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379 results on '"Substances d'Origine Naturelle et Analogues Structuraux (SONAS)"'

52. Anti-inflammatory activity of vitamin E derivatives

Author

Dinh, Chau-Phi, Ville, Alexia, Anaïs, Barbe, To, Thuy-Linh, Neukirch, Konstantin, Viault, Guillaume, Koeberle, Andreas, Temml, Veronika, Werz, Oliver, Schuster, Daniela, Helesbeux, Jean-Jacques, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), and Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany]

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019

53. SEMISYNTHESIS OF BIOACTIVE C-BENZYLATEDDIHYDROCHALCONES FROM RENEWABLE SOURCES

Author

Cala Peralta, Antonio, Mayr, Fabian, Viault, Guillaume, Temml, Veronika, Schuster, Daniela, Stuppner, Hermann, Seraphin, Denis, Helesbeux, Jean-Jacques, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019

56. Design, Synthesis, Pharmacological Evaluation and Vascular Effects of Delphinidin Analogues

Author

Yannick Abatuci, Olivier Duval, Claire Lugnier, Sébastien Faure, Jean-Jacques Helesbeux, Hélène Justiniano, Samuel Legeay, Kien Trân, Université d'Angers (UA), Biophotonique et Pharmacologie (CNRS UMR 7213), Centre National de la Recherche Scientifique (CNRS), Micro et Nanomédecines Biomimétiques (MINT), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL), and Substances d'Origine Naturelle et Analogues Structuraux (SONAS)

Subjects
Vasodilator Agents, Aorta, Thoracic, Pharmacology, Nitric Oxide, Nitric oxide, Anthocyanins, 03 medical and health sciences, chemistry.chemical_compound, Mice, 0302 clinical medicine, In vivo, Drug Discovery, medicine, Human Umbilical Vein Endothelial Cells, Animals, Humans, Endothelial dysfunction, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Anthocyanidin, 0303 health sciences, Cyclic nucleotide phosphodiesterase, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Estrogen Receptor alpha, Biological activity, medicine.disease, In vitro, chemistry, 030220 oncology & carcinogenesis, Drug Design, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Delphinidin
Abstract

Background: Among polyphenolic compounds suggested to prevent cardiovascular diseases (CVDs) and to explain the “French paradox”, the anthocyanidin delphinidin (Dp) has been reported to support at least partly the vascular beneficial effects of dietary polyphenolic compounds including those from fruits and related products as red wine. It has also been highlighted that Dp interacts directly with the active site of estrogen receptor α (ERα), leading to activation of endothelial NO synthase (eNOS) pathway thus contributing to the prevention of endothelial dysfunction in mice aorta. However, anthocyanidins have very low bioavailability and despite a well described in vitro efficacy, the very high hydrophilicity and physicochemical instability of Dp might explain the lack of in vivo reported effects. Objective: The aim of this study was to identify new Dp analogues with increased lipophilicity and vasorelaxation potential by a chemical modulation of its structure and to characterize the signaling pathway notably in relation with ERα signaling and nitric oxide (NO) production. Method: OCH3-substituted delphinidin analogues were obtained through the coupling of the corresponding acetophenones with substituted benzaldehydes. Prediction of resorption of the flavylium derivatives was performed with the calculated logP and induction of vasorelaxation was performed by myography on WT and ERαKO mice thoracic aorta rings and compared to Dp. NO production was evaluated in vitro on human primary endothelial cells. Results: Eight Dp analogues were synthesized including four new flavylium derivatives. Two compounds (9 and 11) showed a strong increase of vasorelaxation potential and a theoretically increased bioavailability compared to Dp. Interestingly, 9 and 11 induced increased O2 - or NO endothelial production respectively and revealed a novel NO-dependent ERα-independent relaxation compared to Dp. We suggested that this mechanism may be at least in part supported by the inhibition of vascular cyclic nucleotide phosphodiesterase (PDEs). Conclusion: The current study demonstrated that pharmacomodulation of the Dp backbone by replacement of OH groups by OCH3 groups of the A and B rings led to the identification and characterization of two compounds (9 and 11) with enhanced physio-chemical properties that could be associated to higher permeability capability and pharmacological activity for the prevention of CVDs compared to Dp.

Published
2019

57. Mycolactone as Analgesic: Subcutaneous Bioavailability Parameters

Author

David Guilet, Estelle Marion, Pascal Richomme, Jean-Paul Saint André, Laurent Marsollier, Anne Croué, Dimitri Bréard, Priscille Brodin, Jérémie Babonneau, Marie-Line Reynaert, ATOMycA (CRCINA-ÉQUIPE 6), Centre de Recherche en Cancérologie et Immunologie Nantes-Angers (CRCINA), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), SFR UA 4207 QUAlité et SAnté du Végétal (QUASAV), Université d'Angers (UA)-Institut National de la Recherche Agronomique (INRA)-Université de Nantes (UN)-AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Ecole supérieure d'Agricultures d'Angers (ESA), Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 (CIIL), Centre National de la Recherche Scientifique (CNRS)-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille)-Université de Lille-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Laboratoire d’Anatomie Pathologique [ICO, Angers] (Site Paul Papin), Institut de Cancérologie de l'Ouest [Angers/Nantes] (UNICANCER/ICO), UNICANCER-UNICANCER, This work was supported by the region Pays de la Loire (Kalmos project), the Agence Nationale de Recherche (ANR-17-CE18-0001), the Institut Pasteur of Lille (granted to PB and M-LR), the Inserm Program ATIP avenir (granted to LM), the region Pays de la Loire (Kalmos project) and Angers University., ANR-17-CE18-0001,AT2R-TRAAK-BIOANALGESICS,Caractérisations moléculaires et cellulaires de voies de signalisation de la douleur: contrôle de la douleur dans l'ulcère de buruli comme source d'inspiration pour la conception rationnelle de nouveaux analgésiques puissants(2017), Bernardo, Elizabeth, Caractérisations moléculaires et cellulaires de voies de signalisation de la douleur: contrôle de la douleur dans l'ulcère de buruli comme source d'inspiration pour la conception rationnelle de nouveaux analgésiques puissants - - AT2R-TRAAK-BIOANALGESICS2017 - ANR-17-CE18-0001 - AAPG2017 - VALID, Université d'Angers (UA)-Université de Nantes (UN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Université d'Angers (UA)-Université de Nantes (UN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes), Université d'Angers (UA)-Institut National de la Recherche Agronomique (INRA)-Université de Nantes (UN)-AGROCAMPUS OUEST-Ecole supérieure d'Agricultures d'Angers (ESA), Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille)-Centre National de la Recherche Scientifique (CNRS), ATIP AVENIR / ATOMycA (CRCINA - Département INCIT - Equipe 6), Centre de recherche de Cancérologie et d'Immunologie / Nantes - Angers (CRCINA), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN), Institut National de la Recherche Agronomique (INRA)-Ecole supérieure d'Agricultures d'Angers (ESA)-Université de Nantes (UN)-AGROCAMPUS OUEST-Université d'Angers (UA), Centre d’Infection et d’Immunité de Lille (CIIL) - U1019 - UMR 8204 (CIIL), Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), and Institut de cancérologie de l'Ouest - Paul Papin (ICO - Paul Papin)

