title: Lactones 43. New biologically active lactones: β-cyclocitral derivatives.
abstract: BACKGROUND
  In our previous studies bicyclic γ-lactones with cyclohexane ring exhibited high antifeedant activity against storage pests. The activity was correlated with the type and number of substituents in the cyclohexane ring. One of the most potent group of antifeedant agents was δ-iodo-γ-lactones.
  
  
  RESULTS
  We present the synthesis of new bicyclic γ-lactones with the cyclohexane ring containing different halogen atoms. To determine the impact of halogen type on biological activity the lactone without halogen atom was also synthesized. The lactones were tested for their antifeedant activity toward the granary weevil beetle (Sitophilus granarius L.), the khapra beetle (Trogoderma granarium Everts) and the confused flour beetle (Tribolium confusum Du Val.). The results of the tests proved that the highest activity was observed for chlorolactone (7) towards larvae and adults of Tribolium confusum. Antibacterial activity of new lactones was also evaluated. Lactone without halogen atom (8) was active against Staphylococcus aureus and Listeria monocytogenes.
  
  
  CONCLUSIONS
  Studies on the biological activity of synthesised lactones revealed high selectivity towards insect pests as well as bacterial strains. Only the halolactones exhibited significant antifeedant activity. In contrast, antibacterial activity was shown only by the lactone (8) without halogen.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland.
authors.forename: Marcelina
authors.initials: M
authors.lastname: Mazur
authors.forename: Witold
authors.initials: W
authors.lastname: Gładkowski
authors.forename: Magdalena
authors.initials: M
authors.lastname: Podkowik
authors.forename: Jacek
authors.initials: J
authors.lastname: Bania
authors.forename: Jan
authors.initials: J
authors.lastname: Nawrot
authors.forename: Agata
authors.initials: A
authors.lastname: Białońska
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001517:Coleoptera / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry*; D005247:Feeding Behavior / Q000187:drug effects; D007300:Insect Control; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009812:Odorants; D048889:Weevils / Q000187:drug effects
chemical_list: D000447:Aldehydes; D000900:Anti-Bacterial Agents; D004224:Diterpenes; D007783:Lactones; C516118:beta-cyclocitral
keywords: antibacterial compound; antifeedant activity; feeding deterents; lactones; synthesis