title: Antioxidant, 5-lipoxygenase inhibitory and cytotoxic activities of compounds isolated from the Ferula lutea flowers.
abstract: A phytochemical investigation of the Ferula lutea (Poir.) Maire flowers has led to the isolation of a new compound, (E)-5-ethylidenefuran-2(5H)-one-5-O-β-d-glucopyranoside (1), designated ferunide, 4-hydroxy-3-methylbut-2-enoic acid (2), reported for the first time as a natural product, together with nine known compounds, verbenone-5-O-β-d-glucopyranoside (3), 5-O-caffeoylquinic acid (4), methyl caffeate (5), methyl 3,5-O-dicaffeoylquinate (6), 3,5-O-dicaffeoylquinic acid (7), isorhamnetin-3-O-α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside, narcissin (8), (-)-marmesin (9), isoimperatorin (10) and 2,3,6-trimethylbenzaldehyde (11). Compounds 3-10 were identified for the first time in Ferula genus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments, mass spectroscopy and X-ray diffraction analysis (compound 2), as well as by comparison with literature data. The antioxidant, anti-inflammatory and cytotoxic activities of isolated compounds were evaluated. Results showed that compound 7 exhibited the highest antioxidant activity with IC50 values of 18 ± 0.5 µmol/L and 19.7 ± 0.7 µmol/L by DPPH radical and ABTS radical cation, respectively. The compound 6 exhibited the highest anti-inflammatory activity with an IC50 value of 5.3 ± 0.1 µmol/L against 5-lipoxygenase. In addition, compound 5 was found to be the most cytotoxic, with IC50 values of 22.5 ± 2.4 µmol/L, 17.8 ± 1.1 µmol/L and 25 ± 1.1 µmol/L against the HCT-116, IGROV-1 and OVCAR-3 cell lines, respectively.
authors.affiliation: Université de Toulouse, Faculté de Pharmacie de Toulouse, Laboratoire des IMRCP UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France. Znatimansour@yahoo.fr.
authors.forename: Mansour
authors.initials: M
authors.lastname: Znati
authors.affiliation: Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité (CHPNR), Equipe Chimie Médicinale et Produits Naturels, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisia. hich.benjannet@yahoo.fr.
authors.forename: Hichem
authors.initials: H
authors.lastname: Ben Jannet
authors.affiliation: Université de Toulouse, Faculté de Pharmacie de Toulouse, Laboratoire des IMRCP UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France. sylvie.cazaux2@univ-tlse3.fr.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Cazaux
authors.affiliation: Université de Toulouse, Faculté de Pharmacie de Toulouse, Laboratoire des IMRCP UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France. souchard@chimie.ups-tlse.fr.
authors.forename: Jean Pierre
authors.initials: JP
authors.lastname: Souchard
authors.affiliation: Laboratory of Genetic, Biodiversity and Valorization of Bioresources, Higher Institute of Biotechnology of Monastir, University of Monastir, 5019 Monastir, Tunisia. fethiaprosopis@yahoo.fr.
authors.forename: Féthia
authors.initials: F
authors.lastname: Harzallah Skhiri
authors.affiliation: Université de Toulouse, Faculté de Pharmacie de Toulouse, Laboratoire des IMRCP UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France. jalloul.bouajila@univ-tlse3.fr.
authors.forename: Jalloul
authors.initials: J
authors.lastname: Bouajila
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001094:Arachidonate 5-Lipoxygenase / Q000737:chemistry*; D002109:Caffeic Acids / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D005309:Ferula / Q000737:chemistry*; D035264:Flowers / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D010936:Plant Extracts / Q000494:pharmacology*; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D000975:Antioxidants; D002109:Caffeic Acids; D004791:Enzyme Inhibitors; D010936:Plant Extracts; C472707:caffeoylquinic acid; C538691:methyl 3, 5-O-dicaffeoylquinate; D011801:Quinic Acid; C042405:methyl caffeate; D001094:Arachidonate 5-Lipoxygenase