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7. Looking for Actives in the Haystack: Merging HRMS2-Based Molecular Networking, Chemometrics, and 13C NMR-Based Dereplication Approaches

Author

Meunier, Manon, Bréard, Dimitri, Boisard, Séverine, Blanchard, Patricia, Litaudon, Marc, Awang, Khalijah, Schinkovitz, Andreas, and Derbré, Séverine

Abstract

The identification of bioactive natural products (NPs) in complex mixtures has become an important subject of contemporary NP research. In an attempt to address this challenge, the present work proposes an integrated strategy that combines tandem mass spectrometry (MS2)-based molecular networking (MN), a partial least-squares (PLS) chemometric model, as well as 13C NMR-based dereplication using MixONat software. In addition, an advanced glycation end product (AGEs) assay was used for activity evaluation. The approach was implemented on a Garcinia parvifoliabark extract that comprised a high content of prenylated xanthones and had previously shown a notable inhibitory effect on AGE formation. As a main result, the proposed strategy permitted the identification of potentially active metabolites within complex mixtures and their annotation with a higher level of confidence by NMR data. Overall, this comprehensive approach provides a powerful and efficient solution for the targeting and annotating of active compounds in complex NP mixtures.

Published
2024
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9. Adaptive remodeling of rat adrenomedullary stimulus-secretion coupling in response to a chronic hypertensive environment

Author

Paillé, Vincent, primary, Park, Joohee, additional, Toutain, Bertrand, additional, Bourreau, Jennifer, additional, Fontanaud, Pierre, additional, De Nardi, Frédéric, additional, Gabillard-Lefort, Claudie, additional, Bréard, Dimitri, additional, Guilet, David, additional, Henrion, Daniel, additional, Legros, Christian, additional, and Guérineau, Nathalie C., additional

Published
2023
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10. Chemodiversity of propolis samples collected in various areas of Benin and Congo: Chromatographic profiling and chemical characterization guided by 13 C NMR dereplication

Author

Azonwade, François, primary, Mabanza‐Banza, Balthazar B., additional, Le Ray, Anne‐Marie, additional, Bréard, Dimitri, additional, Blanchard, Patricia, additional, Goubalan, Elvire, additional, Lamine, Baba‐Moussa, additional, Banga‐Mboko, Henri, additional, Richomme, Pascal, additional, Derbré, Séverine, additional, and Boisard, Séverine, additional

Published
2023
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11. Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research

Author

Fox Ramos, Alexander E., Le Pogam, Pierre, Fox Alcover, Charlotte, Otogo N’Nang, Elvis, Cauchie, Gaëla, Hazni, Hazrina, Awang, Khalijah, Bréard, Dimitri, Echavarren, Antonio M., Frédérich, Michel, Gaslonde, Thomas, Girardot, Marion, Grougnet, Raphaël, Kirillova, Mariia S., Kritsanida, Marina, Lémus, Christelle, Le Ray, Anne-Marie, Lewin, Guy, Litaudon, Marc, Mambu, Lengo, Michel, Sylvie, Miloserdov, Fedor M., Muratore, Michael E., Richomme-Peniguel, Pascal, Roussi, Fanny, Evanno, Laurent, Poupon, Erwan, Champy, Pierre, and Beniddir, Mehdi A.

Published
2019
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12. Influence of Maceration Solvent on Chemical Composition of Gemmotherapy Macerates—A Case Study on Olea europaea Young Shoots.

Author

Bréard, Dimitri, Esselin, Hélène, Bugeia, Lucie, Boisard, Séverine, Guilet, David, Richomme, Pascal, Le Ray, Anne-Marie, and Ripoll, Christophe

Subjects
OLIVE varieties, NATUROPATHY, BUDS, PHYTOCHEMICALS, METABOLITES
Abstract

Gemmotherapy, a natural therapy based on bud macerates, has recently gained importance in the field of food supplements. However, two coexisting extraction methods employ a glycerin-based solvent, either in a binary or ternary solvent mixture. The absence of an official method for bud preparation leads to non-standardized bud macerates. Given this context, this study aimed to (i) assess the influence of solvent composition on the chemical profile of olive young shoot macerates obtained using glycerin-based solvents or using different solvent extractions and (ii) to compare the two coexisting traditional bud extraction methods described by Dr Pol Henry and by the European Pharmacopoeia. A comprehensive phytochemical analysis of all macerates was conducted using HPLC-DAD-ELSD-MS2, identifying 50 metabolites divided into 7 classes through dereplication. The extracts obtained with the solvent described by the European Pharmacopoeia (ethanol/glycerin) and by Dr Pol Henry (water/ethanol/glycerin) appeared to be the most diversified in terms of metabolite distribution and possessed higher rates of secondary metabolites. These observations reinforce the interest in a glycerin-based solvent mixture for bud extraction in gemmotherapy. In addition, the difference in composition between the two traditional solvents was highlighted. Indeed, iridoids were predominant in both macerates, representing about 50% of the chemical composition, but differences were observed from one macerate to another regarding the proportions of the other chemical classes. This emphasizes the necessity for standardized gemmotherapy macerates. [ABSTRACT FROM AUTHOR]

Published
2023
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14. Chemodiversity of propolis samples collected in various areas of Benin and Congo: Chromatographic profiling and chemical characterization guided by 13C NMR dereplication.

