Planta Med 2010; 76 - P74
DOI: 10.1055/s-0030-1251836

Absolute Configuration of the Biphenyl Axis in Cyclooctadienyl Neolignans

Y Ding 1, XC Li 1, IA Khan 1, 2, D Ferreira 1, 2
  • 1National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, MS 38677, USA
  • 2Department of Pharmacognosy, School of Pharmacy, University of Mississippi, MS 38677, USA

Theoretical calculation of electronic circular dichroism (ECD) spectra of a series of cyclooctadienyl neolignans [1] using time dependent density functional theory (TDDFT), were performed at the B3LYP/6–31G** level in the gas phase. The effects of basis set and solution have been studied at the B3LYP/6–311++G**//B3LYP/6–31G** level in the gas phase and at the SCRF-B3LYP/6–31G**//B3LYP/6–31G** level in the MeOH phase in the COSMO model, respectively. The experimentally observed Cotton effects at about 230 and 250nm were confirmed to correspond to the axial chirality of the biphenyl chromophores. This study provided new insights in interpreting the experimentally observed ECD spectra of this class of compounds. Acknowledgements: We thank the Mississippi Center for Supercomputing Research (MCSR) for computational facilities. This work was supported in part by the USDA Agricultural Research Service Specific Cooperative Agreement No. 58–6408–2-0009. References: [1] Choi YW, Takamatsu S, et al. (2006)J Nat Prod 69: 356–35.