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25 results on '"Laboratoire des Substances Naturelles"'

1. Fatty acid composition and mechanisms of the protective effects of myrtle berry seed aqueous extract in alcohol-induced peptic ulcer in rat

Author

Mohsen Sakly, Mohamed-Amine Jabri, Lamjed Marzouki, Kais Rtibi, Karim Hosni, Hichem Sebai, Haifa Tounsi, Laboratoire d’Anatomie Pathologique Humaine et Expérimentale, Institut Pasteur de Tunis, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire de Physiologie Intégrée, Faculté des Sciences de Bizerte [Université de Carthage], and Université de Carthage - University of Carthage-Université de Carthage - University of Carthage

Subjects
myrtle berries, Male, 0301 basic medicine, Peptic Ulcer, antioxidant, Antioxidant, Duodenum, Physiology, Iron, medicine.medical_treatment, Alcohol, Berry, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, free acidity, Physiology (medical), medicine, Animals, Food science, Rats, Wistar, Flavonoids, Pharmacology, Aqueous extract, Ethanol, Plant Extracts, Chemistry, Fatty Acids, Stomach, Polyphenols, Water, Hydrogen Peroxide, General Medicine, medicine.disease, Myrtus, Rats, 3. Good health, 030104 developmental biology, Biochemistry, Cytoprotection, 030220 oncology & carcinogenesis, Peptic ulcer, Seeds, Calcium, Lipid Peroxidation, Fatty acid composition, unsaturated fatty acids, [SDV.MHEP]Life Sciences [q-bio]/Human health and pathology
Abstract

This study aimed to investigate the antiulcer and antioxidant activities of myrtle berry seed aqueous extract (MBSAE) in a peptic ulcer model induced by ethanol in male Wistar rats. MBSAE is rich in total polyphenols, total flavonoids, and unsaturated fatty acids, particularly linoleic (18:2) and oleic (18:1) acids. MBSAE also exhibited in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) (IC50= 172.1 μg/mL) and superoxide anion (IC50= 200.24 μg/mL) scavenging activities. In vivo, MBSAE provided dose-dependent protection against ethanol-induced gastric and duodenal macroscopic and histological alterations. Also, it inhibited secretory profile disturbances and lipid peroxidation, and preserved normal antioxidant enzyme activities and nonenzymatic antioxidant levels. More importantly, we showed that acute alcohol intoxication increased gastric and duodenal calcium, hydrogen peroxide, and free iron levels, whereas MBSAE treatment protected against intracellular mediator deregulation. In conclusion, we suggest that MBSAE has potent protective effects against alcohol-induced peptic ulcer in rat. This protection might be related in part to its antioxidant properties as well as its opposite effects on some studied intracellular mediators.

Published
2017
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2. Maturation-related changes in phytochemicals and biological activities of the Brazilian pepper tree (Schinus terebinthifolius Raddi) fruits

Author

Asma Ennigrou, Belgacem Hanchi, Karim Hosni, A. Laarif, Hervé Casabianca, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), UR13AGR09, CRRHAB, Université de Sousse, Université de Tunis El Manar (UTM), and The authors are thankful to the Direction Generale de la Recherche Scientifique (DGRS, Tunisia) and the Centre National de la Recherche Scientifique (CNRS, France) for financial support, Research project PHC-Utique No 13G0904 and the project 'Laboratoire International de Recherche Analytique (LIRA-Tunisia)'.

Subjects
0106 biological sciences, Flavonoid, Plant Science, Biology, 01 natural sciences, law.invention, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, law, Botany, Food science, Spodoptera littoralis, ComputingMilieux_MISCELLANEOUS, Essential oil, 2. Zero hunger, chemistry.chemical_classification, Limonene, Schinus terebinthifolius Raddi, Fruit maturation, Secondary metabolites, Biological activities, 010401 analytical chemistry, Schinus terebinthifolius, Fatty acid, 15. Life on land, biology.organism_classification, Lipids, 0104 chemical sciences, Phthorimaea operculella, chemistry, Antibacterial activity, 010606 plant biology & botany
Abstract

Changes in fatty acid profile, lipid quality, essential oil composition, total phenolic (TPC) and flavonoid (TFC) contents, radical scavenging, antibacterial and insecticidal activities were studied during the maturation of Schinus terebinthifolius Raddi fruits. Total lipids showed their maximum at the earlier and intermediate stage (green and half-red) of maturation, whereas, the highest levels of the main components linoleic and oleic acids were found at the late stage (red). Mature fruits were also distinguished by their high lipid quality as revealed by the lower values of n-3/n-6 ratio, calculated oxidizability (Cox), oxidative susceptibility (OS), atherogenic index (AI) and thromobogenic index (TI). The contents of monoterpenes decreased while those of sesquiterpenes increased during maturation. With the exception of α-pinene which dropped remarkably from immature to mature fruits, the content of the other main components (α-phellandrene, β-phellandrene and limonene) showed irregular variations. The TPC in intact and hydrodistilled fruits was higher at the last stage of maturation, while the maximum of TFC was recorded in the intermediate stage. Concomitantly, extract from residual hydrodistilled fruits was found as the most potent radical scavengers, whereas, the oils were found as the least scavengers. Nevertheless, they showed an appreciable antibacterial activity against Enterococcus feacium and Streptococcus agalactiae and exert a strong insecticidal activity against Spodoptera littoralis and Phthorimaea operculella . Collectively, these results suggest that the fruits of S. terebinthifolius could be considered as consolidated source of lipid and essential fatty acids, which may provide some health benefits to consumers. They also showed that the essential oils of S. terebinthifolius fruits can potentially be used in S. littoralis and P. operculella control in association with integrated pest management practices. Moreover, the use of extracts from intact or hydrodistilled residual fruits for the development of functional ingredients and the production of bio-based preservatives is encouraged.

Published
2017
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3. New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide, and Isoidide

Author

Raouf Medimagh, Mongia Saïd Zina, Sylvain R. A. Marque, Saber Chatti, Asma Saadaoui, Damien Prim, Hervé Casabianca, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Faculté des Sciences Mathématiques, Physiques et Naturelles de Tunis (FST), Université de Tunis El Manar (UTM), Institut Lavoisier de Versailles (ILV), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and the Ministry of Higher Education, Scientific Research, Tunisia, together with EGIDE in the framework of the CMCU project [Project PHC Utique 13G/1211].

Subjects
poly(ether)esters, Materials science, Isosorbide, Polymers and Plastics, General Chemical Engineering, Ether, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Chloride, Article, AB monomers, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Polymer chemistry, Materials Chemistry, medicine, Organic chemistry, semicrystalline, 6-Dianhydrohexitols, Benzoic acid, 4:3, chemistry.chemical_classification, biosourced, Articles, General Chemistry, Polymer, 021001 nanoscience & nanotechnology, lcsh:TP1080-1185, 0104 chemical sciences, Monomer, lcsh:Polymers and polymer manufacture, chemistry, Polymerization, 1,4:3,6-Dianhydrohexitols, Melting point, 0210 nano-technology, medicine.drug
Abstract

International audience; In the present work, we propose the synthesis of a new family of sugar derived 1,4:3,6-dianhydrohexitol based AA/AB-type monomers. Unprecedented diacids based on Isomannide and Isoidide were elaborated with high yields and showed interestingly high melting point ranges (240-375 degrees C). Optimization of reaction conditions (temperature, time of reaction, and reactant ratios) has been investigated to synthesize the key intermediate of a set of AB monomers with acid, ester, and acid chloride functionalities. Isosorbide based ether benzoic acid AB monomer was polymerized and characterized by NMR and DSC techniques. The results show a semicrystalline behavior of the obtained polymer thanks to the controlled stereoregular arrangement of the AB starting monomer.

