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

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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.

Figure Tree structure representing the structuring of the oxygenated aromatic essential-oil compounds by the position and nature of their substituents in the aromatic ring

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Acknowledgements

The authors would like to thank Prof. Dr. Franc Pohleven and Andreja Klinar of the Department of Wood Science and Technology, Biotechnical Faculty, University of Ljubljana, Slovenija for their help and cooperation during the experimental part of this study. Our sincere thanks also goes to Tripos, Inc. (Germany) for allowing us the use of SYBYL 6.7.2 for a time-limited evaluation period. The research was co-founded by the Slovene Ministry of Education, Science and Sport.

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  1. Department of Chemical Education and Informatics, Faculty of Natural Sciences and Engineering, University of Ljubljana, Vegova 4, 1000, Ljubljana, Slovenia

    Karmen Voda, Bojana Boh & Margareta Vrtačnik

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  1. Karmen Voda
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  2. Bojana Boh
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  3. Margareta Vrtačnik
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Correspondence to Karmen Voda.

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Voda, K., Boh, B. & Vrtačnik, M. A quantitative structure–antifungal activity relationship study of oxygenated aromatic essential oil compounds using data structuring and PLS regression analysis. J Mol Model 10, 76–84 (2004). https://doi.org/10.1007/s00894-003-0174-5

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  • DOI: https://doi.org/10.1007/s00894-003-0174-5

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