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2. Bacterial rhamnolipids and their 3-hydroxyalkanoate precursors activate Arabidopsis innate immunity through two independent mechanisms

Author

Schellenberger, Romain, Crouzet, Jérôme, Nickzad, Arvin, Shu, Lin-Jie, Kutschera, Alexander, Gerster, Tim, Borie, Nicolas, Dawid, Corinna, Cloutier, Maude, Villaume, Sandra, Dhondt-Cordelier, Sandrine, Hubert, Jane, Cordelier, Sylvain, Mazeyrat-Gourbeyre, Florence, Schmid, Christian, Ongena, Marc, Renault, Jean-Hugues, Haudrechy, Arnaud, Hofmann, Thomas, Baillieul, Fabienne, Clément, Christophe, Zipfel, Cyril, Gauthier, Charles, Déziel, Eric, Ranf, Stefanie, and Dorey, Stéphan

Published
2021

3. The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Author

McAlpine, James B, Chen, Shao-Nong, Kutateladze, Andrei, MacMillan, John B, Appendino, Giovanni, Barison, Andersson, Beniddir, Mehdi A, Biavatti, Maique W, Bluml, Stefan, Boufridi, Asmaa, Butler, Mark S, Capon, Robert J, Choi, Young H, Coppage, David, Crews, Phillip, Crimmins, Michael T, Csete, Marie, Dewapriya, Pradeep, Egan, Joseph M, Garson, Mary J, Genta-Jouve, Grégory, Gerwick, William H, Gross, Harald, Harper, Mary Kay, Hermanto, Precilia, Hook, James M, Hunter, Luke, Jeannerat, Damien, Ji, Nai-Yun, Johnson, Tyler A, Kingston, David GI, Koshino, Hiroyuki, Lee, Hsiau-Wei, Lewin, Guy, Li, Jie, Linington, Roger G, Liu, Miaomiao, McPhail, Kerry L, Molinski, Tadeusz F, Moore, Bradley S, Nam, Joo-Won, Neupane, Ram P, Niemitz, Matthias, Nuzillard, Jean-Marc, Oberlies, Nicholas H, Ocampos, Fernanda MM, Pan, Guohui, Quinn, Ronald J, Reddy, D Sai, Renault, Jean-Hugues, Rivera-Chávez, José, Robien, Wolfgang, Saunders, Carla M, Schmidt, Thomas J, Seger, Christoph, Shen, Ben, Steinbeck, Christoph, Stuppner, Hermann, Sturm, Sonja, Taglialatela-Scafati, Orazio, Tantillo, Dean J, Verpoorte, Robert, Wang, Bin-Gui, Williams, Craig M, Williams, Philip G, Wist, Julien, Yue, Jian-Min, Zhang, Chen, Xu, Zhengren, Simmler, Charlotte, Lankin, David C, Bisson, Jonathan, and Pauli, Guido F

Subjects
Biological Products, Magnetic Resonance Spectroscopy, Reproducibility of Results, Molecular Conformation, Generic health relevance, Organic Chemistry, Chemical Sciences, Biological Sciences, Medical and Health Sciences
Abstract

Covering: up to 2018With contributions from the global natural product (NP) research community, and continuing the Raw Data Initiative, this review collects a comprehensive demonstration of the immense scientific value of disseminating raw nuclear magnetic resonance (NMR) data, independently of, and in parallel with, classical publishing outlets. A comprehensive compilation of historic to present-day cases as well as contemporary and future applications show that addressing the urgent need for a repository of publicly accessible raw NMR data has the potential to transform natural products (NPs) and associated fields of chemical and biomedical research. The call for advancing open sharing mechanisms for raw data is intended to enhance the transparency of experimental protocols, augment the reproducibility of reported outcomes, including biological studies, become a regular component of responsible research, and thereby enrich the integrity of NP research and related fields.