Published
2016
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4. Enzyme-aided release of bioactive compounds from coriander (Coriandrum sativum L.) seeds and their residue by-products and evaluation of their antioxidant activity

Author

Aïmen Abbassi, Yassine M’rabet, Wafa Zaouali, Hervé Casabianca, Karim Hosni, Hela Mahmoudi, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Unite Physiol & Biochim Reponse Plantes Contraint, Université de Tunis El Manar (UTM), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)

Subjects
0106 biological sciences, DPPH, Coriandrum, Geranyl acetate, Cellulase, 01 natural sciences, law.invention, Terpene, chemistry.chemical_compound, Camphor, 0404 agricultural biotechnology, Linalool, law, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, 010608 biotechnology, Food science, Essential oil, ComputingMilieux_MISCELLANEOUS, 2. Zero hunger, biology, 04 agricultural and veterinary sciences, biology.organism_classification, 040401 food science, chemistry, biology.protein, Food Science
Abstract

Enzyme-assisted extraction has emerged as an attractive green, cost-effective and high bioactive yielding technology by which desired bioactives with preserved or better efficacy are released. In the present study, the ability of cellulase, hemicellulase and their binary mixture (cellulase:hemicellulase; 1:1) in improving the extraction of essential oils from coriander (Coriandrum sativum L.) seeds, or the residue by-products from the distillation process containing value-added phytochemicals (fatty acids and phenolics) were evaluated. Cellulase and the binary mixture improved the extraction of essential oils by 44.2 and 40%, respectively. Application of enzymes was associated with increased amount of oxygenated terpenes in the essential oils derived from enzyme-treated samples. Linalool, camphor and geranyl acetate were the prominent compounds. From the hydrodistillation residues, a better recovery of petroselinic-rich oil with a good nutritional quality was also observed in enzyme-treated seeds. They also contained an appreciable amount of polyphenols and showed an improved antioxidant activity as revealed by the DPPH, FRAP and cellular antioxidant activity assays. The results suggested that enzyme pre-treatment allowed better recovery without alteration of the essential oil composition. The hydrodistillation residues obtained could be potentially exploited for the development of functional food ingredients and nutraceuticals.

Published
2018
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5. Assessing the fatty acid, essential oil composition, their radical scavenging and antibacterial activities of Schinus terebinthifolius Raddi leaves and twigs

Author

Asma Ennigrou, Emmanuelle Vulliet, Belgacem Hanchi, Karim Hosni, Hervé Casabianca, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Unité Ecole Végétale, Université de Tunis - El Manar II, Université de Tunis El Manar (UTM)-Université de Tunis El Manar (UTM), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), TRACES - Technologie et Recherche en Analyse Chimique pour l'Environnement et la Santé, and The authors are thankful to the Direction Generale de la Recherche Scientifique (DGRS, Tunisia) and the Centre National de la Recherche Scientifique (CNRS, France) for financial support, and the project PHC-Utique No. 13G0904 and the project 'Laboratoire International de Recherche Analytique (LIRATunisia)'.

Subjects
0106 biological sciences, Antioxidant, Monoterpene, medicine.medical_treatment, 01 natural sciences, law.invention, chemistry.chemical_compound, Schinus terebinthifolius, law, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, medicine, Food science, Fatty acids, Essential oil, 2. Zero hunger, chemistry.chemical_classification, Limonene, biology, Chemistry, 010401 analytical chemistry, Fatty acid, biology.organism_classification, 0104 chemical sciences, Essential oils, Composition (visual arts), Antibacterial activity, DPPH˙ scavenging activity, 010606 plant biology & botany, Food Science
Abstract

International audience; The fatty acid, essential oil compositions and their respective antioxidant and antibacterial activities was determined in Schinus terebinthifolius Raddi leaves and twigs. The lipid content ranged from 1.75 to 4.65% in twigs and leaves, respectively. Thirteen fatty acids were identified with α-linolenic (C18:3), palmitic (C16:0) and linoleic (C18:2) acids being the main components. The essential oils of both organs were characterized by a high amount of monoterpene hydrocarbons (68.91-74.88%) with α-phellandrene (33.06-36.18%), α-pinene (14.85-15.18%) and limonene (6.62-8.79%) being the chief components. The DPPH˙ radical scavenging assay revealed that both oils have a very weak antiradical activity. In contrast, they showed an appreciable antibacterial activity against the gram-positive Enterococcus feacium (ATCC 19434) and Streptococcus agalactiae (ATCC 13813) bacteria. These results suggest that leaves and twigs of S. terebinthifolius could be considered as an important dietary source of health promoting phytochemicals and has a good potential for use in food industry and pharmacy.

Published
2018
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6. Enzyme-assisted extraction of bioactive compounds from bay leaves (Laurus nobilis L.)

Author

Hervé Casabianca, Karim Hosni, Ines Ben Amor, Imed E. Hassen, Lamia Haouari, Abdennacer Boulila, Feiza Mejri, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire des méthodes et techniques d'analyses, Institut National de Recherche et d'Analyse Physico-Chimique (INRAP), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and The authors are indebted to the Direction Generale de la Recherche Scientifique (DGRST, Tunisia) and the Centre National de la Recherche Scientifique (CNRS, France) and the Laboratoire International Associe (LIA) for financial support (Research Project PHC-Utique No 13G0904)

Subjects
0106 biological sciences, DPPH, Sabinene, CHEMICAL-COMPOSITION, Laurus nobilis L, 01 natural sciences, law.invention, chemistry.chemical_compound, 0404 agricultural biotechnology, Laurus nobilis, food, Antioxidant activity, Methyl eugenol, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, law, 010608 biotechnology, ANTIBACTERIAL, Organic chemistry, PLANTS, Food science, Essential oil, VOLATILE OIL, alpha-Pinene, ABTS, DISTILLATION, Food processing technology, COMPONENTS, 04 agricultural and veterinary sciences, HYDROLYSIS, 040401 food science, food.food, Enzymes, Eugenol, ESSENTIAL OIL, chemistry, Essential oils, Phenolics, OFFICINALIS, Agronomy and Crop Science
Abstract

International audience; Bay leaves (Laurus nobilis L.) are widely used as a condiment and their therapeutic benefits are well known. These biological properties were attributed to a plethora of highly bioactive secondary metabolites namely essential oils and phenolics. However, their recovery from plant matrix is generally limited by the presence of physical barrier (cell wall). Thus, the use of novel extraction procedures to enhance their release is particularly important. Therefore, the aim of this work is to assess the potential use of enzyme treatment (cellulase, hemicellulase, xylanase end the ternary mixture of them) as a tool to improve the extraction efficiency of bioactive compounds from bay leaves. Results showed that enzyme pre-treatment resulted in 243, 227, 240.54 and 0.48% increase in the essential oil yields in samples treated with cellulase, hemicellulase, xylanase and the ternary mixture, respectively. Compositional analysis by GC and GC MS revealed remarkable enrichment of the essential oils derived from enzyme-treated samples with oxygenated monoterpenes, leading hence to better antioxidant activity as revealed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and azino-bis-(3-ethylbenzothiolzoline 6-sulphonic acid) (ABTS) assays. The 1,8-cineole, alpha-terpinyl acetate, methyl eugenol, linalool, a-pinene, sabinene and beta-pinene were found as the most prominent components in all essential oils. Most importantly, enzyme treatment did not induce transformation of the volatile components, but it contributes to the liberation of some glycosidically bound volatiles. Moreover, it significantly enhances the release of phenolic compounds from the hydro distilled residual leaves and consequently their antioxidant activity. These results suggest that enzyme pre-treatment could be useful for extracting valuables components, and hold good potential for use in food, cosmetic and pharmaceutical industries.

