title: Euphorbia dendroides Latex as a Source of Jatrophane Esters: Isolation, Structural Analysis, Conformational Study, and Anti-CHIKV Activity.
abstract: An efficient process was used to isolate six new jatrophane esters, euphodendroidins J (3), K (5), L (6), M, (8), N (10), and O (11), along with seven known diterpenoid esters, namely, euphodendroidins A (4), B (9), E (1), and F (2), jatrophane ester (7), and 3α-hydroxyterracinolides G and B (12 and 13), and terracinolides J and C (14 and 15) from the latex of Euphorbia dendroides. Their 2D structures and relative configurations were established by extensive NMR spectroscopic analysis. The absolute configurations of compounds 1, 11, and 15 were determined by X-ray diffraction analysis. Euphodendroidin F (2) was obtained in 18% yield from the diterpenoid ester-enriched extract after two consecutive flash chromatography steps, making it an interesting starting material for chemical synthesis. Euphodendroidins K and L (5 and 6) showed an unprecedented NMR spectroscopic behavior, which was investigated by variable-temperature NMR experiments and molecular modeling. The structure-conformation relationships study of compounds 1, 5, and 6, using DFT-NMR calculations, indicated the prominent role of the acylation pattern in governing the conformational behavior of these jatrophane esters. The antiviral activity of compounds 1-15 was evaluated against Chikungunya virus (CHIKV) replication.
authors: Laboratoire de Chimie des Produits Naturels, CNRS, UMR SPE 6134, University of Corsica , 20250, Corte, France.|Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Mélissa
authors: M
authors: Esposito
authors: Laboratoire de Chimie des Produits Naturels, CNRS, UMR SPE 6134, University of Corsica , 20250, Corte, France.|Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Louis-Félix
authors: LF
authors: Nothias
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Hirsto
authors: H
authors: Nedev
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Jean-François
authors: JF
authors: Gallard
authors: Laboratory for Virology and Experimental Chemotherapy, Rega Institute for Medical Research, KU Leuven , 3000 Leuven, Belgium.
authors: Pieter
authors: P
authors: Leyssen
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Pascal
authors: P
authors: Retailleau
authors: Laboratoire de Chimie des Produits Naturels, CNRS, UMR SPE 6134, University of Corsica , 20250, Corte, France.
authors: Jean
authors: J
authors: Costa
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Fanny
authors: F
authors: Roussi
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Bogdan I
authors: BI
authors: Iorga
authors: Laboratoire de Chimie des Produits Naturels, CNRS, UMR SPE 6134, University of Corsica , 20250, Corte, France.
authors: Julien
authors: J
authors: Paolini
authors: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, University of Paris-Saclay , 91198, Gif-sur-Yvette, France.
authors: Marc
authors: M
authors: Litaudon
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D065632:Chikungunya Fever / Q000188:drug therapy; D002646:Chikungunya virus / Q000187:drug effects*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004952:Esters; D028481:Euphorbia / Q000737:chemistry*; D005602:France; D007840:Latex / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013329:Structure-Activity Relationship; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D004224:Diterpenes; D004952:Esters; D007840:Latex; C530345:jatrophane