In silico investigations of some Cyperus rotundus compounds as potential anti-inflammatory inhibitors of 5-LO and LTA4H enzymes.

The present study aimed to experimentally identify the essential oil of Algerian Cyperus rotundus L. and to model the interaction of some known anti-inflammatory molecules with two key enzymes involved in inflammation, 5-Lypoxygenase (5-LO) and leukotriene A4 hydrolase (LTA4H). Gas chromatography/gas chromatography-mass spectrometry (GC/GC-MS) revealed that 92.7% of the essential oil contains 35 compounds, including oxygenated sesquiterpenes (44.2%), oxygenated monoterpenes (30.2%), monoterpene hydrocarbons (11.8%) and sesquiterpene hydrocarbons (6.5%). The major identified oxygenated terpenes are humulene oxide II, caryophyllene oxide, khusinol, agarospirol, spathulinol and trans-pinocarveol Myrtenol and α-terpineol are known to exhibit anti-inflammatory activities. Several complexes obtained after docking the natural terpenes with 5-LO and LTA4H have shown strong hydrogen bonding interactions. The best docking energies were found with α-terpineol, Myrtenol and khusinol. The interaction between the natural products and amino-acid residues HIS367, ILE673 and GLN363 appears to be critical for 5-LO inhibition, while the interaction with residues GLU271, HIS295, TYR383, TYR378, GLU318, GLU296 and ASP375 is critical for LTA4H inhibition. Molecular dynamics (MD) trajectories of the selected docked complexes showed stable backbone root mean square deviation (RMSD), supporting the stability of the natural product-enzyme interaction.Communicated by Ramaswamy H. Sarma.

Chemical Composition, Anti-Quorum Sensing, Enzyme Inhibitory, and Antioxidant Properties of Phenolic Extracts of Clinopodium nepeta L. Kuntze.

Phenolic extracts of Clinopodium nepeta were prepared and their preliminary phenolic profiles determined using HPLC-DAD with 26 phenolic standards. Apigenin (21.75 ± 0.41 µg/g), myricetin (72.58 ± 0.57 µg/g), and rosmarinic acid (88.51 ± 0.55 µg/g) were the most abundant compounds in DCM (dichloromethane), AcOEt (ethyl acetate), and BuOH (butanol) extracts, respectively. The DCM and AcOEt extracts inhibited quorum-sensing mediated violacein production by C. violaceum CV12472. Anti-quorum-sensing zones on C. violaceum CV026 at MIC (minimal inhibitory concentration) were 10.3 ± 0.8 mm for DCM extract and 12.0 ± 0.5 mm for AcOEt extract. Extracts showed concentration-dependent inhibition of swarming motility on flagellated P. aeruginosa PA01 and at the highest test concentration of 100 µg/mL, AcOEt (35.42 ± 1.00%) extract displayed the best activity. FRAP assay indicated that the BuOH extract (A0.50 = 17.42 ± 0.25 µg/mL) was more active than standard α-tocopherol (A0.50 = 34.93 ± 2.38 µg/mL). BuOH extract was more active than other extracts except in the ABTS●+, where the DCM extract was most active. This antioxidant activity could be attributed to the phenolic compounds detected. C. nepeta extracts showed moderate inhibition on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase, and α-amylase. The results indicate that C. nepeta is a potent source of natural antioxidants that could be used in managing microbial resistance and Alzheimer's disease.

Chemical Composition, Acetylcholine Esterase and Anti-bacterial Activities of Essential Oils of Elaeosilenum thapsioides (Desf.) Maire from Algeria.