Published
2015
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7. Myrtle berry seed aqueous extract inhibits human neutrophil myeloperoxidase in vitro and attenuates acetic acid-induced ulcerative colitis in rats

Author

Haifa Tounsi, Abdelaziz Souli, Mohsen Sakly, Mohamed-Amine Jabri, Jamel El-Benna, Karim Hosni, Kais Rtibi, Lamjed Marzouki, Hichem Sebai, Centre de recherche sur l'Inflammation (CRI (UMR_S_1149 / ERL_8252 / U1149)), Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Diderot - Paris 7 (UPD7), Laboratoire de Physiologie Intégrée, Faculté des Sciences de Bizerte, Université de Jendouba (UJ), Laboratoire d'Epidémiologie Moléculaire et de Pathologie Expérimentale Appliquée aux Maladies Infectieuses (LR11IPT04), Université Tunis El Manar (UTM)-Institut Pasteur de Tunis, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique (Ariana, Tunisie) (INRAP), Université Paris Diderot - Paris 7 (UPD7)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Faculté des Sciences de Bizerte [Université de Carthage], Université de Carthage - University of Carthage-Université de Carthage - University of Carthage, Université de Tunis El Manar (UTM)-Institut Pasteur de Tunis, and Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP)

Subjects
chemistry.chemical_classification, Antioxidant, biology, Chemistry, Superoxide, [SDV]Life Sciences [q-bio], General Chemical Engineering, medicine.medical_treatment, Glutathione peroxidase, General Chemistry, Glutathione, Pharmacology, Superoxide dismutase, Lipid peroxidation, chemistry.chemical_compound, Biochemistry, Catalase, Myeloperoxidase, biology.protein, medicine
Abstract

International audience; We aimed in the present study to investigate the protective effect of a myrtle (Myrtus communis L.) berry seed aqueous extract (MBSAE) on acetic acid (AA)-induced colitis in rats as well as the mechanism implicated in this coli-protection. The use of the LC/MS technique allowed us to identify 18 phenolic compounds in the MBSAE. Secondly, we found that the MBSAE inhibited the luminol-amplified chemiluminescence of resting neutrophils and N-formyl-methionylleucyl-phenylalanine (fMLF) or phorbolmyristate acetate (PMA) stimulated neutrophils in a dose-dependent manner. The MBSAE had no effect on superoxide anions, but it inhibited H2O2 production in the cell free system stimulated with horseradish peroxidase (HRPO) and MPO release from the neutrophils. In vivo, the pre-treatment of rats with sulfasalazine (100 mg kg(-1)) and the MBSAE (25, 50, and 100 mg kg(-1)) significantly reduced AA-induced colonic mucosa lesions as well as histopathological changes. The MBSAE counteracted AA-induced lipid peroxidation and the depletion of the activity of antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx). We also found that the myrtle extract inhibited the increase of the plasma scavenging activity (PSA) and preserved the content of non-enzymatic antioxidants such as sulfhydryl groups (-SH) and reduced glutathione (GSH). More importantly, acetic acid administration increased colonic hydrogen peroxide (H2O2), free iron and calcium levels, while the MBSAE pre-treatment reversed all intracellular mediator perturbations. In conclusion, our data suggests that the MBSAE exerted a potential protective effect against AA-induced injury and oxidative stress in the rat colon. This coli-protection might be related in part to its antioxidant and ROS scavenging activities or by negatively regulating Fenton reaction components such as H2O2 and free iron, which are known to lead to cytotoxicity mediated by intracellular calcium deregulation.

Published
2015
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8. Profiling of phenolic compounds and antioxidant activity of Melia azedarach L. leaves and fruits at two stages of maturity

Author

Yassine M’rabet, Nesrine Rokbeni, Abdennacer Boulila, Hervé Casabianca, Karim Hosni, Tristan Richard, Stéphanie Cluzet, Lamjed Marzouki, Stéphanie Krisa, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique (Ariana, Tunisie) (INRAP), Unité de Recherche Oenologie [Villenave d'Ornon], Institut National de la Recherche Agronomique (INRA)-Université de Bordeaux (UB)-Institut des Sciences de la Vigne et du Vin (ISVV), Université de Jendouba (UJ), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), The authors are thankful to the 'Direction Generale de la Recherche Scientifique' (DGRS, Tunisia) and the 'Centre National de la Recherche Scientifique' (CNRS, France) for financial support, Project 'Laboratoire International de Recherche Analytique' (LIRA-Tunisia)., Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Metal chelating activity, Antioxidant, Chromatography, Oxygen radical absorbance capacity, biology, 010405 organic chemistry, DPPH, Melia azedarach, medicine.medical_treatment, 010401 analytical chemistry, biology.organism_classification, 01 natural sciences, 0104 chemical sciences, Rutin, chemistry.chemical_compound, Flavonols, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, medicine, Trolox, Food science, Agronomy and Crop Science
Abstract

International audience; The present work aims to investigate the maturation-related changes in phenolic profile of Melia azedarach (L.) leaves (young and old) and fruits (pulp and kernel) at two developmental stages. A total of 26 phenolic compounds were identified by high-performance liquid chromatography-diode-array detector-hyphenated with tandem mass spectromdtry (HPLC-DAD-ESI MS/MS). They include phenolic acids, flavonols and flavanols which were found mostly in glycosylated forms. The main phenolic compounds were found to be rutin (5.86-21.33%, of total integrated peak area at 280 nm), quercetin-3-O-neohesperidoside (3.95-8.76%), kaempferol-3-O-rutinoside (2.73-11.23%), feruloylglucaric acid (0.85-11.84%) and feruloylquinic acid derivative (1.94-11.07%). The pattern distribution of phenolic compounds was organ-specific, and somewhat variable depending on the stage of maturation. Additionally, the total phenol content was determined as well as the antioxidant capacity using different in vitro assays. The extracts of young leaves demonstrated the highest total phenol content (85.4 mg GAE/g extract), and exhibited the strongest scavenging activity against 2,2-diphenyl-1-picrylhydrazyl DPPH and the highest oxygen radical absorbance capacity ORAC (235 and 328 mg Trolox equivalents/g extract, respectively) compared to old leaves and immature/mature fruit parts. In contrast, the highest metal chelating activity (MCA) was observed in immature pulp extracts (22.85 mg EDTA equivalents/g extract). Pearson's correlation and principal component analysis (PCA) showed that quercetin-3-O-neohesperidoside, rutin and kaempferol-3-O-rutinoside were the main contributors on the antioxidant capacity. On the basis of these results, M. azedarach could serve as an excellent source of natural antioxidants which could be used for pharmaceutical and cosmeceutical applications.

Published
2017
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9. Copolyethersulfones of 1,4:3,6-dianhydrohexitols and bisphenol A

Author

Raouf Medimagh, Saber Chatti, Chaouki Belgacem, Hans R. Kricheldorf, Hatem Ben Romdhane, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Institut fur Technische und Makromolekulare Chemie/Fachbereich Chemie TMC, Universität Hamburg (UHH), Laboratoire de Chimie Organique Structurale et Macromoléculaire (LR99ES14), Université de Tunis El Manar (UTM), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)

Subjects
MALDI-TOF, Bisphenol A, Materials science, Isosorbide, Condensation polymer, Polymers and Plastics, General Chemical Engineering, 02 engineering and technology, 010402 general chemistry, dianhydrohexitols, 01 natural sciences, chemistry.chemical_compound, Differential scanning calorimetry, polyethersulfones, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Materials Chemistry, medicine, Copolymer, Organic chemistry, ComputingMilieux_MISCELLANEOUS, Polycondensation, Comonomer, General Chemistry, Nuclear magnetic resonance spectroscopy, 021001 nanoscience & nanotechnology, NMR, 0104 chemical sciences, Monomer, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, 0210 nano-technology, medicine.drug
Abstract

The synthesis of biosourced copolyethersulfones by polycondensation of 1,4:3,6-dianhydrohexitol monomers and bisphenol A is reported. Structures and properties of these copolymers were investigated in each case. In the first part, the impact of the position of the two hydroxyl groups of isosorbide, isomannide, and isoidide is discussed. In the second part, we focused on improving the cost/thermal properties balance by introducing controlled proportions of bisphenol A as comonomer. The addition of bisphenol A serves two purposes. The first one is to maintain good thermal and mechanical properties of resulting copolymers. The second reason is to insure low-cost route to copolyethersulfones for a potential use in industrial applications. All the products have been fully characterized by NMR spectroscopy, MALDI-TOF spectrometry, and viscosimetry. The thermal properties were studied by differential scanning calorimetry (DSC).

