Molecular modelling and QSAR analysis of the estrogenic activity of terpenoids isolated from Ferula plants
The relationship between chemical structure and estrogenic activity in a series of terpenoid esters with aromatic and aliphatic acid substituents isolated from Ferula plants, was studied. The fragments of the terpenoid structure that are potentially responsible for estrogenic activity
were revealed. A quantitative structure-estrogenic activity study has been carried out using the QSAR approach with use of data derived from quantum-chemical calculations as well as data generated from three-dimensional structures of terpenoids. A number of molecular descriptors was obtained
from the density functional theory (DFT) at the B3LYP/6-31G(d, p) level of calculation. Comparative analysis of the quantum-chemical computational data was also performed to confirm hypothesis concerning importance of the distance between the oxygen of alcohol hydroxyl group and the functional
group in the para-position of the benzene ring (the hydroxyl or methoxy group). Use of the Genetic Algorithm in the QSAR analysis allowed the structural and physicochemical parameters of the terpenoids responsible for estrogenic activity to be determined. A significant QSAR model was obtained
with an r2 value of 0.892. The resulting model showed a reliable dependence of estrogenic activity of the terpenoids on such parameters as molecular shape, number of phenolic groups, surface polarity and the energy of the highest occupied molecular orbital.
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Terpenoid acid esters;
Document Type: Research Article
Computational Center for Molecular Structure and Interactions, Jackson State University, Mississippi 39217-0510, USA,Institute of the Chemistry of Plant substances, Tashkent, 700170, Uzbekistan
Institute of the Chemistry of Plant substances, Tashkent, 700170, Uzbekistan
Computational Center for Molecular Structure and Interactions, Jackson State University, Mississippi 39217-0510, USA
Publication date: December 1, 2007