BACKGROUND: Traditionally, the Algerian medicinal plant Elaeosilenum thapsioides (Desf.) Maire has been used for many diseases. The present research work aims to explore the chemical and biological characterization of its essential oil. METHODS: The essential oils were obtained by hydrodistillation of different Elaeosilenum thapsioides (Apiaceae) aerial parts samples collected from two different regions (Mahouane and Megres) from Setif, Eastern Algeria. The chemical characterization of the obtained essential oils is reported here for the first time. Besides, they were evaluated for their in vitro Acetylcholinesterase (AChE) inhibitory activity involved in Alzheimer's disease using Ellman's spectrophotometric method. RESULTS: Additionally, their in vitro antimicrobial activity was assessed by the disc diffusion method. Both activities were performed at various oil concentrations. The GC/MS analysis of the essential oils from aerial parts (leaves, stems, flowers, and seeds) of E. thapsioides identified 47 constituents. Monoterpene hydrocarbons were the main components, ranging from 72.78 to 99.13%. Oxygenated monoterpenes and oxygenated sesquiterpenes ranged between 1.37 and 17.25% and 0.12 and 3.53% in essential oils from leaves and stems. Sesquiterpene hydrocarbons were present in small to large quantities in the essential oils of both populations, ranging from 0.69 to 13.44%. The presence of m-Methoxybenzyl isothiocyanate was recorded in stems essential oils from Mahouane and leaves essential oils from Merges, which was 9.73% and 3.72%, respectively. CONCLUSION: The stems essential oils obtained from plants collected in Mahouane showed the highest AChE inhibitory activity. The highest anti-bacterial activity was shown by the essential oil obtained from Megres leaves against Bacillus cereus ATCC 11778. The oils exhibited a moderate inhibitory activity in both tests.

In vitro antioxidant, anticholinesterases, anti-α-amylase, and anti-α-glucosidase effects of Algerian Salvia aegyptiaca and Salvia verbenaca.

In this study, Salvia aegyptiaca and Salvia verbenaca aerial part decoction and methanol extracts (SAE DE, SAE ME, SVR DE, and SVR ME) were screened for their in vitro antioxidant, anti-Alzheimer, and antidiabetic enzymes inhibition activities. The antioxidant properties of Salvia extracts were determined using DPPH radical scavenging, ABTS radical scavenging, Alkaline DMSO superoxide radical scavenging, ß-carotene bleaching, reducing power, and metal chelating activity assays. All extracts showed high antioxidant capacity and the antioxidant properties with the best performance were detected in the SAE ME and SVR ME. The extracts of S. aegyptiaca and S. verbenaca showed a low inhibitory activity of acetylcholinesterase (AChE), whereas, the methanol extract of S. aegyptiaca had the highest inhibitory activity on butyrylcholinesterase (BChE) (71.60 ± 4.33% for 100 µg/ml) compared to the other extracts. In vitro inhibitory effect on diabetic enzymes showed that the ME inhibited α-amylase enzyme with an IC50 86 and 101 µg/ml for SAE and SVR, respectively. Similarly, both extracts inhibited α-glucosidase with (IC50 97 and 150 µg/ml, respectively). The decoction extracts exhibited lower activity on both enzymes. PRACTICAL APPLICATIONS: It is becoming evident that oxidative stress is involved in several acute and chronic diseases. Counteracting free radical generation has become one of the widest fields of research worldwide. This study deals with the in vitro antioxidant activity of two plants from the Salvia genus as well as the assessment of their in vitro inhibitory properties of four key enzymes implicated in diabetes and Alzheimer's disease. Concerning the practical applications of our work, it can be explored in its antioxidant part as a food supplement to prevent the excess of free radicals in the body and also in other industrial practices. Another potential use is in the prevention and amelioration of both diabetes and Alzheimer's disease symptoms for the extracts that had enzyme inhibitory activity, but this deserves further toxicological and in vivo studies.

Senecipyrrolidine, an unusual pyrrolidine alkaloid isolated from Jacobaea gigantea (Desf.) Pelser (Asteraceae).

Alkaloids and phenolic compounds are among the most biologically active natural products from the Jacobaea/Senecio genera (Asteraceae). To isolate original natural products directly from Jacobaea gigantea crude polar extracts, centrifugal partition chromatography (CPC) was used. Previously, we reported the phytochemical study of J. gigantea (syn. Senecio giganteus) n-butanol extract using various classical chromatographical techniques combined with CPC. Herein major constituents from the J. gigantea crude ethyl acetate extract and further compounds from the n-butanol extract were purified in only one step using this technique. A new pyrrolidine alkaloid, named senecipyrrolidine was isolated along with thirteen known compounds - chiro-inositol, three phenolic acids, six flavonoids, two quinones and emiline, another pyrrolidine alkaloid - from crude n-butanol or ethyl acetate extracts. Pyrrolidine alkaloids were isolated for the first time in the Jacobaea/Senecio genera and were probably biogenetically related to the two isolated quinones derivatives jacaranone and 3a-hydroxy-3,3a,7,7a-tetrahydrobenzofuran-2,6-dione, isolated in this species.