Author

Azonwade, François, Mabanza‐Banza, Balthazar B., Le Ray, Anne‐Marie, Bréard, Dimitri, Blanchard, Patricia, Goubalan, Elvire, Baba‐Moussa, Lamine, Banga‐Mboko, Henri, Richomme, Pascal, Derbré, Séverine, and Boisard, Séverine

Abstract

Introduction: Propolis is a resinous natural substance collected by honeybees from buds and exudates of various trees and plants; it is widely accepted that the composition of propolis depends on the phytogeographic characteristics of the site of collection. Objectives: The aim of this study was to determine the phytochemical composition of ethanolic extracts from eight propolis batches collected in different regions of Benin (north, center, and south) and Congo, Africa. Material and methods: Characterization of propolis samples was performed by using different hyphenated chromatographic methods combined with carbon‐13 nuclear magnetic resonance (13C NMR) dereplication with MixONat software. Their antioxidant or anti‐advanced glycation end‐product (anti‐AGE) activity was then evaluated by using diphenylpicrylhydrazyl and bovine serum albumin assays, respectively. Results: Chromatographic analyses combined with 13C NMR dereplication showed that two samples from the center of Benin exhibited, in addition to a huge amount of pentacyclic triterpenes, methoxylated stilbenoids or phenanthrenoids, responsible for the antioxidant activity of the extract for the first one. Among them, combretastatins might be cytotoxic. For the second one, the prenylated flavanones known in Macaranga‐type propolis were responsible for its significant anti‐AGE activity. The sample from Congo was composed of many triterpene derivatives belonging to Mangifera indica species. Conclusion: Therefore, propolis from the center of Benin seems to be of particular interest, due to its antioxidant and anti‐AGE properties. Nevertheless, as standardization of propolis is difficult in tropical zones due to its great chemodiversity, a systematic phytochemical analysis is required before promoting the use of propolis in food and health products in Africa. The composition of propolis depends on the phytogeographic characteristics of the collection site, including the plant species in the area. Propolis samples were analyzed using chromatographic methods combined with 13C NMR dereplication and MixONat software. Two Beninese ethanolic extracts showed common pentacyclic triterpenes and methoxylated stilbenoids or phenanthrenoids responsible for the antioxidant activity, and prenylated flavanones with significant anti‐AGE activity. The sample from Congo contained triterpene derivatives belonging to Mangifera indica species. [ABSTRACT FROM AUTHOR]

Published
2023
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16. Screening an In-House Isoquinoline Alkaloids Library for New Blockers of Voltage-Gated Na+ Channels Using Voltage Sensor Fluorescent Probes: Hits and Biases

Author

Coquerel, Quentin, primary, Legendre, Claire, additional, Frangieh, Jacinthe, additional, Waard, Stephan, additional, Montnach, Jérôme, additional, Cmarko, Leos, additional, Khoury, Joseph, additional, Hassane, Charifat, additional, Bréard, Dimitri, additional, Siegler, Benjamin, additional, Fajloun, Ziad, additional, De Pomyers, Harold, additional, Mabrouk, Kamel, additional, Weiss, Norbert, additional, Henrion, Daniel, additional, Richomme, Pascal, additional, Mattei, César, additional, Waard, Michel, additional, Le Ray, Anne-Marie, additional, and Legros, Christian, additional

Published
2022
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17. A Descriptive Chemical Composition of Concentrated Bud Macerates through an Optimized SPE-HPLC-UV-MS2 Method—Application to Alnus glutinosa, Ribes nigrum, Rosa canina, Rosmarinus officinalis and Tilia tomentosa

Author

Charpentier, Thomas, primary, Boisard, Séverine, additional, Le Ray, Anne-Marie, additional, Bréard, Dimitri, additional, Chabrier, Amélie, additional, Esselin, Hélène, additional, Guilet, David, additional, Ripoll, Christophe, additional, and Richomme, Pascal, additional

Published
2022
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20. Behavioral and Antennal Responses of Tribolium confusum to Varronia globosa Essential Oil and Its Main Constituents: Perspective for Their Use as Repellent

Author

Badji, Cesar Auguste, Dorland, Jean, Kheloul, Lynda, Bréard, Dimitri, Richomme, Pascal, Kellouche, Abdellah, Azevedo de Souza, Claudio Roberto, Bezerra, Antônio Lourenço, Anton, Sylvia, Institut de Génétique, Environnement et Protection des Plantes (IGEPP), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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), Universidade Federal Rural de Pernambuco (UFRPE), Université Mouloud Mammeri [Tizi Ouzou] (UMMTO), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), grant finance code 001, Coordenação de Aperfeiçamento de Pessoal de Nivel Superior-Brasil, Université de Rennes (UR)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-INSTITUT AGRO 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)

