162 results on '"Beniddir, Mehdi A."'
Search Results
152. Streamlined targeting of Amaryllidaceae alkaloids from the bulbs of Crinum scillifolium using spectrometric and taxonomically-informed scoring metabolite annotations.
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N'Tamon AD, Okpekon AT, Bony NF, Bernadat G, Gallard JF, Kouamé T, Séon-Méniel B, Leblanc K, Rharrabti S, Mouray E, Grellier P, Ake M, Amin NC, Champy P, Beniddir MA, and Le Pogam P
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- Humans, Molecular Structure, Plant Extracts, Plant Roots, Alkaloids pharmacology, Amaryllidaceae Alkaloids pharmacology, Crinum
- Abstract
Four undescribed alkaloids have been isolated from the bulbs of the previously unstudied Crinum scillifolium. These compounds were targeted following a state-of-the-art molecular networking strategy comprising a dereplication against in silico databases and re-ranking of the candidate structures based on taxonomically informed scoring. The unreported structures span across a variety of Amaryllidaceae alkaloids appendages. Their structures were unambiguously elucidated by thorough interpretation of their HRESIMS and 1D and 2D NMR data, and comparison to literature data. DFT-NMR calculations were performed to support the determined relative configurations of scillitazettine and scilli-N-desmethylpretazettine and their absolute configurations were mitigated by comparison between experimental and theoretically calculated ECD spectra. The lack of a methyl group on the nitrogen atom in the structure of scilli-N-desmethylpretazettine series is highly unusual in the pretazettine/tazettine series but the most original structural feature in it lies in its 11α disposed hydrogen, which is new to pretazettines. The antiplasmodial as well as the cytotoxic activities against the human colon cancer cell line HCT116 were evaluated, revealing mild to null activities., (Copyright © 2020 Elsevier Ltd. All rights reserved.)
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- 2020
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153. A thorough evaluation of matrix-free laser desorption ionization on structurally diverse alkaloids and their direct detection in plant extracts.
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Le Pogam P, Richomme P, Beniddir MA, Duong TH, Bernadat G, and Schinkovitz A
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- Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization methods, Alkaloids analysis, Atropa belladonna chemistry, Cinchona chemistry, Colchicum chemistry, Plant Extracts chemistry
- Abstract
Alkaloids represent a major group of natural products (NPs), derived from highly diverse organisms. These structurally varied specialized metabolites are widely used for medicinal purposes and also known as toxic contaminants in agriculture and dietary supplements. While the detection of alkaloids is generally facilitated by GC- or LC-MS, these techniques do require considerable efforts in sample preparation and method optimization. Bypassing these limitations and also reducing experimental time, matrix-free laser desorption ionization (LDI) and related methods may provide an interesting alternative. As many alkaloids show close structural similarities to matrices used in matrix-assisted laser desorption ionization (MALDI), they should ionize upon simple laser irradiation without matrix support. With this in mind, the current work presents a systematic evaluation of LDI properties of a wide range of structurally diverse alkaloids. Facilitating a direct comparison between LDI and ESI-MS fragmentation, all tested compounds were further studied by electrospray ionization (ESI). Moreover, crude plant extracts of Atropa belladonna, Cinchona succirubra, and Colchicum autumnale were analyzed by LDI in order to evaluate direct alkaloid detection and dereplication from complex mixtures. Finally, dose-dependent evaluation of MALDI and LDI detection using an extract of Rosmarinus officinalis spiked with atropine, colchicine, or quinine was conducted. Overall, present results suggest that LDI provides a versatile analytical tool for analyzing structurally diverse alkaloids as single compounds and from complex mixtures. It may further serve various potential applications ranging from quality control to the screening for toxic compounds as well as the build up of MS databases. Graphical abstract.
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- 2020
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154. In Silico Anticipation of Metabolic Pathways Extended to Organic Chemistry Reactions: A Case Study with Caffeine Alkaline Hydrolysis and The Origin of Camellimidazoles.
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Turpin V, Beniddir MA, Genta-Jouve G, Skiredj A, Gallard JF, Leblanc K, Le Pogam P, and Poupon E
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- Chemistry, Organic, Computer Simulation, Hydrolysis, Imidazoles, Metabolic Networks and Pathways, Caffeine chemistry
- Abstract
Camellimidazoles A-C were recently reported as natural substances in Keemun black tea. Although a "biosynthetic" route to these intriguing imidazole dimers was proposed from caffeine by the authors in this seminal report, we envisioned that a artefactual scenario, consisting of alkaline hydrolysis of caffeine and spontaneous cascade reactions with a methylene donor such as formaldehyde or methylene chloride, could also have led to their formation. To capture the diversity of molecules obtained under these conditions (i.e. alkaline treatment of caffeine/formaldehyde), an in silico MetWork-based pipeline was implemented, highlighting the sought-after camellimidazoles B and C. A wealth of further compounds were also tagged, notably comprising the herein newly described and unnatural camellimidazoles D-F that were subsequently confirmed as anticipated in silico upon extensive spectroscopic analyses. Likewise, camellimidazoles B and C could also be obtained using methylene chloride as an alternative methylene donor which may also have occurred in the initial phytochemical pipeline that implied this solvent. The current investigation emphasizes the fitness of MetWork tagging to extend the logic of in silico anticipation of metabolic pathways to organic chemistry reactions., (© 2020 Wiley-VCH GmbH.)
