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Background and aim: Traditional medicine relies heavily on the use of compounds-rich plants, like those of the Asteraceae family, many of such species are commercially available in the form of herbal preparations. These are particularly rich in a wide range of natural terpenoids named sesquiterpene lactones, the active principles in some cases. Inula viscosa(L.) Aiton (Family Asteraceae, Tribe Inuleae), currently classified as Dittrichia viscose (L.) Greuter, is an invasive weed widely distributed in the Mediterranean region. This species and its components present a broad range of biological activities (anti-inflammatory, antifungal, antiulcer, antiviral, antiparasitic). Its extracts are particularly rich in terpenoids, in particular eudesmane acids, notably α-isocostic acid (present in the aerial parts but not in the roots).Methods: Bioguided assays on the studied plant parts (aerial parts, flowers, streams, roots) have been undertaken, then in vitroBiological assays were investigated through: quantification of Bioactive compounds as total phenols and flavonoids, isolation and characterization of main compound α-isocostic acid by 1H and 2D COSY NMR analysis, assessment of antioxidant activity via Reducing power, CUPRAC, hydrogen peroxide and hydroxyl, DPPH, ABTS free radicals scavenging tests, and antimicrobial activity.Results: Phytochemical analysis reveled flower extract as the richest extract in phenols, flavonoids and α-isocostic acid, root extract is the poorest one, obtained results showed a high correlation with in vitro antioxidant activities, which were assessed by the indirect antioxidant potent, Ferric reducing power FRAP as it is a widely used preliminary test to evaluate reducing capacity of oxygen generating species OGS (H2O2), which can in turn generate free radicals (OH), in addition to CUPRAC test, DPPH and ABTS free radicals scavenging, the main responsible of oxidative stress associated with several pathologies like cardiovascular, neurodegenerative, cancer and aging, The antimicrobial potent evaluated against 4 referential bacteria Escherichia coliATCC 25922, Pseudomonas aeruginosaATCC 27853and Klebsiella pneumoniaATCC 700603 Gram-negative, Staphylococcus aureusATCC 25923 Gram-positive and one fungi Trichoderma harzianum Rifai (usually used as biopesticid) exhibit root part almost as better extract.Conclusion: The hypothesis that sesquiterpens as α-isocostic acid, widely present in Inula viscosaare responsible of its biological activity was proposed. We demonstrate by bioguided assays on different plant parts, that it is not reliable for all tested applications, in case of antimicrobial ones, results suggest that it is mediated by roots system.

Thirteen undescribed triterpenoid saponins named monellosides A-M, were isolated from the aerial parts of Anagallis monelli ssp. linifolia (L.) Maire, together with ten known oleanane-type glycosides. Their structures were elucidated by 1D and 2D-NMR spectroscopy (COSY, TOCSY, HSQC, HMBC and ROESY) as well as high resolution mass spectrometry (HR-ESI-MS) and acid hydrolysis. Monellosides A-M have a carbohydrate chain linked on the C-3 of the aglycone with a common β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyl sequence which was further glycosylated by a glucose and/or a xylose. The sequence β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)-]α-l-arabinopyranosyl was common to all the 13,28-epoxy-oleanane core skeleton except one compound. In order to discuss the reclassification of Anagallis in Primulaceae, we compared saponins from species of Myrsinaceae and Primulaceae families and showed that these species were characterized by a pentacyclic triterpenoid saponin with a 13,28-epoxy bridge skeleton. Our phytochemical results increase the knowledge of saponins of the genus Anagallis, their chemotaxonomy and stimulate the evaluation of the biological activities of these saponins.

One new natural monoterpene, 5-O-β-d-glucopyranosyl-2-hydroxy-p-cymene (1), and 11 known compounds were isolated through a biologically oriented approach from the aerial parts of Phagnalon sordidum L. The most active extract and fractions were selected using 3 complementary antioxidant activity assays. Results and the different methods were compared by relative antioxidant capacity index. In addition, the most active extract of P. sordidum was subjected to liquid chromatography coupled with electrospray ionization hybrid linear ion trap quadrupole Orbitrap mass spectrometry to quantify secondary metabolites. Antioxidant activities of ethyl acetate extract, and purified 3,4-dihydroxyacetophenone (3) and nebrodenside A (7) were demonstrated by in vitro cell free model assays, and their protective effect against H2O2-induced oxidative stress in a HepG2 (human hepatocellular carcinoma) cell line was established.

The fresh aerial parts of Thymus willdenowii Boiss. & Reut. (syn. Thymus hirtus Willd.) were hydrodistilled in a Clevenger type apparatus and analyzed by GC and GC-MS. 44 Components were identified representing 97.3%, with 1,8-cineole (34.62%), camphor (18.55%), α-pinene (9.46%) and camphene (5.38%) as the main components. T. willdenowii essential oil was not cytotoxic (CC50 = 97.65 µg/mL) towards Vero non-tumoural cells, exhibiting good antibacterial and antiproliferative (30.8 ± 3.1% inhibition) potentials against four tested pathogenic bacteria and Human colorectal cell line HT-29, respectively. The essential oil did not show a DPPH radical scavenging activity, by Electron Spin Resonance spectroscopy (ESR), and it lacks antiviral effect towards coxsackievirus B3.