Published
2019

4. Correction: The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

Author

McAlpine, James B, Chen, Shao-Nong, Kutateladze, Andrei, MacMillan, John B, Appendino, Giovanni, Barison, Andersson, Beniddir, Mehdi A, Biavatti, Maique W, Bluml, Stefan, Boufridi, Asmaa, Butler, Mark S, Capon, Robert J, Choi, Young H, Coppage, David, Crews, Phillip, Crimmins, Michael T, Csete, Marie, Dewapriya, Pradeep, Egan, Joseph M, Garson, Mary J, Genta-Jouve, Grégory, Gerwick, William H, Gross, Harald, Harper, Mary Kay, Hermanto, Precilia, Hook, James M, Hunter, Luke, Jeannerat, Damien, Ji, Nai-Yun, Johnson, Tyler A, Kingston, David GI, Koshino, Hiroyuki, Lee, Hsiau-Wei, Lewin, Guy, Li, Jie, Linington, Roger G, Liu, Miaomiao, McPhail, Kerry L, Molinski, Tadeusz F, Moore, Bradley S, Nam, Joo-Won, Neupane, Ram P, Niemitz, Matthias, Nuzillard, Jean-Marc, Oberlies, Nicholas H, Ocampos, Fernanda MM, Pan, Guohui, Quinn, Ronald J, Reddy, D Sai, Renault, Jean-Hugues, Rivera-Chávez, José, Robien, Wolfgang, Saunders, Carla M, Schmidt, Thomas J, Seger, Christoph, Shen, Ben, Steinbeck, Christoph, Stuppner, Hermann, Sturm, Sonja, Taglialatela-Scafati, Orazio, Tantillo, Dean J, Verpoorte, Robert, Wang, Bin-Gui, Williams, Craig M, Williams, Philip G, Wist, Julien, Yue, Jian-Min, Zhang, Chen, Xu, Zhengren, Simmler, Charlotte, Lankin, David C, Bisson, Jonathan, and Pauli, Guido F

Subjects
Organic Chemistry, Chemical Sciences, Clinical Research, Biological Sciences, Medical and Health Sciences, Medicinal and biomolecular chemistry, Traditional, complementary and integrative medicine
Abstract

Correction for 'The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research' by James B. McAlpine et al., Nat. Prod. Rep., 2018, DOI: .

Published
2019

5. Resistance of Pseudomonas aeruginosa and Staphylococcus aureus to the airway epithelium oxidative response assessed by a cell-free in vitro assay.

Author

Petithomme-Nanrocki, Maïwenn, Nicolau-Guillaumet, Nathan, Borie, Nicolas, Haudrechy, Arnaud, Renault, Jean-Hugues, Moussalih, Sophie, Muggeo, Anaëlle, and Guillard, Thomas

Subjects
REACTIVE oxygen species, PSEUDOMONAS aeruginosa, STAPHYLOCOCCUS aureus, HIGH throughput screening (Drug development), HYDROGEN peroxide, SUPRACHIASMATIC nucleus
Abstract

The antibacterial oxidative response, which relies on the production of hydrogen peroxide (H2O2) and hypothiocyanite (OSCN-), is a major line of defense protecting the human airway epithelium (HAE) from lesions when infected. The in vitro studies of the oxidative responses are performed mainly by one-shot H2O2 exposure that does not recapitulate the complex H2O2/LPO/SCN- system releasing the reactive oxygen species in airway secretions. A cell-free in vitro assay mimicking this system has been described but was not fully characterized. Here, we comprehensively characterized the hourly H2O2/OSCN- concentrations produced within this in vitro assay and assessed the resistance of Pseudomonas aeruginosa and Staphylococcus aureus clinical strains to the HAE oxidative response. We found that H2O2/OSCN- were steadily produced from 7h and up to 25h, but OSCN- was detoxified in 15 minutes by bacteria upon exposure. Preliminary tests on PA14 showed survival rates at 1-hour post-exposure (hpe) to H2O2 of roughly 50% for 105 and 107 colony-forming unit (CFU)/mL inocula, while 102 and 104 CFU/mL inocula were cleared after one hpe. Thirteen clinical strains were then exposed, highlighting that conversely to P. aeruginosa, S. aureus showed resistance to oxidative stress independently of its antibiotic resistance phenotype. Our results demonstrated how this in vitro assay can be helpful in assessing whether pathogens can resist the antibacterial oxidative HAE response. We anticipate these findings as a starting point for more sophisticated in vitro models that could serve as high-throughput screening for molecules targeting the bacterial antioxidant response. [ABSTRACT FROM AUTHOR]

Published
2024
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11. Anti-Toxoplasma gondii effect of lupane-type triterpenes from the bark of black alder (Alnus glutinosa) and identification of a potential target by reverse docking

