The study of molecular descriptors of the alkaloids of leaves of Pedicularis Olgae Regel
Abstract
Alkaloids have acquired a special value, among the natural compounds, due to their enormous structural diversity and high physiological activity. They have an important position for the development of organic chemistry, especially chemistry of heterocyclic compounds. The aim of the present study is to investigate the geometric configurations and electronic structures of the aerial part of Pedicularis Olgae Regel ( Scrophulariaceae Juss. ): pediculine (C10H11NO), pediculidine (C10H9NO), pediculinine (C10H13NO), pedicularine (C10H11NO2), pedicularidine (C10H11NO) and plantagonine (C10N1H11O2) alkaloids as well as calculation and establishment of the data of molecular descriptors for prediction of pharmacological activity. In addition, the parameters of the quantitative structure-activity relationship (QSAR) for each alkaloid were investigated. The alkaloid molecules were studied by the molecular orbital method in semiempirical manner with account for 61, 57, 61, 63, 59 and 63 molecular orbitals, respectively. The stable minimum energy configuration of alkaloids were estimated on the base of indicators of energy molecules by quantum-chemical calculation of the electronic structure of the molecules and their configuration features. PM3 method allowed to determine the energy of each alkaloid molecule in an acceptable configuration. Moreover, based on the difference between the values of HOMO (the highest occupied molecular orbital) and LUMO (the lowest unoccupied molecular orbital) were determined the width value of the HOMO-LUMO gap. The HOMO-LUMO energy gap of molecules were -7,865 eV for pediculine, -9,159 eV for pediculidine, -9,717 eV for pediculinine, -9,75 eV for pedicularine, -9,769 eV for pedicularidine, and -9,318 eV for plantagonine, respectively.
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