The fractions (Fr.1-5) of the hydromethanolic extract of Abies numidica cones were studied for their polyphenol constituents, antioxidant, and anticholinesterase activities. The beta-carotene-linoleic acid, cupric reducing power (CUPRAC), DPPH scavenging, and ABTS radical scavenging assays were used to determine antioxidant activity. Fr.3 exhibited the highest antioxidant activity in ABTS test (IC50: 1.29 mu g/mL), b-carotene-linoleic acid test (IC50: 18.6 mu g/mL) and CUPRAC (A(0.5): 33.8 mu g/mL) assays. Three fractions (Fr.2-4) promising antioxidant activity were analyzed using LC-MS/MS for their phenolic compositions. Taxifolin (155.9-2816.2 mu g analyte/g extract), hyperoside (353.0-2045.5 mu g/g), vanillin (1488.9-1529.9 mu g/g), tannic acid (1281.6-1416.8 mu g/g), rosmarinic acid (1063.1-1149.3 mu g/g), coumarin (683.0-772.6 mu g/g), quercetin (881.0 mu g/g), and catechin (277.7-400.2 mu g/g) were identified in the antioxidant fractions. Moreover, the anticholinesterase activity was also performed using the in vitro spectroscopic Ellman method. The antioxidant fractions exhibited moderate butyrylcholinesterase inhibitory activity. The multi-ware analysis was performed to understand the origin of bioactivities. According to principal component analysis, it is detected that the hyperoside, catechin, taxifolin, and tannic acid were responsible for the antioxidant activity. Therefore, the cones of Abies numidica can be considered as potent antioxidant and anticholinesterase sources in food and pharmaceutical industries, commercially. DGRSDT-MESRS (Algeria) 15/116 Mugla Sitki Kocman University 15/116

Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β - d -glucose or β - d -glucuronic acid which could be substituted at C-3 by a β - d -galactose and/or C-2 by a supplementary β - d -galactose or a β - d -glucose. The sugar moiety linked to C-28 was determined as β - d -glucose. The antibacterial evaluation of compounds 1 – 20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC 50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively.

International audience; Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1–11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-d-glucuronic acid or β-d-galactopyranosyl-(1 → 3)-β-d-glucuronopyranoside and at C-28 by a β-d-fucopyranose substituted at C-2 by a β-d-glucose and at C-3 by a β-d-glucose or a β-d-quinovose.

International audience; Five undescribed ursane-type triterpenes, identified as 1β,3β,15α-trihydroxy-urs-9(11)-12-diene (1), 1β,3β,15α,28-tetrahydroxy-urs-9(11),12-diene (2), 1β,3β-dihydroxy-urs-9(11),12-dien-28-al (3), 1β,3β,7β,15α,28-pentahydroxy-urs-12-ene (4), and 1β,3β,15α-trihydroxy-urs-11-en-28-al (5), together with five known compounds (6–10), were isolated from the acetone extract of the dried aerial parts of Salvia argentea L. var. aurasiaca (Pomel) Batt. et Trab. (Lamiaceae). Structures were elucidated on the basis of extensive spectroscopic analysis including HR-ESI-MS, 1D- and 2D-NMR techniques and comparison with literature data. The antibacterial evaluation of compounds 1–10 of the acetone extract of the dried aerial parts, in addition to nine compounds (11–19) previously isolated from the extract of the fresh aerial parts, by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against five bacteria, revealed that two compounds have an antibacterial effect comparable to antibiotics.The cytotoxic activity evaluation of compounds 1–19 showed that Six compounds exhibited an antiproliferative activity against K562 and HT1080 cells with IC50 values ranging from 30.25 to 70.32 μM.

The fresh aerial parts of

In this paper, the isolation of five new guaianolides (1 – 5) and four (6 – 9) known sesquiterpenes from Ormenis mixta aerial parts is reported. The structural determination of the guaianolides was obtained by NMR spectroscopic data, as well as MS experiments. Their relative configurations were assigned by a combined quantum mechanical/NMR approach, comparing the experimental 13C/1H NMR chemical shift data and 1 J H-H homonuclear coupling constants with the related predicted values. The isolates were assayed for their anti-inflammatory potential evaluating nitric oxide release and cyclooxygenase-2 expression in J774A.1 macrophages treated with lipopolysaccharide from Escherichia coli. Our results indicated that, among the tested compounds, 1 – 3, and 7 were able to inhibit nitric oxide release, while all were able to inhibit cyclooxygenase-2 expression with different potencies.

A new C-glycosylflavone, identified as 6"'-O-acetylisospinosin (1), was isolated from the aerial parts of Cladanthus mixtus together with 30 known compounds. The structures of these compounds were established by interpretation of their spectral data, mainly UV, 1D and 2D NMR spectroscopic methods including (1H and 13C NMR, COSY, ROESY, HSQC and HMBC experiments), ESI-MS, and by comparison with the literature data.

One new flavonol glycoside, patuletin-7-Ο-[6-Ο-caffeoyl-2-Ο-[(S)-3-hydroxyisobutanoyl]glucopyranoside] (astermaritimoside) (1) and four known flavonoids, patuletin-7-Ο-β-[-6-Ο-[(S)-3-hydroxyisobutanoyl]glucopyranoside] (2), patuletin-7-Ο-[6-Ο-caffeoylglucopyranoside] (3), patuletin-7-Ο-β-D- glucopyranoside (4) and quercetin-3-Ο-β-rutinoside (5) have been isolated from Asteriscus maritinus (L.) Less. Chemical structures were elucidated by mass spectrometric, and ¹H NMR, ¹³C NMR, COSY, HMQC and HMBC spectroscopic techniques. The antioxidative effect was evaluated using an electronic spin resonance (ESR) method in order to visualize the inhibition of the DPPH radical. The n-butanol fraction was found to possess a remarkable antioxidant activity that was correlated with the total amount of phenolics. The isolated compounds exhibited good antioxidant activity.

