Molecular design of multifunctional food additives: antioxidative antifungal agents.

A series of alkyl 3,4-dihydroxybenzoates (protocatechuates) was synthesized, and their fungicidal activity against Saccharomyces cerevisiae was assayed using a 2-fold serial broth dilution method. Nonyl and octyl 3,4-dihydroxybenzoate were noted to be the most effective against this yeast with the minimum fungicidal concentration of 12.5 microg/mL each. The activity was found to correlate with the hydrophobic alkyl chain length. The time-kill curve study showed that nonyl 3,4-dihydroxybenzoate was fungicidal against S. cerevisiae at any growth stage and this activity was not influenced by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.