Author: "Didier Stien" / Topic: organic chemistry - Searchworks@Jio Institute Digital Library Search Results

Your search keyword '"Didier Stien"' showing total 72 results

Start Over Author "Didier Stien" Topic organic chemistry

72 results on '"Didier Stien"'

1. Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

Author: Jonathan Sorres, Téo Hebra, Nicolas Elie, Charlotte Leman-Loubière, Tatyana Grayfer, Philippe Grellier, David Touboul, Didier Stien, and Véronique Eparvier
Subjects: Pseudallescheria boydii, ovalicin, molecular networking, symbiotic fungus, genome, biosynthesis, Organic chemistry, QD241-441
Abstract: Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 µM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.
Published: 2022
Full Text: View/download PDF

2. Antimicrobial Activity and Synergy Investigation of Hypericum scabrum Essential Oil with Antifungal Drugs

Author: Layal Fahed, Marc El Beyrouthy, Naïm Ouaini, Véronique Eparvier, Didier Stien, Sara Vitalini, and Marcello Iriti
Subjects: Hypericum scabrum, essential oil, chemical composition, antimicrobial activity, synergy, Organic chemistry, QD241-441
Abstract: The chemical composition of Lebanese Hypericum scabrum essential oil (EO) was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GG-MS). Its antimicrobial activity was evaluated by determining its minimal inhibitory concentrations (MICs) against a Gram-negative and a Gram-positive bacterium, one yeast, and five dermatophytes. H. scabrum EO was most active on filamentous fungi (MIC values of 32–64 µg/mL). Synergy within the oil was investigated by testing each of the following major components on Trichophyton rubrum: α-pinene, limonene, myrcene, β-pinene and nonane, as well as a reconstructed EO. The antifungal activity of the natural oil could not be reached, meaning that its activity might be due, in part, to minor constituent(s). The interactions between H. scabrum EO and commercially available antifungals were assessed by the checkerboard test. A synergistic effect was revealed in the combination of the EO with amphotericin B.
Published: 2021
Full Text: View/download PDF

3. Potent and Non-Cytotoxic Antibacterial Compounds Against Methicillin-Resistant Staphylococcus aureus Isolated from Psiloxylon mauritianum, A Medicinal Plant from Reunion Island

Author: Jonathan Sorres, Amandine André, Elsa Van Elslande, Didier Stien, and Véronique Eparvier
Subjects: Aspidin derivatives, acylphloroglucinol, Psiloxylon mauritianum, Staphylococcus aureus, antibacterial compounds, Organic chemistry, QD241-441
Abstract: With the occurrence of antibiotic-resistant Staphylococcus aureus strains, identification of new anti-staphylococcal drugs has become a necessity. It has long been demonstrated that plants are a large and diverse source of antibacterial compounds. Psiloxylon mauritianum, an endemic medicinal plant from Reunion Island, was chemically investigated for its reported biological activity against S. aureus. Aspidin VB, a phloroglucinol derivative never before described, together with Aspidin BB, were first isolated from the ethyl acetate extract of P. mauritianum leaves. Their structures were elucidated from spectroscopic data. Aspidin VB exhibited strong antibacterial activity against standard and methicillin-resistant S. aureus strains, with a minimal inhibition concentration (MIC) of 0.25 μg/mL, and no cytotoxicity was observed at 10−5 M in MRC5 cells. Due to its biological activities, Aspidin VB appears to be a good natural lead in the fight against S. aureus.
Published: 2020
Full Text: View/download PDF

4. Antimicrobial Activity and Synergy Investigation of Hypericum scabrum Essential Oil with Antifungal Drugs

Author: Naim Ouaini, Véronique Eparvier, Layal Fahed, Didier Stien, Sara Vitalini, Marcello Iriti, Marc El Beyrouthy, Université Libanaise, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Holy-Spirit University of Kaslik [Jounieh], Laboratoire de Biochimie et de Biologie Moléculaire (Université d'Abomey Calavi, Cotonou, Bénin) (LBBM), University of Abomey Calavi (UAC), Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Università degli Studi di Milano [Milano] (UNIMI), and Università degli studi di Napoli Federico II
Subjects: Antifungal Agents, Hypericum scabrum, Pharmaceutical Science, synergy, Organic chemistry, Microbial Sensitivity Tests, Trichophyton rubrum, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Gram-Positive Bacteria, 01 natural sciences, Article, essential oil, Analytical Chemistry, law.invention, 03 medical and health sciences, chemistry.chemical_compound, QD241-441, law, Gram-Negative Bacteria, Drug Discovery, Oils, Volatile, chemical composition, Food science, Physical and Theoretical Chemistry, Essential oil, 030304 developmental biology, 0303 health sciences, Limonene, antimicrobial activity, biology, Chemistry, Fungi, [SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics, biology.organism_classification, Antimicrobial, Yeast, Anti-Bacterial Agents, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, Chemistry (miscellaneous), Myrcene, Molecular Medicine, Gas chromatography, Hypericum, Bacteria
Abstract: The chemical composition of Lebanese Hypericum scabrum essential oil (EO) was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GG-MS). Its antimicrobial activity was evaluated by determining its minimal inhibitory concentrations (MICs) against a Gram-negative and a Gram-positive bacterium, one yeast, and five dermatophytes. H. scabrum EO was most active on filamentous fungi (MIC values of 32–64 µg/mL). Synergy within the oil was investigated by testing each of the following major components on Trichophyton rubrum: α-pinene, limonene, myrcene, β-pinene and nonane, as well as a reconstructed EO. The antifungal activity of the natural oil could not be reached, meaning that its activity might be due, in part, to minor constituent(s). The interactions between H. scabrum EO and commercially available antifungals were assessed by the checkerboard test. A synergistic effect was revealed in the combination of the EO with amphotericin B.
Published: 2021
Full Text: View/download PDF

5. Four lignans from Portulaca oleracea L. and its antioxidant activities

Author: Ma Yifei, Xixiang Ying, Didier Stien, Yongrui Bao, Wenjie Zhang, University of Science and Technology LiaoNing (USTL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: DPPH, Electrospray ionization, antioxidant activity, Plant Science, Portulaca, Mass spectrometry, 01 natural sciences, Biochemistry, Analytical Chemistry, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Lignan, Quenching (fluorescence), biology, 010405 organic chemistry, Organic Chemistry, Portulaca oleracea L, lignans, biology.organism_classification, Anisole, 0104 chemical sciences, 3. Good health, 010404 medicinal & biomolecular chemistry, chemistry, Two-dimensional nuclear magnetic resonance spectroscopy, Nuclear chemistry
Abstract: International audience; A new lignan, named oleralignan (1) and three known compounds (+)-syringaresinol (2), (+)-lirioresinol A (3) and monomethyl 3,30,4,40-tetrahydroxy-δ-truxinate (4) were isolated from the P. oleracea for the first time. The compound (1) were identified by 1D, 2D NMR spectroscopic methods and high resolution electrospray ionization time-of-flight mass spectrometry. In addition, it was found that the four lignans presented the scavenging activities in 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical quenching assay more than that of hydroxyl anisole (BHA).
Published: 2018
Full Text: View/download PDF

6. A new alkaloid from Portulaca oleracea L. and its antiacetylcholinesterase activity

Author: Didier Stien, Xixiang Ying, Fen Xiu, Wenjie Zhang, Xuetao Li, Fan He, University of Science and Technology LiaoNing (USTL), Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: biology, 010405 organic chemistry, Stereochemistry, Alkaloid, Organic Chemistry, Plant Science, Portulaca, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, 3. Good health, Analytical Chemistry, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Benzamide, Two-dimensional nuclear magnetic resonance spectroscopy, ComputingMilieux_MISCELLANEOUS
Abstract: A new alkaloid, (10E, 12E)-9-ureidooctadeca-10, 12-dienoic acid, named oleraurea (1) and 10 known compounds, p-hydroxybenzaldehyde (2), p-hydroxybenzoic acid (3), p-hydroxyacetophenone (4), benzamide (5), (E)-p-coumaramide (6), (E)-ferulamide (7), soyalkaloid A (8), β-carboline-3-carboxylic acid (9), 2, 3, 4, 9-tetrahydro-1H-pyrido [3, 4-b] indole-3-carboxylic acid (10), (1S, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (11) were obtained from Portulaca oleracea L., in which, compounds 4, 5, 8-11 were isolated from the plant for the first time. The structure of the compound 1 was identified using spectroscopic methods including 1D and 2D NMR, HR-ESI-TOF-MS. The compounds 1, 5-11 presented anticholinesterase activities, but the P. oleracea extract (POE) presented very low anticholinesterase activity.
Published: 2018
Full Text: View/download PDF

