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.
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.