Subjects
0301 basic medicine, Buruli ulcer, [SDV.CAN]Life Sciences [q-bio]/Cancer, mycolactone, Pharmacology, medicine.disease_cause, 03 medical and health sciences, chemistry.chemical_compound, Subcutaneous injection, 0302 clinical medicine, [SDV.CAN] Life Sciences [q-bio]/Cancer, biological action, medicine, Pharmacology (medical), Mycolactone, Original Research, Mycobacterium ulcerans, biology, Toxin, lcsh:RM1-950, analgesia, Hypoesthesia, biology.organism_classification, medicine.disease, 3. Good health, lcsh:Therapeutics. Pharmacology, 030104 developmental biology, Nociception, chemistry, 030220 oncology & carcinogenesis, medicine.symptom, bioavailability, Panniculitis
Abstract

Jérémie Babonneau, Dimitri Bréard and Marie-Line Reynaert have contributed equally to this work. Priscille Brodin, Pascal Richomme and Laurent Marsollier are co-senior authors.; International audience; Mycobacterium ulcerans is the bacillus responsible for Buruli ulcer, an infectious disease and the third most important mycobacterial disease worldwide, after tuberculosis and leprosy. M. ulcerans infection is a type of panniculitis beginning mostly with a nodule or an oedema, which can progress to large ulcerative lesions. The lesions are caused by mycolactone, the polyketide toxin of M. ulcerans. Mycolactone plays a central role for host colonization as it has immunomodulatory and analgesic effects. On one hand, mycolactone induces analgesia by targeting type-2 angiotensin II receptors (AT 2 R), causing cellular hyperpolarization and neuron desensitization. Indeed, a single subcutaneous injection of mycolactone into the mouse footpad induces a long-lasting hypoesthesia up to 48 h. It was suggested that the long-lasting hypoesthesia may result from the persistence of a significant amount of mycolactone locally following its injection, which could be probably due to its slow elimination from tissues. To verify this hypothesis, we investigated the correlation between hypoesthesia and mycolactone bioavailability directly at the tissue level. Various quantities of mycolactone were then injected in mouse tissue and hypoesthesia was recorded with nociception assays over a period of 48 h. The hypoesthesia was maximal 6 h after the injection of 4 µg mycolactone. The basal state was reached 48 h after injection, which demonstrated the absence of nerve damage. Surprisingly, mycolactone levels decreased strongly during the first hours with a reduction of 70 and 90% after 4 and 10 h, respectively. Also, mycolactone did not diffuse in neighboring skin tissue and only poorly into the bloodstream upon direct injection. Nevertheless, the remaining amount was sufficient to induce hypoesthesia during 24 h. Our results thus demonstrate that intact mycolactone is rapidly eliminated and that very small amounts of mycolactone are sufficient to induce hypoesthesia. Taken together, our study points out that mycolactone ought to be considered as a promising analgesic.

Published
2019

58. Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research

Author

Laurent Evanno, Mariia S. Kirillova, Fanny Roussi, Gaëla Cauchie, Pierre Champy, Marc Litaudon, Guy Lewin, Anne-Marie Le Ray, Raphaël Grougnet, Erwan Poupon, Marina Kritsanida, Lengo Mambu, Alexander E. Fox Ramos, Antonio M. Echavarren, Fedor M. Miloserdov, Pascal Richomme-Peniguel, Michel Frederich, Khalijah Awang, Sylvie Michel, Hazrina Hazni, Dimitri Bréard, Pierre Le Pogam, Christelle Lémus, Marion Girardot, Elvis Otogo N’Nang, Michael E. Muratore, Mehdi A. Beniddir, Charlotte Fox Alcover, Thomas Gaslonde, Institut de Recherches sur les lois Fondamentales de l'Univers (IRFU), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Université de Liège, Synthèse et structure de molécules d'interet pharmacologique (SSMIP), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Microbiologie de l'Eau (MDE), Ecologie et biologie des interactions (EBI), Université de Poitiers-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Centre National de la Recherche Scientifique (CNRS), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), PEIRENE (PEIRENE), Institut Génomique, Environnement, Immunité, Santé, Thérapeutique (GEIST), Université de Limoges (UNILIM)-Université de Limoges (UNILIM), Institut de Recherche en Gestion des Organisations (IRGO), Université de Bordeaux (UB)-Institut d'Administration des Entreprises (IAE) - Bordeaux, Équipe 'Pharmacognosie-Chimie des Substances Naturelles' BioCIS, Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11), Université de Rennes (UR), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Statistics and Probability, Data descriptor, Data Descriptor, 010504 meteorology & atmospheric sciences, Monoterpene, Library and Information Sciences, Tandem mass spectrometry, Mass spectrometry, 01 natural sciences, Education, 03 medical and health sciences, chemistry.chemical_compound, Life Science, [CHIM]Chemical Sciences, Metabolomics, Organic chemistry, lcsh:Science, 030304 developmental biology, 0105 earth and related environmental sciences, Indole test, Natural products, 0303 health sciences, Natural product, Indole alkaloid, Accession number (library science), Data acquisition, Computer Science Applications, chemistry, 13. Climate action, lcsh:Q, Statistics, Probability and Uncertainty, Information Systems
Abstract