7. Potent and Non-Cytotoxic Antibacterial Compounds Against Methicillin-Resistant Staphylococcus aureus Isolated from Psiloxylon mauritianum, A Medicinal Plant from Reunion Island

Author: Elsa Van Elslande, Amandine André, Didier Stien, Jonathan Sorres, Véronique Eparvier, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Staphylococcus aureus, Phloroglucinol, Ethyl acetate, Pharmaceutical Science, Psiloxylon, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010403 inorganic & nuclear chemistry, medicine.disease_cause, 01 natural sciences, Psiloxylon mauritianum, Analytical Chemistry, lcsh:QD241-441, chemistry.chemical_compound, acylphloroglucinol, lcsh:Organic chemistry, Drug Discovery, medicine, Physical and Theoretical Chemistry, Cytotoxicity, Traditional medicine, biology, 010405 organic chemistry, Organic Chemistry, Biological activity, antibacterial compounds, biology.organism_classification, Methicillin-resistant Staphylococcus aureus, 0104 chemical sciences, chemistry, Chemistry (miscellaneous), [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Molecular Medicine, Antibacterial activity, Aspidin derivatives
Abstract: With the occurrence of antibiotic-resistant Staphylococcus aureus strains, identification of new anti-staphylococcal drugs has become a necessity. It has long been demonstrated that plants are a large and diverse source of antibacterial compounds. Psiloxylon mauritianum, an endemic medicinal plant from Reunion Island, was chemically investigated for its reported biological activity against S. aureus. Aspidin VB, a phloroglucinol derivative never before described, together with Aspidin BB, were first isolated from the ethyl acetate extract of P. mauritianum leaves. Their structures were elucidated from spectroscopic data. Aspidin VB exhibited strong antibacterial activity against standard and methicillin-resistant S. aureus strains, with a minimal inhibition concentration (MIC) of 0.25 μg/mL, and no cytotoxicity was observed at 10−5 M in MRC5 cells. Due to its biological activities, Aspidin VB appears to be a good natural lead in the fight against S. aureus.
Published: 2020
Full Text: View/download PDF

8. Carneic Acids from an Endophytic Phomopsis sp. as Dengue Virus Polymerase Inhibitors

Author: Cécilia Eydoux, Laure-Anne Peyrat, Véronique Eparvier, Jean-Claude Guillemot, Didier Stien, Marc Litaudon, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Architecture et fonction des macromolécules biologiques (AFMB), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), ANR-10-LABX-0025,CEBA,CEnter of the study of Biodiversity in Amazonia(2010), and Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
Subjects: viruses, Pharmaceutical Science, Dengue virus, medicine.disease_cause, 01 natural sciences, Analytical Chemistry, Zika virus, Dengue fever, Microbiology, Drug Discovery, medicine, Ic50 values, Cytotoxicity, Polymerase, Pharmacology, biology, 010405 organic chemistry, Organic Chemistry, virus diseases, Nuclear magnetic resonance spectroscopy, biology.organism_classification, medicine.disease, 3. Good health, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, Complementary and alternative medicine, Phomopsis sp, biology.protein, Molecular Medicine, [CHIM.OTHE]Chemical Sciences/Other
Abstract: International audience; Thirteen carneic acids were isolated from the fungal endophyte Phomopsis sp. SNB-LAP1-7-32. Their structures were identified by mass spectrometry and extensive one- and two-dimensional NMR spectroscopy and through comparison with data reported in the literature. Compounds 1-13 were investigated for their antipolymerase activities against DENV polymerase and Zika NS5. Five of them exhibited significant inhibition of dengue polymerase with IC50 values in the 10 to 20 mu M range without cytotoxicity. None inhibited Zika virus NS5 protein.
Published: 2020
Full Text: View/download PDF

9. A novel alkaloid from Portulaca oleracea L. and its anti-inflammatory activity

Author: Xixiang Ying, Didier Stien, Aijing Leng, Wenjie Zhang, Gu Yingying, University of Science and Technology LiaoNing (USTL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: biology, 010405 organic chemistry, medicine.drug_class, Stereochemistry, Chemistry, Alkaloid, Organic Chemistry, Plant Science, Portulaca, Carbon-13 NMR, biology.organism_classification, 01 natural sciences, Biochemistry, Anti-inflammatory, 3. Good health, 0104 chemical sciences, Analytical Chemistry, Oleracein E, 010404 medicinal & biomolecular chemistry, medicine, [CHIM.OTHE]Chemical Sciences/Other, Two-dimensional nuclear magnetic resonance spectroscopy, Flavoglaucin, ComputingMilieux_MISCELLANEOUS
Abstract: A novel alkaloid identified as methyl 8,9-dihydroxy-11-oxo-6,11-dihydro-5H-benzo[d]pyrrolo[1,2-a]azepine-3-carboxylate, named portulacatone A (1) with six known compounds Oleracein E (2), 6,7-dihdroxy-3,4-dihydro-2H-isoquinolin-1-one (3), N-trans-p-coumaroytyramine (4), 9H-carbazole (5), isoaspergin (6) and flavoglaucin (7) were obtained from Portulaca oleracea L., while compounds (5–7) were isolated from the plant for the first time. The new structure was identified by using UHPLC-ESI-Q-TOF/MS, 1D, 2D NMR and the others were proved by 1H-NMR and 13C NMR that comparing with previous reports. It was suggested that the portulacatone A (1) can significantly inhibit the inflammatory factor, interleukin-1β (IL-1β) in the RAW 264.7 cells induced by LPS.
Published: 2020
Full Text: View/download PDF

10. Two amide glycosides from Portulaca oleracea L. and its bioactivities

Author: Xiaojun Tao, Haibo Wu, Xixiang Ying, Didier Stien, Xilong Liu, University of Science and Technology LiaoNing (USTL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Observatoire océanologique de Banyuls (OOB), and 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, biology, 010405 organic chemistry, Stereochemistry, Organic Chemistry, Glycoside, Plant Science, Portulaca, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, 3. Good health, Analytical Chemistry, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Amide, Two-dimensional nuclear magnetic resonance spectroscopy, ComputingMilieux_MISCELLANEOUS
Abstract: Two novel amide glycosides, named oleraciamide E (1) and oleraciamide F (2), were isolated from the Portulaca oleracea L. Their structures were determined by means of 1D and 2D NMR spectroscopic an...
Published: 2019
Full Text: View/download PDF

11. Structural Identification of Antibacterial Lipids from Amazonian Palm Tree Endophytes through the Molecular Network Approach

Author: David Touboul, Morgane Barthélemy, Jean-Luc Wolfender, Léonie Pellissier, Nicolas Elie, Véronique Eparvier, Didier Stien, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Lausanne (UNIL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Models, Molecular, 0301 basic medicine, Astrocaryum sciophilum, Ethyl acetate, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Arecaceae, Tandem mass spectrometry, medicine.disease_cause, 01 natural sciences, Trees, lcsh:Chemistry, chemistry.chemical_compound, Tandem Mass Spectrometry, Depsipeptides, Food science, lcsh:QH301-705.5, Chromatography, High Pressure Liquid, Spectroscopy, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, molecular networking, biology, General Medicine, Staphylococcal Infections, Antimicrobial, Lipids, Anti-Bacterial Agents, Computer Science Applications, Staphylococcus aureus, [SDE]Environmental Sciences, cytotoxicity, Antibacterial activity, Gammaproteobacteria, Methicillin-Resistant Staphylococcus aureus, endophytes, Microbial Sensitivity Tests, fatty acids, Article, Catalysis, Plant use of endophytic fungi in defense, Inorganic Chemistry, 03 medical and health sciences, medicine, Humans, [CHIM]Chemical Sciences, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Physical and Theoretical Chemistry, Molecular Biology, 010401 analytical chemistry, Organic Chemistry, Fatty acid, biology.organism_classification, 0104 chemical sciences, antibacterial, 030104 developmental biology, lcsh:Biology (General), lcsh:QD1-999, chemistry, Bacteria
Abstract: A library of 197 endophytic fungi and bacteria isolated from the Amazonian palm tree Astrocaryum sciophilum was extracted and screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Four out of five antibacterial ethyl acetate extracts were also cytotoxic for the MRC-5 cells line. Liquid chromatography coupled to tandem mass spectrometry (UPHLC-HRMS/MS) analyses combined with molecular networking data processing were carried out to allow the identification of depsipeptides and cyclopeptides responsible for the cytotoxicity in the dataset. Specific ion clusters from the active Luteibacter sp. extract were also highlighted using an MRSA activity filter. A chemical study of Luteibacter sp. was conducted leading to the structural characterization of eight fatty acid exhibiting antimicrobial activity against MRSA in the tens of &micro, g/mL range.
Published: 2019
Full Text: View/download PDF