Structural characterization, antioxidant and antibacterial activities of a novel polysaccharide from Periploca laevigata root barks.

A novel water-soluble polysaccharide named PLP1 was successfully isolated from root barks of Periploca laevigata by hot water extraction and further purified by DEAE-sepharose chromatography. PLP1 has a relative molar mass of 5.57 105 g/mol determined by Ultra-high performance liquid chromatography (UHPLC). The PLP1 structure was investigated by chemical and instrumental analysis including gas chromatography mass spectrometry (GC-MS), methylation analysis, Fourier transform infrared (FT-IR) spectroscopy and nuclear magnetic spectroscopy (1H NMR and 13C NMR). Results showed that PLP1 was mainly composed of glucose, galactose, mannose and glucuronic acid in a molar percent of 62.9, 19.4, 11.8 and 5.9, respectively. The backbone of PLP1 was composed of 1,3-ß-d-Glcp, 1,3,4-α-d-Glcp, 1,4-α-d-Manp, 1,6-α-d-Manp, 1,3-α-d-Galp and 1,6-ß-d-Galp. The thermogravimetry analysis (TGA) and the differential scanning calorimetry (DSC) were used and showed that PLP1 has good thermal stability under 229 °C. Moreover, the purified polysaccharide demonstrated an appreciable in vitro antioxidant potential and high antibacterial activity against several Gram (+) and Gram (-) strains. These finding suggested that PLP1 might be suitable for use as functional foods and as potential therapeutic agents.

In Vitro Assessment of Total Phenolic and Flavonoid Contents, Antioxidant and Photoprotective Activities of Crude Methanolic Extract of Aerial Parts of Capnophyllum peregrinum (L.) Lange (Apiaceae) Growing in Algeria.

Background:Capnophyllum peregrinum (L.) Lange (Apiaceae) is the unique taxon of capnophyllum genus in Algerian flora. It has never been investigated in regards to its total phenolic and flavonoid contents and antioxidant and photoprotective activities. Methods:C. peregrinum aerial parts extracted with absolute methanol. The total flavonoid and phenolic contents of the extract were evaluated to determine their correlation with the antioxidant and photoprotective activities of the extract. Results: The methanolic extract demonstrated a significant amount of phenolics and flavonoids (74.06 ± 1.23 mg GAE/g, 44.09 ± 2.13 mg QE/g, respectively) and exhibited good antioxidant activity in different systems, especially in 1,1-Diphenyl-2-picrylhydrazyl (DPPH), reducing power and total antioxidant capacity assays. Furthermore the extract showed high photoprotective activity with the sun protection factor (SPF) value = 35.21 ± 0.18. Conclusions: The results of the present study show, that the methanolic extract could be used as a natural sunscreen in pharmaceutics or cosmetic formulations and as a valuable source of natural antioxidants.

Chemical characterization of polyphenols from Daucus muricatus growing in Algeria by RP-UHPLC-ESI-QTOF-MS/MS.

In the present work, reversed phase (RP) ultra-high-performance liquid chromatography (UHPLC) coupled to quadrupole-time-of-flight (QTOF) mass spectrometry in tandem has been used for the identification of the main phenolic compounds in the aerial parts of Daucus muricatus. The characterisation of the compounds was carried out taking into account retention time, mass accurate measurements, the generated molecular formulae and fragmentation pattern. These data were contrasted with literature and databases, as well as with those of authentic standards when possible. The proposed method provided tentative identification of 30 phenolic and other polar compounds, including hydroxycinnamic acid derivatives, flavonoids and hydroxybenzoic acid derivatives. As a note, hydroxycinnamic acid derivatives were found to be the most diverse phenolic class of Daucus muricatus.

Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae).

