Natural triterpenoids are of great interest to researchers of various fields as they possess diverse physicochemical and biological properties. In medicinal chemistry, detailed information about the chemical structures of bioactive triterpenoids often helps find new lead compounds. Herein, the low-energy structures of (20S)-protopanaxadiol and (20S)-protopanaxatriol, the aglycones of various triterpenoid saponins found in Panax ginseng, and their (20R)-epimers have been predicted by the geometry optimization of the conformers extracted from molecular dynamics simulations with the self-consistent-charge density functional tight-binding method. By performing quantum mechanical calculations on the low-energy conformers, we have estimated the NMR chemical shifts of the compounds, which display good agreement with the most recently reported experimental values within an expected range of errors. Our results indicate that theoretical estimation of the NMR parameters of a relatively large molecule with a molecular mass of 500 is feasible.
Keywords: 1H and 13C; NMR; conformer; molecular dynamics; protopanaxadiol; protopanaxatriol; self-consistent-charge density functional tight-binding.
Copyright © 2015 John Wiley & Sons, Ltd.