12. Insects-entomopathogens interactions to discover new insecticidal and antimicrobial compounds

Author: Isabelle Dusfour, Seindé Touré, Didier Stien, and Véronique Eparvier
Subjects: Pharmacology, Complementary and alternative medicine, Traditional medicine, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Biology, Antimicrobial, Analytical Chemistry
Published: 2016
Full Text: View/download PDF

13. Search for anti-dengue secondary metabolites from two Diospyros endophytes, Aspergillus sp. and Phomopsis sp

Author: Cécilia Eydoux, Laure-Anne Peyrat, Véronique Eparvier, Didier Stien, Marc Litaudon, and Jean-Claude Guillemot
Subjects: Pharmacology, Aspergillus, biology, Organic Chemistry, Pharmaceutical Science, Diospyros, biology.organism_classification, medicine.disease, Analytical Chemistry, Microbiology, Dengue fever, Complementary and alternative medicine, Drug Discovery, Phomopsis sp, medicine, Molecular Medicine
Published: 2016
Full Text: View/download PDF

14. Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues

Author: Sandy Desrat, Didier Stien, Jean-Luc Wolfender, Pierre-Marie Allard, Seindé Touré, Léonie Pellissier, Véronique Eparvier, Isabelle Dusfour, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Université de Genève (UNIGE), Institut Pasteur de la Guyane, Réseau International des Instituts Pasteur (RIIP), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Aedes aegypti, Stereochemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, medicine.disease_cause, Catalysis, Inorganic Chemistry, lcsh:Chemistry, 03 medical and health sciences, Minimum inhibitory concentration, 0302 clinical medicine, medicine, Bioassay, Structure–activity relationship, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, bacteria, Molecular Biology, lcsh:QH301-705.5, Spectroscopy, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, biology, Organic Chemistry, Fatty acid, General Medicine, biology.organism_classification, Antimicrobial, hydroxyacyl-phenylalanine, entomopathogen, 3. Good health, Computer Science Applications, 030104 developmental biology, chemistry, lcsh:Biology (General), lcsh:QD1-999, Staphylococcus aureus, [SDE]Environmental Sciences, antimicrobial, lipoamino acid, larvicidal, 030217 neurology & neurosurgery, Bacteria
Abstract: A biological evaluation of a library of extracts from entomopathogen strains showed that Pantoea sp. extract has significant antimicrobial and insecticidal activities. Three hydroxyacyl-phenylalanine derivatives were isolated from this strain. Their structures were elucidated by a comprehensive analysis of their NMR and MS spectroscopic data. The antimicrobial and insecticidal potencies of these compounds were evaluated, and compound 3 showed 67% mortality against Aedes aegypti larvae at a concentration of 100 ppm, and a minimum inhibitory concentration (MIC) of 16 &micro, g/mL against methicillin-resistant Staphylococcus aureus. Subsequently, hydroxyacyl-phenylalanine analogues were synthesized to better understand the structure-activity relationships within this class of compounds. Bioassays highlighted the antimicrobial potential of analogues containing saturated medium-chain fatty acids (12 or 14 carbons), whereas an unsaturated long-chain fatty acid (16 carbons) imparted larvicidal activity. Finally, using a molecular networking-based approach, several close analogues of the isolated and newly synthesized lipoamino acids were discovered in the Pantoea sp. extract.
Published: 2019
Full Text: View/download PDF

15. Chemical Variability of the Essential Oil of Origanum ehrenbergii Boiss. from Lebanon, Assessed by Independent Component Analysis (ICA) and Common Component and Specific Weight Analysis (CCSWA)

Author: Raviella Zgheib, Sylvain Chaillou, Naim Ouaini, Amine Kassouf, Marcello Iriti, Marc El-Beyrouthy, Didier Stien, Marco Leonti, Douglas N. Rutledge, Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Holy-Spirit University of Kaslik [Jounieh], Ingénierie, Procédés, Aliments (GENIAL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Lebanese University [Beirut], Universita degli Studi di Cagliari [Cagliari], University of Milan, Lebanese University [Beirut] (LU), National Council for Scientific Research (CNRS) -Lebanon, and Iriti, Marcello
Subjects: Time Factors, Origanum ehrenbergii, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 01 natural sciences, law.invention, lcsh:Chemistry, Soil, chemistry.chemical_compound, law, Origanum, Carvacrol, Lebanon, lcsh:QH301-705.5, Chemical composition, Spectroscopy, Principal Component Analysis, Geography, biology, Component (thermodynamics), Altitude, Specific weight, Discriminant Analysis, General Medicine, 6. Clean water, Computer Science Applications, Horticulture, independent component analysis, Composition (visual arts), chemical variability, Article, Catalysis, Inorganic Chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Oils, Volatile, Desiccation, Physical and Theoretical Chemistry, Molecular Biology, essential oils, Essential oil, Chemotype, 010401 analytical chemistry, Organic Chemistry, biology.organism_classification, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, common component and specific weight analysis, lcsh:Biology (General), lcsh:QD1-999, chemistry, origanum ehrenbergii
Abstract: Origanum ehrenbergii Boiss., an endemic plant to Lebanon, is widely acknowledged in Lebanese traditional medicine. The aim of the present study was to evaluate the influence of the drying method, region, and time of harvest on yield and chemical composition of O. ehrenbergii essential oils (EOs). Plants were harvested monthly throughout 2013 and 2014, from two different regions, Aabadiye and Qartaba, then dried using two drying methods: lyophilization and shade-drying at 4 &deg, C. EO was extracted by hydrodistillation and analyzed by GC/MS. GC-MS data, combined with independent component analysis (ICA) and common component and specific weight analysis (CCSWA), showed that drying techniques, region of harvest, and soil composition have no effect on the chemical composition of O. ehrenbergii EOs. Of the factors analyzed, only harvesting time affected the EO composition of this species. High and stable amounts of carvacrol, associated with reliable antimicrobial activities, were detected in material harvested between March and October. EOs obtained from plants harvested in Aabadiye in January and February showed high amounts of thymoquinone, related to anti-inflammatory and cytotoxic effects. The use of ICA and CCSWA was proven to be efficient, and allowed the development of a discriminant model for the classification of O. ehrenbergii chemotype and the determination of the best harvesting time.
Published: 2019
Full Text: View/download PDF

16. The antifungal potential of (Z)-ligustilide and the protective effect of eugenol demonstrated by a chemometric approach

Author: Nadine Amusant, Emeline Houël, Alice M. S. Rodrigues, Didier Stien, Véronique Eparvier, Guillaume Odonne, Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Laboratoire Ecologie, évolution, interactions des systèmes amazoniens (LEEISA), Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire Ecologie, Evolution, Interactions des Systèmes amazoniens (LEEISA), Centre National de la Recherche Scientifique (CNRS)-Université de Guyane (UG)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER), 'Investissements d'avenir' of the French National Agency for Research (Labex CEBA) [ANR-10-LABX-25-01], Stien, Didier, and Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)
Subjects: 0301 basic medicine, Antifungal, Candida parapsilosis, medicine.drug_class, lcsh:Medicine, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Citral, Article, Terpene, 03 medical and health sciences, chemistry.chemical_compound, Minimum inhibitory concentration, 0302 clinical medicine, 4-Butyrolactone, Candida albicans, Eugenol, medicine, Organic chemistry, Metabolomics, lcsh:Science, Thymol, Antifungal agents, [SDV.MP.MYC]Life Sciences [q-bio]/Microbiology and Parasitology/Mycology, Multidisciplinary, biology, lcsh:R, biology.organism_classification, Eugénol, 3. Good health, Propriété antifongique, 030104 developmental biology, chemistry, S50 - Santé humaine, Maladie infectieuse, Huile essentielle, lcsh:Q, U30 - Méthodes de recherche, 030217 neurology & neurosurgery
Abstract: Mankind is on the verge of a postantibiotic era. New concepts are needed in our battle to attenuate infectious diseases around the world and broad spectrum plant-inspired synergistic pharmaceutical preparations should find their place in the global fight against pathogenic microorganisms. To progress towards the discovery of potent antifungal agents against human pathologies, we embarked upon developing chemometric approach coupled with statistical design to unravel the origin of the anticandidal potential of a set of 66 essential oils (EOs). EOs were analyzed by GC-MS and tested against Candida albicans and C. parapsilosis (Minimal Inhibitory Concentration, MIC). An Orthogonal Partial Least Square (OPLS) analysis allowed us to identify six molecules presumably responsible for the anticandidal activity of the oils: (Z)-ligustilide, eugenol, eugenyl acetate, citral, thymol, and β-citronellol. These compounds were combined following a full factorial experimental design approach in order to optimize the anticandidal activity and selectivity index (SI = IC50(MRC5 cells)/MIC) through reconstituted mixtures. (Z)-Ligustilide and citral were the most active compounds, while (Z)-ligustilide and eugenol were the two main factors that most contributed to the increase of the SI. These two terpenes can, therefore, be used to construct bioinspired synergistic anticandidal mixtures.
Published: 2019
Full Text: View/download PDF