This Data Descriptor announces the submission to public repositories of the monoterpene indole alkaloid database (MIADB), a cumulative collection of 172 tandem mass spectrometry (MS/MS) spectra from multiple research projects conducted in eight natural product chemistry laboratories since the 1960s. All data have been annotated and organized to promote reuse by the community. Being a unique collection of these complex natural products, these data can be used to guide the dereplication and targeting of new related monoterpene indole alkaloids within complex mixtures when applying computer-based approaches, such as molecular networking. Each spectrum has its own accession number from CCMSLIB00004679916 to CCMSLIB00004680087 on the GNPS. The MIADB is available for download from MetaboLights under the identifier: MTBLS142 (https://www.ebi.ac.uk/metabolights/MTBLS142)., Design Type(s)mass spectrometry data transformation objective • mass spectrometry data analysis objective • data integration objectiveMeasurement Type(s)mass spectrumTechnology Type(s)liquid chromatography-tandem mass spectrometryFactor Type(s)Sample Characteristic(s)Strychnos usambarensis • Picralima nitida • Geissospermum laeve • Pleiocarpa mutica • Alstonia • Callichilia inaequalis • Chimarris cymosa • Mostuea brunonis • Gonioma • Cinchona • Catharanthus roseus • Voacanga grandifolia Machine-accessible metadata file describing the reported data (ISA-Tab format)

Published
2019

59. Anti-inflammatory activity of w-oxidized tocotrienols

Author

Dinh, Chau-Phi, Ville, Alexia, BARBE, Anaïs, TO, Thuy Linh, Viault, Guillaume, Koeberle, Andreas, Werz, Oliver, Temml, Veronika, Schuster, Daniela, Helesbeux, Jean-Jacques, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], and Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019

60. Mesua sp.: chemical aspects and pharmacological relevance of prenylated polyphenols

Author

Séverine Derbré, Caroline Rouger, Pascal Richomme, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
0106 biological sciences, Antioxidant, medicine.medical_treatment, Plant Science, immunomodulation, 01 natural sciences, chemistry.chemical_compound, Prenylation, medicine, [CHIM]Chemical Sciences, xanthones, Cytotoxicity, biology, Chemistry, biology.organism_classification, Coumarin, Calophyllaceae, Antimicrobial, Mammea coumarins, 0104 chemical sciences, Mesua, 010404 medicinal & biomolecular chemistry, Biochemistry, Polyphenol, prenylated polyphenols, 010606 plant biology & botany, Biotechnology, Mesua L
Abstract

International audience; The genus Mesua L. (Calophyllaceae) comprises approximately 50 species that grow in the restrictive area of South East Asia. Investigations of Mesua species reported the chemodiversity and pharmacological relevance of their phytoconstituents, in particular polyphenolic compounds. To date, about 170 secondary metabolites have been identified from 13 Mesua species, predominantly xanthones and coumarins. Most of them hold a prenylated skeleton and display activities such as antitumor and antimicrobial, antioxidant, anti-inflammatory or immunomodulating properties, which were evaluated using either in vitro assay or, in rare cases, in vivo animal studies. Prenylation of aromatic compounds appears as a key element to enhance their biological activities, including their cytotoxicity and, could be involved in their inhibitory potential towards enzymes playing crucial roles in inflammatory and immune cascades. The aim of this review is to provide a systematic and comprehensive overview of Mesua polyphenolic secondary metabolites and their pharmacological properties. Among them, the structure of coumarin beccamarin T is herein revised and attributed to lepidotol A based on a careful examination of the 1D and 2D NMR spectra of the respective compounds. A considerable attention is also given to the place of prenylated polyphenols as anti-inflammatory and immunomodulatory molecules, to highlight the interest of Mesua metabolites as chemical probes for target discovery.

Published
2019

61. Analysis of Complex Mixtures

Author

Skopikova, Michaela, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019

62. Efficient Semi-Synthesis of Natural δ-( R )-Tocotrienols from a Renewable Vegetal Source

Author

Denis Séraphin, Jean-Jacques Helesbeux, Pascal Richomme, Guillaume Viault, David Guilet, Alexia Ville, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
Subfamily, medicine.medical_treatment, Pharmaceutical Science, Computational biology, 01 natural sciences, Natural (archaeology), Analytical Chemistry, Drug Discovery, medicine, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, Pharmacology, 010405 organic chemistry, business.industry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Tocotrienols, Vitamin E, Organic Chemistry, Biological potential, 0104 chemical sciences, Renewable energy, 010404 medicinal & biomolecular chemistry, Complementary and alternative medicine, Molecular Medicine, Garcinia, business
Abstract

Recent studies have highlighted the biological potential of tocotrienols, a vitamin E subfamily. The major natural sources of tocotrienols are complex mixtures requiring particularly challenging purification processes. The present study describes efficient semi-synthetic strategies toward relevant δ-( R)-tocotrienol derivatives, using as a starting material δ-( R)-garcinoic acid, the major vitamin E derivative isolated from Garcinia kola nuts, a renewable vegetal source.