International audience; Eight known abietane diterpenes (1-8) were isolated for the first time from Abies numidica cones (Pinaceae). The structures of all compounds were established by means of 1D and 2D NMR, and UV spectral analyses. The hydromethanolic extract of A. numidica cones was tested for its antimicrobial activity against 17 gram-positive and gram-negative bacteria and against five yeasts by the use of liquid and solid medium and bioautography methods. The best antimicrobial activity was found against gram-positive bacteria (MIC ≤ 0.3 mg/mL) Bacillus subtilis, Enterococcus faecalis ATCC 1034, Staphylococcus aureus 8325.4, S. aureus CIP 53.154, Micrococcus luteus and Listeria innocua and against Candida yeasts. The determination of MIC's of isolated products showed a high activity of compounds 4 and 6 against S. aureus, L. innocua (MIC = 62.5 μg/mL) and E. faecalis (MIC = 125 μg/mL).

International audience; Eight undescribed triterpenoid saponins, scabiostellatosides A-H, together with three known compounds were isolated from the whole plant of Scabiosa stellata L. Their structures were established by spectroscopic analyses (1D, 2D-NMR and HRESIMS) and chemical methods. Scabiostellatosides A-H were evaluated for their cytotoxicity against human fibrosarcoma cell line (HT1080). Scabiostellatoside F, a heptasaccharide derivative of oleanolic acid, exhibited moderate cytotoxicity against HT1080 cell line with IC50 value of 12.0 μM.

International audience; This study presents the chemical profile investigation of a 70% ethanol extract obtained from Scabiosa stellata, a medicinal herbaceous traditionally used to treat heel cracks. A 13C NMR-based dereplication methodology was firstly applied on centrifugal partition chromatography-generated fractions in order to quickly identify the major compounds of the extract. The dereplication process was then completed by semi-preparative high-performance liquid chromatography in order to identify unknown or minor compounds. Two new bis-iridoids, namely 7-O-caffeoyl-sylvestroside I (1) and 7-O-(p-coumaroyl)-sylvestroside I (2), together with ten known compounds (3 − 12) were isolated. Their structures were elucidated by spectroscopic methods including NMR and HR-ESI-MS. The antibacterial, anti-tyrosinase and DPPH radical scavenging activities of the crude extract, fractions, and isolated compounds were evaluated. A significant antibacterial activity was observed for nine isolated compounds, particularly 1 and 2 which yielded MIC values of 31.2 μg/mL against Enterococcus faecalis and 62.5 μg/mL against Staphylococcus epidermidis. The cytotoxic activity of these new bis-iridoids was evaluated on a fibrosarcoma cell line (HT1080) and only compound 1 exhibited a moderate cytotoxic activity (IC50 35.9 μg/mL).

From the aerial parts of Salvia barrelieri Etl. (Lamiaceae), 12 compounds including a new triterpene, 3β-acetoxy-olean-18-ene-2α-ol, were isolated. Their structures were established by the combination analyses of spectroscopy including 1D-, 2D-NMR and HRESIMS and in comparison with the reported data in the literature. The antibacterial activity of these compounds was evaluated by bioautography on Staphylococcus aureus followed by the determination of MIC values by serial dilution technique against five bacteria. Three compounds were active against Enterococcus faecalis, S. aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas aeruginosa (MIC 15.1 to 125 μg/mL). Two compounds showed moderate DPPH radical scavenging activity (IC50 79.1 and 21.2 μg/mL). These compounds did not show significant tyrosinase inhibitory activities (IC50> 1.5 mg/mL). Their cytotoxic activity was evaluated against promyelocytic leukaemia (HL60), human erythromyeloblastoid leukaemia (K562) and fibrosarcoma (HT1080) cell lines and four compounds exhibited a moderate cytotoxic activity (IC50 28.75 to 85.0 μM).

International audience; Context: Phytochemical study and biological potential of Evax pygmaea (L.) Brot. (Asteraceae) are reported for the first time.Objective: To identify the secondary metabolites of Evax pygmaea and to determine its antioxidant, antibacterial and cytotoxic activities.Materials and methods: Dried aerial parts (1 kg) were macerated in 70% MeOH (5 L) during 72 h. The concentrated hydromethanolic extract was subjected to extractions with chloroform (3 × 300 mL), ethyl acetate (3 × 300 mL) and n-butanol (3 × 300 mL), successively. VLC of combined ethyl acetate (EAEP) and n-butanol (BEP) fractions was followed by column purifications. Antioxidant activity was investigated using DPPH, CUPRAC, and metal chelating, β-carotene/linoleic acid and ABTS assays. Agar method was used in the antibacterial study. Cytotoxic activity was determined by Brine shrimp lethality test in DMSO and ethanol, at varying concentrations (2, 1 and 0.2%) and (1, 0.2 and 0.1%) successively.Results: Quercetin (1), isorhamnetin 3-O-β-d-xyloside (2), isorhamnetin 3-O-β-d-glucoside (3), quercetin 3-O-β-d-glucoside (4), quercetin 7-O-β-D-glucoside (5), patuletin 3-O-β-d-glucoside (6) were isolated from for the first time from Evax genus. The EAEP was the most active in ABTS (IC50: 80 µg/mL).Discussion and conclusions: Six flavonoids were isolated for the first time from Evax pygmaea which exhibited good antioxidant and antibacterial activities.

