Modes of antifungal action of (2E)-alkenals against Saccharomyces cerevisiae.
A series of aliphatic (2E)-alkenals from C(5) to C(14) were tested for their antifungal activity against Saccharomyces cerevisiae ATCC 7754. (2E)-Undecenal (C(11)) was found to be the most effective with the minimum fungicidal concentration (MFC) of 6.25 microgram/mL, followed by (2E)-decenal (C(10)) with an MFC of 12.5 microgram/mL. The time-kill curve study showed that (2E)-undecenal was fungicidal against S. cerevisiae at any growth stage, and this activity was not influenced by pH values. The (2E)-alkenals inhibited glucose-induced acidification by inhibiting the plasma membrane H(+)-ATPase. The primary antifungal action of medium-chain (C(9)-C(12)) (2E)-alkenals against S. cerevisiae comes from their ability to function as nonionic surface-active agents (surfactants), disrupting the native membrane-associated function nonspecifically. Hence, the antifungal activity of (2E)-alkenals is mediated by biophysical processes, and the maximum activity can be obtained when the balance between the hydrophilic and hydrophobic portions becomes the most appropriate.
Kubo
Isao
I
Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA. ikubo@uclink.berkeley.edu
Fujita
Ken-Ichi
K
Kubo
Aya
A
Nihei
Ken-Ichi
K
Lunde
Christopher S
CS
D000447:Aldehydes / Q000008:administration & dosage / Q000032:analysis / Q000494:pharmacology*; D000475:Alkenes / Q000008:administration & dosage / Q000032:analysis / Q000494:pharmacology*; D000935:Antifungal Agents / Q000008:administration & dosage / Q000494:pharmacology*; D004791:Enzyme Inhibitors; D006863:Hydrogen-Ion Concentration; D006180:Proton-Translocating ATPases / Q000037:antagonists & inhibitors; D012441:Saccharomyces cerevisiae / Q000187:drug effects*
C476489:(2E)-decenal; D000447:Aldehydes; D000475:Alkenes; D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D006180:Proton-Translocating ATPases; C476488:(2E)-undecenal