Subjects
olfactometry, Arthropod Antennae, Tribolium, Behavior, Animal, [SDV]Life Sciences [q-bio], caatinga plant, fungi, alternative pest control, Organic chemistry, stored insect pest, repellent effect, Article, essential oil, Magnoliopsida, QD241-441, electroantennogram, Insect Repellents, Oils, Volatile, Animals, aggregation pheromone
Abstract

Essential oils of aromatic plants represent an alternative to classical pest control with synthetic chemicals. They are especially promising for the alternative control of stored product pest insects. Here, we tested behavioral and electrophysiological responses of the stored product pest Tribolium confusum, to the essential oil of a Brazilian indigenous plant, Varronia globosa, collected in the Caatinga ecosystem. We analyzed the essential oil by GC-MS, tested the effects of the entire oil and its major components on the behavior of individual beetles in a four-way olfactometer, and investigated responses to these stimuli in electroantennogram recordings (EAG). We could identify 25 constituents in the essential oil of V. globosa, with anethole, caryophyllene and spathulenole as main components. The oil and its main component anethole had repellent effects already at low doses, whereas caryophyllene had only a repellent effect at a high dose. In addition, the essential oil abolished the attractive effect of the T. confusum aggregation pheromone. EAG recordings revealed dose-dependent responses to the individual components and increasing responses to the blend and even more to the entire oil. Our study reveals the potential of anethole and the essential oil of V. globosa in the management of stored product pests.

Published
2021
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22. Exploration of Long-Chain Vitamin E Metabolites for the Discovery of a Highly Potent, Orally Effective, and Metabolically Stable 5-LOX Inhibitor that Limits Inflammation

Author

Neukirch, Konstantin, primary, Alsabil, Khaled, additional, Dinh, Chau-Phi, additional, Bilancia, Rossella, additional, Raasch, Martin, additional, Ville, Alexia, additional, Cerqua, Ida, additional, Viault, Guillaume, additional, Bréard, Dimitri, additional, Pace, Simona, additional, Temml, Veronika, additional, Brunner, Elena, additional, Jordan, Paul M., additional, Marques, Marta C., additional, Loeser, Konstantin, additional, Gollowitzer, André, additional, Permann, Stephan, additional, Gerstmeier, Jana, additional, Lorkowski, Stefan, additional, Stuppner, Hermann, additional, Garscha, Ulrike, additional, Rodrigues, Tiago, additional, Bernardes, Gonçalo J. L., additional, Schuster, Daniela, additional, Séraphin, Denis, additional, Richomme, Pascal, additional, Rossi, Antonietta, additional, Mosig, Alexander S., additional, Roviezzo, Fiorentina, additional, Werz, Oliver, additional, Helesbeux, Jean-Jacques, additional, and Koeberle, Andreas, additional

Published
2021
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23. Fumigant toxicity of some essential oils and eucalyptol on different life stages of Tribolium confusum(Coleoptera: Tenebrionidae)

Author

Kheloul, Lynda, Anton, Sylvia, Bréard, Dimitri, and Kellouche, Abdellah

Abstract

ABSTRACTEssential oils of aromatic plants have a high potential for the development of alternative insect pest management strategies. Especially for the control of stored product pests, alternative methods to replace synthetic insecticides are urgently needed. We evaluate the fumigant toxicity of Myrtus communis, Eucalyptus globulus, Syzygium aromaticum, Thymus saturejoidesessential oils, and the main natural compound of two of them, eucalyptol, on different life stages of the confused flour beetle (Tribolium confusum) under laboratory conditions. Whereas eucalyptol and the essential oils of M. communisand E. globulushave rather strong toxic effects on all developmental stages, apart from the eggs of T. confusum, the essential oil of S. aromaticum caused the highest egg toxicity. Our results indicate that eucalyptol or essential oils containing large amounts of this compound might be efficient as potential alternative control agents for T. confusum, but tests under more natural conditions need to be performed.

Published
2023
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24. Oxostephanine, Thalmiculine, and Thaliphyline—Three Isoquinoleine Alkaloids That Inhibit L-Type Voltage-Gated Ca 2+ Channels.

