2. Academic Validation
  3. DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

  • J Nat Prod. 2015 Dec 24;78(12):2896-907. doi: 10.1021/acs.jnatprod.5b00492.
Serge Lavoie 1,  Charles Gauthier 1 2,  Vakhtang Mshvildadze 1,  Jean Legault 1,  Benoit Roger 1,  André Pichette 1
Affiliations

Affiliations

  • 1 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.
  • 2 Institut de Chimie IC2MP, CNRS-UMR 7285, Équipe Synthèse Organique, Université de Poitiers , 4 Rue Michel Brunet, 86073 Poitiers Cedex 9, France.
PMID: 26592897 DOI: 10.1021/acs.jnatprod.5b00492
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.

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