17. A trace alkaloid, oleraisoindole A from Portulaca oleracea L. and its anticholinesterase effect

Author: Didier Stien, Xuetao Li, Xixiang Ying, Ma Yifei, Wenjie Zhang, University of Science and Technology LiaoNing (USTL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Centre National de la Recherche Scientifique (CNRS)-EDF (EDF)-PIERRE FABRE-Université Pierre et Marie Curie - Paris 6 (UPMC)-Observatoire océanologique de Banyuls (OOB), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Lignan, biology, 010405 organic chemistry, Alkaloid, Organic Chemistry, Plant Science, Portulaca, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, 3. Good health, Analytical Chemistry, Trace (semiology), 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Botany, ComputingMilieux_MISCELLANEOUS
Abstract: A new trace alkaloid possessing the lignan structure, named oleraisoindole A, was obtained from the extract of the Portulaca oleracea L.. The structure of oleraisoindole A was elucidated by 1D and 2D NMR and high resolution electrospray ionization time-of-flight mass spectroscopic methods. The compound presented an anticholinesterase effect with the IC50 value of 60.4 μM.
Published: 2019
Full Text: View/download PDF

18. Mucorolactone, a Macrolactone from Mucor sp. SNB-VECD13A, a Fungus Isolated from the Cuticle of a Vespidae Species

Author: Morgane Barthélemy, Seindé Touré, Grégory Genta-Jouve, Isabelle Dusfour, Didier Stien, Jonathan Sorres, Véronique Eparvier, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Institut Pasteur de la Guyane, Réseau International des Instituts Pasteur (RIIP), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Mucor, Circular dichroism, Magnetic Resonance Spectroscopy, biology, Molecular Structure, 010405 organic chemistry, Chemistry, Stereochemistry, Cuticle, Circular Dichroism, Organic Chemistry, Ethyl acetate, Nuclear magnetic resonance spectroscopy, Carbon-13 NMR, 010402 general chemistry, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Molecule, Physical and Theoretical Chemistry, Two-dimensional nuclear magnetic resonance spectroscopy
Abstract: International audience; The newly discovered macrolactone mucorolactone, along with 8 known compounds, was isolated from an ethyl acetate extract of the insect-born fungus Mucor sp. All structures were elucidated using 1D and 2D NMR and MS spectroscopic experiments. Relative and absolute configurations of the original skeleton of mucorolactone was deduced from NOESY experiment , from the 13 C NMR chemical shifts calculation based on the DP4 probability method, and from the comparison of experimental and calculated electronic circular dichroism spectra.
Published: 2018
Full Text: View/download PDF

19. Two new tetrahydrofuran derivatives from the fungus Mucor spp. SNB-VECD11D isolated from the Chrysomelidae Acalymma bivittula

Author: Isabelle Dusfour, Seindé Touré, Véronique Eparvier, Didier Stien, and Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Fungus, Aedes aegypti, medicine.disease_cause, 01 natural sciences, Biochemistry, Microbiology, 03 medical and health sciences, chemistry.chemical_compound, Drug Discovery, medicine, Acalymma, [CHIM]Chemical Sciences, Tetrahydrofuran, ComputingMilieux_MISCELLANEOUS, Mucor, biology, 010405 organic chemistry, Organic Chemistry, biology.organism_classification, Antimicrobial, 0104 chemical sciences, 3. Good health, 030104 developmental biology, chemistry, Staphylococcus aureus, Antibacterial activity
Abstract: Two new tetrahydrofuran derivatives, mucorinic acids A ( 1 ) and B ( 2 ) as well as the three known secondary metabolites dehydroabietic acid ( 3 ), Δ8-dihydroabietic acid ( 4 ) and 8-pimarenic acid ( 5 ) were isolated from a solid culture of the fungus Mucor spp. isolated on insect Acalymma bivittula . The structure of these compounds was elucidated by analysis of NMR and MS spectroscopic data. Compounds were tested in antimicrobial and insecticidal assays. Dehydroabietic acid exhibited moderate larvicidal activity on Aedes aegypti larvae with 65% mortality at 10 ppm. Both new compounds 1 and 2 showed interesting antibacterial activity on Staphylococcus aureus and methicillin resistant S. aureus with MIC values in the 8–16 μg/ml.
Published: 2017
Full Text: View/download PDF

20. New acorane sesquiterpenes isolated from the endophytic fungus Colletotrichum gloeosporioides SNB-GSS07

Author: Kaatio Touré, Didier Stien, Amandine André, Nathalie Wojtowicz, Véronique Eparvier, and Centre National de la Recherche Scientifique (CNRS)
Subjects: Circular dichroism, biology, 010405 organic chemistry, Stereochemistry, Chemistry, Organic Chemistry, Endophytic fungus, biology.organism_classification, Mass spectrometry, 01 natural sciences, Biochemistry, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, Sabicea cinerea, Colletotrichum gloeosporioides, Drug Discovery, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract: Looking for new anti-glycation compounds, four new acorane sesquiterpenes together with seven known molecules were isolated from Colletrotrichum gloeosporioides , an endophytic fungus of Sabicea cinerea . Their structures were established based on mass spectrometry and NMR, together with circular dichroism for their absolute configurations.
Published: 2017
Full Text: View/download PDF

21. Cytotoxic indole alkaloids from Pseudovibrio denitrificans BBCC725

Author: Marcelino T. Suzuki, Clémence Rohée, François Sautel, Alice M. S. Rodrigues, Thibaut Fabre, Nicole Batailler, Didier Stien, Stéphanie Nogues, Isabelle Carletti, Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Observatoire océanologique de Banyuls (OOB), 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS), Centre de Recherche Pierre Fabre (Centre de R&D Pierre Fabre), and PIERRE FABRE
Subjects: Pseudovibrio denitrificans, Stereochemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, Drug Discovery, medicine, Cytotoxic T cell, Indole test, A549 cell, biology, Strain (chemistry), Cytotoxic activity, 010405 organic chemistry, Chemistry, Organic Chemistry, Cresol, biology.organism_classification, [SDV.MP.BAC]Life Sciences [q-bio]/Microbiology and Parasitology/Bacteriology, 0104 chemical sciences, 3. Good health, Indole alkaloids, Marine natural products, Tetra, medicine.drug
Abstract: In this study, we investigated a culture supernatant of a Pseudovibrio denitrificans strain isolated from sea water. Five indole alkaloids were isolated from this culture. These include four known compounds, arundine ( 1 ), vibrindole A ( 2 ), 1,1,1-tris(indol-3-yl)methane ( 3 ), 7,7-bis(indol-3-yl)- p -cresol ( 4 ) and the new tetra(indol-3-yl)ethanone ( 5 ). Compound 5 showed interesting cytotoxic effect against L929 cells (EC 50 = 7 µM) and A549 cells (EC 50 = 8 µM).
Published: 2017
Full Text: View/download PDF