Author

Darme Pierre, Escotte-Binet Sandie, Cordonnier Julien, Remy Simon, Hubert Jane, Sayagh Charlotte, Borie Nicolas, Villena Isabelle, Voutquenne-Nazabadioko Laurence, Dauchez Manuel, Baud Stéphanie, Renault Jean-Hugues, and Aubert Dominique

Subjects
toxoplasma gondii, alnus glutinosa, triterpene, betulone, inverse docking, target hypothesis, Infectious and parasitic diseases, RC109-216
Abstract

Toxoplasmosis is a worldwide parasitosis that is generally benign. The infestation may pose a risk to immunocompromized patients and to fetuses when pregnant women have recently seroconverted. Current treatments have numerous side effects and chemoresistance is emerging, hence the need to find new anti-Toxoplasma gondii substances. This study focuses on the antiparasitic potential of lupane-type pentacyclic triterpenes isolated from the bark of black alder (Alnus glutinosa), as well as the hypothesis of their macromolecular target by an original method of reverse docking. Among the isolated triterpenes, betulone was the most active compound with an IC50 of 2.7 ± 1.2 μM, a CC50 greater than 80 μM, and a selectivity index of over 29.6. An additional study of the anti-T. gondii potential of commercially available compounds (betulonic acid methyl ester and betulonic acid) showed the important role of the C3 ketone function and the C28 oxidation level on the lupane-type triterpene in the antiparasitic activity since their IC50 and CC50 were similar to that of betulone. Finally, the most active compounds were subjected to the AMIDE reverse docking workflow. A dataset of 87 T. gondii proteins from the Protein Data Bank was created. It identified calcium-dependent protein kinase CDPK3 as the most likely target of betulin derivatives.

Published
2022
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12. Combining Laccase-Mediated Dimerization of Resveratrol and Centrifugal Partition Chromatography: Optimization of E-Labruscol Production and Identification of New Resveratrol Dimers

Author

Sursin, Emmanuel, primary, Flourat, Amandine L., additional, Akissi, Z. L. Evariste, additional, Martinez, Agathe, additional, Borie, Nicolas, additional, Peyrot, Cedric, additional, Courot, Eric, additional, Nuzillard, Jean-Marc, additional, Renault, Jean-Hugues, additional, Voutquenne-Nazabadioko, Laurence, additional, and Allais, Florent, additional

Published
2023
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16. Versa DB: Assisting 13C NMR and MS/MS Joint Data Annotation Through On‐Demand Databases.

Author

Cordonnier, Julien, Remy, Simon, Renault, Jean‐Hugues, and Nuzillard, Jean‐Marc

Subjects
GRAPHICAL user interfaces, DATABASES, OPEN source software, ELECTRONIC data processing, SOFTWARE development tools
Abstract

Compound identification in complex mixtures by NMR and MS is best achieved through experimental databases (DB) mining. Experimental DB frequently show limitations regarding their completeness, availability or data quality, thus making predicted database of increasing common use. Querying large databases may lead to select unlikely structure candidates. Two approaches to dereplication are thus possible: filtering of a large DB before search or scoring of the results after a large scale search. The present work relies on the former approach. As far as we know, nmrshiftdb2 is the only open‐source 13NMR chemical shift predictor that can be freely operated in batch mode. CFM‐ID 4.0 is one of the best‐performing open‐source tools for ESI‐MS/MS spectra prediction. LOTUS is a freely usable and comprehensive collection of secondary metabolites. Integrating the open source database and software LOTUS, CFM‐ID, and nmrshiftdb2 in a dereplication workflow requires presently programming skills, owing to the diversity of data encoding and processing procedures. A graphical user interface that integrates seamlessly chemical structure collection, spectral data prediction and database building still does not exist, as far as we know. The present work proposes a stand–alone software tool that assists the identification of mixture components in a simple way. [ABSTRACT FROM AUTHOR]

Published
2024
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20. Production of high molecular-ordered stilbene oligomers for the study of their biological activity: total synthesis, bio-catalyzed synthesis and production by plant systems

Author

Jeandet, Philippe, primary, Uddin, Md. Sahab, additional, Clément, Christophe, additional, Aziz, Aziz, additional, Jacquard, Cédric, additional, Khan, Haroon, additional, Shah, Muhammad Ajmal, additional, Barka, Essaid Ait, additional, Koffas, Mattheos, additional, Nabavi, Seyed Mohammad, additional, Sobarzo-Sánchez, Eduardo, additional, and Renault, Jean-Hugues, additional

