title: DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea.
abstract: Eight non-carotenoid tetraterpenoids, abibalsamins C-J (3-10), were isolated from the oleoresin of Abies balsamea. Their chemical structures were determined based on analysis of 1D/2D NMR and MS data. The assignment of their relative configurations was accomplished using homonuclear coupling constants in tandem with ROESY data. However, the presence of two stereogenic centers on a flexible side chain complicated the characterization. In silico models and ROESY data were analyzed in order to assign relative configurations of the isolated tetraterpenoids. Abibalsamins B and H-J showed moderate cytotoxicity against human A549 lung carcinoma cells, with IC50 values ranging between 6.7 and 10 μM.
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.
authors.forename: Serge
authors.initials: S
authors.lastname: Lavoie
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.|Institut de Chimie IC2MP, CNRS-UMR 7285, Équipe Synthèse Organique, Université de Poitiers , 4 Rue Michel Brunet, 86073 Poitiers Cedex 9, France.
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.
authors.forename: Vakhtang
authors.initials: V
authors.lastname: Mshvildadze
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.
authors.forename: Jean
authors.initials: J
authors.lastname: Legault
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.
authors.forename: Benoit
authors.initials: B
authors.lastname: Roger
authors.affiliation: Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi , 555 Boulevard de l'Université, Chicoutimi, Québec, Canada , G7H 2B1.
authors.forename: André
authors.initials: A
authors.lastname: Pichette
mesh_terms: D028202:Abies / Q000737:chemistry*; D000465:Algorithms; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002170:Canada; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013141:Spiro Compounds; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D013141:Spiro Compounds; D013729:Terpenes; C572543:abibalsamin B