Conformational studies of dammarane-type triterpenoids using computational and NMR spectroscopic methods

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‐e...

Full description

Saved in:
Bibliographic Details
Published in:Magnetic resonance in chemistry 2015-12, Vol.53 (12), p.1035-1042
Main Authors: Shin, Byong-kyu, Lee, Jihyung, Choi, Tae Hoon
Format: Article
Language:English
Subjects:
1H and 13C
Accuracy
conformer
Dammaranes
Density
Low energy
Magnetic resonance
Magnetic Resonance Spectroscopy - methods
Mathematical analysis
Models, Chemical
Molecular Conformation
Molecular dynamics
Molecular Dynamics Simulation
Molecular structure
Molecular Weight
NMR
Nuclear magnetic resonance
Panax - chemistry
Plant Extracts - chemistry
protopanaxadiol
protopanaxatriol
Quantum Theory
self-consistent-charge density functional tight-binding
Triterpenes - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Copyright © 2015 John Wiley & Sons, Ltd. Stable conformers of two triterpenoids are found by SCC‐DFTB‐based MD. The NMR chemical shifts of the stable conformers are estimated by QM calculations. The calculated chemical shifts show good agreement with the experimental values.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.4302