22. Aedes aegypti larvicidal sesquiterpene alkaloids from Maytenus oblongata

Author: Véronique Eparvier, Isabelle Dusfour, Seindé Touré, Maïra Coke, Arnaud Jahn-Oyac, Guillaume Odonne, Isabelle Boulogne, Didier Azam, Michaël Falkowski, Céline Moriou, Charlotte Nirma, Romain Girod, Didier Stien, Emeline Houël, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Institut Pasteur de la Guyane, Réseau International des Instituts Pasteur (RIIP), Laboratoire de Glycobiologie et Matrice Extracellulaire Végétale (Glyco-MEV), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU), Unité d'Ecologie et Ecotoxicologie Aquatiques (UEEA), Institut National de la Recherche Agronomique (INRA), Laboratoire Ecologie, évolution, interactions des systèmes amazoniens (LEEISA), Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Observatoire océanologique de Banyuls (OOB), 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Ecologie, Evolution, Interactions des Systèmes amazoniens (LEEISA), La Région Guyane, Air Liquide Fondation, ANR 11-INBS-0001, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA), Centre National de la Recherche Scientifique (CNRS)-EDF (EDF)-PIERRE FABRE-Université Pierre et Marie Curie - Paris 6 (UPMC)-Observatoire océanologique de Banyuls (OOB), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Stereochemistry, [SDV]Life Sciences [q-bio], Ethyl acetate, Pharmaceutical Science, Aedes aegypti, Sesquiterpene, 01 natural sciences, Analytical Chemistry, Maytenus oblongata, 03 medical and health sciences, chemistry.chemical_compound, Alkaloids, Triterpenoid, Aedes, Drug Discovery, Animals, Organic chemistry, Nuclear Magnetic Resonance, Biomolecular, ComputingMilieux_MISCELLANEOUS, Pharmacology, Molecular Structure, Plant Stems, biology, 010405 organic chemistry, Organic Chemistry, Maytenus, biology.organism_classification, Triterpenes, French Guiana, 3. Good health, 0104 chemical sciences, 030104 developmental biology, Complementary and alternative medicine, chemistry, Larva, Molecular Medicine, Sesquiterpenes, Two-dimensional nuclear magnetic resonance spectroscopy
Abstract: International audience; Four new sesquiterpene alkaloids (1-4) with a beta-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.
Published: 2017
Full Text: View/download PDF

23. An isoindole alkaloid from Portulaca oleracea L

Author: Haoran Xu, Didier Stien, Xixiang Ying, Fen Xiu, Xu Yang, Wenjie Zhang, Mingyue Jiang, University of Science and Technology LiaoNing (USTL), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: China, Isoindoles, Coumaric Acids, Stereochemistry, Plant Science, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Portulaca, Coumaric acid, Nitric Oxide, 01 natural sciences, Biochemistry, Analytical Chemistry, Nitric oxide, Ferulic acid, chemistry.chemical_compound, Mice, Alkaloids, Animals, nitric oxide (NO), RAW 264.7 Cells, Portulaca oleracea L, biology, Molecular Structure, 010405 organic chemistry, Plant Extracts, Alkaloid, Macrophages, Organic Chemistry, Dipeptides, biology.organism_classification, alkaloid, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry, Isoindole
Abstract: A novel isoindole alkaloid named oleraisoindole (1), together with six known compounds, 7′-ethoxy-trans-feruloyltyramine (2), N-trans-feruloyltyramine (3), N-trans-feruloyl-3-methoxytyramine (4), N-trans-p-coumaroyltyramine (5) aurantiamide (6) and ferulic acid methyl ester (7) were isolated from Portulaca oleracea L. Compounds 2 and 7 were isolated for the first time from this plant. Compound 1 was identified using spectroscopic methods including HR-ESI-TOF-MS, 1D-NMR, 2D-NMR. It was tested in a nitric oxide (NO) inhibition assay and was shown to inhibit NO production in RAW 264.7 cells induced by LPS.
Published: 2017
Full Text: View/download PDF

24. How can plant defences lead to valuable products? Inspiration from plant complexity in phytochemistry

Author: German Gonzalez, Véronique Eparvier, Eric Deharo, Guillaume Odonne, A Rodrigues, Jean-Marie Bessière, A Jahn-Oyac, Emeline Houël, Didier Stien, Laila S. Espindola, Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Laboratoire Ecologie, Evolution, Interactions des Systèmes amazoniens (LEEISA), Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS), Pharmacochimie et Biologie pour le Développement (PHARMA-DEV), Institut de Recherche pour le Développement (IRD)-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)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Universidade de Brasilia [Brasília] (UnB), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-10-LABX-0025,CEBA,CEnter of the study of Biodiversity in Amazonia(2010), ANR-07-CP2D-0019,XYLOTECH,Valorisation des déchets de scierie et des ressources sylvicoles sous-exploitées en Guyane Française - évaluation du potentiel industriel des molécules extractibles(2007), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Ecole Polytechnique Universitaire de l'Université Pierre et Marie Curie (Polytech‘ Paris - UPMC), UMR 5076, Laboratoire Ecologie, évolution, interactions des systèmes amazoniens (LEEISA), Université de Toulouse, Universidade de Brasília (UnB), Centre National de la Recherche Scientifique (CNRS), Institut de Recherche pour le Développement (IRD)-Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT), Centre National de la Recherche Scientifique (CNRS)-Université de Guyane (UG)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-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), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
Subjects: 2. Zero hunger, Pharmacology, Phytochemistry, 010405 organic chemistry, Chemistry, [SDV]Life Sciences [q-bio], 010401 analytical chemistry, Organic Chemistry, Pharmaceutical Science, 15. Life on land, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, Lead (geology), Complementary and alternative medicine, biomimetic design, Drug Discovery, Molecular Medicine, antifungal agents, antiparasitic agents, Biochemical engineering, therapeutic switching, essential oils
Abstract: International audience; If plants are known for centuries as a valuable source of molecules, complexity remains and can open up numerous perspectives. Plants have indeed evolved a wide range of secondary metabolites as defense, competition or attraction compounds [1]. More particularly, the exceptional biodiversity encountered in the tropics, along with the presence of various pathogens and a strong herbivory especially linked to a rich entomofauna, leads to a promising chemodiversity, due to the constant and dynamic interactions between plants and their environment. Taking into account the role and “raison d'être”[2] of natural products, and the fact that all these molecules work together as complex mixtures can therefore lead to a new point of view, by shifting from the “magic bullet” classical approach to a “herbal shotgun” strategy[3]. We will illustrate the fact that, inspired by their ecological functions, and taking into account synergistic interactions, some therapeutic applications can be found for these versatile mixtures of compounds. In particular we examined whether the antidermatophytic activity of essential oils (EOs) obtained from particularly fragrant plant species from French Guiana could be used as an indicator for the discovery of active natural products against Leishmania amazonensis. A significant correlation was observed between antidermatophytic and antileishmanial activity, confirming the “alternative use” strategy in the case of EOs, and allowed us to highlight P. hispidum Sw. (Piperaceae) EO as a promising antileishmanial product [4]. We also illustrated the importance of synergistic effects through the example of the antifungal EO of Otacanthus azureus (Linden) Ronse (Plantaginaceae) [5] and the biomimetic design of optimized synergistic mixtures thanks to a full factorial experiment approach.
Published: 2016
Full Text: View/download PDF

25. Isolation and characterization of santolinoidol, a bisabolene sesquiterpene from Achillea santolinoides subsp wilhelmsii (K. Koch) Greuter

Author: Naim Ouaini, Marc El Beyrouthy, Didier Stien, Véronique Eparvier, Layal Fahed, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Department of Agricultural Sciences, Holy Spirit University of Kaslik, Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Centre National de la Recherche Scientifique (CNRS)-EDF (EDF)-PIERRE FABRE-Université Pierre et Marie Curie - Paris 6 (UPMC)-Observatoire océanologique de Banyuls (OOB), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Observatoire océanologique de Banyuls (OOB), and 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0106 biological sciences, 0301 basic medicine, Structural determination, Achillea, Stereochemistry, 030106 microbiology, Antimicrobial activity, medicine.disease_cause, Sesquiterpene, 01 natural sciences, Biochemistry, Essential oil, law.invention, 03 medical and health sciences, chemistry.chemical_compound, law, Drug Discovery, medicine, [CHIM]Chemical Sciences, Traditional medicine, biology, Organic Chemistry, Achillea santolinoides subsp wilhelmsii, biology.organism_classification, Antimicrobial, chemistry, Staphylococcus aureus, Mic values, Santolinoidol, Bisabolene, Trichophyton species, 010606 plant biology & botany
Abstract: International audience; The essential oil (EO) obtained by hydrodistillation of aerial parts of Lebanese Achillea santolinoides subsp wilhelmsii (K. Koch) Greuter was analyzed by GC and GC–MS. The identity of the second major compound was uncertain. Its structure was elucidated using 1D and 2D NMR spectroscopy as well as MS data. It appeared to be a new sesquiterpene with a 1-oxa-bicyclo[5,4,0]-undecane skeleton which was named santolinoidol. The EO revealed interesting antimicrobial potential particularly against Trichophyton species, Staphylococcus aureus and Methicillin-resistant Staphylococcus aureus (MRSA) with MIC values ranging from 16 to 128 μg/ml.
Published: 2016
Full Text: View/download PDF