Published
2023
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35. Investigation of Antiparasitic Activity of 10 European Tree Bark Extracts on Toxoplasma gondii and Bioguided Identification of Triterpenes in Alnus glutinosa Barks

Author

Darme, Pierre, Spalenka, Jérémy, Hubert, Jane, Escotte-Binet, Sandie, Debelle, Laurent, Villena, Isabelle, Sayagh, Charlotte, Borie, Nicolas, Martinez, Agathe, Bertaux, Benjamin, Voutquenne-Nazabadioko, Laurence, Renault, Jean-Hugues, and Aubert, Dominique

Subjects
Alnus glutinosa, bark, Antiparasitic Agents, Plant Extracts, Toxoplasma gondii, Alnus, Triterpenes, Betulaceae, apicomplexa, triterpene, Plant Bark, Humans, Experimental Therapeutics, Toxoplasma
Abstract

Toxoplasmosis is a worldwide parasitosis that affects one-third of the population. People at risk, such as immunocompromised patients (AIDS, chemotherapy treatment) or fetuses (maternal-fetal transmission) can develop severe forms of the disease. The antiparasitic activity of extracts of different polarities (n-heptane, MeOH, MeOH/H2O) of 10 tree species endemic to temperate regions was investigated against Toxoplasma gondii infection in vitro. Our results showed that the n-heptane extract of the black alder (Alnus glutinosa) exhibited a significant antiparasitic activity without any cytotoxicity at the tested concentrations, with an IC50 of up to 25.08 μg/mL and a selectivity index higher than 3.99. The chemical profiling of this extract revealed triterpenes as major constituents. The ability of commercially available triterpene (betulin, betulinic acid, and betulone) to inhibit the growth of T. gondii was evaluated and showed growth inhibition rates of 44%, 49%, and 99% at 10 μM, respectively.

Published
2022

39. Abundant Extractable Metabolites from Temperate Tree Barks: The Specific Antimicrobial Activity of Prunus Avium Extracts

Author

Abedini, Amin, Colin, Marius, Hubert, Jane, Charpentier, Émilie, Angelis, Apostolis, Bounasri, Heithem, Bertaux, Benjamin, Kotland, Alexis, Reffuveille, Fany, Nuzillard, Jean-Marc, Renault, Jean-Hugues, Gangloff, Sophie, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Biomatériaux et inflammation en site osseux - EA 4691 (BIOS), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Renault, Jean-Hugues, Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
dihydrowogonin, [CHIM.ANAL] Chemical Sciences/Analytical chemistry, antimicrobial activity, natural products, [CHIM.ORGA]Chemical Sciences/Organic chemistry, lcsh:RM1-950, Prunus avium, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Article, centrifugal partition chromatography, lcsh:Therapeutics. Pharmacology, barks, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, 13 C nuclear magnetic resonance chemical profiling, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, antibiofilm activity, [SDV.MP] Life Sciences [q-bio]/Microbiology and Parasitology, ComputingMilieux_MISCELLANEOUS, 13C nuclear magnetic resonance chemical profiling
Abstract

Tree barks are mainly considered as wood wastes from forestry activities, but represent valuable resources as they may contain antimicrobial compounds. Here, we aimed to evaluate the possible antimicrobial activities of bark extracts and to characterize the chemical composition of the most active extract. Ten methanol bark extracts were tested in vitro against 17 bacterial strains and 5 yeast strains, through minimum inhibitory concentration (MIC) and minimum bactericidal (or fungicidal) concentration (MBC/MFC) assays. The extract from Prunus avium (E2-4) displayed the largest bactericidal activity against Gram-positive bacteria, with a lethal effect on 6 out of 8 strains. Antibiofilm assays of E2-4 were performed by crystal violet staining and enumeration of adhered bacteria. Assays demonstrated a biofilm inhibitory effect of E2-4 against Staphylococcus aureus CIP 53.154 at concentrations equal to or higher than 250 µg/mL. Chemical profiling of E2-4 by 13C nuclear magnetic resonance (NMR) revealed the presence of dihydrowogonin as a major constituent of the extract. E2-4 was fractionated by centrifugal partition chromatography and the three fractions containing dihydrowogonin were tested for their antibacterial and antibiofilm activities, revealing similar activities to those of E2-4. Dihydrowogonin was positively assessed as an interesting antimicrobial compound, which could be valued from wastes of Prunus avium barks.

