Three-dimensional quantitative structure-activity relationship study on gas chromatographic retention index of the fragrance compounds of Liliumspp

Abstract

Quantitative structure-activity relationship models on the gas chromatographic retention index of the 38 volatile fragrance compounds of Liliumspp were investigated and established by comparative molecular field analysis (CoMFA) and comparative molecular similarity index (CoMSIA) methods. The robustness and predictive performance of the developed models were assessed using external test set validation and leave-one-out cross validation. Further, the effects of the molecular structure on the gas chromatographic retention indices of these compounds were intuitively studied in light of the three-dimensional contour maps of molecular fields provided by the developed CoMSIA and CoMFA models. The validation results demonstrated that both the models could accurately predict the retention indices of the investigated components. The influence of the molecular structure on the retention indices could be reasonably explained by these models. Moreover, the prediction accuracy of the CoMSIA model was slightly higher than that of the CoMFA model. Obviously, the proposed CoMSIA model is more promising for the analysis of the volatile fragrance compounds of Lilium spp.