The aims of this study were to compare the chemical composition and antibacterial activity of four hydrodistilled oils of Ferula vesceritensis Coss. & Dur . Essential oils were obtained from the hydrodistillation of fresh flowers ( FF), dry flowers (DF), fresh stems (FS) and dry stems (DS). The GC-MS analyses of the oils revealed the presence of forty two compounds for FF, thirty seven compounds for DF, forty eight compounds for FS and thirty six components for DS. The total yields of the volatile essential oils were respectively: 97.9% (FF), 88.6% (DF), 96.4% (FS) and 87.4% (DS) with the prevalence of α -pinene (FF 32%, DF 16.1%, FS 11.5%, DS 17.4%), β-pinene (FS 8.1%, DS 8.9%), α - phellandrene (FF 8.5%, DF 24.3%), fenchylacetate (FF 10.4%, FS 7.3%, DS 8.8%), elixene (DF 6.3%, FS 5.4%), aristolene (FF 5.4%, FS 7.2%, DS 6.8%), caryophyllene oxide (FS 7.6%) and carotol (FF 13.9%, DF 10.7% FS 18.8%, DS 10.8%). The essential oils were tested againest 9 bacteria and showed a good antibacterial activity against almost food-borne pathogens and clinical isolated microorganisms at a concentration of 128 µ g/mL Minimum inhibitory concentration (MIC) values for all the bacteria were ranged between16 µ g/mL and 80 µ g/mL.

International audience; A new 2-alkylhydroquinone glucoside, 1-O-β-d-glucopyranosyl-1,4-dihydroxy-2-((E) 2-oxo-3-butenyl)benzene (1), in addition to nine known compounds were isolated from the aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae). Their structures were identified based on spectroscopic methods including 1D and 2D NMR, mass spectrometry (HR-ESI-MS), UV spectral analyses and by comparison with literature data. The cytotoxic activity of three isolated compounds (1–3) was evaluated against fibrosarcoma (HT1080), human lung cancer (A549) and breast cancer (MCF7) cell lines.

This is the first study on the phytochemistry and antioxidant activity of Ferula longipes Coss. ex Bonnier and Maury (Apiaceae). A new flavonoid quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-[2-O-caffeoyl]-glucopyranoside (1), along with 10 known compounds kaempferol-3-O-α-L-rhamnopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), kaempferol-3-O-ß-D-glucopyranoside-7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (5), quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (6), isorhamnetin-3,7-di-O-β-D-glucopyranoside (7), apigenin (8), apigenin-7-O-ß-D-glucopyranoside (9), 3,5-dicaffeoylquinic acid (10), deltoin (11) were isolated from the aerial parts of Ferula longipes Coss. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The compounds 1, 3, 4, 6, 7 and 10 were evaluated for their antioxidant activity, compound 1 exhibited the best antiradical activity potential and showed IC50 and A0.5 values 5.70, 7.25, 5.00, and 2.63 μg/mL towards DPPH free radical-scavenging, ABTS, CUPRAC, and reducing power assays, respectively compared with BHA, BHT and ascorbic acid which were used as positive controls.

International audience; A new phorbol-type diterpene ester, 4,20-dideoxy-4α-phorbol-12β-acetate-13α-isobutyrate, in addition to 11 known compounds were isolated from the latex and roots of Euphorbia clementei Boiss. Structure elucidation was performed by comprehensive 1D and 2D NMR analyses (1H and 13C NMR, COSY, ROESY, HSQC and HMBC experiments), mass spectrometry (HR-ESI-MS) and by comparison with literature data. The inhibitory activity of all isolated compounds was evaluated against promyelocytic leukemia HL60 and human erythromyeloblastoid leukemia K562 cell lines and seven of these compounds exhibited a weak cytotoxicity with IC50 values ranging from 40 to 97 μM.

International audience; One new cardenolide, 3-O-β-D-allopyranosylcoroglaucigenin (salsotetragonin) (1), was isolated from the aerial parts of Salsola tetragona Delile with four known cardenolides (2–5), two known flavonoids (6–7), three known phenolic compounds (8–10) and two known fatty acids (11–12). Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. Compounds 1–5, 7, 10 and 12 were isolated from the genus Salsola for the first time. This is the first report on cardenolides identified in the Amaranthaceae family.

A previously undescribed phenolic sulphate ester, potassium 34-dihydroxy-3-methoxybenzoic acid methyl ester-5-sulphate (1), along with nine known flavonoids, kaempferol-3-O-potassium sulphate-4′,7-dimethyl ether (2), kaempferol-4′,7-dimethyl ether (3), rhamnocitrin-3-O-potassium sulphate (4), rhamnocitrin (5), kaempferol (6), quercetin (7), afzelin (8), quercetin-3-O-α-l-rhamnopyranoside (9) and luteolin-3′-O-potassium sulphate (10) were isolated from the aerial parts of Tamarix balansae. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The antibacterial assay against Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas aeruginosa bacteria showed a good activity for 2, 3, 7 and 9, with MICs ranging from 62.5 to 250 μg/mL. The abilities of these compounds to scavenge the DPPH were evaluated. Compounds 1, 7, 9 and 10 exhibited a good antiradical activity potential with IC50 values ranging from 3.0 to 115.5 μg/mL, compared with ascorbic acid (IC50 7.4 μg/mL) which was used as positive control.