Published
2019

63. New Developments of Laser Desorption Ionization Mass Spectrometry in Natural Products Research

Author

Andreas Schinkovitz, Denis Séraphin, Pascal Richomme, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
Ionization, Mass spectrometry, Chemistry, secondary metabolites, Electrospray ionization, [SDV]Life Sciences [q-bio], 010401 analytical chemistry, Analytical chemistry, Laser, Atmospheric-pressure chemical ionization, 02 engineering and technology, 021001 nanoscience & nanotechnology, 01 natural sciences, Small molecule, 0104 chemical sciences, law.invention, law, Desorption, desorption, Gas chromatography, 0210 nano-technology
Abstract

Mass spectrometry (MS) represents an indispensable tool for the structural identification of natural products (NPs) and is one of the major focus areas of analytical chemistry research. The technique has long been used to obtain molecular weights and further molecular formulae. In the past, former ionization sources such as electronic impact (EI) limited MS analysis to predominately volatile, polar, and thermostable compounds. However, the development of soft ionization techniques such as electrospray ionization (ESI), atmospheric pressure chemical ionization (APCI), and laser desorption/ionization (LDI) have gradually extended the scope of MS analysis to a much wider range of chemical entities. Moreover, the hyphenation of liquid and gas chromatography with MS (LC‐MS, GC‐MS) has provided a most powerful tool for the analysis of complex mixtures and NPs. In fact, LC‐MS is often considered as a method of first choice particularly when studying complex mixtures of small molecules. On the other hand, recent developments in matrix‐assisted laser desorption/ionization (MALDI) and LDI may provide useful supplements and potential alternatives to this approach. Both methods share similar, though slightly different ionization mechanisms. While MALDI uses small molecules comprising strong UV chromophores (matrices) to transfer laser energy to the sample material, LDI targets compounds that can be directly ionized by laser irradiation without any matrix support. Moreover, certain compounds showing LDI properties may also work as MALDI matrices. With regard to NPs research, MALDI and LDI may help overcoming certain limitations encountered in LC‐MS such as the indispensable use of buffer solutions when analyzing alkaloids. Moreover, as (MA)LDI hardly requires any sample conditioning, analysis time can be significantly shortened.With all this in mind, the subsequent article will highlight some interesting MALDI and LDI applications, which focus on the detection of NPs in complex mixtures. This includes the use of specifically adapted matrices for the selective detection of alkaloids (i), the study of the inherent LDI and matrix properties of phenolic compounds (ii) as well of evaluation on the reproducibility of LDI signal patterns (iii). Eventually, a statistical approach toward LDI profiling, which may provide a future tool for quality control of large sample batches will be presented (iv).

Published
2019

64. Characterization of glycosylated flavonoids obtained from enzymatic reaction by matrix free laser desorption ionization mass spectrometry (LDI-MS)

Author

J Guerry, Andreas Schinkovitz, Pascal Richomme, C Miral, Michaela Skopikova, David Guilet, C Solleux, B Offmann, Ingrid Freuze, T Brouté, Séverine Boisard, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Plateforme d'Ingénierie et d'Analyses Moléculaires (PIAM), Unité de Biotechnologie, Biocatalyse et Biorégulation (U3B), Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS), Unité de fonctionnalité et ingénierie de protéines (UFIP), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), and Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Matrix (chemical analysis), Chromatography, Enzyme, Chemistry, Laser desorption ionization mass spectrometry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, Characterization (materials science)
Abstract

International audience

Published
2019

65. Use of 3-phenyl-prop-2-enoic acid esters from papaya as biodegradable anti-scaling agents to inhibit formation of limestone deposits

Author

Richomme, Pascal, Derbré, Séverine, Binachon, Christophe, Dejoie, Stéphane, Boulmane, Rim, Cheap-Charpentier, Hélène, Horner, Olivier, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), EPF-Graduate School of Engineering, Laboratoire Interfaces et Systèmes Electrochimiques (LISE), and Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[SDV]Life Sciences [q-bio], [CHIM]Chemical Sciences
Published
2019

67. Botanical origin of triterpenoids from Yucatecan propolis

Author

Martha Leyte-Lugo, Luis M. Peña-Rodríguez, Andreas Schinkovitz, Mercedes G. Herrera-López, Luz María Calvo-Irabién, Evelyn I. Rubio-Hernández, Pascal Richomme, Centro de Investigacion Cientifica de Yucatan (CICY), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
Yucatan peninsula, Flora, Traditional medicine, 010405 organic chemistry, Bursera simaruba, [SDV]Life Sciences [q-bio], Mangifera indica, Dammarenediol II, Plant Science, Biology, Propolis, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, Cycloartanes, Triterpenoid, Close relationship, Pentacyclic Triterpenes, Agronomy and Crop Science, Biotechnology, Dammarennediols
Abstract

International audience; Propolis is a resinous material produced by bees from plant exudates; the most common secondary metabolites found in propolis are poliphenolics with different biological activities. Nevertheless, to date, there are a number of reports describing the presence of triterpenoids in propolis. This work describes the isolation and identification of the triterpenoids mangiferolic acid (1), iso-mangiferolic acid (2), and dammarenediol II (3), together with a number of ubiquitous pentacyclic triterpenes, from the extract of a propolis sample collected in Yucatan, Mexico. While the cycloartanes 1 and 2 have been reported previously from propolis samples collected in Africa, Asia and South America, this is the first report of 3 as a component in propolis. The botanical origin of 3 and the pentacyclic triterpenes has been traced to the resin of Bursera simaruba, a tree commonly found in Yucatan peninsula. The results of this investigation confirm the close relationship between the flora surrounding the beehive and the chemical composition of propolis

Published
2019

69. 13C-NMR dereplication of complex mixtures using a custom software

Author

Bruguière, Antoine, Derbré, Séverine, Dietsch, Joël, Leguy, Jules, Rahier, Valentine, Pottier, Quentin, Saubion, Frédéric, Richomme, Pascal, Viault, Guillaume, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and Laboratoire d'Etudes et de Recherche en Informatique d'Angers (LERIA)

Subjects
[CHIM] Chemical Sciences, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2019

70. Targeting MHC Regulation Using Polycyclic Polyprenylated Acylphloroglucinols Isolated from Garcinia bancana

Author

Khalijah Awang, Pascal Richomme, Antoine Bruguière, Nathalie Gérard, Séverine Derbré, Chau Phi Dinh, Sow Tein Leong, Caroline Rouger, Chloé Coste, Béatrice Charreau, AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro), Centre de Recherche en Transplantation et Immunologie (U1064 Inserm - CRTI), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and University of Malaya [Kuala Lumpur, Malaisie]

