title: Chemical constituents of Anacolosa pervilleana and their antiviral activities.
abstract: In an effort to identify novel inhibitors of Chikungunya (CHIKV) and Dengue (DENV) virus replication, a systematic study with 820 ethyl acetate extracts of Madagascan plants was performed in a virus-cell-based assay for CHIKV and a DENV NS5 RNA-dependant RNA polymerase (RdRp) assay. The extract obtained from the leaves of Anacolosa pervilleana was selected for its significant activity in both assays. One new (E)-tridec-2-en-4-ynedioic acid named anacolosine (1), together with three known acetylenic acids, the octadeca-9,11,13-triynoic acid (2), (13E)-octadec-13-en-9,11-diynoic acid (3), (13E)-octadec-13-en-11-ynoic acid (4), two terpenoids, lupenone (5) and β-amyrone (6), and one cyanogenic glycoside, (S)-sambunigrin (7) were isolated. Their structures were elucidated by comprehensive analyses of NMR spectroscopy and mass spectrometry data. The inhibitory potency of these compounds was evaluated on CHIKV, DENV RdRp and West-Nile polymerase virus (WNV RdRp). Both terpenoids showed a moderate activity against CHIKV (EC(50) 77 and 86 μM, respectively) and the acetylenic acids produced IC(50) values around 3 μM in the DENV RdRp assay.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles (ICSN), CNRS, LabEx LERMIT, Gif sur Yvette, France.
authors.forename: Mélanie
authors.initials: M
authors.lastname: Bourjot
authors.forename: Pieter
authors.initials: P
authors.lastname: Leyssen
authors.forename: Cécilia
authors.initials: C
authors.lastname: Eydoux
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Guillemot
authors.forename: Bruno
authors.initials: B
authors.lastname: Canard
authors.forename: Philippe
authors.initials: P
authors.lastname: Rasoanaivo
authors.forename: Françoise
authors.initials: F
authors.lastname: Guéritte
authors.forename: Marc
authors.initials: M
authors.lastname: Litaudon
mesh_terms: D000480:Alkynes / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D000818:Animals; D000998:Antiviral Agents / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D002646:Chikungunya virus / Q000187:drug effects*; D002522:Chlorocebus aethiops; D012321:DNA-Directed RNA Polymerases / Q000378:metabolism; D003716:Dengue Virus / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D008270:Madagascar; D015394:Molecular Structure; D031656:Olacaceae / Q000737:chemistry*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D018515:Plant Leaves; D012327:RNA Virus Infections / Q000188:drug therapy*; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use; D014709:Vero Cells; D014902:West Nile virus / Q000187:drug effects*; D000094042:Lupanes
chemical_list: D000480:Alkynes; D000998:Antiviral Agents; D012321:DNA-Directed RNA Polymerases; D010936:Plant Extracts; D014315:Triterpenes; C511312:amyrone; C470592:lupenone; D000094042:Lupanes