Chemical investigation of the leaves of Bupleurum lancifolium led to the isolation and identification of two triterpenoid saponins previously undescribed named 3-O-[α-L-rhamnopyranosyl (1 â†’ 4)-ß-D-glucopyranosyl] echinocystic acid 28-O-ß-D-glucopyranosyl ester (1) and 3-O-[α-L-rhamnopyranosyl (1 â†’ 4)-ß-D-glucopyranosyl] oleanolic acid 28-O-ß-D-glucopyranosyl ester (2) along with the two known compounds isorhamnetin 3-rutinoside (3) and rutin (4). Their structures were elucidated by different spectroscopic methods, including HRESIMS analysis as well as 1D and 2D NMR experiments.

Chemical analysis, antimicrobial and anti-oxidative properties of Daucus gracilis essential oil and its mechanism of action

Objective: To evaluate the essential oils (EO) composition, antimicrobial and antioxi-dant power of a local plant, Daucus gracilis (D. gracilis). Methods: The aerial parts of D. gracilis were subjected to hydro distillation by a Cle-venger apparatus type to obtain the EO which had been analyzed by gas chromatography and gas chromatography coupled with mass spectrometry, and screened for antimicrobial activity against five bacteria and three fungi by agar diffusion method. The mechanism of action of the EO was determined on the susceptible strains by both of time kill assay and lysis experience. The minimal inhibitory concentrations were determined by agar macro-dilution and micro-dilution methods. Anti-oxidative properties of the EO were also studied by free diphenyl-2-picrylhydrazyl radical scavenging and reducing power techniques. Results: The EO yielded 0.68 (v/w). The chemical analysis presented two dominant constituents which were the elemicin (35.3%) and the geranyl acetate (26.8%). D. gracilis EO inhibited the growth of Bacillus cereus and Proteus mirabilis significantly with minimal inhibitory concentrations of 17.15 mg/mL by the agar dilution method and 57.05 mg/mL and 114.1 mg/mL, respectively by liquid micro-dilution. A remarkable decrease in a survival rate as well as in the absorbance in 260 nm was recorded, which suggested that the cytoplasm membrane was one of the targets of the EO. The EO showed, also, important anti-oxidative effects with an IC50 of 0.002 mg/mL and a dose-dependent reducing power. Conclusions: D. gracilis EO showed potent antimicrobial and anti-oxidative activities and had acted on the cytoplasm membrane. These activities could be exploited in the food industry for food preservation.

Mediterranean essential oils as effective weapons against the West Nile vector Culex pipiens and the Echinostoma intermediate host Physella acuta: what happens around? An acute toxicity survey on non-target mayflies.

Mosquitoes (Diptera: Culicidae) represent a threat for millions of people worldwide, since they act as vectors for important pathogens, including malaria, yellow fever, dengue and West Nile. Second to malaria as the world's most widespread parasitic disease, infection by trematodes is a devastating public health problem. In this study, we proposed two essential oils from plants cultivated in Mediterranean regions as effective chemicals against mosquitoes and freshwater snails vectors of Echinostoma trematodes. Chemical composition of essential oils from Achillea millefolium (Asteraceae) and Haplophyllum tuberculatum (Rutaceae) was investigated. Acute toxicity was evaluated against larvae of the West Nile vector Culex pipiens (Diptera: Culicidae) and the invasive freshwater snail Physella acuta (Mollusca: Physidae), an important intermediate host of many parasites, including Echinostoma revolutum (Echinostomidae). Acute toxicity of essential oils was assessed also on a non-target aquatic organism, the mayfly Cloeon dipterum (Ephemeroptera: Baetidae). Achillea millefolium and H. tuberculatum essentials oils were mainly composed by oxygenated monoterpenes (59.3 and 71.0 % of the whole oil, respectively). Chrysanthenone and borneol were the two major constituents of Achillea millefolium essential oil (24.1 and 14.2 %, respectively). Major compounds of H. tuberculatum essential oil were cis-p-menth-2-en-1-ol and trans-p-menth-2-en-1-ol (22.9 and 16.1 %, respectively). In acute toxicity assays, C. pipiens LC50 was 154.190 and 175.268 ppm for Achillea millefolium and H. tuberculatum, respectively. P. acuta LC50 was 112.911 and 73.695 ppm for Achillea millefolium and H. tuberculatum, respectively, while the same values were 198.116 and 280.265 ppm for C. dipterum. Relative median potency analysis showed that both tested essential oils were more toxic to P. acuta over C. dipterum. This research adds knowledge on plant-borne chemicals toxic against invertebrates of medical importance, allowing us to propose the tested oils as effective candidates to develop newer and safer vector control tools.

