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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.

Chemo-Enzymatic Synthesis of Optically Active γ- and δ-Decalactones and Their Effect on Aphid Probing, Feeding and Settling Behavior