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. Epub 2015 Nov 23.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abies / chemistry*
  • Algorithms
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Canada
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Spiro Compounds
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Spiro Compounds
  • Terpenes
  • abibalsamin B