Published
2016
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10. Responses of Nigella sativa L. to Zinc Excess: Focus on Germination, Growth, Yield and Yield Components, Lipid and Terpene Metabolism, and Total Phenolics and Antioxidant Activities

Author

Hervé Casabianca, Saloua Ouerghemmi, Ahmed Marichali, Houcine Sebei, Sana Dallali, Karim Hosni, Ecole Super Agr Mograne, Inst Super Agron Chott Mariem, PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), and We are thankful to the Direction Generale de la Recherche Scientifique (DGRS, Tunisia) and the Centre National de la Recherche Scientifique (CNRS, France) for financial support, Research Project PHC-Utique 13G0904, and the project 'Laboratoire International de Recherche Analytique (LIRA-Tunisia)'.

Subjects
0106 biological sciences, 0301 basic medicine, Antioxidant, medicine.medical_treatment, Nigella sativa L, growth, Nigella sativa, chemistry.chemical_element, antioxidant activity, Germination, Zinc, 01 natural sciences, Antioxidants, law.invention, Terpene, lipids, 03 medical and health sciences, Phenols, law, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Botany, medicine, Radicle, Food science, Essential oil, 2. Zero hunger, Chemistry, secondary metabolites, Terpenes, food and beverages, Lipid metabolism, General Chemistry, Lipid Metabolism, 030104 developmental biology, Seeds, General Agricultural and Biological Sciences, [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition, 010606 plant biology & botany
Abstract

International audience; A comprehensive analysis of the responses of Nigella sativa L. to elevated zinc concentrations was assessed in pot experiments. Zn excess supply did not affect the germination but drastically reduced radicle elongation. A concentration-dependent reduction in all growth parameters, yield, and yield components was observed. With the increasing Zn concentrations, total lipid contents decreased and changes in fatty composition toward the production of saturated ones were underscored. Despite the reduction in the seeds essential oil yield, a redirection of the terpene metabolism toward the synthesis of oxygenated compounds has been evidenced. A significant increase in the total phenols and flavonoids contents concomitant with improved antioxidant activities has also been found. Collectively, these results highlight the possible use of N. sativa L. in phytoremediation applications, on the one hand, and that Zn excess could represent an excellent alternative to improve the nutritional attributes of this important species, on the other hand.

Published
2016
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11. Synthesis and characterization of novel biosourced building blocks from isosorbide

Author

Raouf Medimagh, Eric Drockenmuller, Malek M'sahel, Ayoub Elmahdi, Mongia Saïd Zina, Ingénierie des Matériaux Polymères (IMP), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire de Chimie des Matériaux et Catalyse, Faculté des Sciences Mathématiques, Physiques et Naturelles de Tunis (FST), and Université de Tunis El Manar (UTM)-Université de Tunis El Manar (UTM)-Département de Chimie

Subjects
Isosorbide, Polymers and Plastics, isosorbide, General Chemical Engineering, 4: 3, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Acylation, chemistry.chemical_compound, Materials Chemistry, medicine, Organic chemistry, 6-Dianhydrohexitols, Addition reaction, biosourced, novel diols, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, NMR, 0104 chemical sciences, Solvent, Monomer, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymerization, 0210 nano-technology, Selectivity, Two-dimensional nuclear magnetic resonance spectroscopy, medicine.drug
Abstract

International audience; New biosourced unprotected diols were prepared by acylation reaction of aminoalcohol based on 1,4: 3,6-dianhydrosorbitol (Isosorbide Is) with several aliphatic and aromatic diacyl chlorides (sebacoyl, adipoyl, and terephthaloyl). Optimization of reaction conditions (solvent, base nature, and addition mode) has been investigated with protected alcohols. The use of hindered bases was needful to ensure the selectivity of the addition reaction when starting from unprotected aminoalcohol, and selectively led to bis amides products with good yields. 1D and 2D NMR techniques were used to ascertain the structures of the unprecedented monomers. These novel building blocks were successfully polymerized using succinic and terephthalic spacers and studied by NMR and DSC techniques.

Published
2016
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12. Biosourced 1,2,3-triazolium ionic liquids derived from isosorbide

Author

Raouf Medimagh, Eric Drockenmuller, Anatoli Serghei, Malek M'sahel, Mona M. Obadia, Mongia Saïd Zina, Ingénierie des Matériaux Polymères (IMP), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire de Chimie des Matériaux et Catalyse, Faculté des Sciences Mathématiques, Physiques et Naturelles de Tunis (FST), and Université de Tunis El Manar (UTM)-Université de Tunis El Manar (UTM)-Département de Chimie

Subjects
Thermogravimetric analysis, Isosorbide, CLICK CHEMISTRY POLYADDITION, GREEN, SALTS, Alkylation, 010402 general chemistry, Metathesis, 01 natural sciences, ISOMANNIDE, chemistry.chemical_compound, Differential scanning calorimetry, Materials Chemistry, medicine, Organic chemistry, Ionic conductivity, 010405 organic chemistry, Chemistry, CATALYSIS, DEEP-EUTECTIC SOLVENTS, VERSATILE, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, POLY(IONIC LIQUID)S, Ionic liquid, RENEWABLE RESOURCES, CATIONS, medicine.drug, Methyl iodide
Abstract

International audience; Two series of 1,2,3-triazolium chiral ionic liquid (CIL) stereoisomers are synthesized from isosorbide by combining the robust attributes of the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), alkylation of the resulting 1,2,3-triazoles by methyl iodide and further anion metathesis with different fluorinated salts. These novel biosourced CILs are characterized in details by H-1 and C-13 NMR spectroscopy, high-resolution mass spectrometry (ESI-HRMS), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and broadband dielectric spectroscopy (BDS). The effect of stereochemistry on their physical, thermal and ion conducting properties is discussed. Markedly, it is demonstrated for the first time that stereochemistry can drastically influence ionic conductivity by several orders of magnitude.

Published
2016
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13. Biosourced Cyclic and Multicyclic Polyesters Based on 1,4:3,6-Dianhydrohexitols: Application to Metal Ions Uptake in Aqueous Media

Author

Hans R. Kricheldorf, Raouf Medimagh, Saber Chatti, Mongia Saïd Zina, Aurélie Fildier, Haythem Bennour, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), TRACES - Technologie et Recherche en Analyse Chimique pour l'Environnement et la Santé, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut fur Technische und Makromolekulare Chemie/Fachbereich Chemie TMC, Universität Hamburg (UHH), Laboratoire de Chimie des Materiaux, Faculte ́ des Sciences de Tunis, Universite ́ de Tunis El Manar, Laboratoire de Chimie des Materiaux, and the Tunisian Ministry of Higher Education and Research for financial support together with EGIDE (Project 'PHC Utique' 13G/1211).

