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Environmentally Friendly Procedure Based on Supercritical Fluid Chromatography and Tandem Mass Spectrometry Molecular Networking for the Discovery of Potent Antiviral Compounds from Euphorbia semiperfoliata

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† Institut de Chimie des Substances Naturelles, CNRS UPR 2301, University of Paris-Saclay, 91198 Gif-sur-Yvette, France
‡ Laboratoire de Chimie des Produits Naturels, CNRS, UMR SPE 6134, University of Corsica, 20250 Corte, France
§ Collaborative Mass Spectrometry Innovation Center, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California 92093, United States
∥ Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California 92093, United States
⊥ Laboratoire de Pharmacognosie, UMR 8638 COMETE CNRS, Faculté de Pharmacie, University of Paris Descartes, Sorbonne Paris Cité, 75270 Paris, France
▽ 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
# Laboratory for Virology and Experimental Chemotherapy, Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium
*Tel: +33 1 69 82 30 85. E-mail: [email protected]
*Tel: +33 1 69 82 30 94. E-mail: [email protected]
Cite this: J. Nat. Prod. 2017, 80, 10, 2620–2629
Publication Date (Web):September 19, 2017
https://doi.org/10.1021/acs.jnatprod.7b00113
Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    A supercritical fluid chromatography-based targeted purification procedure using tandem mass spectrometry and molecular networking was developed to analyze, annotate, and isolate secondary metabolites from complex plant extract mixture. This approach was applied for the 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 phorbol esters, were present in the samples. The purification procedure using semipreparative supercritical fluid chromatography led to the isolation and identification of two new jatrophane esters (13 and 14) and one known (15) and three new 4-deoxyphorbol esters (16–18). The structure and absolute configuration of compound 16 were confirmed by X-ray crystallography. This compound was found to display antiviral activity against Chikungunya virus (EC50 = 0.45 μM), while compound 15 proved to be a potent and selective inhibitor of HIV-1 replication in a recombinant virus assay (EC50 = 13 nM). This study showed that a supercritical fluid chromatography-based protocol and molecular networking can facilitate and accelerate the discovery of bioactive small molecules by targeting molecules of interest, while minimizing the use of toxic solvents.

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