Characterisation and antimicrobial activity of the volatile components of the flowers of Magydaris tomentosa (Desf.) DC. collected in Sicily and Algeria.

The essential oils of the flowers of Magydaris tomentosa (Desf.) DC. (Apiaceae) collected in Sicily (MSi) and Algeria (MAl), respectively, were obtained by hydrodistillation, and their compositions were analysed. The analyses allowed the identification and quantification of 23 components in MSi and 60 compounds in MAl, respectively, showing a very different profile in the composition of the two populations. The main components of MSi were cembrene (28.2%), α-springene (17.5%) and ß-springene (14.8%), also present in MAl but in lesser amount (0.4%, 1.8% and 0.9%, respectively), whereas the principal constituents of MAl were (E)-nerolidol (35.4%), α-costol (13.3%) and ß-costol (6.8%). Both MSi and MAl exhibited a significant antibacterial activity against Staphylococcus epidermidis (minimum inhibitory concentration = 25 and 12.5 µg/mL, respectively). The chemotaxonomy markers of the species were identified.

Fucans from a Tunisian brown seaweed Cystoseira barbata: structural characteristics and antioxidant activity.

Sulfated polysaccharides from brown seaweeds are known to be a topic of numerous studies, due to their beneficial biological properties including antioxidant activity. Fucans were isolated from the brown seaweed Cystoseira barbata harvested in Tunisia. ATR-FTIR and (1)H-NMR spectroscopies demonstrated that C. barbata sulfated polysaccharides (CBSPs) consisted mainly of 3-linked-α-l-fucopyranosyl backbone, acetylated and mostly sulfated at C-4. Molar degrees of sulfation and acetylation of CBSPs were 0.79 and 0.27, respectively. Neutral sugars analysis determined by gas chromatography-mass spectrometry (GC-MS) showed that CBSPs were mainly composed of fucose (44.6%) and galactose (34.32%) with few amounts of other sugars such as glucose (7.55%), rhamnose (6.41%), xylose (4.21%) and mannose (2.91%). CBSPs were examined for in vitro antioxidant properties using various antioxidant assays. CBSPs exhibited important DPPH radical-scavenging activity (100% inhibition at a concentration of 1.5mg/ml) and considerable ferric reducing potential (24.62 mg ascorbic acid equivalents). Effective chelating activity and significant protection activity against hydroxyl radical induced DNA breakage were also recorded for CBSPs. However, in the linoleate-ß-carotene system, CBSPs exerted moderate antioxidant activity (62% inhibition at a concentration of 1.5mg/ml). Therefore, CBSPs can be used as a potent natural antioxidant in food industry or in the pharmaceutical field.

Flavonoids from Algerian endemic Centaurea microcarpa and their chemotaxonomical significance.

Six flavonoids, namely 6-methoxykaempferol (1), 6-methoxykaempferol 7-O-glucoside (2), kaempferol 7-O-glucoside (3), 6-methoxyluteolin (4), patuletin 7-O-glucoside (5), and hispidulin 7-O-glucoside (6), were isolated from a n-butanolic fraction of Centaurea microcarpa Coss et Dur. flowers. This work describes for the first time the phytochemical composition of this endemic Algerian plant.

Bioactive phenylpropanoids from Daucus crinitus Desf. from Algeria.

The volatile constituents of Daucus crinitus Desf. from Algeria were analyzed by GC and GC-MS, The main constituent was isochavicol isobutyrate (39.0%), an uncommon phenylpropanoid. By synthesis of a series of homologous esters, it was also possible to determine the presence of small amounts of isochavicol propionate, which has never been described previously as a natural product. The antibacterial and antifungal activities of the whole essential oil, of these two esters, and of isochavicol itself were investigated against a wide range of bacteria and fungi. Additionally, their antimalarial and antiradical properties were also evaluated, showing an interesting antiplasmodial activity of isochavicol.

Chemical composition and antimicrobial activity of essential oil of Bupleurum montanum and B. plantagineum.