Subjects
MALDI-TOF, Condensation polymer, Isosorbide, ADSORPTION, Polymers and Plastics, Metal ions in aqueous solution, Inorganic chemistry, Diol, DICARBOXYLIC-ACID, polyesters, Mass spectrometry, multicyclic, chemistry.chemical_compound, MALDI ToF, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Polymer chemistry, SUCCINIC ACID, Materials Chemistry, Magic angle spinning, medicine, metal uptake, Organic chemistry, POLYCONDENSATION, Physical and Theoretical Chemistry, FREE SAMPLE PREPARATION, POLY(ETHER ESTER)S, Organic Chemistry, MASS-SPECTROMETRY, Condensed Matter Physics, STATE, Polyester, Matrix-assisted laser desorption/ionization, ISOSORBIDE, chemistry, medicine.drug
Abstract

Authors want to thank all INRAP staff for analysis and helpful discussion. M. Mezni is acknowledged for NMR experiments, R. Jebali and N. Chaabane for ICP analysis.; International audience; Isosorbide and isomannide are polycondensed in solution with trimesoyl chloride at a concentration of 0.06 mol L-1 for the synthesis of cyclic and multicyclic polyesters. The feed ratio diol/trimesoyl chloride is varied from 1.0/1.0 to 1.6/1.0. As all obtained polyesters prove insoluble, innovative solvent-free matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI ToF MS) is performed for their characterization. The influence of the stereochemistry is shown to be of great importance for the cyclization trend. Both isosorbide and isomannide lead mainly to cyclic and multicyclic structures at a feed ratio of 1.0/1.0 and 1.1/1.0. Isomannide gives higher fractions of multicyclic structures. The products are characterized by complementary techniques such as C-13 cross polarization magic angle spinning nuclear magnetic resonance (C-13 CP-MAS NMR) and differential scanning calorimetry measurements. Application as a cryptands for the uptake of metal ions in aqueous media is followed by inductively coupled plasma atomic emission spectroscopy (ICP AES) analysis and reveal efficient toward large range of metals with tunable selectivity depending on the starting diol.

Published
2015
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14. Synthesis and characterization of isosorbide-based α,ω-dihydroxyethersulfone oligomers

Author

Raouf Medimagh, Audrey Buleté, Hans R. Kricheldorf, Saber Chatti, Hatem Ben Romdhane, Aurélie Fildier, Chaouki Belgacem, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), TRACES - Technologie et Recherche en Analyse Chimique pour l'Environnement et la Santé, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut für Technische und Makromolekulare Chemie, Universität Hamburg (UHH), Laboratoire de Chimie Organique Structurale et Macromoléculaire (LR99ES14), Université de Tunis El Manar (UTM), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, and Institut fur Technische und Makromolekulare Chemie/Fachbereich Chemie TMC

Subjects
Materials science, Condensation polymer, Isosorbide, Polymers and Plastics, isosorbide, PHASE-TRANSFER CATALYSIS, General Chemical Engineering, DIOLS, Size-exclusion chromatography, DIANHYDROHEXITOLS, Hydroxylation, chemistry.chemical_compound, Differential scanning calorimetry, polyethersulfones, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Materials Chemistry, medicine, Organic chemistry, MICROWAVE, oligomers, chemistry.chemical_classification, MALDI-ToF, POLYURETHANES, General Chemistry, Polymer, Nuclear magnetic resonance spectroscopy, NMR, Monomer, chemistry, ACID, POLYMERS, polycondensation, medicine.drug
Abstract

International audience; Functionalization of bio-based oligomers is a relevant approach in order to allow these materials to replace more conventional and nonbiodegradable polymers in a wider range of applications. This article will report on the hydroxylation of isosorbide-based ethersulfone oligomers. The hydroxy end-group was controlled by the variation of polycondensation parameters. Comparative study was conducted to assess the effect of isosorbide excess and the monomer concentration on structural composition and molecular weights of produced oligomers. Depending on reaction conditions, various products were synthesized, mainly alpha,omega-dihydroxyethersulfone oligomers. The characterization of the synthesized polyethersulfone was demonstrated by MALDI-TOF, NMR spectroscopy, differential scanning calorimetry, and size exclusion chromatography.

Published
2015
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15. Ecballium elaterium (L.) A. Rich. seed oil: Chemical composition and antiproliferative effect on human colonic adenocarcinoma and fibrosarcoma cancer cell lines

Author

Belgacem Hanchi, Olfa Kallech-Ziri, Saloua Fatnassi, Abdennacer Boulila, José Luis, Imen Touihri, Naziha Marrakchi, Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire des Venins et Biomolécules Thérapeutiques - Laboratory of Venoms and Therapeutic Biomolecules (LR11IPT08), Institut Pasteur de Tunis, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Faculté de Médecine de Tunis, Université de Tunis El Manar (UTM), Centre de Recherches en Oncologie biologique et Oncopharmacologie (CRO2), Aix Marseille Université (AMU)- Hôpital de la Timone [CHU - APHM] (TIMONE)-Institut National de la Santé et de la Recherche Médicale (INSERM), Aix Marseille Université (AMU), Faculté des Sciences Mathématiques, Physiques et Naturelles de Tunis (FST), This research was supported by Tunisian Ministry of High Education and Scientific Research (MESRS), the Institut National de Recherche et d’Analyse Physico-chimique (INRAP), Tunisia, and the Institut national de la santé et de la recherche médicale (INSERM), France., and Authors would like to thank Professor S. BEN SAAD, botanist in the Faculty of Sciences of Tunisia for his contribution in the identification of plants. The authors thank Professor Khaoula Khwaldia biologist in INRAP for helpful discussions.

Subjects
Chemistry(all), General Chemical Engineering, Linoleic acid, Chemical composition, [SDV.CAN]Life Sciences [q-bio]/Cancer, Antiproliferative activity, lcsh:Chemistry, chemistry.chemical_compound, medicine, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, [INFO]Computer Science [cs], Tocopherol, Fibrosarcoma, chemistry.chemical_classification, Punicic acid, biology, Elaterium, Ecballium elaterium, General Chemistry, biology.organism_classification, medicine.disease, 3. Good health, Colon cancer, chemistry, Biochemistry, lcsh:QD1-999, Chemical Engineering(all), lipids (amino acids, peptides, and proteins), HT1080, Seed oil, Polyunsaturated fatty acid
Abstract

In this work the physicochemical characteristics including fatty acids, tocopherols and sterols composition of Ecballium elaterium (L.) A. Rich seed oil was determined. Results showed that linoleic acid (48.64%) and punicic acid (22.38%) were the major polyunsaturated fatty acids. Among the phytosterols, β-sitosterol was the most abundant (396.25 mg/100 g), while the major tocopherol form was γ-tocopherol (44.23 mg/100 g). In addition, we evaluated for the first time the effect of E. elaterium seed oil on the growth of human colonic adenocarcinoma (HT29) and fibrosarcoma (HT1080) cell lines. The original finding was its potent antiproliferative effect on both tumour cell lines. This effect was dose-dependent, with half-maximal inhibition values of IC50 = 4.86 μg/ml and 4.16 μg/ml respectively. This pilot study opens the way for further investigation about the potential use of E. elaterium as an anticancer agent. Keywords: Ecballium elaterium, Seed oil, Chemical composition, Antiproliferative activity, Colon cancer

Published
2015
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16. Chemodiversity of volatile oils in Thapsia garganica L. (Apiaceae)

Author

Ons Kesraoui, Chaouki Belgacem, Yassine M’rabet, Hervé Casabianca, Karim Hosni, Imed E. Hassen, Laboratoire des méthodes et techniques d'analyses, Institut National de Recherche et d'Analyse Physico-Chimique (INRAP), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), PNBS - Produits naturels et biosourcés - Natural & Bio-based Products, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), and the Direction Generale de la Recherche Scientifique (DGRST, Tunisia), the Centre National de la Recherche Scientifique (CNRS, France), and the Laboratoire International Associe (LIA) for financial support (Research Project PHC-Utique N813G0904).