Published
2020

40. AMIDE v2: High-Throughput Screening Based on AutoDock-GPU and Improved Workflow Leading to Better Performance and Reliability

Author

Darme, Pierre, primary, Dauchez, Manuel, additional, Renard, Arnaud, additional, Voutquenne-Nazabadioko, Laurence, additional, Aubert, Dominique, additional, Escotte-Binet, Sandie, additional, Renault, Jean-Hugues, additional, Villena, Isabelle, additional, Steffenel, Luiz-Angelo, additional, and Baud, Stéphanie, additional

Published
2021
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41. Dereplication of Natural Extracts Diluted in Propylene Glycol, 1,3-Propanediol and Glycerin. Comparison of Leontopodium alpinum Cass. (Edelweiss) Extracts as a Case Study

Author

Canton, Marine, Poigny, Stéphane, Roe, Richard, Nuzillard, Jean-Marc, Renault, Jean-Hugues, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Pharmacochimie Pierre Fabre Dermo-Cosmétique, Centre de Recherche Pierre Fabre (Centre de R&D Pierre Fabre), PIERRE FABRE-PIERRE FABRE, Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), and Centre de Recherche Pierre Fabre

Subjects
glycerin, dereplication, NMR, mixture analysis, lcsh:Chemistry, centrifugal partition chromatography, lcsh:QD1-999, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, propylene glycol, Leontopodium alpinum, natural extract analysis, 1,3-propanediol, ComputingMilieux_MISCELLANEOUS, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

Many natural extracts used as cosmetic ingredients are available as solutions prepared in high-boiling-point solvents, called carrier solvents, such as propylene glycol (1,2-propanediol), propanediol (1,3-propanediol) and glycerin. The upstream chemical profiling of these extracts represents a major asset for the cosmetic industry, because it accelerates product development. A new workflow for the rapid characterization of the main metabolites present in natural extracts diluted in propylene glycol and 1,3-propanediol is presented here as an extension of previous works on glycerin-containing extracts. This method is an optimized version of a well-established dereplication procedure and consists of a fractionation by centrifugal partition chromatography followed by 13C nuclear magnetic resonance analysis and dedicated data processing. The concentration by evaporation under reduced pressure was considered as a pertinent preliminary step, particularly adapted to the analysis of highly diluted extracts. A dried hydro-ethanolic extract of Leontopodium alpinum Cass. was prepared at laboratory scale and used for method validation. Three solutions at 5% wt. of dry extract were prepared with propylene glycol/water (1:1), 1,3-propanediol/water (1:1) and glycerin/water (1:1) as carrier solvents. The dereplication workflow was applied to the three resulting L. alpinum extracts. Each study led to the quick identification of 26 metabolites including five flavonoids (luteolin and its derivatives), five hydroxycinnamic acids (among which are leontopodic acids), sugars and organic acids.

Published
2021

42. Rhamnolipids and their 3-(3-hydroxyalkanoyloxy)alkanoic acid precursors activate Arabidopsis innate immunity through two independent mechanisms

Author

Schellenberger, Romain, Crouzet, Jérôme, Nickzad, Arvin, Kutschera, Alexander, Gerster, Tim, Borie, Nicolas, Dawid, Corinna, Cloutier, Maude, Villaume, Sandra, Dhondt‐Cordelier, Sandrine, Hubert, Jane, Cordelier, Sylvain, Mazeyrat-Gourbeyre, Florence, Schmid, Christian, Ongena, Marc, Renault, Jean-Hugues, Haudrechy, Arnaud, Hofmann, Thomas, Baillieul, Fabienne, Clément, Christophe, Zipfel, Cyril, Gauthier, Charles, Déziel, Eric, Ranf, Stefanie, Dorey, Stephan, Résistance Induite et Bioprotection des Plantes - EA 4707 (RIBP), Université de Reims Champagne-Ardenne (URCA)-SFR Condorcet, and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[SDV]Life Sciences [q-bio], food and beverages
Abstract