The phytochemical and antimicrobial properties of the cones of Cedrus atlantica (Endl) Manetti ex Carriere were investigated. Two new compounds ( 1,2 ) and nineteen known compounds ( 3 – 21 ) were isolated. Their structures were established by mass spectrometry (HRESIMS), 1D, 2D NMR and by comparison with literature data. Antimicrobial activity of hydromethanolic extract against a panel of 22 bacteria and yeasts showed an interesting antimicrobial activity. All compound purified from this extract were tested against S. aureus by bioautography. MIC values of the most active compounds were determined using a serial dilution technique. The results showed strong antibacterial activity of the abietane diterpenes 10, 11, 14, 15, 16 and 17 . Dehydroabietic acid ( 17) was the most potent against Enterococcus faecalis (MIC = 15.1 = μg/mL), a multi-resistant commensal bacterium which can cause the fatal infections in humans.

WOS: 000390846600032 PubMed ID: 27927090 Context: Stachys guyoniana Noe ex. Batt. and Mentha aquatica L. are two Algerian Lamiaceae used in folk medicine. Objective: To investigate their antioxidant, anticholinesterase and antibacterial activities. Material and methods: n-Butanol (BESG), ethyl acetate (EESG) and chloroform (CESG) extracts of S. guyoniana and methanol (MEMA) and chloroform (CEMA) aerial part extracts of M. aquatica and methanol (MERMA) and acetone (AERMA) roots extracts of M. aquatica were evaluated for their antioxidant activity by the beta-carotene-linoleic acid, DPPH center dot and ABTS(center dot+) scavenging, CUPRAC and metal chelating assays. The anticholinesterase activity was tested against AChE and BChE. The antibacterial activity was assessed by MICs determination against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella heidelberg, Klebsiella pneumoniae, Enterobacter aerogenes and Morganella morganii strains. Results: In the b-carotene test, the CESG (IC50: 2.3 +/- 1.27 mu g/mL) exhibited the highest activity. The BESG was the best scavenger of DPPH center dot (IC50: 2.91 +/- 0.14 mu g/mL). In the ABTS test, AERMA was the most active (IC50: 4.21 +/- 0.28 mu g/mL). However, with the CUPRAC, the BESG exhibited the best activity (A(0.50): 0.15 +/- 0.05 mu g/mL) and was active in metal chelating assay with 48% inhibition at 100 mu g/mL. The BESG was the best AChE inhibitor (IC50: 5.78 +/- 0.01 mu g/mL) however, the AERMA showed the highest BChE inhibitory activity (IC50: 19.23 +/- 1.42 mu g/mL). The tested extracts exhibited a good antibacterial activity. Conclusion: This study demonstrated good antioxidant, anticholinesterase and antibacterial potential of S. guyoniana and M. aquatica, which fits in well with their use in folk medicine. MESRS-Algeria; Mugla Sitki Kocman University, Department of ChemistryMugla Sitki Kocman University The authors thank the MESRS-Algeria and the Mugla Sitki Kocman University, Department of Chemistry for financial support.

The essential oil of the fresh aerial parts of Inula graveolens (L.) Desf. (Asteraceae), obtained by hydrodistillation in a Clevenger-type apparatus, was analyzed by GC-MS. Thirty compounds were characterized representing 89.9 % of the essential oil with isobornylacetate (50.8 %), borneol (18.3 %) and τ- cadinol (6.2.%) as main components.

© 2011 Production and hosting by Elsevier B.V. on behalf of King Saud University, One diterpenoid, horminone 1, two flavonoid glycosides, apigenin-7-O-(6″-E-p-coumaroyl)-β-d-glucopyranoside 2, isoscutellarein-7-O-(6″′-O-acetyl-β-d-allopyranosyl-(1 → 2)-β-d-glucopyranoside) 3, were isolated from n-butanolic extract of the aerial parts of Stachys mialhesi de Noé (BESM). Their structures were established on the basis of physical and spectroscopic analysis, and by comparison with the literature data. Antioxidant activity of this extract and the compound 3 was evaluated by the use of the Electron Spin Resonance method in order to visualize the inhibition of the DPPH radical. In this study, we also investigated the anti-inflammatory, anti-ulcer and antinociceptive activities of the BESM in experimental animal models at different doses. Our results showed that the BESM showed a strongest antioxidant activity. It decreased acetic acid induced writhing times; inhibited carrageenan-induced hind paw edema. All of these results suggested that the BESM possesses significant antioxidant, antinociceptive and anti-inflammatory activities., The authors are grateful to the ANDRS and DG-RSDT/MESRS for the financial support.