Subjects
0301 basic medicine, HLA-E, Acylation, [SDV]Life Sciences [q-bio], lcsh:QR1-502, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, polycyclic polyprenylated acylphloroglucinols, Biochemistry, lcsh:Microbiology, 0302 clinical medicine, Tapasin, p300-CBP Transcription Factors, STAT1, Garcinia, biology, Chemistry, Nuclear Proteins, Garcinia bancana, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, major histocompatibility complex, 3. Good health, GATA2 Transcription Factor, Molecular Docking Simulation, STAT1 Transcription Factor, 030220 oncology & carcinogenesis, endothelium, Primary Cell Culture, Down-Regulation, Phloroglucinol, Major histocompatibility complex, Article, histone acetyltransferase, Benzophenones, Interferon-gamma, 03 medical and health sciences, Clusiaceae, xanthochymol, CIITA, Humans, Polycyclic Compounds, ATP Binding Cassette Transporter, Subfamily B, Member 2, Molecular Biology, Transcription factor, Prenylation, Terpenes, Endothelial Cells, Membrane Transport Proteins, guttiferone J, Histone acetyltransferase, biology.organism_classification, guttiferone F, 030104 developmental biology, Trans-Activators, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, biology.protein
Abstract

Modulation of major histocompatibility complex (MHC) expression using drugs has been proposed to control immunity. Phytochemical investigations on Garcinia species have allowed the isolation of bioactive compounds such as polycyclic polyprenylated acylphloroglucinols (PPAPs). PPAPs such as guttiferone J (1), display anti-inflammatory and immunoregulatory activities while garcinol (4) is a histone acetyltransferases (HAT) p300 inhibitor. This study reports on the isolation, identification and biological characterization of two other PPAPs, i.e., xanthochymol (2) and guttiferone F (3) from Garcinia bancana, sharing structural analogy with guttiferone J (1) and garcinol (4). We show that PPAPs 1&ndash, 4 efficiently downregulated the expression of several MHC molecules (HLA-class I, -class II, MICA/B and HLA-E) at the surface of human primary endothelial cells upon inflammation. Mechanistically, PPAPs 1&ndash, 4 reduce MHC proteins by decreasing the expression and phosphorylation of the transcription factor STAT1 involved in MHC upregulation mediated by IFN-&gamma, Loss of STAT1 activity results from inhibition of HAT CBP/p300 activity reflected by a hypoacetylation state. The binding interactions to p300 were confirmed through molecular docking. Loss of STAT1 impairs the expression of CIITA and GATA2 but also TAP1 and Tapasin required for peptide loading and transport of MHC. Overall, we identified new PPAPs issued from Garcinia bancana with potential immunoregulatory properties.

Published
2020

71. Structure-based design, semi-synthesis and anti-inflammatory activity of tocotrienolic amides as 5-lipoxygenase inhibitors

Author

Jean-Jacques Helesbeux, Andreas Koeberle, Pascal Richomme, Denis Séraphin, Veronika Temml, Konstantin Neukirch, Hermann Stuppner, Oliver Werz, Guillaume Viault, Daniela Schuster, Chau Phi Dinh, Alexia Ville, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], and Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI)

Subjects
medicine.drug_class, medicine.medical_treatment, Inflammation, Pharmacology, 01 natural sciences, Anti-inflammatory, law.invention, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, law, Drug Discovery, medicine, [CHIM]Chemical Sciences, Humans, Vitamin E, Lipoxygenase Inhibitors, IC50, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, 0303 health sciences, Arachidonate 5-Lipoxygenase, Dose-Response Relationship, Drug, Molecular Structure, biology, 010405 organic chemistry, Anti-Inflammatory Agents, Non-Steroidal, Organic Chemistry, General Medicine, Lipid signaling, Amides, Recombinant Proteins, 3. Good health, 0104 chemical sciences, Molecular Docking Simulation, chemistry, Drug Design, Arachidonate 5-lipoxygenase, Recombinant DNA, biology.protein, Arachidonic acid, medicine.symptom
Abstract

Inflammation contributes to the development of various pathologies, e.g. asthma, cardiovascular diseases, some types of cancer, and metabolic disorders. Leukotrienes (LT), biosynthesized from arachidonic acid by 5-lipoxygenase (5-LO), constitute a potent family of pro-inflammatory lipid mediators. δ-Garcinoic acid (δ-GA) (1), a natural vitamin E analogue, was chosen for further structural optimization as it selectively inhibited 5-LO activity in cell-free and cell-based assays without impairing the production of specialized pro-resolving mediators by 15-LO. A model of semi-quantitative prediction of 5-LO inhibitory potential developed during the current study allowed the design of 24 garcinamides that were semi-synthesized. In accordance with the prediction model, biological evaluations showed that eight compounds potently inhibited human recombinant 5-LO (IC50

Published
2020

72. Xanthone derivatives from NPs library as potential UPR inhibitors for alternative crop protection: Molecular modelling and biological activity

Author

Viault, Guillaume, Bréard, Dimitri, Dinh, Chau-Phi, Nadège, Blon, Bruguière, Antoine, Le Ray, Anne-Marie, Bataille-Simoneau, Nelly, Guillemette, Thomas, Simoneau, Philippe, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Institut de Recherche en Horticulture et Semences (IRHS), Université d'Angers (UA)-AGROCAMPUS OUEST, and Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
[SDV]Life Sciences [q-bio], [SDE]Environmental Sciences, [CHIM]Chemical Sciences, [SDV.BID]Life Sciences [q-bio]/Biodiversity, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

73. 13C-NMR dereplication of complex mixtures: building a custom search algorithm

Author

Bruguière, Antoine, Derbré, Séverine, Dietsch, Joël, Saubion, Frédéric, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and Laboratoire d'Etudes et de Recherche en Informatique d'Angers (LERIA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

75. Endogenous metabolites of vitamin E limit inflammation by targeting 5-lipoxygenase

Author

Pein, Helmut, Pace, Simona, Temml, Veronika, Garscha, Ulrike, Waltenberger, Birgit, Stuppner, Hermann, Roviezzo, Fiorentina, Helesbeux, Jean-Jacques, Seraphin, Denis, Mosig, Alexander, Schuster, Daniela, Rossi, Antonietta, Richomme, Pascal, Werz, Oliver, Koeberle, Andreas, Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Department of Experimental Pharmacology, University of Naples Federico II, Jena University, and Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany]