Subjects
0106 biological sciences, Principal-component analysis (PCA), 01 natural sciences, Biochemistry, Thapsia garganica, Plant Roots, chemistry.chemical_compound, Sesquiterpenes, Germacrane, Linalool, Cluster Analysis, Chemical composition, FRUITS, Thapsia, education.field_of_study, Principal Component Analysis, biology, Plant Stems, General Medicine, Biodiversity, Molecular Medicine, Composition (visual arts), Sesquiterpenes, Tunisia, Acyclic Monoterpenes, Population, Bioengineering, Flowers, Naphthalenes, Sesquiterpene, CHEMICAL-COMPOSITION, Gas Chromatography-Mass Spectrometry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Botany, Oils, Volatile, Plant Oils, education, Molecular Biology, Apiaceae, Epicubenol, General Chemistry, biology.organism_classification, 0104 chemical sciences, Plant Leaves, 010404 medicinal & biomolecular chemistry, chemistry, Hierarchical-cluster analysis (HCA), Monoterpenes, CONSTITUENTS, Volatile oils, 010606 plant biology & botany
Abstract

International audience; The chemical composition of the volatile oils obtained from the roots, leaves, flowers, and stems of Thapsia garganica of Tunisian origin was investigated by GC-FID and GC/MS analyses. Sesquiterpene hydrocarbons and oxygenated monoterpenes were predominant in the oils of all plant parts. Bicyclogermacrene (21.59-35.09%) was the main component in the former compound class, whereas geranial (3.31-14.84%) and linalool (0.81-10.9%) were the most prominent ones in the latter compound class. Principal-component (PCA) and hierarchical-cluster (HCA) analyses revealed some common constituents, but also significant variability amongst the oils of the different plant parts. This organ-specific oil composition was discussed in relation to their biological and ecological functions. For the evaluation of the intraspecific chemical variability in T. garganica, the composition of the flower volatile oils from four wild populations was investigated. Bicyclogermacrene, linalool, and geranial were predominant in the oils of three populations, whereas epicubenol, -sesquiphellandrene, and cadina-1,4-diene were the most prominent components of the oil of one population. PCA and HCA allowed the separation of the flower oils into three distinct groups, however, no relationship was found between the volatile-oil composition and the geographical distribution and pedoclimatic conditions of the studied populations.

Published
2014
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17. The leaf essential oil ofMurraya crenulata (Turcz.) Oliver from New Caledonia

Author

Gerhard Buchbauer, Josiane Patissou, Jean Waikedre, Pierre Cabalion, Chantal Menut, Edouard Hnawia, I. Raunicher, Université de la Nouvelle-Calédonie (UNC), Laboratoire des Substances Naturelles et Savoirs Traditionnels, Institute of Pharmaceutical Chemistry, University of Vienna [Vienna], Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)

Subjects
Limonene, Murraya, biology, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Monoterpene, General Chemistry, Perillaldehyde, biology.organism_classification, 01 natural sciences, Terpenoid, 0104 chemical sciences, law.invention, Steam distillation, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, Rutaceae, law, Botany, ComputingMilieux_MISCELLANEOUS, Essential oil, Food Science
Abstract

The essential oil of Murraya crenulata (Turcz.) Oliver (Rutaceae) was obtained from fresh leaves by hydrodistillation of plant material collected in Lifou, Loyalty Islands, New Caledonia. Analysis by a combination of GC and GC–MS indicates a characteristic chemical composition dominated by p-menthane derivatives, mainly perilla aldehyde (73.2%), limonene (8.2%), perilla alcohol (6.5%) and its acetate (6.0%). Copyright © 2006 John Wiley & Sons, Ltd.

Published
2006
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18. Protective effect of Artemisia campestris extract against aspirin-induced gastric lesions and oxidative stress in rat

Author

Slimen Selmi, Hichem Sebai, Haifa Tounsi, Karim Hosni, Olfa Tebourbi, Mohamed-Amine Jabri, Abdelaziz Souli, Jamel El-Benna, Mohsen Sakly, Samir Boubaker, Pasteur Tunis, Institut, Faculté des Sciences de Bizerte [Université de Carthage], Université de Carthage - University of Carthage, Institut Supérieur de Biotechnologie Béja, Université de Jendouba (UJ), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Laboratoire d'Epidémiologie Moléculaire et de Pathologie Expérimentale Appliquée aux Maladies Infectieuses (LR11IPT04), Université de Tunis El Manar (UTM)-Institut Pasteur de Tunis, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Institut Pasteur de Tunis, Réseau International des Instituts Pasteur (RIIP), Centre de recherche biomédicale Bichat-Beaujon (CRB3), and Université Paris Diderot - Paris 7 (UPD7)-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
Antioxidant, General Chemical Engineering, medicine.medical_treatment, [SDV]Life Sciences [q-bio], Pharmacology, medicine.disease_cause, Superoxide dismutase, chemistry.chemical_compound, medicine, Hydrogen peroxide, [SDV.BV.PEP] Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy, chemistry.chemical_classification, biology, Glutathione peroxidase, food and beverages, [SDV.MHEP.HEG]Life Sciences [q-bio]/Human health and pathology/Hépatology and Gastroenterology, General Chemistry, Malondialdehyde, [SDV.MHEP.HEG] Life Sciences [q-bio]/Human health and pathology/Hépatology and Gastroenterology, 3. Good health, [SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy, [SDV] Life Sciences [q-bio], stomatognathic diseases, Mechanism of action, chemistry, Biochemistry, Catalase, biology.protein, medicine.symptom, Oxidative stress
Abstract

International audience; The present study aims at evaluating the antiulcer and antioxidant effect of Artemisia campestris aqueous extract (ACAE) as well as the mechanism of action involved in such gastroprotection. The use of LC/MS allowed the identification of 11 phenolic compounds and the colorimetric analysis demonstrated that the ACAE exhibited an important in vitro antioxidant activity. We first showed that in vivo ACAE protected against macroscopic and histological changes induced by aspirin in stomach mucosa. Aspirin administration was accompanied by an oxidative stress status assessed by an increase in malondialdehyde (MDA) level, a decrease in the content of sulfhydryl -(SH) groups and a depletion of antioxidant enzyme activities such as superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx). Pre-treatment with ACAE protected against aspirin-induced gastric oxidative stress. More importantly, aspirin administration increased plasma and tissue hydrogen peroxide (H2O2), free iron and calcium levels, while the ACAE pre-treatment reversed all the effects of aspirin-induced intracellular mediators. In conclusion, we suggest that Artemisia campestris aqueous extract has potent antiulcer and antioxidant properties. This gastroprotection offered by ACAE might be related partly to the safety of sulfhydryl group as well as its opposite effect on some intracellular mediators such as hydrogen peroxide, free iron and calcium.

Published
2014
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19. Synthesis of biosourced polyether-amides from 1,4-3,6-dianhydrohexitols: Characterization by NMR and MALDI-ToF mass spectrometry

Author

Guy Raffin, Hans R. Kricheldorf, Salma Mghirbi, Marlène Desloir-Bonjour, Aurélie Fildier, Saber Chatti, Raouf Medimagh, Asma Saadaoui, Institut National de Recherche et d'Analyse Physico-Chimique (INRAP), TRACES - Technologie et Recherche en Analyse Chimique pour l'Environnement et la Santé, Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut fur Technische und Makromolekulare Chemie/Fachbereich Chemie TMC, Universität Hamburg (UHH), the Tunisian Ministry of Higher Education and Research, Ingénierie des Matériaux Polymères (IMP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Jean Monnet [Saint-Étienne] (UJM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des Substances Naturelles (LR02INRAP10), Institut National de Recherche et d'Analyse Physico-chimique [Ariana, Tunisie] (INRAP), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Institut für Technische und Makromolekulare Chemie

Subjects
Polyether-amides, Isosorbide, Condensation polymer, General Chemical Engineering, 02 engineering and technology, 010402 general chemistry, MALDI-ToF mass spectrometry, 01 natural sciences, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, 4-3, medicine, [CHIM]Chemical Sciences, Organic chemistry, 6-Dianhydrohexitols, ComputingMilieux_MISCELLANEOUS, Polycondensation, Chemistry, General Chemistry, Nuclear magnetic resonance spectroscopy, 021001 nanoscience & nanotechnology, MALDI-TOF Mass Spectrometry, 0104 chemical sciences, Characterization (materials science), 0210 nano-technology, Biobased, medicine.drug
Abstract

International audience; New series of polyether-amides were prepared by polycondensation in solution of three diamines based on 1,4-3,6-dianhydrohexitols with two types of diacyl chlorides (sebacoyl and isophtaloyl). Unprecedented diamines based on isomannide and isoidide were elaborated. The corresponding polyether-amides (PeA) were obtained with high yields. They were characterized by different analytical techniques (NMR, MALDI-ToF MS, DSC). The combination of MALDI-ToF MS with NMR spectroscopy allowed us to confirm structure types. DSC measurements revealed an amorphous character for the isophtaloyl family with a high Tg value. The sebacoyl series proved to be semi-crystalline with a high Tm value. Isosorbide-based PeAs demonstrated interesting properties (Tg above 210 °C and Tm above 240 °C) and high viscosity (0.32).