WOS: 000389443300031 PubMed ID: 27431425 Context: The phytochemical study and biological activities of Astragalus armatus Willd. subsp. numidicus (Fabaceae) pods, an endemic shrub of Maghreb, are reported. Objective: This study isolates the secondary metabolites and determines the bioactivities of Astragalus armatus pods. Materials and methods: The chloroform, ethyl acetate and n-butanol extracts of hydro-ethanolic extracts were studied. Antioxidant activity was investigated using DPPH and ABTS radical scavenging, CUPRAC and ferrous chelating assays at concentrations ranging from 3 to 200 mu g/mL. Anticholinesterase activity was determined against acetylcholinesterase and butyrylcholinesterase enzymes at 50, 100 and 200 mu g/mL. Antibacterial activity was performed according to minimum inhibitory concentration (MIC) method. Carbon clearance method in albino mice was used for the phagocytic activity at concentrations 50, 70 and 100mg/kg body weight. Spectroscopic techniques were used to elucidate the compounds. Results: Ethyl acetate extract afforded a flavonoid (1) while the n-butanol extract gave four flavonoids (2-5), a cyclitol (6) and a cycloartane-type saponin (7). The ethyl acetate extract exhibited highest antioxidant activity in DPPH (IC50: 67.90 +/- 0.57 mu g/mL), ABTS (IC50: 11.30 +/- 0.09 mu g/mL) and CUPRAC (A(0.50): 50.60 +/- 0.9 mu g/mL) assays. The chloroform extract exhibited the best antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, each with 80 mu g/mL MIC values. The n-butanol extract enhanced phagocytic activity. Discussion and conclusion: Isorhamnetin (1), isorhamnetin-3-O-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-galactopyranoside (2), isorhamnetin-3-O-beta-D-apiofuranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-galactopyranoside (3), kaempferol-3-O-(2,6-di-O-alpha-L-rhamnopyranosyl)-beta-D-galactopyranoside (4), kaempferol-3-O-(2,6-di-O-alpha-L-rhamnopyranosyl)- beta-D-glucopyranoside (5), pinitol (6) and cyclomacroside D (7) were isolated whereas 1, 2, 6 and 7 are reported for the first time from A. armatus. ATRSS-DGRSDT (MESRS, Algeria); Mugla Sitki Kocman University, Department of Chemistry; Groupe Isolement et Structure of the Institut de Chimie Moleculaire de Reims (ICMR), France The authors are grateful to ATRSS-DGRSDT (MESRS, Algeria), Mugla Sitki Kocman University, Department of Chemistry and Groupe Isolement et Structure of the Institut de Chimie Moleculaire de Reims (ICMR), France for providing their financial support and facilities during the study.

A new sulfonyl flavonol glucoside, 5,7,4′,5′-tetrahydoxyflavonol 2′-[propanoic acid-(2″′-acetoxy-1″′-sulfonyl)]-5′-O-β-d-glucopyranoside (1) was isolated from the aerial parts of Cotula anthemoides L. in addition to 15 known compounds (2–16). The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D-, 2D-NMR and HR-ESI-MS techniques and by comparing their NMR data with those reported in the literature. These compounds were evaluated for their DPPH radical scavenging and tyrosinase inhibitory activity. Compound 6 showed a high DPPH radical scavenging with EC50 value of 9.1 ± 0.4 μM. Compound 11, 9 and 1 exhibited a mild tyrosinase inhibitory activity with IC50 values of 85 ± 0.8, 95 ± 1.5 and 100 ± 0.5 μM, respectively.

International audience; Two new phenolic glucosides, together with six known compounds, were isolated from the aerial part of Eryngium tricuspidatum L. (Apiaceae). The structures of the new compounds were established as 2-hydroxy- 3,5-dimethyl-acetophenon-4-O-β-d-glucopyranoside (1) and 2,3-dimethyl-4-hydroxymethylphenyl-1-hydroxymethyl-O-β-d-glucopyranoside (2) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The antibacterial, tyrosinase inhibitory and DPPH radical scavenging activities of hydromethanolic extract, fractions, and the eight isolated compounds were evaluated. The antibacterial assay showed a moderate activity for magnolioside (4) against Staphylococcus aureus CIP 53.154. Compound 7 (quercetin 3-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-galactopyranoside) had moderate DPPH radical scavenging activity whereas compounds 2 exhibited good inhibitory effect against mushroom tyrosinase.

The essential oil obtained by hydrodistillation of fresh aerial parts of Ferula lutea Poiret (Apiaceae) was analyzed by GC and GC-MS. Twenty one compounds were characterized representing 84.9 % of the essential oil with the prevalence of 2,3,6-trimethylbenzene (25.0 %), cis-chrysanthenol (20.8 %), α- pinene (10.9 %) and thymol (10.2 %).

Essential oil extracted from fresh aerial parts ofAthamanta siculaL. (syn.Tingara sicula) was analysed by gas phase chomatography coupled to mass spectrometry (GC-MS). The main constituents were: germacrene B (88.5%) and apiol (4.9%). Comparing with the tested bacteria, the growth ofEscherichia coliandKlebsiella pneumoniaestrains was more inhibited by the essential oil ofA. sicula.

Eleven flavonols have been isolated from the aerial parts of Ammi visnaga L. from which four aglycones, four monoglycosides, two diglycosides and one triglycoside. The flavonoid aglycones were distributed into one hydroxylated, quercetin (1) and three methoxylated, namely, rhamnetin (2), isorhamnetin (3) and rhamnazin (4). Among the monoglycosides, we found three 3-O-glucosides respectively linked to rhamnetin (5), isorhamnetin (6) and rhamnazin (7) and one 7-O-glucoside of isorhamnetin (8). The two diglycosides were 3-O-rutin of quercetin (9) and isorhamnetin (10) while the single trioside was quercetin 7,3,3’-O-triglucoside (11). These flavonols are reported for the first time from A. visnaga L . Free radical DPPH scavenging potential of the butanolic extract was investigated.

