Structure-Antifungal Activity Relationships among Volatile C6 and C9 Aliphatic Aldehydes, Ketones, and Alcohols

Roger A. Andersen, Thomas R. Hamilton-Kemp, David F. Hildebrand, Charles T. McCracken, Randall W. Collins, Pierce D. Fleming

Research output: Contribution to journalArticlepeer-review

95 Scopus citations

Abstract

Antifungal potentials of volatile oxygenated alkyl compounds were determined by bioassay of Alternaria alternata germ tube growth. Compounds were naturally occurring lipoxygenase enzyme system products or related to them chemically. Results were based on headspace concentrations of test compounds. Among six-and nine-carbon aldehydes and ketones related to hexanal, nonanal, 3-hexanone, and 2-nonanone, respectively, the presence of an α,β-unsaturated bond adjacent to the carbonyl moiety generally enhanced antifungal activity. Among six-carbon alcohols related to 1-hexanol, however, an α,β-unsaturated bond enhanced antifungal activity only slightly. Abundant, naturally occurring (E)-2-hexenal that higher plants emit as a response to wounding tested negatively for mutagenicity; a volatile compound modification of the Ames test with several strains of Salmonella typhimurium was used.

Original languageEnglish
Pages (from-to)1563-1568
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume42
Issue number7
DOIs
StatePublished - Jul 1 1994

Keywords

  • (E)-hexenal
  • Alternaria
  • Antifungal
  • aldehydes
  • bioassay
  • ketones
  • lipoxygenase products
  • mutagenicity
  • volatiles
  • α,β-unsaturated

ASJC Scopus subject areas

  • General Chemistry
  • General Agricultural and Biological Sciences

Fingerprint

Dive into the research topics of 'Structure-Antifungal Activity Relationships among Volatile C6 and C9 Aliphatic Aldehydes, Ketones, and Alcohols'. Together they form a unique fingerprint.

Cite this