26. Two new isopimarane diterpenoids from the endophytic fungus Xylaria sp. SNB-GTC2501

Author: Charlotte Nirma, Jonathan Sorres, Seindé Touré, Didier Stien, Véronique Eparvier, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA), Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), and Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA)
Subjects: Ergosterol peroxide, 010405 organic chemistry, Stereochemistry, Chemistry, Organic Chemistry, Absolute configuration, Endophytic fungus, Xylaria sp, Antimicrobial, 01 natural sciences, Biochemistry, 3. Good health, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, ComputingMilieux_MISCELLANEOUS
Abstract: Two new isopimarane diterpenoids, xylabisboein A (1) and B (2), as well as three known secondary metabolites (i.e., (−)-5-methylmellein (3), mellein-5-carboxylic acid (4) and ergosterol peroxide (5)), were isolated from a solid culture of the endophytic fungus Xylaria sp. SNB-GTC2501. The structures were elucidated by spectroscopic analysis and the absolute configuration of xylabisboein A (1) was determined by X-ray crystallographic analysis. All of the compounds were tested for their antimicrobial and cytotoxic activities.
Published: 2015
Full Text: View/download PDF

27. Secondary Metabolites Isolated from the Amazonian Endophytic Fungus Diaporthe sp. SNB-GSS10

Author: Hugues Mandavid, Laila S. Espindola, Alice M. S. Rodrigues, Véronique Eparvier, Didier Stien, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Universidade de Brasilia [Brasília] (UnB), Observatoire océanologique de Banyuls (OOB), 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-EDF (EDF)-PIERRE FABRE-Université Pierre et Marie Curie - Paris 6 (UPMC)-Observatoire océanologique de Banyuls (OOB), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Bridged-Ring Compounds, Pharmaceutical Science, Antineoplastic Agents, 01 natural sciences, Diaporthe pseudomangiferae, KB Cells, Analytical Chemistry, Microbiology, 03 medical and health sciences, Sabicea cinerea, Ascomycota, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Botany, Endophytes, [CHIM]Chemical Sciences, Humans, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Pharmacology, 0303 health sciences, biology, Molecular Structure, 010405 organic chemistry, Organic Chemistry, Endophytic fungus, Human cell, biology.organism_classification, 3. Good health, 0104 chemical sciences, Diaporthe sp, Complementary and alternative medicine, Pyrones, [SDE]Environmental Sciences, Molecular Medicine, Drug Screening Assays, Antitumor, Mycoepoxydiene, Sesquiterpenes
Abstract: International audience; We describe a Sabicea cinerea endophytic fungus closely related to Diaporthe pseudomangiferae that produces two known metabolites, mycoepoxydiene and altiloxin A, as well as enamidin and eremofortin F, two compounds not previously described in the literature. The structure of these four metabolites was elucidated using spectroscopic analysis, and their cytotoxic activities were measured against the human cell lines KB,MRC-5, and MDA-MB-435.
Published: 2015
Full Text: View/download PDF

28. Dicorynamine and harmalan-N-oxide, two new β-carboline alkaloids from Dicorynia guianensis Amsh heartwood

Author: Jean-Baptiste Say Anouhe, Didier Stien, Augustin Amissa Adima, Séraphin Kati-Coulibaly, Nadine Amusant, Jean-Luc Pirat, Pierre-Alain Blandinières, Florence Bobelé Niamké, David Virieux, Brise Kassi Amian, Groupe de recherche en Chimie des Eaux et des Substances Naturelles, Institut National Polytechnique Houphoue¨t Boigny, BP 1313 Yamoussoukro, Cote d’Ivoire (INPHB), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Université des Antilles (UA)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-AgroParisTech-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), France embassy in Cote d'Ivoire, CIRAD, and Agence Nationale de la Recherche (CEBA) [ANR-10-LABX-0025]
Subjects: K50 - Technologie des produits forestiers, Antioxidant, medicine.medical_treatment, Plant Science, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Spiroindolone, K01 - Foresterie - Considérations générales, Organic chemistry, Forêt tropicale humide, Biogenesis, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, ABTS, Chemistry, Composition chimique, Antioxydant, 3. Good health, Produit forestier non ligneux, Biotechnology, ABTS antioxidant, Stereochemistry, F60 - Physiologie et biochimie végétale, Bois de coeur, Oxide, 010402 general chemistry, Nitrone, Alcaloïde, medicine, [CHIM]Chemical Sciences, Arbre forestier, Indole test, 010405 organic chemistry, Extrait de bois, Dicorynia guianensis, 0104 chemical sciences, Agronomy and Crop Science
Abstract: International audience; The chemical investigations of Dicorynia guianensis heartwood led to the isolation of four new indole alkaloids for the first time in this plant. Compound (1) identified as spiroindolone 2',3',4',9'-tetrahydrospiro [indoline-3,1'pyrido[3,4-b]-indol]-2-one, and compound (3) described as nitrone 1-methyl-4,9-dihydro-3H-pyrido [3,4-b] indole 2-oxide and were isolated for the first time as natural products. ABTS antioxidant activity guided their isolation. (C) 2015 Phytochemical Society of Europe.
Published: 2015
Full Text: View/download PDF

29. Quaternary Ammonium-Supported Scavenger Reagents for Acids and Electrophiles

Author: Noha Ghanem, Jean Martinez, and Didier Stien
Subjects: Aqueous solution, Organic Chemistry, Scavenger (chemistry), law.invention, Solvent, chemistry.chemical_compound, chemistry, law, Reagent, Electrophile, Organic chemistry, Methanol, Physical and Theoretical Chemistry, Diethyl ether, Filtration
Abstract: The present article describes how we devised new quaternary ammonium-supported quench reagents (TAMA-Cl and BAX-sulfate) for scavenging acids and excess electrophiles from crude reaction mixtures. TAMA-Cl is liquid at room temperature, but is very glutinous and has to be used in aqueous solution. It removes unchanged electrophiles very efficiently. An aqueous preparation of TAMA-Cl may be easily added in automated syntheses, and high-throughput phase-separation techniques should allow purification of scavenger-containing reaction mixtures. However, workup with TAMA-Cl is more complex than simple filtration. Recognizing this major advantage of solid-phase syntheses, we designed BAX-sulfate, a highly crystalline scavenger reagent that allows reaction workup to be simplified to a single filtration and evaporation of solvent. BAX-sulfate reacts with electrophiles, quenches acids and precipitates quantitatively when diethyl ether is added. It even precipitates from methanol solutions. With BAX-sulfate the workup stage uses simple filtration to make crude separations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Published: 2004
Full Text: View/download PDF

30. Synthesis of (±)- and (−)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals

Author: Robert Nouguier, Olivier Andrey, Felix Villar, Stéphane Gastaldi, Philippe Renaud, Michèle P. Bertrand, and Didier Stien
Subjects: Inorganic Chemistry, chemistry.chemical_compound, chemistry, Botryodiplodin, Intramolecular force, Organic Chemistry, Organic chemistry, Stereoselectivity, General Medicine, Physical and Theoretical Chemistry, Combinatorial chemistry, Catalysis, Derivative (chemistry)
Abstract: Three different routes for the stereoselective synthesis of botryodiplodin have been investigated. The intramolecular allylation of acetals proved to be unsatisfactory due to unstable intermediates and poor stereocontrol. Zard intramolecular radical allylation of a 2-iodopropionate derivative allows the development of an expeditious synthesis of racemic botryodiplodin. The relative configuration within the final product was corrected by a deprotonation–reprotonation step. The cyclization of allenyl bromoacetals was investigated next and proved to be satisfactory for the synthesis of racemic and enantiomerically pure botryodiplodin. Good stereocontrol was achieved by cyclizing a gem -dibromide followed by the stereoselective reduction of the thus formed cyclic monobromide.
Published: 2003
Full Text: View/download PDF

31. Antibacterial Ilicicolinic Acids C and D and Ilicicolinal from Neonectria discophora SNB-CN63 Isolated from a Termite Nest

