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.
Nihei
Ken-ichi
K
Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA.
Nihei
Atsuko
A
Kubo
Isao
I
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D005503:Food Additives / Q000737:chemistry*; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects
D000975:Antioxidants; D005503:Food Additives; D005659:Fungicides, Industrial