Author

Frangieh, Jacinthe, Legendre, Claire, Bréard, Dimitri, Richomme, Pascal, Henrion, Daniel, Fajloun, Ziad, Mattei, César, Le Ray, Anne-Marie, and Legros, Christian

Subjects
ISOQUINOLINE alkaloids, PHYTOCHEMICALS, CARDIOVASCULAR diseases, CALCIUM ions, ION channel inhibition
Abstract

The isoquinoline alkaloids (IAs) represent a large and diverse subfamily of phytochemicals in terms of structures and pharmacological activities, including ion channel inhibition. Several IAs, such as liriodenine (an oxoaporphine) and curine (a bisbenzylisoquinoline (BBIQ), inhibit the L-type voltage-gated Ca2+ channels (LTCC). In this study, we aimed to search for new blockers of LTCC, which are therapeutic targets in neurological and cardiovascular diseases. We set up a screening assay using the rat pituitary GH3b6 cell line, which expresses two LTCC isoforms, CaV1.2 and CaV1.3. Both LTCC subtypes can be indirectly activated by KCl concentration elevation or directly by the dihydropyridine (DHP), BAY K8644, leading to an increase in the intracellular Ca2+ concentration ([Ca2+]i). These Ca2+ responses were completely blocked by the selective LTCC DHP inhibitor, nifedipine. Thereby, 16 selected IAs were tested for their ability to inhibit KCl and BAY K8644-induced Ca2+ responses. We then identified three new potent LTCC blockers, namely, oxostephanine, thaliphyline, and thalmiculine. They inhibited LTCC with IC50 values in the micromolar range through interaction to a binding site different to that of dihydropyridines. The two subfamilies of IAs, oxoaporphine with oxostephanine, and BBIQs with both thalyphilline and thalmiculine, constitute interesting pharmacophores for the development of future therapeutic leads for neurological and cardiovascular diseases. [ABSTRACT FROM AUTHOR]

Published
2022
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26. Screening an In-House Isoquinoline Alkaloids Library for New Blockers of Voltage-Gated Na + Channels Using Voltage Sensor Fluorescent Probes: Hits and Biases.

Author

Coquerel, Quentin, Legendre, Claire, Frangieh, Jacinthe, Waard, Stephan De, Montnach, Jérôme, Cmarko, Leos, Khoury, Joseph, Hassane, Charifat Said, Bréard, Dimitri, Siegler, Benjamin, Fajloun, Ziad, De Pomyers, Harold, Mabrouk, Kamel, Weiss, Norbert, Henrion, Daniel, Richomme, Pascal, Mattei, César, Waard, Michel De, Le Ray, Anne-Marie, and Legros, Christian

Subjects
ISOQUINOLINE alkaloids, FLUORESCENT probes, SODIUM channels, VOLTAGE, DETECTORS, ALKALOIDS, INHIBITORY postsynaptic potential, BRUGADA syndrome
Abstract

Voltage-gated Na+ (NaV) channels are significant therapeutic targets for the treatment of cardiac and neurological disorders, thus promoting the search for novel NaV channel ligands. With the objective of discovering new blockers of NaV channel ligands, we screened an In-House vegetal alkaloid library using fluorescence cell-based assays. We screened 62 isoquinoline alkaloids (IA) for their ability to decrease the FRET signal of voltage sensor probes (VSP), which were induced by the activation of NaV channels with batrachotoxin (BTX) in GH3b6 cells. This led to the selection of five IA: liriodenine, oxostephanine, thalmiculine, protopine, and bebeerine, inhibiting the BTX-induced VSP signal with micromolar IC50. These five alkaloids were then assayed using the Na+ fluorescent probe ANG-2 and the patch-clamp technique. Only oxostephanine and liriodenine were able to inhibit the BTX-induced ANG-2 signal in HEK293-hNaV1.3 cells. Indeed, liriodenine and oxostephanine decreased the effects of BTX on Na+ currents elicited by the hNaV1.3 channel, suggesting that conformation change induced by BTX binding could induce a bias in fluorescent assays. However, among the five IA selected in the VSP assay, only bebeerine exhibited strong inhibitory effects against Na+ currents elicited by the hNav1.2 and hNav1.6 channels, with IC50 values below 10 µM. So far, bebeerine is the first BBIQ to have been reported to block NaV channels, with promising therapeutical applications. [ABSTRACT FROM AUTHOR]

Published
2022
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27. MixONat, a Software for the Dereplication of Mixtures Based on 13C NMR Spectroscopy

Author

Bruguière, Antoine, primary, Derbré, Séverine, additional, Dietsch, Joël, additional, Leguy, Jules, additional, Rahier, Valentine, additional, Pottier, Quentin, additional, Bréard, Dimitri, additional, Suor-Cherer, Sorphon, additional, Viault, Guillaume, additional, Le Ray, Anne-Marie, additional, Saubion, Frédéric, additional, and Richomme, Pascal, additional

Published
2020
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28. MixONat: Assistance aux analyses déréplicatives par RMN-13C

Author

Derbré, Séverine, Bruguière, Antoine, Dietsch, Joël, Leguy, J., Rahier, V, Bréard, Dimitri, Suor-Cherer, Sorphon, Viault, Guillaume, Ray, Anne-Marie Le, Saubion, F., Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Laboratoire d'Etudes et de Recherche en Informatique d'Angers (LERIA), and Viault, Guillaume

