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

By Serge Lavoie, Charles Gauthier, Vakhtang Mshvildadze, Jean Legault, Benoit Roger, André Pichette

July 28, 2017

  • Year

  • Technique

  • Industry

Title

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

Author

Serge Lavoie, Charles Gauthier, Vakhtang Mshvildadze, Jean Legault, Benoit Roger, André Pichette

Year

2015

Journal

Journal of Natural Products

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.

Full Article

http://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.5b00492

Instrument

J-815

Keywords

Circular dichroism, Absolute configuration, Natural products