Plant innate immunity is activated upon perception of invasion pattern molecules by plant cell-surface immune receptors. Several bacteria of the genera Pseudomonas and Burkholderia produce rhamnolipids (RLs) from L-rhamnose and ( R )-3-hydroxyalkanoate precursors (HAAs). RL and HAA secretion is required to modulate bacterial swarming motility behavior. The bulb-type lectin receptor kinase LIPOOLIGOSACCHARIDE-SPECIFIC REDUCED ELICITATION/S-DOMAIN-1-29 (LORE/SD1-29) mediates medium-chain 3-hydroxy fatty acid (mc-3-OH-FA) sensing in the plant Arabidopsis thaliana . Here, we show that the lipidic secretome from Pseudomonas aeruginosa comprising RLs, HAAs and mc-3-OH-FAs stimulates Arabidopsis immunity. HAAs, like mc-3-O-FAs, are sensed by LORE and induce canonical immune signaling and local resistance to plant pathogenic Pseudomonas infection. By contrast, RLs trigger an atypical immune response and resistance to Pseudomonas infection independent of LORE. Thus, the glycosyl moieties of RLs, albeit abolishing sensing by LORE, do not impair their ability to trigger plant defense. In addition, our results show that RL-triggered immune response is affected by the sphingolipid composition of the plasma membrane. In conclusion, RLs and their precursors released by bacteria can both be perceived by plants but through distinct mechanisms.

Published
2021

43. Investigation of antiparasitic activity of ten European tree bark extracts on Toxoplasma gondii and bioguided identification of triterpenes in Alnus glutinosa barks

Author

Darme, Pierre, Spalenka, Jérémy, Hubert, Jane, Escotte-Binet, Sandie, Debelle, Laurent, Villena, Isabelle, Sayagh, Charlotte, Borie, Nicolas, Martinez, Agathe, Renault, Jean-Hugues, Bertaux, Benjamin, Voutquenne-Nazabadioko, Laurence, Aubert, Dominique, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Epidémiosurveillance de protozooses à transmission alimentaire et vectorielle (ESCAPE), Université de Reims Champagne-Ardenne (URCA)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Agence nationale de sécurité sanitaire de l'alimentation, de l'environnement et du travail (ANSES), NatExplore, Matrice extracellulaire et dynamique cellulaire - UMR 7369 (MEDyC), Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Alnus glutinosa, bark, antiparasitic, toxoplasma gondii, Betulaceae, apicomplexa, triterpene, [SDV.MP.PAR]Life Sciences [q-bio]/Microbiology and Parasitology/Parasitology, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, [SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics
Abstract

International audience; Toxoplasmosis is a worldwide parasitosis that affects one-third of the population. People at risk, such as immunocompromised patients (AIDS, chemotherapy treatment) or fetuses (maternal-fetal transmission) can develop severe forms of the disease. The antiparasitic activity of extracts of different polarities ( n -heptane, MeOH, MeOH/H 2 O) of ten tree species endemics to temperate regions was investigated against Toxoplasma gondii infection in vitro . Our results showed that the n -heptane extract of the black alder ( Alnus glutinosa ) exhibited a significant antiparasitic activity without any cytotoxicity at the tested concentrations, with an IC 50 of up to 25.08 μg/mL and a selectivity index higher than 3.99. The chemical profiling of this extract revealed triterpenes as major constituents. The ability of commercially available triterpene (betulin, betulinic acid, and betulone) to inhibit the growth of T. gondii was evaluated and showed growth inhibition rates of 44%, 49%, and 99% at 10 μM, respectively.

Published
2021

44. Anti-tumoral Effect of Thymelaea hirsutaL. Extracts in Colorectal Cancer Cells

Author

Toumi, Iheb, Yatouji, Sonia, Borie, Nicolas, Remy, Simon, Renault, Jean-Hugues, Chazee, Lise, Hammami, Mohamed, Martiny, Laurent, Devarenne-Charpentier, Emmanuelle, and El Btaouri, Hassan