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

International audience

Published
2019

29. MIADB: Monoterpene Indole Alkaloid MS/MS Spectral Database

Author

Fox Ramos, Alexander E., Le Pogam, Pierre, Alcover, Charlotte, Otogo N'Nang, Elvis, Cauchie, Gaëla, Hazni, Hazrina, Awang, Kalijah, Bréard, Dimitri, Echavarren, Antonio M., Frederich, Michel, Gaslonde, Thomas, Girardot, Marion, Grougnet, Raphael, Kirillova, Mariia S., Kritsanida, Marina, Lémus, Christelle, Le Ray, Anne-Marie, Lewin, Guy, Litaudon, Marc, Mambu, Lengo, Michel, Sylvie, Miloserdov, Fedor M., Muratore, Michael E., Richomme-Peniguel, Pascal, Roussi, Fanny, Evanno, Laurent, Poupon, Erwan, Champy, Pierre, and Beniddir, Mehdi A.

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 has 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).

Published
2019

30. 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

31. 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

34. Mycolactone as Analgesic: Subcutaneous Bioavailability Parameters

Author

Babonneau, Jérémie, primary, Bréard, Dimitri, additional, Reynaert, Marie-Line, additional, Marion, Estelle, additional, Guilet, David, additional, Saint André, Jean-Paul, additional, Croué, Anne, additional, Brodin, Priscille, additional, Richomme, Pascal, additional, and Marsollier, Laurent, additional

Published
2019
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35. 13 C NMR Dereplication Using MixONat Software: A Practical Guide to Decipher Natural Products Mixtures#.

Author

Bruguière, Antoine, Derbré, Séverine, Bréard, Dimitri, Tomi, Félix, Nuzillard, Jean-Marc, and Richomme, Pascal

Subjects
CHEMICAL alcohol analysis, COMPUTER software, ESSENTIAL oils, TERPENES, PEPPERMINT, NUCLEAR magnetic resonance spectroscopy, PHYTOCHEMICALS, GAS chromatography, MASS spectrometry, DESCRIPTIVE statistics, PLANT extracts, MOLECULAR structure, DATA analysis software, ALGORITHMS
Abstract

The growing use of herbal medicines worldwide requires ensuring their quality, safety, and efficiency to consumers and patients. Quality controls of vegetal extracts are usually undertaken according to pharmacopeial monographs. Analyses may range from simple chemical experiments to more sophisticated but more accurate methods. Nowadays, metabolomic analyses allow a fast characterization of complex mixtures. In the field, besides mass spectrometry (MS), nuclear magnetic resonance spectroscopy (NMR) has gained importance in the direct identification of natural products in complex herbal extracts. For a decade, automated dereplication processes based on13 C-NMR have been emerging to efficiently identify known major compounds in mixtures. Though less sensitive than MS,13 C-NMR has the advantage of being appropriate to discriminate stereoisomers. Since NMR spectrometers nowadays provide useful datasets in a reasonable time frame, we have recently made available MixONat, a software that processes13 C as well as distortionless enhancement by polarization transfer (DEPT)-135 and -90 data, allowing carbon multiplicity (i.e., CH3 , CH2 , CH, and C) filtering as a critical step. MixONat requires experimental or predicted chemical shifts (δ C) databases and displays interactive results that can be refined based on the userʼs phytochemical knowledge. The present article provides step-by-step instructions to use MixONat starting from database creation with freely available and/or marketed δ C datasets. Then, for training purposes, the reader is led through a 30 – 60 min procedure consisting of the13 C-NMR based dereplication of a peppermint essential oil. [ABSTRACT FROM AUTHOR]

Published
2021
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36. 13 C NMR Dereplication Using MixONat Software: A Practical Guide to Decipher Natural Products Mixtures#.

Author

Bruguière, Antoine, Derbré, Séverine, Bréard, Dimitri, Tomi, Félix, Nuzillard, Jean-Marc, and Richomme, Pascal

Subjects
COMPUTER software, ESSENTIAL oils, BIOLOGICAL products, HERBAL medicine, PEPPERMINT, METABOLOMICS, NUCLEAR magnetic resonance spectroscopy, PHYTOCHEMICALS, DESCRIPTIVE statistics, PLANT extracts
Abstract