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- 2020
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155. Corynanthean-Epicatechin Flavoalkaloids from Corynanthe pachyceras .
- Author
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Kouamé T, Okpekon AT, Bony NF, N'Tamon AD, Gallard JF, Rharrabti S, Leblanc K, Mouray E, Grellier P, Champy P, Beniddir MA, and Le Pogam P
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- Inhibitory Concentration 50, Magnetic Resonance Spectroscopy, Mass Spectrometry, Molecular Structure, Monoterpenes chemistry, Pausinystalia chemistry, Plant Bark chemistry, Plant Stems chemistry, Anthelmintics pharmacology, Catechin chemistry, Flavonoids chemistry, Indole Alkaloids chemistry
- Abstract
Epicatechocorynantheines A and B, and epicatechocorynantheidine were isolated from the stem bark of Corynanthe pachyceras . These molecules were pinpointed, and their isolation streamlined, by a molecular networking strategy. The structural elucidation was unambiguously accomplished from HRMS and 1D/2D NMR data. These compounds represent the first examples of corynanthean-type alkaloids tethered with a flavonoid. Epicatechocorynantheidine notably instigated two connections between the monoterpene indole alkaloid and the flavonoid, yielding an unprecedented octacyclic appendage. These flavoalkaloids exerted moderate antiplasmodial activities.
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- 2020
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156. A database of high-resolution MS/MS spectra for lichen metabolites.
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Olivier-Jimenez D, Chollet-Krugler M, Rondeau D, Beniddir MA, Ferron S, Delhaye T, Allard PM, Wolfender JL, Sipman HJM, Lücking R, Boustie J, and Le Pogam P
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- Tandem Mass Spectrometry, Databases, Factual, Lichens chemistry, Metabolomics
- Abstract
While analytical techniques in natural products research massively shifted to liquid chromatography-mass spectrometry, lichen chemistry remains reliant on limited analytical methods, Thin Layer Chromatography being the gold standard. To meet the modern standards of metabolomics within lichenochemistry, we announce the publication of an open access MS/MS library with 250 metabolites, coined LDB for Lichen DataBase, providing a comprehensive coverage of lichen chemodiversity. These were donated by the Berlin Garden and Botanical Museum from the collection of Siegfried Huneck to be analyzed by LC-MS/MS. Spectra at individual collision energies were submitted to MetaboLights (https://www.ebi.ac.uk/metabolights/MTBLS999) while merged spectra were uploaded to the GNPS platform (CCMSLIB00004751209 to CCMSLIB00004751517). Technical validation was achieved by dereplicating three lichen extracts using a Molecular Networking approach, revealing the detection of eleven unique molecules that would have been missed without LDB implementation to the GNPS. From a chemist's viewpoint, this database should help streamlining the isolation of formerly unreported metabolites. From a taxonomist perspective, the LDB offers a versatile tool for the chemical profiling of newly reported species.
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- 2019
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157. Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research.
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Fox Ramos AE, Le Pogam P, Fox Alcover C, Otogo N'Nang E, Cauchie G, Hazni H, Awang K, Bréard D, Echavarren AM, Frédérich M, Gaslonde T, Girardot M, Grougnet R, Kirillova MS, Kritsanida M, Lémus C, Le Ray AM, Lewin G, Litaudon M, Mambu L, Michel S, Miloserdov FM, Muratore ME, Richomme-Peniguel P, Roussi F, Evanno L, Poupon E, Champy P, and Beniddir MA
- 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 ).
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- 2019
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158. Correction: The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.
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McAlpine JB, Chen SN, Kutateladze A, MacMillan JB, Appendino G, Barison A, Beniddir MA, Biavatti MW, Bluml S, Boufridi A, Butler MS, Capon RJ, Choi YH, Coppage D, Crews P, Crimmins MT, Csete M, Dewapriya P, Egan JM, Garson MJ, Genta-Jouve G, Gerwick WH, Gross H, Harper MK, Hermanto P, Hook JM, Hunter L, Jeannerat D, Ji NY, Johnson TA, Kingston DGI, Koshino H, Lee HW, Lewin G, Li J, Linington RG, Liu M, McPhail KL, Molinski TF, Moore BS, Nam JW, Neupane RP, Niemitz M, Nuzillard JM, Oberlies NH, Ocampos FMM, Pan G, Quinn RJ, Reddy DS, Renault JH, Rivera-Chávez J, Robien W, Saunders CM, Schmidt TJ, Seger C, Shen B, Steinbeck C, Stuppner H, Sturm S, Taglialatela-Scafati O, Tantillo DJ, Verpoorte R, Wang BG, Williams CM, Williams PG, Wist J, Yue JM, Zhang C, Xu Z, Simmler C, Lankin DC, Bisson J, and Pauli GF
- 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: .