Abstract

Background: Conventional chemotherapeutic treatment of colorectal cancer has low efficiency because of its high toxicity. Several studies identified natural compounds as potential antitumor agents by inducing cancer cell cycle arrest or apoptosis and exhibiting a potential synergy in drug combination therapy. Natural compounds derived from plants represent an important source of pharmacologic agents toward several diseases. For example, the Tunisian Thymelaeaceae plants are used in folk medicine for the treatment of different pathologies such as diabetes and hypertension. Objective: The Thymelaea hirsuta L. extracts were evaluated for their anti-tumoral activities and their adjuvant potential that could be used in conventional colorectal cancer therapy. Methods: Fractionation of total methanolic extract from the plant leaves provided 4 fractions using vacuum liquid chromatography. The cytotoxic activities of these fractions were tested toward colorectal cancer cells. Results: Ethyl acetate fraction (E2 fraction) induced cell cycle arrest and apoptosis by activating caspase-3. E2 fraction inhibited cell invasion by reducing integrin α5 expression and FAK phosphorylation. Moreover, E2 fraction potentialized colorectal cancer cells to 5-FU treatment. Conclusion: The selected plant Thymelaea hirsuta is the source of natural compounds that inhibited cell growth and invasion and induced cell cycle arrest in colorectal cancer cells. The most interesting result was their potential synergy in 5-FU combination treatment. Further analysis will identify the active compounds and confirm their role in chemotherapeutic treatment by sensitizing colorectal cancer cell to anti-cancer drugs.

Published
2023
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47. Multiple solvent signal presaturation and decoupling artifact removal in 13C{1H} nuclear magnetic resonance

Author

Canton, Marine, Roe, Richard, Poigny, Stéphane, Renault, Jean-Hugues, Nuzillard, Jean-Marc, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Pharmacochimie Pierre Fabre Dermo-Cosmétique, Centre de Recherche Pierre Fabre (Centre de R&D Pierre Fabre), and PIERRE FABRE-PIERRE FABRE

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

The analysis by proton-decoupled carbon-13 nuclear magnetic resonance spectroscopy of samples dissolved in solvents presenting strong multiple resonances can be facilitated by the suppression of these resonances by multisite presaturation. The advantage drawn from this operation is the elimination of the possible artifacts that arise from the solvent signals in non-optimized decoupling conditions. Solvent presaturation was implemented on glycerol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, and 1,3-butanediol with at least 94 % on-resonance efficiency and a bandwidth of less than 50 Hz measured at 50 % signal intensity decrease. The experimental measurement of the signal suppression bandwidth leads to unexpected selectivity profiles for close-frequency resonances. Computer resolution of the Bloch equations during multisite presaturation provide an insight into the origin of the observed profile perturbations.

Published
2020

48. Multiple solvent signal presaturation in 13C NMR

Author

Canton, Marine, Roe, Richard, Poigny, Stéphane, Renault, Jean-Hugues, Nuzillard, Jean-Marc, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Pharmacochimie Pierre Fabre Dermo-Cosmétique, Centre de Recherche Pierre Fabre (Centre de R&D Pierre Fabre), and PIERRE FABRE-PIERRE FABRE

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

The analysis by proton-decoupled carbon-13 nuclear magnetic resonance spectroscopy of samples dissolved in solvents presenting strong multiple resonances can be facilitated by the suppression of these resonances by multi–site presaturation. The advantage drawn from this operation is the elimination of the possible artifacts that arise from the solvent signals in non–optimized decoupling conditions. Solvent presaturation was implemented on glycerol, 1,2–propanediol, 1,3–propanediol, 1,2–butanediol, 1,3–butanediol with at least 94 % on–resonance efficiency and a bandwidth of less 5 than 50 Hz measured at 50 % signal intensity decrease. The experimental measurement of the signal suppression bandwidth leads to unexpected selectivity profiles for frequency close resonances. Computer resolution of the Bloch equations during multi–site presaturation provide an insight into the origin of the observed profile perturbations.; The analysis by proton-decoupled carbon-13 nuclear magnetic resonance spectroscopy of samples dissolved in solvents presenting strong multiple resonances can be facilitated by the suppression of these resonances by multi-site presatu-ration. The advantage drawn from this operation is the elimination of the possible artifacts that arise from the solvent signals in non-optimized decoupling conditions. Solvent presaturation was implemented on glycerol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol with at least 94 % on-resonance efficiency and a bandwidth of less than 50 Hz measured at 5 50 % signal intensity decrease. The experimental measurement of the signal suppression bandwidth leads to unexpected se-lectivity profiles for frequency close resonances. Computer resolution of the Bloch equations during multi-site presaturation provide an insight into the origin of the observed profile perturbations.