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

76. Omega-oxidized terpenoids: from traditional African medicine to novel insights into human vitamin physiology

Author

Pein, Helmut, Pace, Simona, Temml, Veronika, Garscha, Ulrike, Waltenberger, Birgit, Stuppner, Hermann, Roviezzo, Fiorentina, Helesbeux, Jean-Jacques, Seraphin, Denis, Mosig, Alexander, Schuster, Daniela, Rossi, Antonietta, Richomme, Pascal, Werz, Oliver, Koeberle, Andreas, Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Department of Experimental Pharmacology, University of Naples Federico II, Jena University, and Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany]

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

77. Additional Insights into Hypericum perforatum Content: Isolation, Total Synthesis, and Absolute Configuration of Hyperbiphenyls A and B from Immunomodulatory Root Extracts

Author

Séverine Derbré, Dimitri Bréard, Béatrice Charreau, Guillaume Viault, Antoine Bruguière, Sylvain Pagie, Pascal Richomme, Marie-Charlotte Mezier, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Centre de Recherche en Transplantation et Immunologie (U1064 Inserm - CRTI), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN), Institut de transplantation urologie-néphrologie (ITUN), Université de Nantes (UN)-Centre hospitalier universitaire de Nantes (CHU Nantes), Immunoregulation And Immunointervention in Transplantation and Autoimmunity (Team 4 - U1064 Inserm - CRTI), Université de Nantes (UN)-Université de Nantes (UN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Region Pays de la Loire (HYPROTEC project). Nantes Metropole., Grants from the Ministère de l’Enseignement Supérieur et de la Recherche., The 'Fondation Centaure' (RTRS)., ANR-10-IBHU-0005,CESTI (TSI-IHU),Centre Européen des Sciences de la Transplantation et de l'Immunothérapie (TSI-IHU)(2010), ANR-11-LABX-0016,IGO,Immunothérapies Grand Ouest(2011), ANR-10-IDEX-0002,UNISTRA,Par-delà les frontières, l'Université de Strasbourg(2010), Le Bihan, Sylvie, Instituts Hospitalo-Universitaires B - Centre Européen des Sciences de la Transplantation et de l'Immunothérapie (TSI-IHU) - - CESTI (TSI-IHU)2010 - ANR-10-IBHU-0005 - IBHU - VALID, Laboratoires d'excellence - Immunothérapies Grand Ouest - - IGO2011 - ANR-11-LABX-0016 - LABX - VALID, and Initiative d'excellence - Par-delà les frontières, l'Université de Strasbourg - - UNISTRA2010 - ANR-10-IDEX-0002 - IDEX - VALID

Subjects
Spectrometry, Mass, Electrospray Ionization, Magnetic Resonance Spectroscopy, Stereochemistry, Pharmaceutical Science, Stereoisomerism, Fluorine-19 NMR, 01 natural sciences, Plant Roots, Analytical Chemistry, chemistry.chemical_compound, Drug Discovery, Xanthone, Human Umbilical Vein Endothelial Cells, Humans, Immunologic Factors, Benzopyrans, Nuclear Magnetic Resonance, Biomolecular, Benzofurans, Pharmacology, [SDV.MHEP] Life Sciences [q-bio]/Human health and pathology, 010405 organic chemistry, Chemistry, Organic Chemistry, Biphenyl Compounds, Absolute configuration, Hypericum perforatum, Total synthesis, Nuclear magnetic resonance spectroscopy, 0104 chemical sciences, Biphenyl compound, 010404 medicinal & biomolecular chemistry, Complementary and alternative medicine, Molecular Medicine, Spectrophotometry, Ultraviolet, Hypericum, [SDV.MHEP]Life Sciences [q-bio]/Human health and pathology
Abstract

International audience; Phytochemical investigation of the root extracts of Hypericum perforatum led to the isolation of two biphenyl derivatives named hyperbiphenyls A and B (1 and 2) and four known xanthones (3−6). These structures were elucidated by spectroscopic and spectrometric methods including UV, NMR, and HRMS. The absolute configuration of the biphenyl derivatives was defined by two different approaches: biomimetic total synthesis of racemic hyper-biphenyl A followed [1]H and [19]F NMR Mosher's esters analysis and stereoselective total synthesis of hyperbiphenyl B, permitting assignment of the S absolute configuration for both compounds. The bioactivity of compounds 1−6 toward a set of biomolecules, including major histocompatibility complex (MHC) molecules expressed on vascular endothelial cells, was measured. The results showed that the major xanthone, i.e., 5-O-methyl-2-deprenylrheediaxanthone B (3), is a potent inhibitor of MHC that efficiently reduces HLA-E, MHC-II, and MICA biomolecules on cell surfaces.

Published
2018

78. Extraction and purification of antifungal xanthones from Garcinia mangostana (Clusiaceae)

Author

Viault, Guillaume, Suor-Cherer, Sorphon, Bréard, Dimitri, Dinh, Chau-Phi, Nadège, Blon, Le Ray, Anne-Marie, Bataillé, Nelly, Guillemette, Thomas, Simoneau, Philippe, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Institut de Recherche en Horticulture et Semences (IRHS), AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de la Recherche Agronomique (INRA)-Université d'Angers (UA), Université d'Angers (UA)-AGROCAMPUS OUEST, and Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

80. Secondary metabolites from lichens as promising inhibitors of the formation of pentosidine like advanced glycosylation end products

Author

Schinkovitz, Andreas, Le Pogam, Pierre, Derbré, Séverine, Legouin, Béatrice, Le Lamer, Anne-Cécile, Blanchard, Patricia, Aumond, Marie-Christine, Tomasi, Sophie, Boustie, Joël, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), and Université de Rennes (UR)

Subjects
[SDV]Life Sciences [q-bio]
Published
2018

81. Computational analysis of the interaction between vitamin E derivatives and 5-lipoxygenase

Author

Temml, Veronika, Pein, Helmut, Pace, Simona, Garscha, Ulrike, Waltenberger, Birgit, Stuppner, Hermann, Roviezzo, Fiorentina, Helesbeux, Jean-Jacques, Seraphin, Denis, Rossi, Antonietta, Richomme, Pascal, Werz, Oliver, Koeberle, Andreas, Schuster, Daniela, Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Department of Experimental Pharmacology, University of Naples Federico II, Jena University, and Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany]

