title: A quantitative structure-antifungal activity relationship study of oxygenated aromatic essential oil compounds using data structuring and PLS regression analysis.
abstract: 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.
authors.affiliation: Department of Chemical Education and Informatics, Faculty of Natural Sciences and Engineering, University of Ljubljana, Vegova 4, 1000 Ljubljana, Slovenia. karmen.voda@uni-lj.si
authors.forename: Karmen
authors.initials: K
authors.lastname: Voda
authors.forename: Bojana
authors.initials: B
authors.lastname: Boh
authors.forename: Margareta
authors.initials: M
authors.lastname: Vrtacnik
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000935:Antifungal Agents / Q000737:chemistry*; D035843:Biomedical Research; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004987:Ethers / Q000737:chemistry; D005658:Fungi / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D016018:Least-Squares Analysis; D008031:Lignin / Q000737:chemistry; D016014:Linear Models; D008954:Models, Biological; D008956:Models, Chemical; D008962:Models, Theoretical; D015394:Molecular Structure; D015999:Multivariate Analysis; D000442:Octanols / Q000737:chemistry; D009822:Oils, Volatile / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D012044:Regression Analysis; D012984:Software; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D000935:Antifungal Agents; D004987:Ethers; D000442:Octanols; D009822:Oils, Volatile; D010636:Phenols; D008031:Lignin; D010100:Oxygen