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- 2019
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159. The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.
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McAlpine JB, Chen SN, Kutateladze A, MacMillan JB, Appendino G, Barison A, Beniddir MA, Biavatti MW, Bluml S, Boufridi A, Butler MS, Capon RJ, Choi YH, Coppage D, Crews P, Crimmins MT, Csete M, Dewapriya P, Egan JM, Garson MJ, Genta-Jouve G, Gerwick WH, Gross H, Harper MK, Hermanto P, Hook JM, Hunter L, Jeannerat D, Ji NY, Johnson TA, Kingston DGI, Koshino H, Lee HW, Lewin G, Li J, Linington RG, Liu M, McPhail KL, Molinski TF, Moore BS, Nam JW, Neupane RP, Niemitz M, Nuzillard JM, Oberlies NH, Ocampos FMM, Pan G, Quinn RJ, Reddy DS, Renault JH, Rivera-Chávez J, Robien W, Saunders CM, Schmidt TJ, Seger C, Shen B, Steinbeck C, Stuppner H, Sturm S, Taglialatela-Scafati O, Tantillo DJ, Verpoorte R, Wang BG, Williams CM, Williams PG, Wist J, Yue JM, Zhang C, Xu Z, Simmler C, Lankin DC, Bisson J, and Pauli GF
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- Molecular Conformation, Reproducibility of Results, Biological Products chemistry, Magnetic Resonance Spectroscopy methods
- 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.
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- 2019
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160. Resolving the (19 R) Absolute Configuration of Lanciferine, a Monoterpene Indole Alkaloid from Alstonia boulindaensis.
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Beniddir MA, Genta-Jouve G, and Lewin G
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- Crystallography, X-Ray methods, Nuclear Magnetic Resonance, Biomolecular methods, Alkaloids chemistry, Alstonia chemistry, Indole Alkaloids chemistry, Monoterpenes chemistry
- Abstract
Reinvestigation of the structure of lanciferine (1a) through extensive spectroscopic analysis in conjunction with a detailed computational study led to the unambiguous assignment of its (19 R) absolute configuration, thus leading to the full (2 R, 3 S, 7 S, 15 R, 16 R, 19 R, 20 S) assignment of lanciferine 45 years after its isolation.
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- 2018
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161. Pleiokomenines A and B: Dimeric Aspidofractinine Alkaloids Tethered with a Methylene Group.
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N'Nang Obiang EO, Genta-Jouve G, Gallard JF, Kumulungui B, Mouray E, Grellier P, Evanno L, Poupon E, Champy P, and Beniddir MA
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Pleiokomenines A and B (1 and 2), first examples of dimeric aspidofractinine alkaloids linked by a methylene bridge, were isolated from the stem bark of Pleiocarpa mutica. Their structures were elucidated by a combination of spectroscopic analyses and semisynthetic derivatization of pleiocarpinine (3) and a formaldehyde equivalent mediated by scandium trifluoromethanesulfonate. Pleiokomenines A (1) and B (2) showed moderate antiplasmodial activities in the micromolar range against the FcB1 strain.
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- 2017
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162. An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H.
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Bonneau N, Chen G, Lachkar D, Boufridi A, Gallard JF, Retailleau P, Petek S, Debitus C, Evanno L, Beniddir MA, and Poupon E
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- Animals, Biological Products chemical synthesis, Biological Products chemistry, Biological Products isolation & purification, Chlortetracycline chemical synthesis, Chlortetracycline isolation & purification, Chromatography, High Pressure Liquid, Crystallography, X-Ray, Magnetic Resonance Spectroscopy, Molecular Conformation, Porifera metabolism, Quinones chemistry, Sesquiterpenes chemistry, Tandem Mass Spectrometry, Chlortetracycline analogs & derivatives, Porifera chemistry
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Guided by a "chemistry first" approach using molecular networking, eight new bright-blue colored natural compounds, namely dactylocyanines A-H (3-10), were isolated from the Polynesian marine sponge Dactylospongia metachromia. Starting from ilimaquinone (1), an hemisynthetic phishing probe (2) was prepared for annotating and matching structurally related natural substances in D. metachromia crude extract network. This strategy allowed characterizing for the first time in Nature the blue zwitterionic quinonoid chromophore. The solvatochromic properties of the latter are reported., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
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- 2017
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