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Environmentally-Friendly Workflow Based on Supercritical Fluid Chromatography and Tandem Mass Spectrometry Molecular Networking For the Discovery of Potent Anti-Viral Leads From Plants

Louis-Félix Nothias, Stéphanie Boutet-Mercey, Xavier Cachet, Erick De La Torre, Laurent Laboureur, Jean-François Gallard, Pascal Retailleau, Alain Brunelle, Pieter C. Dorrestein, Jean Costa, Luis M. Bedoya, Fanny Roussi, Pieter Leyssen, José Alcami, Julien Paolini, Marc Litaudon, David Touboul
doi: https://doi.org/10.1101/106153
Louis-Félix Nothias
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
‡Laboratoire de Chimie de Produits Naturels, UMR CNRS SPE 6134, Université de Corse, 20250, Corte, France
§Collaborative Mass Spectrometry Innovation Center, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA 92093, USA
∥Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California, CA 92093, USA
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Stéphanie Boutet-Mercey
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Xavier Cachet
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
⊥Laboratoire de Pharmacognosie, UMR 8638 COMETE CNRS, Faculté de Pharmacie, Université Paris Descartes, Sorbonne Paris Cité, Paris, France
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Erick De La Torre
#Departamento de Inmunopatología del SIDA, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Ctra. Pozuelo Km.2, 28220, Majadahonda, Madrid, Spain
+Departamento de Farmacología, Facultad de Farmacia, Universidad Complutense de Madrid. Pz. Ramon y Cajal s/n, 28040, Madrid, Spain
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Laurent Laboureur
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Jean-François Gallard
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Pascal Retailleau
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Alain Brunelle
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Pieter C. Dorrestein
§Collaborative Mass Spectrometry Innovation Center, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA 92093, USA
∥Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California, CA 92093, USA
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Jean Costa
‡Laboratoire de Chimie de Produits Naturels, UMR CNRS SPE 6134, Université de Corse, 20250, Corte, France
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Luis M. Bedoya
#Departamento de Inmunopatología del SIDA, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Ctra. Pozuelo Km.2, 28220, Majadahonda, Madrid, Spain
+Departamento de Farmacología, Facultad de Farmacia, Universidad Complutense de Madrid. Pz. Ramon y Cajal s/n, 28040, Madrid, Spain
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Fanny Roussi
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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Pieter Leyssen
×Laboratory for Virology and Experimental Chemotherapy, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium
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José Alcami
#Departamento de Inmunopatología del SIDA, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Ctra. Pozuelo Km.2, 28220, Majadahonda, Madrid, Spain
+Departamento de Farmacología, Facultad de Farmacia, Universidad Complutense de Madrid. Pz. Ramon y Cajal s/n, 28040, Madrid, Spain
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Julien Paolini
‡Laboratoire de Chimie de Produits Naturels, UMR CNRS SPE 6134, Université de Corse, 20250, Corte, France
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Marc Litaudon
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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  • For correspondence: marc.litaudon@cnrs.fr
David Touboul
†Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la terrasse, 91198 Gif-sur-Yvette, France
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  • For correspondence: david.touboul@cnrs.fr
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ABSTRACT

A supercritical fluid chromatography-based targeted purification workflow using tandem mass spectrometry and molecular networking was developed to analyze, annotate and isolate secondary metabolites from complex mixture. This approach was applied for targeted isolation of new antiviral diterpene esters from Euphorbia semiperfoliata whole plant extract. The analysis of bioactive fractions revealed that unknown diterpene esters, including jatrophane esters and phorboids esters, were present in the samples. The purification procedure using semi-preparative-supercritical fluid chromatography led to the isolation and identification of two jatrophane esters (13 and 14) and four 4-deoxyphorbol esters (15-18). Compound 16 was found to display antiviral activity against chikungunya virus (EC50 = 0.45 µM), while compound 15 was found to be a potent and selective inhibitor of HIV-1 replication in a recombinant virus assay (EC50 = 13 nM). This study showed that supercritical fluid chromatography-based workflow and molecular networking can facilitate and accelerate the discovery of bioactive small molecules by targeted molecules of interest, while minimizing the use of toxic solvents.

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  • The authors declare no competing financial interest.

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The copyright holder for this preprint is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. All rights reserved. No reuse allowed without permission.
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Posted February 05, 2017.
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Environmentally-Friendly Workflow Based on Supercritical Fluid Chromatography and Tandem Mass Spectrometry Molecular Networking For the Discovery of Potent Anti-Viral Leads From Plants
Louis-Félix Nothias, Stéphanie Boutet-Mercey, Xavier Cachet, Erick De La Torre, Laurent Laboureur, Jean-François Gallard, Pascal Retailleau, Alain Brunelle, Pieter C. Dorrestein, Jean Costa, Luis M. Bedoya, Fanny Roussi, Pieter Leyssen, José Alcami, Julien Paolini, Marc Litaudon, David Touboul
bioRxiv 106153; doi: https://doi.org/10.1101/106153
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Environmentally-Friendly Workflow Based on Supercritical Fluid Chromatography and Tandem Mass Spectrometry Molecular Networking For the Discovery of Potent Anti-Viral Leads From Plants
Louis-Félix Nothias, Stéphanie Boutet-Mercey, Xavier Cachet, Erick De La Torre, Laurent Laboureur, Jean-François Gallard, Pascal Retailleau, Alain Brunelle, Pieter C. Dorrestein, Jean Costa, Luis M. Bedoya, Fanny Roussi, Pieter Leyssen, José Alcami, Julien Paolini, Marc Litaudon, David Touboul
bioRxiv 106153; doi: https://doi.org/10.1101/106153

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