Substituent and solvent effects on the structural bioactivity and anticancer characteristic of catechin as a bioactive constituent of green tea

In this study, quantum chemical calculations using density functional theory and 6‐311G (d) basis set have been applied to analyze the substituent effect on the electronic structural properties including thermochemical parameters as well as anticancer characteristics of catechin as a bioactive constituent of green tea. It has been found out that different substituents with two kinds of electron donating and electron withdrawing groups including ? NO₂, ? NH₂, ? Cl, ? OCH₃, and ? CH₃ leaded to different structural stabilities. The catechin with chloro substituents has been referred to the most stable catechin derivatives based on the minimum energy of investigated compounds. In this study, the calculated values have been compared in gas phase and different solvent media with a wide range of solvent dielectrics using the self‐consistent reaction field method with polarizable continuum model. Relative interaction energies between solute and solvent as well as dipole moment values have been analyzed. The results of solvent effect study revealed that the formation of hydrogen bonds accounts for the stabilization of catechin. These calculated data were found to be a logical way in predicting the relative stability of catechin derivatives and can be useful for drug design of anticancer drugs and would open a new door for the researchers who are interested in natural products. The results presented in this article will be helpful to improve existing model and will open up a whole new arena of study to understand the anticancer characteristic of these antioxidant drugs derived from natural products against the photosensitizing DNA damage induce by catechin extracts and enable a much clearer understanding of how anticancer drugs mediate their effects on the specific spot. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011