The essential oil obtained by hydrodistillation of aerial parts of Ruta chalepensis subsp. angustifolia (Rutaceae) was analyzed by GC and GC-MS. Fourteen compounds were characterized representing 98.2 % of the essential oil with the great prevalence of undecan-2-one (83.4 %).

yellowish essential oil, having an intense and penetrating odor. Forty-one components were identified, representing 99.8% of the essential oil mainly characterized by camphor (27.4%), santolina triene (13.0%), thujone (12.9%), camphene (10.7%), and -curcumene (5.3%) (Table 1). Gas Chromatography-Mass Spectrometry. GC-MS was performed using a Shimadzu QP5050 mass selective detector and a cross-linked DB5-MS column (40 m 0.18 mm, film thickness 0.18 m). The oven temperature was programmed as isothermal at 60C for 5 min, then raised to 275C at 5C/min and held at this temperature for 5 min. Helium was used as the carrier gas at a rate of 1 ml/min. The oil (0.1 L) was introduced directly into the source of the MS via a transfer line (280C) with a split ratio of 1:50 and a linear velocity of 30.0 cm/sec. Ionization was obtained by electron impact (70 eV, source temperature 200C, resolution 1000). The present composition is quite different from the reported essential oil of Cotula coronopifolia L. leaves, which are mainly characterized by agarospirol (10.4%), and by hexacosane (31.7%) in flowers, and by 1-eicosanol (17.1%) in stems. The major constituents identified in the root oils were heptacosane (28.4%), 1-eicosanol (14.6%), octacosane (5.4%), and -amorphen (5.2%) [5].

(2000 g) were macerated three times with 70% MeOH solution. Thehydroalcoholic solution was concentrated under reduced pressure to dryness, and the residue was dissolved in hot water(1000 mL) and kept in the cold overnight. After filtration, the aqueous solution was successively extracted with EtOAc onceand with

The genus Eryngium belongs to the Apiaceae family (Umbelliferae), subfamily Saniculoideae, which consists of about 300 species [1]. Plants of this genus have shown various activities such as anti-inflammatory [2], antimalaria and antifungal [3], antioxidant and antimicrobial [4], antidiabetic [5], and analgesic properties [6]. Air-dried and powdered aerial parts (1.5 kg) of Eryngium triquetrum Vahl. were macerated at room temperature with MeOH–H2O (70:30, v/v) for 24 h three times. After filtration and concentration, the residue was dissolved in water (600 mL). The resulting solution was extracted successively with CHCl3, EtOAc, and n-butanol. Concentration in vacuo led to the following extracts: CHCl3 (0.8 g), EtOAc (1.3 g), and n-butanol (11 g). The butanolic extract of Eryngium triquetrum (11 g) was column chromatographed on polyamide SC6 with a gradient of toluene–MeOH with increasing polarity; Fr. 4 (70 mg), obtained from 85% toluene, was subjected to silica gel column chromatography eluted with EtOAc–MeOH–H2O (10:1:0.5), leading to two subfractions: Fr. 1 and Fr. 2. Subfraction 1 was separated by silica gel column chromatography eluted with CH2Cl2–MeOH (8:2) to afford compound 1 (10 mg). Subfraction 2 yielded compound 2 (60 mg), which was obtained as a yellow precipitate. Fraction 6 (70 mg), obtained from 80% toluene, was further subjected to silica gel column chromatography eluted with EtOAc–MeOH–H2O (10:1:0.5) to give compound 3 (40 mg). The ethyl acetate extract (1.3 g) was column chromatographed on silica gel with a gradient of CHCl3–MeOH with increasing polarity. Fraction 2 (30 mg) and Fr. 3 (35 mg), obtained from 95% and 90% CHCl3 successively, were separated by silica gel column chromatography eluted with EtOAc–MeOH–H2O (10:1:0.5) to afford compounds 4 (9 mg) and 5 (8.5 mg). The structures of compounds 1–5 were established by chemical and spectral analysis, UV, NMR, acid hydrolysis, and HPLC-UVDAD-MS, as well as by comparing their spectroscopic data with those reported in the literature. Acid Hydrolysis. The pure compounds were treated with 2M HCl at 100 C for 1 h. The hydrolysates were extracted with EtOAc, and the aglycons were identified by their UV spectra in methanol and by comparison of their Rf with authentic samples. Sugars were identified in the aqueous residue by comparison with authentic samples on silica gel TLC impregnated with 0.2 M NaH2PO4, solvent Me2CO–H2O (9:1), revealed with aniline malonate. Compound 1. C21H20O11. UV (MeOH, max, nm): 267, 347; +NaOH: 275, 325, 401; +AlCl3: 273, 398; +AlCl3/HCl: 273, 397; +NaOAc: 274, 377; +H3BO3: 268, 355. 1H NMR (250 MHz, CD3OD, , ppm, J/Hz): 8.09 (2H, d, J = 8.9, H-6 , 2 ), 6.91 (2H, d, J = 8.9, H-5 , 3 ), 6.42 (1H, d, J = 1.9, H-8), 6.22 (1H, d, J = 1.9, H-6), 5.28 (1H, d, J = 7.3, Glc H-1 ), 3.26–4.14 (sugar protons). This compound was characterized as kaempferol 3-O-D-glucoside [7]. Compound 2. C30H26O13. UV (MeOH, max, nm): 267, 315; +NaOH: 274, 368; +AlCl3: 274, 403; +AlCl3/HCl: 273, 403; +NaOAc: 274, 372; +H3BO3: 272, 371. 1H NMR (400 MHz, CD3OD, , ppm, J/Hz): 7.97 (2H, d, J = 8.9, H-6 , 2 ), 7.39 (1H, d, J = 15.9, H-7 ), 7.28 (2H, d, J = 8.6, H-2 , 6 ), 6.79 (2H, d, J = 8.9, H-5 , 3 ), 6.77 (2H, d, J = 8.6, H-3 , 5 ), 6.27 (1H, d, J = 1.7, H-8), 6.11 (1H, d, J = 1.7, H-6), 5.24 (1H, d, J = 7.2, Glc H-1 ), 4.32 (1H, d, J = 11.5, H-6 a), 4.19 (1H, dd, J = 12.5, 5.6, H-6 b), 3.20–4.40 (sugar protons). In addition, HPLC-UV-DAD permitted the characterization of the compound as kaempferol 3-O-[6 -O-E-p-coumaroyl]-D-glucopyranoside [8]. Compound 3. C27H30O16. UV (MeOH, max, nm): 269, 314; +NaOH: 276, 321, 365; +AlCl3: 276, 399; +AlCl3/HCl: 277, 399; +NaOAc: 275, 374; +H3BO3: 275, 372. 1H NMR (400 MHz, CD3OD, , ppm, J/Hz): 7.95 (2H, d, J = 8.9, H-6 , 2 )