The hydrodistilled oils from the aerial parts of Bupleurum montanum and B. plantagineum, which are endemic to North Africa, including Algeria, were analyzed by gas chromatography-mass spectrometry (GC-MS). Ninety-eight compounds were detected in the oil of B. montanum, representing 98.6% of the total oil, and 68 in the oil of B. plantagineum, representing 99.8% of the total. Megastigma-4,6-(E),8(2)-triene was the major constituent of B. montana oil (25.3%). Other important compounds were myrcene, alpha-pinene and benzyl tiglate. Conversely, the major constituents of the oil of B. plantagineum were alpha-pinene (31.9%), cis-chrysanthenyl acetate (28.2%), and myrcene (24.8%), followed by the monoterpene hydrocarbon limonene (5.1%). The mutagenic, antiplasmodial and antimicrobial activities of the essential oils were individually evaluated against eleven microorganisms, using the agar diffusion method, by determination of MIC values. The investigated oils exhibited moderate antimicrobial activity. Maximum activity of the oils was observed against Nocardia asteroides, Staphylococcus aureus and Enterococcus faecalis. Fungicidal activity against Candida albicans was also found for both oils.

Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae).

Phenolic derivatives such as quinones, acid-phenols and flavonoids were successfully isolated from a n-butanolic fraction of Senecio giganteus Desf. (Asteraceae) flowers, namely jacaranone (1), 3a-hydroxy-3,3a,7,7a-tetrahydrobenzofuran-2,6-dione (2), chlorogenic acid (3), hyperoside (4), quercetin 3-O-beta-D-robinobioside (5), isorhamnetin-3-O-beta-D-glucuronide (6), quercetin-3-O-beta-D-glucuronide (7), and isorhamnetin-3-O-beta-D-glucuronide-6"-methyl ester (8). These compounds were purified through either classical polyamide filtration followed by fractionation on Si gel, or through fast centrifugal partition chromatography (FCPC). Using FCPC, the major compounds could be readily isolated from the crude n-butanolic fraction. Compounds 1-8 were identified by means of spectroscopic and spectrometric analysis (UV, 1H, 13C and 2D NMR, and MS). This work described for the first time the phytochemical composition of this endemic Algerian plant.

Composition, antioxidant and antimicrobial activities of the essential oil of Marrubium deserti.

The essential oil from aerial part of Marrubium deserti De Noé (Lamiaceae), obtained by hydrodistillation was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), and evaluated for in vitro antimicrobial activity. The antioxidant activity was determined using three in vitro assays: scavenging effect on DPPH, the ABTS test and the phosphomolybdenum method. Thirty-seven compounds were identified in the oil, with germacrene D as the major component (45.7%). This oil was characterized by an important hydrocarbon fraction (78.1%) and by the predominance of sesquiterpenes (67.4%). M. deserti essential oil had no activity on the tested microorganisms (Staphylococcus aureus ATCC 25923, Echerichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Candida albicans and Aspergillus flavus). However the oil presented an antioxidant activity.

An antibacterial and antifungal phenylpropanoid from Carum montanum (Coss. et Dur.) Benth. et Hook.

The volatile constituents of the aerial parts of Carum montanum (Coss. et Dur.) Benth. et Hook. were analysed by GC-FID and GC-MS, and the main component was isolated and identified as nothoapiole. The antibacterial and antifungal activities of this compound and of the total oil were investigated against Gram-negative (P. aeruginosa, E. coli), Gram-positive (E. faecalis, S. aureus, S. epidermitis, S. saprophyticus, S. simulans, S. lugdunensis) bacteria and on one strain of fungus (C. tropicalis).

Constituents of the polar extracts from Algerian Pituranthos scoparius.

The methanolic and aqueous extracts of Pituranthos scoparius (Coss. & Dur.) Benth. & Hook. (Apiaceae) have been analyzed and fifteen metabolites were identified: two cinnamic acids (5-O-caffeoyl quinic acid and 5-feruloyl quinic acid), and thirteen known flavonoids (vicenin-2, six quercetin and six isorhamnetin O-glycosylated derivatives). 5-O-caffeoylquinic acid was the main component, while, of the flavonoids, the isorhamnetin derivatives were present to a greater extent.