Author: Véronique Eparvier, Didier Stien, Charlotte Nirma, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), Observatoire océanologique de Banyuls (OOB), 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)-PIERRE FABRE-EDF (EDF)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-EDF (EDF)-PIERRE FABRE-Université Pierre et Marie Curie - Paris 6 (UPMC)-Observatoire océanologique de Banyuls (OOB), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (ECOFOG), and Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS)
Subjects: Ilicicolinal, Pharmaceutical Science, Nasutitermes corniger, Fungus, Isoptera, Benzoates, KB Cells, Analytical Chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Botany, Animals, Humans, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, Benzofurans, Pharmacology, biology, Molecular Structure, Organic Chemistry, biology.organism_classification, Neonectria discophora, 3. Good health, Anti-Bacterial Agents, French Guiana, Complementary and alternative medicine, Hypocreales, Molecular Medicine, Female, Drug Screening Assays, Antitumor, Antibacterial activity, Nest (protein structural motif)
Abstract: International audience; Ilicicolinic acids A, C, and D and ilicicolinal were isolated from a fungus isolated from a Nasutitermes corniger nest in French Guiana. The structures of ilicicolinic acids C and D and ilicicolinal were elucidated using 1D and 2D NMR spectroscopic data as well as MS data. Ilicicolinic acids show antibacterial activity in vitro.
Published: 2015
Full Text: View/download PDF

32. Experimental design optimization of antimicrobial mixtures of active VOCs

Author: A Rodrigues, Véronique Eparvier, Emeline Houël, Guillaume Odonne, Didier Stien, and C Makerri
Subjects: Pharmacology, Complementary and alternative medicine, Chemistry, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Antimicrobial, Combinatorial chemistry, Analytical Chemistry
Published: 2014
Full Text: View/download PDF

33. Bio-inspired design of antimicrobial synergistic mixtures

Author: Naim Ouaini, Didier Stien, M El Beyrouthy, Véronique Eparvier, and Madona Khoury
Subjects: Pharmacology, Complementary and alternative medicine, Chemistry, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Antimicrobial, Combinatorial chemistry, Analytical Chemistry
Published: 2014
Full Text: View/download PDF

34. Search for anti-dengue secondary metabolites from Diospyros species and their endophytes

Author: Didier Stien, Marc Litaudon, Cécilia Eydoux, Jean-Claude Guillemot, J Letienne, Laure-Anne Peyrat, and Véronique Eparvier
Subjects: Pharmacology, biology, Organic Chemistry, Pharmaceutical Science, Diospyros, biology.organism_classification, medicine.disease, Analytical Chemistry, Dengue fever, Complementary and alternative medicine, Drug Discovery, Botany, medicine, Molecular Medicine
Published: 2014
Full Text: View/download PDF

35. Symbioses: An environmentally-relevant source of natural substances in the search for antimicrobial compounds

Author: Jonathan Sorres, Véronique Eparvier, Charlotte Nirma, and Didier Stien
Subjects: Pharmacology, Complementary and alternative medicine, Symbiosis, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Biochemical engineering, Biology, Antimicrobial, Combinatorial chemistry, Natural (archaeology), Analytical Chemistry
Published: 2014
Full Text: View/download PDF

36. TakamalaImë (Psidium acutangulum Mart ex. DC): Understanding the use of an antimalarial traditional remedy from French Guiana

Author: Eric Deharo, Valérie Jullian, Véronique Eparvier, Marie Fleury, Pascal Villa, Didier Stien, Emeline Houël, Guillaume Odonne, Flore Nardella, Catherine Vonthron-Sénécheau, Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), Patrimoines Locaux et Gouvernance (PALOC), Muséum national d'Histoire naturelle (MNHN)-Institut de Recherche pour le Développement (IRD), Pharmacochimie et Biologie pour le Développement (PHARMA-DEV), Institut de Recherche pour le Développement (IRD)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT), Laboratoire d'Innovation Thérapeutique (LIT), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Plate-forme de chimie biologique intégrative de Strasbourg (PCBiS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Ecologie, Evolution, Interactions des Systèmes amazoniens (LEEISA), Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), CNRS, UMR Ecol Forets Guyane, Kourou, France, Partenaires INRAE, UMR Botanique et bioinformatique de l'architecture des plantes, 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 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)-Institut de Chimie du CNRS (INC)-Institut de Recherche pour le Développement (IRD), Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC), PCBIS Plate-forme de chimie biologique intégrative de Strasbourg, UMS 3286, CNRS, Université de Strasbourg, Labex Medalis, 300 boulevard Sebastien Brant, F-67000 Strasbourg, France, CNRS Guyane (USR 3456), and Centre National de la Recherche Scientifique (CNRS)
Subjects: Pharmacology, Psidium, Traditional medicine, business.industry, [SDV]Life Sciences [q-bio], Organic Chemistry, Pharmaceutical Science, Analytical Chemistry, Complementary and alternative medicine, Drug Discovery, Molecular Medicine, Medicine, business, ComputingMilieux_MISCELLANEOUS
Abstract: International audience
Published: 2014
Full Text: View/download PDF

37. Bioprospection in French Guiana for the discovery of potential agrochemical and cosmetic agents

Author: Emeline Houël, A Rodrigues, Véronique Eparvier, O Sorgenfrei, Didier Stien, M Ralli, and Jonathan Sorres
Subjects: Pharmacology, Complementary and alternative medicine, business.industry, Agrochemical, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Medicine, business, Analytical Chemistry, Biotechnology
Published: 2014
Full Text: View/download PDF

38. Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals

Author: Didier Stien, Gerald D. Artman, Xichen Lin, and Steven M. Weinreb
Subjects: Diphenyl disulfide, chemistry.chemical_compound, chemistry, Radical, Organic Chemistry, Drug Discovery, medicine, Biochemistry, Combinatorial chemistry, Diphenyl diselenide, Chloride, medicine.drug
Abstract: New methodology has been devised for the generation and subsequent cyclization of iminyl and amidyl radicals under mild conditions. The process involves either the treatment of oximes with 2,6-dimethylbenzenesulfinyl chloride, or the treatment of hydroxamic acids with tert-butylsulfinyl chloride (−50°C to rt), to give the corresponding nitrogen radicals, followed by cyclization onto pendant olefins. Radical traps such as diphenyl diselenide, diphenyl disulfide, and TEMPO can be used to terminate the cyclizations, thus introducing functionality that provides multiple options for further manipulation. In a more convenient procedure, both iminyl and amidyl radical cyclizations can be initiated using commercially available diethyl chlorophosphite which generally provides similar (with diphenyl disulfide and TEMPO) or significantly higher (with diphenyl diselenide) yields of products.
Published: 2001
Full Text: View/download PDF

39. A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine

Author: Steven M. Weinreb, Xichen Lin, and Didier Stien
Subjects: Diphenyl disulfide, Hydroxamic acid, Indole alkaloid, Radical, Organic Chemistry, Total synthesis, Biochemistry, Radical cyclization, Chloride, Medicinal chemistry, chemistry.chemical_compound, chemistry, Drug Discovery, medicine, Diphenyl diselenide, medicine.drug
Abstract: Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride and Hunig’s base from −50°C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6-azabicyclo[3.2.1]octane-containing indole alkaloid peduncularine.
Published: 2000
Full Text: View/download PDF

40. A New Method for the Generation and Cyclization of Iminyl Radicals via the Hudson Reaction

Author: Steven M. Weinreb, Didier Stien, and Xichen Lin
Subjects: Free Radicals, Chemistry, Radical, Organic Chemistry, Alkenes, Photochemistry, Biochemistry, Chloride, Cyclization, Reagent, medicine, Surface modification, Imines, Physical and Theoretical Chemistry, medicine.drug
Abstract: [formula: see text] A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50 degrees C to room temperature (Hudson reaction).
Published: 1999
Full Text: View/download PDF

41. Highly-loaded amphiphilic polyimino resin: quench reagent and solid support for peptide synthesis

Author: Didier Stien and Houcine Rahali
Subjects: Aqueous solution, Organic Chemistry, Condensation, Xylene, Ethylenediamine, Biochemistry, Combinatorial chemistry, chemistry.chemical_compound, chemistry, Reagent, Drug Discovery, Electrophile, Amphiphile, Peptide synthesis, Organic chemistry
Abstract: We demonstrate herein that polyimino resin 4a prepared by condensation of α,α′-dichloro- p -xylene, ethylenediamine and tris-(2-aminoethyl)-amine can be successfully exploited as a quench reagent for acids and electrophiles both in aqueous and organic solutions. Scope and limitations of such a resin as a solid support for peptide synthesis were also investigated.
Published: 2006
Full Text: View/download PDF