The growing use of herbal medicines worldwide requires ensuring their quality, safety, and efficiency to consumers and patients. Quality controls of vegetal extracts are usually undertaken according to pharmacopeial monographs. Analyses may range from simple chemical experiments to more sophisticated but more accurate methods. Nowadays, metabolomic analyses allow a fast characterization of complex mixtures. In the field, besides mass spectrometry (MS), nuclear magnetic resonance spectroscopy (NMR) has gained importance in the direct identification of natural products in complex herbal extracts. For a decade, automated dereplication processes based on13 C-NMR have been emerging to efficiently identify known major compounds in mixtures. Though less sensitive than MS,13 C-NMR has the advantage of being appropriate to discriminate stereoisomers. Since NMR spectrometers nowadays provide useful datasets in a reasonable time frame, we have recently made available MixONat, a software that processes13 C as well as distortionless enhancement by polarization transfer (DEPT)-135 and -90 data, allowing carbon multiplicity (i.e., CH3 , CH2 , CH, and C) filtering as a critical step. MixONat requires experimental or predicted chemical shifts (δ C) databases and displays interactive results that can be refined based on the userʼs phytochemical knowledge. The present article provides step-by-step instructions to use MixONat starting from database creation with freely available and/or marketed δ C datasets. Then, for training purposes, the reader is led through a 30 – 60 min procedure consisting of the13 C-NMR based dereplication of a peppermint essential oil. [ABSTRACT FROM AUTHOR]

Published
2021
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37. Monitoring the Secretory Behavior of the Rat Adrenal Medulla by High-Performance Liquid Chromatography-Based Catecholamine Assay from Slice Supernatants

Author

De Nardi, Frédéric, Lefort, Claudie, Bréard, Dimitri, Richomme, Pascal, Legros, Christian, Guérineau, Nathalie, MitoVasc - 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), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), This work was supported by the Centre National de la Recherche Scientifique, Institut National de la Santé et de la Recherche Médicale, Institut Universitaire de Technologie d’Angers-Cholet, Université d’Angers, Fondation pour la Recherche Médicale., Guerineau, Nathalie C., and Physiopathologie Cardiovasculaire et Mitochondriale (MITOVASC)

Subjects
adrenal gland, lcsh:RC648-665, Endocrinology, Diabetes and Metabolism, acute adrenal slice, acute slice, medullary tissue, hexamethonium, lcsh:Diseases of the endocrine glands. Clinical endocrinology, acetylcholine, fluorescence derivatization, Endocrinology, stimulus-secretion coupling, catecholamine release, [SDV.NEU]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], [SDV.NEU] Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC], HPLC, high-performance liquid chromatography, chromaffin cells, Original Research
Abstract

International audience; Catecholamine (CA) secretion from the adrenal medullary tissue is a key step of the adaptive response triggered by an organism to cope with stress. Whereas molecular and cellular secretory processes have been extensively studied at the single chromaffin cell level, data available for the whole gland level are much scarcer. We tackled this issue in rat by developing an easy to implement experimental strategy combining the adrenal acute slice supernatant collection with a high-performance liquid chromatography-based epinephrine and norepinephrine (NE) assay. This technique affords a convenient method for measuring basal and stimulated CA release from single acute slices, allowing thus to individually address the secretory function of the left and right glands. Our data point that the two glands are equally competent to secrete epinephrine and NE, exhibiting an equivalent epinephrine:NE ratio, both at rest and in response to a cholinergic stimulation. Nicotine is, however, more efficient than acetylcholine to evoke NE release. A pharmacological challenge with hexamethonium, an α3-containing nicotinic acetylcholine receptor antagonist, disclosed that epinephrine-and NE-secreting chromaffin cells distinctly expressed α3 nicotinic receptors, with a dominant contribution in NE cells. As such, beyond the novelty of CA assays from acute slice supernatants, our study contributes at refining the secretory behavior of the rat adrenal medullary tissue, and opens new perspectives for monitoring the release of other hormones and transmitters, especially those involved in the stress response.

Published
2017
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38. Total synthesis and determination of the absolute configuration of Hyperbiphenyl A and B, isolated from the roots of Hypericum perforatum

Author

Bréard, Dimitri, Viault, Guillaume, Bruguière, Antoine, Charreau, Béatrice, Richomme, Pascal, Derbré, Séverine, 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), and Université de Nantes (UN)-Université de Nantes (UN)

Subjects
[SDV]Life Sciences [q-bio]
Published
2017

39. Identifying natural products (NPs) as potential UPR inhibitors for crop protection

Author

Benbelkacem, Z., Le Ray, Anne-Marie, Bruguière, Antoine, Suor-Cherer, Sorphon, Bréard, Dimitri, Blon, N, Marchi, Muriel, Rolland, Aurélia, Simoneau, Philippe, Bataille-Simoneau, Nelly, Guilllemette, T., 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-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]Life Sciences [q-bio], ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2017

42. Screening an in house alkaloids library using Voltage-Sensor Probes for new modulators of voltage-gated sodium channels

Author

Coquerel, Quentin, Le Ray, Anne-Marie, Mattei, César, Guérineau, Nathalie C., Bréard, Dimitri, Siegler, Benjamin, Richomme, Pascal, Legros, Christian, Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and Plateforme d'Ingénierie et d'Analyses Moléculaires (PIAM)

Subjects
[SDV]Life Sciences [q-bio], Voltage-gated sodium channel, Voltage-Sensor Probes, [CHIM]Chemical Sciences, plant alkaloids, GH3b6 cell line
Abstract

