title: Lactones 46. Synthesis, antifeedant and antibacterial activity of γ-lactones with a p-methoxyphenyl substituent.
abstract: BACKGROUND
  Lactones are well known for their biological activity. Grosheimin and repin are potent deterrents against storage pests. The unsaturated lactones have exhibited a wide spectrum of antibacterial activity. In our study we focused on the synthesis and evaluation of the biological activity of anisaldehyde derivatives containing lactone function.
  
  
  RESULTS
  Four new lactones were synthesized in one-step reductive dehalogenation or dehydrohalogenation reactions. These compounds, together with halolactones synthesized earlier, were tested for their antifeedant activity towards Sitophilus granaries, Trogoderma granarium and Tribolium confusum. The results of the tests showed that the highest activity, comparable with that of azadirachtin, towards all tested pests (total coefficient of deterrence 143.3-183.9) was observed for lactone with a vinyl substituent. The antibacterial activity of these compounds was also evaluated. The most potent lactone was active towards gram-positive bacteria strains.
  
  
  CONCLUSIONS
  The results of biological tests showed that halogen atom removal significantly increased the antifeedant properties of γ-lactones with a p-methoxyphenyl substituent. Unsaturated lactones are most promising in the context of their possible industrial application as crop protection agents. Further structural modifications of lactones with aromatic rings are needed to find important structural factors increasing the antibacterial activity.
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Marcelina
authors: M
authors: Mazur
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Andrzej
authors: A
authors: Skrobiszewski
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Witold
authors: W
authors: Gładkowski
authors: Department of Food Hygiene and Consumer Health Protection, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Magdalena
authors: M
authors: Podkowik
authors: Department of Food Hygiene and Consumer Health Protection, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Jacek
authors: J
authors: Bania
authors: Institute of Plant Protection - National Reasearch Institute, Poznań, Poland.
authors: Jan
authors: J
authors: Nawrot
authors: Institute of Plant Protection - National Reasearch Institute, Poznań, Poland.
authors: Tomasz
authors: T
authors: Klejdysz
authors: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors: Czesław
authors: C
authors: Wawrzeńczyk
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001517:Coleoptera / Q000187:drug effects* / Q000254:growth & development; D005247:Feeding Behavior / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis / Q000494:pharmacology*; D007783:Lactones / Q000138:chemical synthesis / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects / Q000254:growth & development; D048889:Weevils / Q000187:drug effects / Q000254:growth & development
chemical_list: D000900:Anti-Bacterial Agents; D007306:Insecticides; D007783:Lactones
keywords: anisaldehyde derivatives; antibacterial lactones; antifeedant activity; dehalogenation