Published
2013
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20. Amphiphilic polyesters derived from silylated and germylated fatty compounds

Author

Annie Castel, Mohamed Dahrouch, Zahra Benmaarouf, Pierre Riviere, Abdelkrim El Kadib, Nicolás Gatica, Nadia Katir, LABORATOIRE DES SUBSTANCES NATURELLES, UNIVERSITE IBN ZO, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, DEPARTAMENTO DE QUIMICA ORGANICA, and Universidad de Concepción [Chile]

Subjects
Condensation polymer, Magnetic Resonance Spectroscopy, Polymers and Plastics, Siloxanes, Hydrosilylation, Polymers, Polyesters, Bioengineering, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Biomaterials, chemistry.chemical_compound, Glycols, Surface-Active Agents, Polymer chemistry, Amphiphile, Materials Chemistry, Copolymer, Organic chemistry, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Germanium, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Polymer, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Polyester, Monomer, chemistry, Fatty Acids, Unsaturated, 0210 nano-technology, Hybrid material
Abstract

New classes of amphiphilic polyesters were prepared from metallated (Si, Ge) fatty methyl ester (FAME) precursors and poly(tetramethylene oxide) glycol. Hydrosilylation of 10-undecenoic methyl ester by tetramethyldisiloxane occurred at 80 degrees C in the presence of Karstedt's catalyst, and hydrogermylation of the same FAME derivative was obtained at the same temperature under radical AIBN initiation. These diester precursors, obtained in high yields (approximately 90%), reacted with poly(tetramethylene oxide) glycol under free solvent to give silicon polymers or germanium oligomers. These condensed materials display both the characteristic of organic-inorganic hybrid materials and those of amphiphilic polymers. The nature of organometallic fragment (hydrophobicity of tetramethyldisiloxy and sterical hindrance of diphenylgermyl) was shown to influence the chemical reactivity of the polymerizable monomers and the physical properties of the resulting copolymers. The amphiphilicity of these materials provides a driving force for the formation of small objects (approximately 1 nm), making them very attractive as hybrid nanocontainers.

Published
2009

21. New biosurfactants based on germylated fatty compounds

Author

Nadia Katir, Annie Castel, Pierre Rivière, Zahra Benmaarouf, A. El Kadib, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), LABORATOIRE DES SUBSTANCES NATURELLES, and UNIVERSITE IBN ZO

Subjects
chemistry.chemical_classification, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Fatty acid, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Monomer, chemistry, Amphiphile, Organic chemistry, Self-assembly, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract

A simple and efficient method for producing amphiphilic germylated compounds has been developed by hydrogermylation of fatty acid methyl esters. The germylated precursors afford a micelle-type assembly in various solvents as evident by the formation of nano-objects, micrometer spheres and lamellar forms. This offers a promising route to synthetically useful monomers for structured materials. Copyright © 2008 John Wiley & Sons, Ltd.

Published
2008

22. Wood essential oils of two endemic trees from New Caledonia : Callitris sulcata (Parl.) Schltr. and Callitris neocaledonica Dummer

Author

Chantal Menut, Abdelhamid Agrebi, Pierre Cabalion, Edouard Hnawia, BUNC, Pole ID, Laboratoire Insulaire du Vivant et de l'Environnement (LIVE), Université de la Nouvelle-Calédonie (UNC), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), and Laboratoire des Substances Naturelles et Savoirs Traditionnels

Subjects
Guaiol, Cupressaceae, Dummer, [SDV]Life Sciences [q-bio], 01 natural sciences, Biochemistry, Essential oil, law.invention, chemistry.chemical_compound, law, Callitris sulcata (Parlatore) Schlechter, Botany, Thujopsene, Callitris neocaledonica, Eudesmols, ComputingMilieux_MISCELLANEOUS, Ecology, Evolution, Behavior and Systematics, biology, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, biology.organism_classification, 0104 chemical sciences, [SDV] Life Sciences [q-bio], 010404 medicinal & biomolecular chemistry, chemistry, Callitris sulcata, beta-Barbatene
Abstract

The essential oils obtained by hydrodistillation of pieces of dead trunks of Callitris sulcata (Parlatore) Schlechter and Callitris neocaledonica Dummer were investigated by gas chromatography, mass spectrometry and NMR spectroscopy. Analyses evidenced the presence of rare natural compounds: both essential oils are exclusively sesquiterpenic with nevertheless remarkable difference: C. sulcata essential oil was dominated by β-barbatene and thujopsene while C. neocaledonica was characterized by high levels of guaiane- and eudesmane-type structures (eudesmols, guaiol and related components). The biochemical correlations between the major components of each species are discussed and the relationship between the two species is commented.

Published
2008
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23. Antimalarial potential of xestoquinone, a protein kinase inhibitor isolated from a Vanuatu marine sponge Xestospongia sp

Author

Olivier Lozach, Laurent Meijer, Arnaud Parenty, Dominique Laurent, Frédéric Alby, Nicolas Lebouvier, Christian Doerig, Martine Knibiehler, Maryvonne Frostin, Séverine Maurel, Sophie Schmitt, Dominique Dorin, Valérie Jullian, Michel Sauvain, Institut Non Linéaire de Nice Sophia-Antipolis (INLN), Université Nice Sophia Antipolis (1965 - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physique de la matière condensée (LPMC), Pharmacochimie des substances naturelles et pharmacophores redox, Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT), Laboratoire des Substances Naturelles, Synapse Développement, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Insulaire du Vivant et de l'Environnement (LIVE), Université de la Nouvelle-Calédonie (UNC), UMS 2646 Pierre Fabre-CNRS, Institut de Sciences et Technologies du Médicament de Toulouse, 3, rue des satellites, 31400 Toulouse, France, Centre de Recherche Pierre Fabre (Centre de R&D Pierre Fabre), PIERRE FABRE-PIERRE FABRE-Centre National de la Recherche Scientifique (CNRS), Controle de la Proliferation Cellulaire Chez Plasmodium Falciparum, Institut National de la Santé et de la Recherche Médicale (INSERM), Recherches Epistémologiques et Historiques sur les Sciences Exactes et les Institutions Scientifiques (REHSEIS (UMR_7596)), Université Paris Diderot - Paris 7 (UPD7)-Centre National de la Recherche Scientifique (CNRS), Molécules et cibles thérapeutiques (MCT), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Nice Sophia Antipolis (... - 2019) (UNS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Université Paris Diderot - Paris 7 (UPD7), Centre National de la Recherche Scientifique (CNRS), UMS 2646, PIERRE FABRE-Centre National de la Recherche Scientifique (CNRS), Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Mer et santé (MS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche Pierre Fabre-Centre National de la Recherche Scientifique (CNRS), faculte des sciences pharmaceutiques (umr 152 IRD), Faculte des Sciences Pharmaceutiques, Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and BUNC, Pole ID

