A quantitative structure-antifungal activity relationship study of oxygenated aromatic essential oil compounds using...

Area of Science:

• Mycology
• Natural Products Chemistry
• Computational Chemistry

Background:

• Wood-decaying fungi, Trametes versicolor and Coniophora puteana, cause significant material degradation.
• Essential oils contain oxygenated aromatic compounds with potential antimicrobial properties.

Purpose of the Study:

• To evaluate the antifungal activity of 22 oxygenated aromatic essential oil compounds against T. versicolor and C. puteana.
• To establish a relationship between the molecular structures of these compounds and their antifungal efficacy.
• To perform a quantitative structure-activity relationship (QSAR) analysis to identify key structural determinants of activity.

Main Methods:

• Minimal inhibitory concentrations (MICs) were determined using the agar dilution method.
• Dimethyl sulfoxide (DMSO) was used as a solvent, and potato-dextrose agar (PDA) as the growth medium.
• QSAR analysis was performed using the partial least squares (PLS) method.

Main Results:

• A tree structure revealed a correlation between compound structure and antifungal activity.
• Statistically significant PLS models were developed for both fungi.
• Key molecular descriptors identified for T. versicolor included 1-octanol-water partition coefficient (C log P), energy of the highest occupied molecular orbital (E(HOMO)), and hydrogen-bond donor atoms (Donor).
• For C. puteana, significant descriptors were C log P and fractional negative surface area (FNSA1).

Conclusions:

• A clear relationship exists between the molecular structure of oxygenated aromatic essential oil compounds and their antifungal activity against wood-decaying fungi.
• QSAR modeling provides valuable insights for designing more potent antifungal agents from essential oils.