Published
2020

49. Multilevel chemotyping of microalgae, a necessary tool for chemodiversity exploration and blue biotechnology development : the i-chemalgae project

Author

Coat, Rémy, Chollet, Sébastien, BERNARD, Sylvie, Humeau, Anne, Sockalingum, Ganesh, Untereiner, Valérie, Marchal, Luc, Gonçalves, Olivier, Renault, Jean-Hugues, Bioprocédés Appliqués aux Microalgues (GEPEA-BAM), Laboratoire de génie des procédés - environnement - agroalimentaire (GEPEA), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-IMT Atlantique Bretagne-Pays de la Loire (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Ecole Polytechnique de l'Université de Nantes (EPUN), Université de Nantes (UN)-Université de Nantes (UN)-Institut Universitaire de Technologie - Nantes (IUT Nantes), Université de Nantes (UN)-Institut Universitaire de Technologie Saint-Nazaire (IUT Saint-Nazaire), Université de Nantes (UN)-Institut Universitaire de Technologie - La Roche-sur-Yon (IUT La Roche-sur-Yon), Université de Nantes (UN)-Ecole Nationale Vétérinaire, Agroalimentaire et de l'alimentation Nantes-Atlantique (ONIRIS)-Université Bretagne Loire (UBL)-Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Ecole Nationale Vétérinaire, Agroalimentaire et de l'alimentation Nantes-Atlantique (ONIRIS)-Université Bretagne Loire (UBL), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), SOLIENCE, Biospectroscopie Translationnelle - EA 7506 (BIOSPECT), Université de Reims Champagne-Ardenne (URCA), Matrice extracellulaire et dynamique cellulaire - UMR 7369 (MEDyC), Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Mines Nantes (Mines Nantes)-Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Ecole Nationale Vétérinaire, Agroalimentaire et de l'alimentation Nantes-Atlantique (ONIRIS)-Centre National de la Recherche Scientifique (CNRS), and Gonçalves, Olivier

Subjects
[SPI]Engineering Sciences [physics], [SPI] Engineering Sciences [physics], [SPI.GPROC] Engineering Sciences [physics]/Chemical and Process Engineering, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2020

50. Chemical Profile and Antimicrobial Activity of the Fungus-Growing Termite Strain Macrotermes Bellicosus Used in Traditional Medicine in the Republic of Benin

Author

Hammoud Mahdi, Dima, Hubert, Jane, Renault, Jean-Hugues, Martinez, Agathe, Schubert, Andreas, Engel, Kathrin Monika, Koudogbo, Blaise, Vissiennon, Zacharie, Ahyi, Virgile, Nieber, Karen, Vissiennon, Cica, Inter-Regional University of Industrial Engineering Biotechnologies and Applied Sciences, IRGIB Africa, NatExplore, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fraunhofer Institute for Cell Therapy and Immunology (Fraunhofer IZI), Fraunhofer (Fraunhofer-Gesellschaft), and Institute of Medical Physics and Biophysics - Leipzig University

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, Republic of Benin, Macrotermes bellicosus, termite, traditional medicine, antibacterial activity, hydroquinone, methylhydroquinone, lcsh:QD241-441, lcsh:Organic chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, ddc:540, Antibacterial activity
Abstract

The fungus growing termite species Macrotermes bellicosus (M. bellicosus) is used in nutrition and traditional medicine in the Republic of Benin for the treatment of infectious and inflammatory diseases. Previous findings demonstrated evidence of anti-inflammatory and spasmolytic properties of M. bellicosus. The aim of the present study was to evaluate the antimicrobial potential of different extracts of M. bellicosus samples and determine the chemical profile of an ethanolic M. bellicosus extract. Chemical profiling was conducted using centrifugal partition chromatography and 13C-NMR, followed by MALDI-TOF MS. Major identified compounds include hydroquinone (HQ), methylhydroquinone (MHQ), 3,4-dihydroxyphenethyl glycol (DHPG), N-acetyldopamine (NADA) and niacinamide. The fatty acid mixture of the extract was mainly composed of linoleic and oleic acid and highlights the nutritional purpose of M. bellicosus. Using the Kirby&ndash, Bauer disc diffusion and broth microdilution assay, an antibacterial activity of M. bellicosus samples was observed against various clinical strains with a highest growth inhibition of S. aureus. In addition, HQ and MHQ as well as fractions containing DHPG, niacinamide and NADA inhibited S. aureus growth. The reported antimicrobial activity of M. bellicosus and identified active substances provide a rationale for the traditional medicinal use of M. bellicosus.

Published
2020

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