Introduction The phytochemical and biological studies carried out on Salvia species showed that their extracts and constituents have various biological activities. Objective The aim of this study was the isolation of diterpenoids from the roots of Salvia barrelieri Ettling and the determination of the antioxidant activity. Methodology Chromatographic methods were used for fractionation and isolation, respectively. Structure elucidation was established by spectroscopic methods. Five antioxidant assays were performed. Results Three new abietane diterpenoids barreliol, royleanone 12-methyl ether and 7-epi-salviviridinol, and six known diterpenoids, with a known dammarane triterpenoid, pyxinol were isolated. The absolute stereochemistry of pyxinol was confirmed by X-ray analysis. Conclusion Taxodione exhibited the highest antioxidant activity among the tested compounds. Copyright © 2009 John Wiley & Sons, Ltd.

The root extract of endemic Algerian Salvia species Salvia barrelieri Ettling and its diterpenoids were investigated for potential antioxidant activity. From its acetone extract, a new natural abietane diterpenoid 7-oxoroyleanone-12-methyl ether ( 1 ) and six known diterpenoids 7 α -acetoxyroyleanone-12-methyl ether ( 2 ), royleanone ( 3 ), horminone ( 4 ), 7-acetylhorminone ( 5 ), cryptojaponol ( 6 ) and inuroyleanol ( 7 ) were isolated, and their structures were elucidated by spectroscopic means. Among the diterpenoids, the new diterpenoid 7-oxoroyleanone-12-methyl ether ( 1 ) showed highest superoxide anion scavenging activity while inuroyleanol ( 7 ) showed both the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity and inhibition of lipid peroxidation in β-carotene–linoleic acid system. These findings indicate that S. barrelieri extract as well as isolated abietane diterpenes, particularly inuroyleanol are promising antioxidants which can be used as food additives.

Starting from tetrahydroquinolines a straightforward and eco-friendly two-step access to functionalized julolidines is elaborated.

Different extracts of the aerial parts of Biscutella raphanifolia (Brassicaceae), which has not been the subject of any study, were screened for the phytochemical content, anti-microbial, antioxidant and anti-cholinesterase activities. We used four methods to identify the antioxidant activity namely, ABTS(•+), DPPH• scavenging, CUPRAC and ferrous-ions chelating methods. Since there is a relationship between antioxidants and cholinesterase enzyme inhibitors, we used two methods to determine the in vitro anti-cholinesterase activity by the use of the basic enzymes that occur in causing Alzheimer's disease: acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The extracts were also tested in vitro antimicrobial activity against various bacteria. The phytochemical study of B. raphanifolia afforded four flavonol glycosides; namely, quercetin-3-O-β-D-g1ucoside, quercetin-3-O-[β-D-glucosyl(1→2)-O-β-D-glucoside], quercetin-3-O-[β-D-glucosyl(1→3)-O-β-D-glucoside] and kaempferol-3-O-[β-D-glucosyl(1→2)-[(6'''p-coumaroyl)- β-D-glucoside], being isolated here for the first time from Biscutella raphanifolia and the genus. The ethyl acetate extract showed the highest activity in ABTS(•+), DPPH• and CUPRAC assays, while the petroleum ether extract demonstrated optimum efficiency metal chelating activity. The dicloromethane and petroleum ether extracts showed a mild inhibition against AChE and BChE. However, the petroleum ether extract showed a good antibacterial activity against the pathovars Enteropathogenic E. coli (EPEC), Enterotoxigenic E. coli (ETEC) and Enterococcus feacalis, whereas the Enterohemorrhagic E. coli (EHEC) strain was more sensitive to dichloromethane and n-butanol extracts.

International audience; The straightforward and ecofriendly preparation of functionalized julolidines starting from tetrahydroquinoline, diols, and aldehydes, for which water is produced as the only side product was investigated. To achieve this task, several well-defined ruthenium and iridium complexes including three new complexes were prepared from the corresponding phosphine–sulfonates, phosphine–carboxylates, and phosphine–phosphonates. The first transformation involved in situ generation of enaminoiminium intermediates, which allowed the formation of the julolidines through formal N,C(sp2)-cyclization of tetrahydroquinoline and the propane-1,3-diols. The influence of the chelate acidity points out that [Cp*IrIII]-based catalysts (Cp*=C5Me5) featuring phosphine–carboxylate and phosphine–sulfonate ligands were suitable for the cyclization, whereas the acidic phosphinophosphonate-containing complex favored the formation of reduced N-alkylated tetrahydroquinoline. We found that substitution of the propane-1,3-diols was crucial for the generation of enaminoiminium ions, which accounts for the efficiency and selectivity of the reaction. Applying another hydrogen autotransfer process, the prepared julolidines were easily functionalized at the C2 position.