Subjects
antiplasmodial drug, Plasmodium, [SDV]Life Sciences [q-bio], Clinical Biochemistry, Pharmaceutical Science, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Pharmacognosy, 01 natural sciences, Biochemistry, Mice, chemistry.chemical_compound, Antimalarial drug, Drug Discovery, MESH: Protein Kinase Inhibitors, MESH: Animals, MESH: Plasmodium falciparum, MESH: Inhibitory Concentration 50, 0303 health sciences, biology, Kinase, Quinones, Biological activity, 3. Good health, Xestospongia, [SDV] Life Sciences [q-bio], Enzyme inhibitor, Molecular Medicine, Biological Assay, Antiplasmodial drug, antimalarial drug, Plasmodium falciparum, MESH: Biological Assay, MESH: Quinones, Antimalarials, Inhibitory Concentration 50, 03 medical and health sciences, parasitic diseases, Animals, Xestoquinone, Plasmodium berghei, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Protein kinase A, Protein Kinase Inhibitors, Molecular Biology, MESH: Mice, 030304 developmental biology, 010405 organic chemistry, Organic Chemistry, biology.organism_classification, MESH: Antimalarials, 0104 chemical sciences, MESH: Xestospongia, xestoquinone, chemistry, biology.protein
Abstract

As part of our search for new antimalarial drugs, we have screened for inhibitors of Pfnek-1, a protein kinase of Plasmodium falciparum, in south Pacific marine sponges. On the basis of a preliminary screening, the ethanolic crude extract of a new species of Xestospongia collected in Vanuatu was selected for its promising activity. A bioassay-guided fractionation led us to isolate xestoquinone which inhibits Pfnek-1 with an IC50 around 1 mu M. Among a small panel of plasmodial protein kinases, xestoquinone showed modest protein kinase inhibitory activity toward PfPK5 and no activity toward PfPK7 and PfGSK-3. Xestoquinone showed in vitro antiplasmodial activity against a FCB1 P. falciparum strain with an IC50 of 3 mu M and a weak selectivity index (SI 7). Xestoquinone exhibited a weak in vivo activity at 5 mg/kg in Plasmodium berghei NK65 infected mice and was toxic at higher doses. (c) 2006 Elsevier Ltd. All rights reserved.

Published
2006
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24. Radical hydrometalation of functional ethylenic compounds: radical autoinhibition changes the regioselectivity

Author

Monique Rivière-Baudet, Mohamed Ahra, A. Hasnaoui, Francisco Burgos, Annie Castel, Abdelkrim El Kadib, Ivone Chavez, Fabien Delpech, Pierre Rivière, Amal Feddouli, Juan M. Manriquez, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Facultad de Quimica [Santiago], Pontificia Universidad Católica de Chile (UC), Laboratoire de chimie Organique et Organométallique Faculte des Sciences, Université Ibn Zohr [Agadir], Laboratoire des Substances Naturelles et des Hétérocycles, Faculté des Sciences Semlalia Marrakech, Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
chemistry.chemical_classification, Radical trapping, Double bond, Hydroquinone, Stereochemistry, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Regioselectivity, 010402 general chemistry, Carbonyl group, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Galvinoxyl, Normal reaction, Physical and Theoretical Chemistry, Hydrometalation, ComputingMilieux_MISCELLANEOUS
Abstract

Hydrometalation of carbon−carbon double bonds by group 14 hydrides is inhibited by carbonyl compoundsmainly by α,β-unsaturated carbonyl groupsas efficiently as by classical radical trapping compounds, such as galvinoxyl and hydroquinone. This phenomenon, in the case of polyfunctional CC- and CO-containing compounds, such as carvone, leads to an autoinhibition of the exocyclic alkenylic hydrometalation under normal reaction conditions, while under drastic conditions, the O-metalation of the α,β-unsaturated carbonyl group occurs.

Published
2005

25. A new omega-conotoxin that targets N-type voltage-sensitive calcium channels with unusual specificity

Author

Philippe Favreau, Bournaud R, Laboute P, Lamthanh H, Shimahara T, Letourneux Y, Le Gall F, Molgó J, Bouet F, Gilles N, Ménez A, Laboratoire de neurobiologie cellulaire et moléculaire (NBCM), Centre National de la Recherche Scientifique (CNRS), Institut de Neurobiologie Alfred Fessard (INAF), Département d'Ingénierie et d'Etudes des Protéines, Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire des Substances Naturelles, Laboratoire de Synthèse et Etudes de Substances Naturelles à Activités Biologiques, La Rochelle Université (ULR), and Université de La Rochelle (ULR)

Subjects
Guanidinium chloride, Male, Patch-Clamp Techniques, MESH: Sequence Homology, Amino Acid, Chromaffin Cells, Snails, MESH: Calcium Channel Blockers, Venom, Peptide, MESH: Amino Acid Sequence, MESH: Muscle, Smooth, Biochemistry, MESH: Radioligand Assay, omega-Conotoxins, Membrane Potentials, MESH: Dose-Response Relationship, Drug, chemistry.chemical_compound, Cyprinodontiformes, Mice, Radioligand Assay, Calcium Channels, N-Type, MESH: Structure-Activity Relationship, MESH: Chromaffin Cells, MESH: Animals, MESH: Snails, MESH: omega-Conotoxins, chemistry.chemical_classification, biology, Voltage-dependent calcium channel, Brain, Rana esculenta, Calcium Channel Blockers, MESH: Rana esculenta, [SDV.NEU]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], MESH: Injections, Intraventricular, Protein Binding, MESH: Rats, Stereochemistry, Molecular Sequence Data, Cone snail, Structure-Activity Relationship, MESH: Brain, MESH: Cyprinodontiformes, MESH: Calcium Channels, N-Type, MESH: Patch-Clamp Techniques, Animals, MESH: Membrane Potentials, MESH: Protein Binding, Amino Acid Sequence, MESH: Mice, Injections, Intraventricular, MESH: Molecular Sequence Data, Dose-Response Relationship, Drug, Sequence Homology, Amino Acid, Calcium channel, Muscle, Smooth, biology.organism_classification, Omega-Conotoxins, MESH: Male, Rats, chemistry, Conus consors
Abstract

A new specific voltage-sensitive calcium channel (VSCC) blocker has been isolated from the venom of the fish-hunting cone snail Conus consors. This peptide, named omega-Ctx CNVIIA, consists of 27 amino acid residues folded by 3 disulfide bridges. Interestingly, loop 4, which is supposed to be crucial for selectivity, shows an unusual sequence (SSSKGR). The synthesis of the linear peptide was performed using the Fmoc strategy, and the correct folding was achieved in the presence of guanidinium chloride, potassium buffer, and reduced/oxidized glutathione at 4 degrees C for 3 days. Both synthetic and native toxin caused an intense shaking activity, characteristic of omega-conotoxins targeting N-type VSCC when injected intracerebroventricularly to mice. Binding studies on rat brain synaptosomes revealed that the radioiodinated omega-Ctx CNVIIA specifically and reversibly binds to high-affinity sites with a K(d) of 36.3 pM. Its binding is competitive with omega-Ctx MVIIA at low concentration (K(i) = 2 pM). Moreover, omega-Ctx CNVIIA exhibits a clear selectivity for N-type VSCCs versus P/Q-type VSCCs targeted respectively by radioiodinated omega-Ctx GVIA and omega-Ctx MVIIC. Although omega-Ctx CNVIIA clearly blocked N-type Ca(2+) current in chromaffin cells, this toxin did not inhibit acetylcholine release evoked by nerve stimuli at the frog neuromuscular junction, in marked contrast to omega-Ctx GVIA. omega-Ctx CNVIIA thus represents a new selective tool for blocking N-type VSCC that displays a unique pharmacological profile and highlights the diversity of voltage-sensitive Ca(2+) channels in the animal kingdom.

Published
2001
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