title: Chemo-Enzymatic Synthesis of Optically Active γ- and δ-Decalactones and Their Effect on Aphid Probing, Feeding and Settling Behavior.
abstract: The enantiomerically enriched γ- and δ-decalactones (4a and 4b) were prepared from corresponding racemic primary-secondary 1,4- and 1,5-diols (1a and 1b), as products of enzymatic oxidation catalyzed by different alcohol dehydrogenases. The results of biotransformations indicated that the oxidation processes catalyzed by alcohol dehydrogenase (HLADH), both isolated from horse liver and recombinant in Escherichia coli, were characterized by the highest degree of conversion with moderate enantioselectivity of the reaction. Useful, environmentally friendly extraction procedure of decalactones (4a and 4b) based on hydrodistillation using a Deryng apparatus was developed. Both racemic lactones (4a and 4b), as well as their enantiomerically enriched isomers, were tested for feeding deterrent activity against Myzus persicae. The effect of these compounds on probing, feeding and settling behavior of M. persicae was studied in vivo. The deterrent activity of decalactones (4a and 4b) against aphids depended on the size of the lactone ring and the enantiomeric purity of the compounds. δ-Decalactone (4b) appeared inactive against M. persicae while γ-decalactone (4a) restrained aphid probing at ingestional phase. Only (-)-(S)-γ-decalactone (4a) had strong and durable (i.e. lasting for at least 24 hours) limiting effect, expressed at phloem level.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors.forename: Filip
authors.initials: F
authors.lastname: Boratyński
authors.affiliation: Department of Biology and Ecology, University of Zielona Góra, Zielona Góra, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Dancewicz
authors.affiliation: Department of Biology and Ecology, University of Zielona Góra, Zielona Góra, Poland.
authors.forename: Marlena
authors.initials: M
authors.lastname: Paprocka
authors.affiliation: Department of Biology and Ecology, University of Zielona Góra, Zielona Góra, Poland.
authors.forename: Beata
authors.initials: B
authors.lastname: Gabryś
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D000426:Alcohol Dehydrogenase / Q000235:genetics / Q000378:metabolism; D000818:Animals; D001042:Aphids / Q000187:drug effects* / Q000502:physiology; D001711:Biotransformation; D001937:Brassica / Q000469:parasitology; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D005247:Feeding Behavior / Q000187:drug effects* / Q000502:physiology; D015870:Gene Expression; D006736:Horses; D007302:Insect Repellents / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D007783:Lactones / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D009904:Optical Rotation; D052585:Phloem / Q000469:parasitology; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D007302:Insect Repellents; D007783:Lactones; D011994:Recombinant Proteins; D000426:Alcohol Dehydrogenase