42. Antifungal Agents from Pseudallescheria boydii SNB-CN73 Isolated from a Nasutitermes sp. Termite

Author: Didier Stien, Véronique Eparvier, Charlotte Nirma, Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Antifungal, Antifungal Agents, Epinephrine, Miconazole, medicine.drug_class, Pharmaceutical Science, Trichophyton rubrum, Isoptera, Microbial Sensitivity Tests, KB Cells, Analytical Chemistry, Microbiology, Pseudallescheria, 03 medical and health sciences, Trichophyton, Tyroscherin, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Candida albicans, Nasutitermes, medicine, Escherichia coli, Animals, Humans, skin and connective tissue diseases, Nuclear Magnetic Resonance, Biomolecular, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Pharmacology, 0303 health sciences, biology, Molecular Structure, 030306 microbiology, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Aspergillus fumigatus, Organic Chemistry, biology.organism_classification, 3. Good health, Pseudallescheria boydii, Complementary and alternative medicine, Molecular Medicine, Drug Screening Assays, Antitumor, Fatty Alcohols
Abstract: International audience; Defense mutualisms between social insects and microorganisms have been described in the literature. The present article describes the discovery of a Pseudallescheria boydii strain isolated from Nasutitermes sp. The microbial symbiont produces two antifungal metabolites: tyroscherin and N-methyltyroscherin, a compound not previously described in the literature. Methylation of tyroscherin has confirmed the structure of N-methyltyroscherin. Both compounds are effective antifungal agents with favorable selectivity indices for Candida albicans and Trichophyton rubrum.
Published: 2013
Full Text: View/download PDF

43. In vitro antifungal activity of Otacanthus azureus (Linden) Ronse essential oil alone and in combination with azoles

Author: Emeline Houël, Didier Stien, Véronique Eparvier, Eric Deharo, Jean-Marie Bessière, A Rodrigues, and Arnaud Jahn-Oyac
Subjects: Pharmacology, Antifungal, Traditional medicine, Chemistry, medicine.drug_class, Stereochemistry, Organic Chemistry, Pharmaceutical Science, In vitro, Analytical Chemistry, law.invention, Complementary and alternative medicine, law, Drug Discovery, medicine, Molecular Medicine, Otacanthus azureus, Essential oil
Published: 2012
Full Text: View/download PDF

44. Development of a statistical tool to predict anticandidal activity of essential oils

Author: Didier Stien, MK El Khil, Emeline Houël, and Véronique Eparvier
Subjects: Pharmacology, Complementary and alternative medicine, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Biochemical engineering, Biology, Analytical Chemistry
Published: 2012
Full Text: View/download PDF

45. Bioactives products from leaves endophytes

Author: Laila S. Espindola, Didier Stien, ML de Mesquita, TM Casella, Véronique Eparvier, and Guillaume Odonne
Subjects: Pharmacology, Complementary and alternative medicine, Organic Chemistry, Drug Discovery, Botany, Pharmaceutical Science, Molecular Medicine, Nanotechnology, Biology, Analytical Chemistry
Published: 2012
Full Text: View/download PDF

46. Evaluation of natural products as potential agrochemical agents with insecticide, fungicide and herbicide activities

Author: O Sorgenfrei, Philippe Rasoanaivo, Didier Stien, Nikolas Fokialakis, Marc Litaudon, Vincent Dumontet, Emeline Houël, Françoise Guéritte, A Espinosa, Florent Olivon, Mahabir P. Gupta, Véronique Eparvier, AL Skaltsounis, Gerda Fouche, D Breuninger, Maria Halabalaki, Cyril Poullain, Dionisio Olmedo, and Matthias Hamburger
Subjects: Pharmacology, Agrochemical, business.industry, Organic Chemistry, Pharmaceutical Science, Natural (archaeology), Analytical Chemistry, Biotechnology, Fungicide, Complementary and alternative medicine, International congress, Drug Discovery, Molecular Medicine, Environmental science, business, Plant Sources
Abstract: The International Congress on Natural Products Research, New York City, 28 July - 1 August 2012
Published: 2012
Full Text: View/download PDF

47. PAH-supported tin hydride: a new tin reagent easily removable from reaction mixtures

Author: Stéphane Gastaldi and Didier Stien
Subjects: Chemistry, Hydride, Radical, Organic Chemistry, Inorganic chemistry, chemistry.chemical_element, equipment and supplies, Biochemistry, Adsorption, Reagent, Drug Discovery, Side product, medicine, Organic chemistry, Tin, Activated carbon, medicine.drug
Abstract: We demonstrate here that a new pyrene-supported tin hydride can be used in radical chemistry. Final products were easily purified by adsorption of the PAH-supported tin side product with activated carbon.
Published: 2002
Full Text: View/download PDF

48. A new high-loading water-soluble scavenger for anhydrides, acid chlorides and isocyanates

Author: Noha Ghanem, Jean Martinez, and Didier Stien
Subjects: chemistry.chemical_classification, Organic Chemistry, High loading, Salt (chemistry), Biochemistry, Scavenger (chemistry), chemistry.chemical_compound, Water soluble, chemistry, Reagent, Drug Discovery, Electrophile, Organic chemistry, Ammonium, After treatment
Abstract: We demonstrate here that a new quaternary ammonium salt bearing three amino functionalities can be used to remove electrophiles. In most cases, final products were essentially pure after treatment of the crude reaction mixture with this new scavenger reagent.
Published: 2002
Full Text: View/download PDF

49. Search for Antifungal Compounds from the Wood of Durable Tropical Trees

Author: Maria do Rosário Rodrigues Silva, Alice M. S. Rodrigues, Laila S. Espindola, Phellipe N. E. T. Theodoro, Didier Stien, Jacques Beauchêne, Véronique Eparvier, Charlie Basset, Laboratoire de Biodiversité et Biotechnologies Microbiennes (LBBM), PIERRE FABRE-EDF (EDF)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Observatoire océanologique de Banyuls (OOB), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2), Universidade de Brasilia [Brasília] (UnB), and Universidade Federal de Goiás [Goiânia] (UFG)
Subjects: K50 - Technologie des produits forestiers, Antifungal Agents, [SDV]Life Sciences [q-bio], Ethyl acetate, Pharmaceutical Science, Human pathogen, Pharmacognosy, L73 - Maladies des animaux, 01 natural sciences, Trees, Analytical Chemistry, Polyporaceae, Mice, chemistry.chemical_compound, Acetals, Maladie des plantes, Drug Discovery, Forêt tropicale humide, Medicinal plants, [SDV.MP.MYC]Life Sciences [q-bio]/Microbiology and Parasitology/Mycology, ComputingMilieux_MISCELLANEOUS, French guiana, Molecular Structure, Plant Stems, biology, Basidiomycota, Biological activity, Lauraceae, Wood, Extrait d'origine végétale, Ocotea, Alkynes, Fongicide, Molecular Medicine, F60 - Physiologie et biochimie végétale, Microbial Sensitivity Tests, Alkenes, 010402 general chemistry, Antifungal, complex mixtures, Bois, Maladie de l'homme, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Botany, Animals, Bois tropical, Pharmacology, 010405 organic chemistry, Organic Chemistry, technology, industry, and agriculture, 15. Life on land, biology.organism_classification, 0104 chemical sciences, Complementary and alternative medicine, chemistry, NIH 3T3 Cells
Abstract: Research on antifungal compounds from the durable wood from French Guiana Amazonian forest trees highlights the correlation between the activity of their extracts against wood-rotting fungi and human pathogens. The fractionation of an ethyl acetate extract of Sextonia rubra wood led to the isolation of rubrenolide (1) and rubrynolide (2). The potential of compounds 1 and 2 is described through the evaluation of their activity against 16 pathogenic fungi and their cytotoxicity toward NIH-3T3 mammalian fibroblast cells.
Published: 2010
Full Text: View/download PDF

50. Research of antifungal compounds from the Amazonian biomass by a bio-inspired approach

Author: L Salmen Espindola, Didier Stien, and Charlie Basset
Subjects: Pharmacology, Antifungal, medicine.drug_class, business.industry, Amazonian, Organic Chemistry, Pharmaceutical Science, Biomass, Biology, Analytical Chemistry, Biotechnology, Complementary and alternative medicine, Drug Discovery, Botany, medicine, Molecular Medicine, business
Published: 2010
Full Text: View/download PDF

Catalog

Books, media, physical & digital resources

See catalog results

Searchworks

Select search scope, currently: Articles Catalog books, media & more in Jio Institute collections Articles journal articles & other e-resources

Search

Search Constraints

Refine your results

Search Limiters

Topic

Publication Year Range

Language

Publication Type

Journal

Database

Publisher

72 results on '"Didier Stien"'

Search Results

Catalog

Select search scope, currently: Articles

Catalog

books, media & more in Jio Institute collections

Articles

journal articles & other e-resources