevalieri. The GC–MS analysis of these four plants species extracts revealed the presence of various compounds, such as Ethyl 2-nonenoate, 2-(2-Hydroxy-2-phenylethyl)-3,5,6-trimethyl pyrazine, Palmitic Acid, Ethyl palmitate, Ethyl linolenate, and N-Acetyltyramine. ConclusionBased on the obtained results, P. chevalieri could be selected for further investigations or ⁄and for the management of malaria after standardization.

Metagenomic Insights into the Regulatory Effects of Microbial Community on the Formation of Biogenic Amines and Volatile Flavor Components during the Brewing of Hongqu Rice Wine.

As one of the typical representatives of Chinese rice wine (Huangjiu), Hongqu rice wine is produced with glutinous rice as the main raw material and Hongqu as the fermentation starter. The complex microbial flora in the brewing process may have a great influence on the formation of the flavor quality and drinking safety of Hongqu rice wine. Previous studies have shown that high biogenic amine (BA) content in rice wine has potential physiological toxicity and has become a bottleneck problem restricting the development of the rice wine industry. This study aimed to evaluate the regulatory effects of the microbial community on the formation of BAs and volatile flavor components during the brewing of Hongqu rice wine. The results demonstrated that histamine, putrescine, cadaverine, tyramine, tryptamine, spermine, and spermidine were the main BAs in Hongqu rice wine. The contents of putrescine, cadaverine, histamine, tyramine, and spermidine in Hongqu rice wine of HBAs (with higher BAs content) were significantly higher than those in LBAs (with lower BAs content). GC-MS testing results showed that there were significant differences in the composition of volatile organic compounds (VOCs) between HBAs and LBAs. Among them, VOCs such as 2-methoxy-4-vinylphenol, ethyl caprate, phenethyl acetate, ethyl lactate, ethyl myristate, ethyl palmitate, ethyl n-octadecanoate, ethyl oleate, and ethyl linoleate were identified as the characteristic volatile components with significant differences between HBAs and LBAs. Microbiome analysis based on metagenomic sequencing revealed that unclassified_g_Pantoea, Klebsiella pneumoniae, Panobacter disperse, unclassified_f_Enterobacteriaceae, Leuconostoc mesenteroides, and Saccharomyces cerevisiae were the dominant microbial species in the HBA brewing process, while Weissella confuse, Pediococcus acidilactici, Saccharomyces cerevisiae, and Aspergillus niger were the dominant microbial species in the LBA brewing process. Furthermore, correlation heatmap analysis demonstrated that BAs were positively related to Lactobacillus curvatus, Lactococcus lactis, and Leuconostoc mesenteroides. Bioinformatical analysis based on the KEGG database revealed that the microbial genes encoding enzymes involved in BAs' synthesis were more abundant in HBAs, and the abundances of microbial genes encoding enzymes related to BAs' degradation and the metabolism of characteristic volatile components were higher in LBAs. Overall, this work provides important scientific data for enhancing the flavor quality of Hongqu rice wine and lays a solid foundation for the healthy development of the Hongqu rice wine industry.

Predicting the mass spectrum of polymerizing linoleates using weighted random graph modeling

Biopolymers and biopolymer networks that form via autoxidation, like in drying of oil paint or fat degradation in food components, contain a large variety of monomeric building blocks. While the monomer variety complicates the modeling itself, obtaining experimental validation of infinite polymer networks is inherently difficult as well. A new model is developed, where an automated reaction network generation (ARNG) procedure is used to automatically generate the monomer components, structures and masses, and their reactions. This methodology is combined with random graph (RG) modeling to predict global polymer properties: distributions of numbers of monomer units and molar masses, gel point and gel fraction. This computational framework is applied to two model systems for linseed oil paint binder: the polymerization of ethyl linoleate (EL) and methyl linoleate (ML). A novel method was constructed to deal with the variability of monomer masses that complicates inferring molar mass from monomer number distribution. By modeling the polymer as a weighted random graph where the nodes contain information about the monomer masses in the system, the total weight of the finite connected components is computed. The predicted mass spectrum of finite connected components is used for validation with experimental data. A size exclusion chromatography (SEC) trace of ML is employed, which after calibration using the proposed framework, proves consistency between model and SEC data. The model provides a practical approach to both characterize complex biopolymers as polymers in terms of molar mass distribution and gel point, while preserving the information down to the level of monomeric units.