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

82. Design, semisynthesis and biological evaluations of garcinoic acid derivatives as novel anti-inflammatory

Author

Dinh, Chau-Phi, Helesbeux, Jean-Jacques, Koeberle, Andreas, Schuster, Daniela, Werz, Oliver, Stuppner, Hermann, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], and Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

84. Synthèse et évaluation biologique de nouveaux actifs potentiels ciblant les dysfonctionnements mitochondriaux

Author

Viault, Guillaume, Benamar, Abdel, Mao, Morgane Le, Andriantsitohaina, R., Helesbeux, Jean-Jacques, Macherel, David, Lenaers, Guy, Richomme, Pascal, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Institut de Recherche en Horticulture et Semences (IRHS), Université d'Angers (UA)-AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Physiopathologie Cardiovasculaire et Mitochondriale (MITOVASC), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Stress Oxydant et Pathologies Métaboliques (SOPAM), and Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

86. New avenues for Good Old Natural Products (NPs)

Author

Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

87. Semisynthesis of δ-(R)-tocotrienols

Author

Ville, Alexia, Viault, Guillaume, Helesbeux, Jean-Jacques, Guilet, David, Richomme, Pascal, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

88. Semi-synthetic derivatives and endogenous metabolites of vitamin E as potent, selective and orally available inhibitors of 5 lipoxygenase

Author

Koeberle, Andreas, Pein, Helmut, Pace, Simona, Temml, Veronika, Garscha, Ulrike, Waltenberger, Birgit, Stuppner, Hermann, Wallert, Marta, Lorkowski, Stefan, Birringer, Mark, Rossi, Antonietta, Helesbeux, Jean-Jacques, Seraphin, Denis, Mosig, Alexander, Schuster, Daniela, Richomme, Pascal, Werz, Oliver, Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Department of Experimental Pharmacology, University of Naples Federico II, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

89. Design, semisynthesis and biological evaluations of garcinoic acid derivatives as novel anti-inflammatory agents

Author

Dinh, Chau-Phi, Viault, Guillaume, Koeberle, Andreas, Stuppner, Hermann, Schuster, Daniela, Werz, Oliver, Helesbeux, Jean-Jacques, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], and Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

90. Garcinia species are potent and selective, allosteric inhibitors of 5-lipoxygenase and provide novel insights into human vitamin E physiology

Author

Koeberle, Andreas, Pein, Helmut, Pace, Simona, Temml, Veronika, Garscha, Ulrike, Waltenberger, Birgit, Stuppner, Hermann, Helesbeux, Jean-Jacques, Seraphin, Denis, Mosig, Alexander, Schuster, Daniela, Rossi, Antonietta, Richomme, Pascal, Werz, Oliver, Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Department of Experimental Pharmacology, and University of Naples Federico II

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

91. Computational binding mode prediction of ω-oxidized tocotrienols as inhibitors of 5-lipoxygenase

Author

Temml, Veronika, Koeberle, Andreas, Garscha, Ulrike, Helesbeux, Jean-Jacques, Waltenberger, Birgit, Seraphin, Denis, Richomme, Pascal, Stuppner, Hermann, Werz, Oliver, Schuster, Daniela, Department of Pharmacology and Toxicology and Center for Molecular Biosciences Innsbruck (CMBI), Jena University, Friedrich-Schiller-Universität = Friedrich Schiller University Jena [Jena, Germany], Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

93. Laser desorption ionization mass spectrometry as an analytical tool for the investigation of Malus X Domestica treated by selected plant resistant inducers

Author

Skopikova, Michaela, Gaucher, Matthieu, Boisard, Séverine, Brisset, Marie-Noelle, Richomme, Pascal, Schinkovitz, Andreas, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Institut de Recherche en Horticulture et Semences (IRHS), Université d'Angers (UA)-AGROCAMPUS OUEST-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Université d'Angers (UA)-AGROCAMPUS OUEST, and Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
[SDV.BID.EVO]Life Sciences [q-bio]/Biodiversity/Populations and Evolution [q-bio.PE], [SDV]Life Sciences [q-bio], fungi, food and beverages, [SDV.BDLR]Life Sciences [q-bio]/Reproductive Biology, [SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy
Abstract

Apple is a very important agricultural plant, and globally cultivated fruit tree. For its protection against pathogens, pesticides are commonly used, which poses a heavy burden on the environment. Therefore alternative methods of crop protection are being widely explored, some of them focusing on the stimulation of the plant’s immune defense (e.g. development of resistant genotypes, use of plant resistant inducers). In this respect, the induced formation of protective plant metabolites (phytoalexins) represents the most interesting strategy. Phytoalexins are monitored mostly by liquid chromatography coupled with mass spectrometry (LC-MS). For phenolic phytoalexins, matrix free laser desorption ionization (LDI) may provide a promising supplement or alternative, particularly as many phenols exhibit close structural similarities to commercial matrices used in matrix assisted laser desorption ionization (MALDI). Contrary to LC-MS, LDI-MS can be performed without time consuming sample preparation or chromatographic method optimization and is not limited to specific solvents.

Published
2018

94. Secondary metabolites from lichen as potent inhibitors of advanced glycation end products and vasodilative agents

Author

Dimitri Bréard, Brigitte Kopp, Séverine Derbré, Hermann Stuppner, Martin Zehl, Amandeep Kaur, Patricia Blanchard, Sophie Tomasi, Ernst Urban, Stefanie Hofer, Pascal Richomme, Daniel Henrion, Denis Séraphin, Pierre Le Pogam, Joël Boustie, Emilie Roy-Vessieres, Sangeetha-Laura Thirumaran, Andreas Schinkovitz, Marie-Chistine Aumond, Isabelle Baglin, Nathalie Jäger, SFR UA 4207 QUAlité et SAnté du Végétal (QUASAV), Institut National de la Recherche Agronomique (INRA)-Ecole supérieure d'Agricultures d'Angers (ESA)-Université de Nantes (UN)-AGROCAMPUS OUEST-Université d'Angers (UA), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS), Physiopathologie Cardiovasculaire et Mitochondriale (MITOVASC), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Angers (UA), Université d'Angers (UA), Technical University of Vienna [Vienna] (TU WIEN), University of Innsbruck, The University of Angers is gratefully acknowledged for funding the FIKETI project., Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), MitoVasc - Physiopathologie Cardiovasculaire et Mitochondriale (MITOVASC), Université d'Angers (UA)-Institut National de la Recherche Agronomique (INRA)-Université de Nantes (UN)-AGROCAMPUS OUEST-Ecole supérieure d'Agricultures d'Angers (ESA), Vienna University of Technology (TU Wien), Leopold Franzens Universität Innsbruck - University of Innsbruck, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université d'Angers (UA)-Institut National de la Recherche Agronomique (INRA)-Université de Nantes (UN)-AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Ecole supérieure d'Agricultures d'Angers (ESA), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)

