A quantitative structure-antifungal activity relationship study of oxygenated aromatic essential oil compounds using data structuring and PLS regression analysis

作者：Voda K^*; Boh B; Vrtacnik M

来源：Journal of Molecular Modeling, 2004, 10(1): 76-84.

DOI：10.1007/s00894-003-0174-5

• QSAR
• oxygenated aromatic compounds
• essential oils
• antifungal activity
• wood degrading fungi

Twenty two oxygenated aromatic essential oil compounds were chosen for the study of the antifungal activity against two wood-decaying fungi, the white-rot Trametes versicolor, which mainly metabolizes lignin, and the brown-rot Coniophoha puteana, which digests cellulose in plant cell walls. Minimal inhibitory concentrations (MICs) were determined by the agar dilution method, using dimethyl sulfoxide (DMSO) as the solvent for the selected compounds and potato-dextrose agar (PDA) as the growth medium for both fungi. The MICs were then used to generate a tree structure, which represents the structuring of the essential oil compounds by the nature and position of the substituents in their aromatic rings, and as dependent variables (log(1/MIC)) in the QSAR analysis. Data structuring proved that a relationship between the molecular structures of the essential oil compounds and their antifungal activity exists, and the hypotheses derived therefrom were complemented by performing a QSAR analysis using the partial least squares (PLS) method. Statistically significant PLS models were obtained with the 1-octanol-water partition coefficient (C log P), the energy of the highest occupied molecular orbital (E-HOMO), and the number of hydrogen-bond donor atoms in the molecules of the compounds studied (Donor) for T. versicolor and with C log P and the fractional negative surface area (FNSA1) for C. puteana.

• 出版日期2004-2