Voltage-gated sodium channels (Nav) are molecular targets of clinically used drugs for treatments of various diseases (epilepsy, chronic pain, cardiac arrhythmia…) and also of numerous animal and plant neurotoxins. The development of easy-to-use screening assays for searching new ligands from chemicals libraries, animal venoms or plant extracts represents a challenge of a great interest to generate therapeutic hits. Here, we used the mammalian GH3B6 pituitary cell line, which constitutively expresses three different neuronal Nav channel isoforms (Nav1.2, Nav1.3 and Nav1.6), to identify novel compounds of pharmacological interest from a library of in-house vegetal alkaloids. The screening is based on a method using Voltage-Sensor Probes (VSPs) that we adapted to detect both activators and blockers of Nav channels. Over the 84 pure alkaloids or plant extracts that were screened, 17 increased the VSP signal. They operated as gating modifier, showing an action mechanism similar to that of batrachotoxin (BTX), known to strongly inhibit Nav channel inactivation. The remaining 67 plant products were assessed for their potency to inhibit BTX-induced VSP signal. We further selected 11 alkaloids as efficient Nav channels inhibitors. We focused our attention on two structural analogs belonging to the aporphine family, liriodenine and oxostephanine, which differ only by a methoxy group. Whereas liriodenine has been already described as a Nav channels blocker, oxostephanine has not been yet documented as an ion channel modulator. In conclusion, the novel VSPs-based screening assay we developed is a suitable method to challenge the discovery and to assess the activity of novel ligands on Nav channels.

Published
2015

43. Acylphloroglucinol Derivatives Synthesis, anti-AGEs, Antioxidant and Vascular Activities

Author

Baglin, Isabelle, Thirumaran, Sangeetha-Laura, Bodero, Lizeth, Derbré, Séverine, Blanchard, Patricia, Bréard, Dimitri, Richomme, Pascal, Vessières, Emilie, Henrion, Daniel, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), and Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Angers (UA)

Subjects
[SDV]Life Sciences [q-bio]
Published
2015
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44. Chemically engineered extracts of Hypericum perforatum (St John’s wort) as sources of bioactive compounds to prevent endothelial dysfunction

Author

Corlay, Nina, Michaud, Aurore, Camara, Aïssata, Mezier, Marie-Charlotte, Dang, Bach Tai, Bréard, Dimitri, Pagie, Sylvain, Richomme, Pascal, Charreau, Béatrice, Derbré, Séverine, 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), and Université de Nantes (UN)-Université de Nantes (UN)

Subjects
[SDV]Life Sciences [q-bio]
Published
2015

45. Voltage Sensor Probes as an efficient tool to screen for new modulators of voltage-gated sodium channels

Author

Coquerel, Quentin, Le Ray, Anne-Marie, Said-Hassane, Charifat, Mattei, César, Guérineau, Nathalie C., Bréard, Dimitri, Siegler, Benjamin, Richomme, Pascal, Legros, Christian, Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), and Plateforme d'Ingénierie et d'Analyses Moléculaires (PIAM)

Subjects
Alkaloids, voltage sensor probes, [SDV]Life Sciences [q-bio], Voltage-gated sodium channel
Abstract

Voltage-gated sodium channels (Nav) constitute the molecular targets of clinically used drugs for treatments of various diseases (epilepsies, chronic pain, cardiac arrythmies…) and also of numerous toxins from animals and plants. The development of useful screening assay for the discovery of new ligands in/ from chemicals libraries or animal venoms and either plant extract still represents a challenge of great interest. Here, we used a mammalian GH3 cells that constitutively express at least three different brain Nav channels isoforms (Nav1.1, Nav1.2, Nav1.3 and Nav1.6) in order to identify in a library of in-house natural alkaloids, novel compounds of therapeutical interest. For this screening, we developed a method based on the use of Voltage Sensor Probes (VSPs) that we adapted to detect both activators and blockers of Nav channels. Among 62 compounds tested, 5 isoquinolines appeared as potent Nav channels inhibitors. Other compounds were characterized as specific gating modifier of Nav channels. While most of these alkaloids have been already described in the literature, their abilities to act on Nav channels were unknown. In conclusion, we demonstrated the potency of this novel screening method using VSPs to identify novel ligands of Nav channels of therapeutical interests.References:1. Salat, K. et al. (2014) EOID 23:1093-11042. Yu, F.H. et al (2003) Genome Biol. 4

Published
2014

46. Phloroglucinol : a simple core for new anti-AGEs derivatives - synthesis, anti-AGEs activity and RSA

Author

Baglin, Isabelle, Bodero, Lizeth, Derbré, Séverine, Blanchard, Patricia, Bréard, Dimitri, Aumond, Marie-Christine, Richomme, Pascal, Ayer, Audrey, Henrion, Daniel, Seraphin, Denis, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), and Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