Subjects
0301 basic medicine, Glycation End Products, Advanced, Male, Antioxidant, Lichens, DPPH, Radical scavenging, medicine.medical_treatment, Vasodilator Agents, Fluorescence assay, Secondary Metabolism, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Pharmacology, 01 natural sciences, Rats, Inbred WKY, 03 medical and health sciences, symbols.namesake, chemistry.chemical_compound, Glycation, Drug Discovery, Ic50 values, medicine, Animals, Declarations of interest none, Lichen, Biological Products, Molecular Structure, 010405 organic chemistry, Lichen metabolites, General Medicine, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, In vitro, Inhibition of Advanced Glycation End Products, 0104 chemical sciences, 3. Good health, Vasodilation, Maillard reaction, 030104 developmental biology, chemistry, symbols
Abstract

Secondary metabolites from lichens are known for exhibiting various biological effects such as anti-inflammatory, antioxidant and antibacterial activities. Despite this wide range of reported biological effects, their impact on the formation of advanced glycation end products (AGEs) remains vastly unexplored. The latter are known contributors to lifestyle and age-related diseases such as Alzheimer and Parkinson. Moreover, the development of atherosclerosis and arterial stiffness is causally linked to the formation of AGEs. With this in mind, the present work evaluated the inhibitory effects of secondary lichen metabolites on the formation of pentosidine-like AGEs' by using an in vitro, Maillard reaction based, fluorescence assay. Overall, thirty-seven natural and five synthetically modified compounds were tested, eighteen of which exhibiting IC50 values in the range of 0.05 to 0.70 mM. This corresponds to 2 to 32 fold of the inhibitory activity of aminoguanidine. Targeting one major inhibiting mechanism of AGEs formation, all compounds were additionally evaluated on their radical scavenging capacities in an DPPH assay. Furthermore, as both AGEs' formation and hypertension are major risk factors for atherosclerosis, compounds that were available in sufficient amounts were also tested for their vasodilative effects. Overall, and though some of the active compounds were previously reported cytotoxic, present results highlight the interesting potential of secondary lichen metabolites as anti-AGEs and vasodilative agents.

Published
2018

95. Matrix for specific detection of alkaloids by MALDI-​TOF mass spectrometry

Author

Seraphin, Denis, Guilet, David, Schinkovitz, Andreas, Richomme, Pascal, Dias, Marylène, Levillain, Eric, Jaber, Ali, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), MOLTECH-Anjou, Université d'Angers (UA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université d'Angers (UA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ANAL]Chemical Sciences/Analytical chemistry, [SDV]Life Sciences [q-bio], [CHIM]Chemical Sciences
Abstract

The présent invention relates to a novel bithiophenic matrix for spécifie détection of alkaloids by MALDI-TOF mass spectrometry; La présente invention concerne une nouvelle matrice bithiophénique pour la détection spécifique des alcaloïdes par spectrométrie de masse de type MALDI-TOF

Published
2018

96. Aldaulactone, a new phytotoxin involved in Alternaria dauci–Daucus carota interaction

Author

Courtial, Julia, Hamama, Latifa, Helesbeux, Jean-Jacques, Lecomte, Mickaël, Renaux, Yann, Guichard, Esteban, Voisine, Linda, Yovanopoulos, Claire, Hamon, Bruno, Ogé, Laurent, Richomme, Pascal, Briard, Mathilde, Boureau, Tristan, Gagné, Séverine, Poupard, Pascal, Berruyer, Romain, Institut de Recherche en Horticulture et Semences (IRHS), Université d'Angers (UA)-AGROCAMPUS OUEST, Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Université d'Angers (UA)-AGROCAMPUS OUEST-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut de Sciences Criminelles et de la Justice (ISCJ), and Université de Bordeaux (UB)

Subjects
[SDV]Life Sciences [q-bio], ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

97. Concise semisynthesis of novel phenazine-vitamin E hybrids via regioselective tocopheryl ortho-quinone formation

Author

Jean-Jacques Helesbeux, Pascal Richomme, Guillaume Viault, Denis Séraphin, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
quinone, natural product, Natural product, 010405 organic chemistry, Stereochemistry, Vitamin E, medicine.medical_treatment, phenazine, [SDV]Life Sciences [q-bio], Organic Chemistry, Phenazine, Regioselectivity, 010402 general chemistry, 01 natural sciences, Biochemistry, Semisynthesis, 0104 chemical sciences, Quinone, chemistry.chemical_compound, chemistry, Drug Discovery, medicine, semisynthesis, Quinone formation
Abstract

International audience; A regioselective method for the semisynthesis of phenazine derivatives has been disclosed through an efficient IBX mediated ortho-quinone formation from vitamin E derivatives. High chemo- and regio-selectivity was observed during the oxidation step and the corresponding 5,6-ortho-quinones could react with various phenylenediamines. Thus, this methodology proves its interest as a concise semisynthetic pathway to phenazine-vitamin E hybrids with moderate to good yields.

Published
2018

98. Analysis of complex phenolic mixtures by matrix free laser desorption ionization

Author

Schinkovitz, Andreas, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)

Subjects
[CHIM.ANAL]Chemical Sciences/Analytical chemistry
Abstract

National audience; The presentation highlights matrix free laser desorption ionization as a versatile tool for the characterization of complex mixtures of phenolic compounds.

Published
2018

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