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

International audience

Published
2014

47. Voltage Sensor Probes (VSPs) as an Efficient Tool to Screen for Inhibitors of Voltage-Gated Sodium Channels

Author

Said-Hassane, Charifat, Coquerel, Quentin, Le Ray, Anne-Marie, Bréard, Dimitri, Siegler, Benjamin, Legros, Christian, Richomme, Pascal, Substances d'Origine Naturelle et Analogues Structuraux (SONAS), Université d'Angers (UA), Biologie Neurovasculaire et Mitochondriale Intégrée (BNMI), Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), and Plateforme d'Ingénierie et d'Analyses Moléculaires (PIAM)

Subjects
Alkaloids, voltage sensor probes, [SDV]Life Sciences [q-bio], Voltage-gated sodium channel
Abstract

Voltage-gated sodium channels (Nav) represent a therapeutically validated group of targets for the development of antiepileptic drugs, analgesics and antiarrhythmics [1]. However most of the existing drugs acting as Nav blockers suffer from multiple side effects, but the existence of a multigene family of Nav [2] suggests that the identification of new compounds that selectively block Nav isoforms might have better therapeutic efficiency and reduced side effects. Due to their molecular interference with numerous ion channels, alkaloids represent a group of natural products of particular interest. This is the reason why we have evaluated the efficiency of an in-house method to screen a library of isoquinoline alkaloids formerly isolated in our laboratory. Mammalian GH3 cells constitutively expressing Nav where used in conjunction with Voltage Sensor Probes (VSPs), the signals being read on a fluorescence plate reader. Thanks to this technique, we were able to precisely detect Nav channels activators or blockers. Among 62 compounds tested, 5 isoquinolines appeared as potent Nav channels inhibitors.References:1. Salat, K. et al. (2014) EOID 23:1093-11042. Yu, F.H. et al (2003) Genome Biol. 4

Published
2014

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

Author

Bréard, Dimitri, Viault, Guillaume, Mezier, Marie-Charlotte, Pagie, Sylvain, Bruguière, Antoine, Richomme, Pascal, Charreau, Béatrice, and Derbré, Séverine

Abstract

Phytochemical investigation of the root extracts of Hypericum perforatumled to the isolation of two biphenyl derivatives named hyperbiphenyls A and B (1and 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 hyperbiphenyl A followed by 1H and 19F NMR Mosher’s esters analysis and stereoselective total synthesis of hyperbiphenyl B, permitting assignment of the Sabsolute configuration for both compounds. The bioactivity of compounds 1–6toward 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
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50. A Descriptive Chemical Composition of Concentrated Bud Macerates through an Optimized SPE-HPLC-UV-MS 2 Method—Application to Alnus glutinosa , Ribes nigrum , Rosa canina , Rosmarinus officinalis and Tilia tomentosa.

Author

Charpentier, Thomas, Boisard, Séverine, Le Ray, Anne-Marie, Bréard, Dimitri, Chabrier, Amélie, Esselin, Hélène, Guilet, David, Ripoll, Christophe, and Richomme, Pascal

Subjects
ALNUS glutinosa, ROSEMARY, HIGH performance liquid chromatography, SOLID phase extraction, LINDENS, GLYCERIN, ANTIOXIDANT analysis
Abstract

Concentrated bud macerates (CBMs) are obtained from meristematic tissues such as buds and young shoots by maceration in a solvent composed of glycerin, water and ethanol (1/1/1/, v/v). Their traditional utilization in gemmotherapy has gained interest in the past years, and the knowledge of their chemical characterization can provide commercial arguments, particularly to secure their quality control. Therefore, an optimized method for phytochemical analysis including glycerol removal by a preliminary solid phase extraction (SPE) followed by compound identification using high performance liquid chromatography coupled with ultra-violet and tandem mass detectors (HPLC-UV-MS2) was developed. This method was applied on 5 CBMs obtained from Alnus glutinosa, Ribesnigrum, Rosmarinus officinalis, Rosa canina and Tilia tomentosa in order to determinate their chemical composition. Their antioxidant effects were also investigated by radical scavenging activity assays (DPPH and ORAC). Glycerol removal improved the resolution of HPLC chemical profiles and allowed us to perform TLC antioxidant screening. Our approach permitted the identification of 57 compounds distributed in eight major classes, three of them being common to all macerates including nucleosides, phenolic acids and glycosylated flavonoids. Quantification of the later class as a rutin equivalent (RE) showed a great disparity between Rosa canina macerate (809 mg RE/L), and the other ones (from 175 to 470 mg RE/L). DPPH and ORAC assays confirmed the great activity of Rosa canina (4857 and 6479 μmol TE/g of dry matter, respectively). Finally, phytochemical and antioxidant analysis of CBMs strengthened their phytomedicinal interest in the gemmotherapy field. [ABSTRACT FROM AUTHOR]

Published
2022
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