ArticlePloS one2016
Chemo-Enzymatic Synthesis of Optically Active γ- and δ-Decalactones and Their Effect on Aphid Probing, Feeding and Settling Behavior.
Article in PloS one, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 27 citations in OpenAlex.
- Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids.Organic letters · 2023Article
- Semiochemicals Associated with the Western Flower Thrips Attraction: A Systematic Literature Review and Meta-Analysis.Insects · 2023Review
- Stereoselective synthesis of whisky lactone isomers catalyzed by bacteria in the genusFrontiers in microbiology · 2023Article
- Ene-reductase transformation of massoia lactone to δ-decalactone in a continuous-flow reactor.Scientific reports · 2021Article
- Characterization of the Key Aroma Constituents in Fry Breads by Means of the Sensomics Concept.Foods (Basel, Switzerland) · 2020Article
- Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture ofMolecules (Basel, Switzerland) · 2020Article
- Biocatalytic synthesis of lactones and lactams.Chemistry, an Asian journal · 2018Review
- Novel Hydroxy- and Epoxy-Molecules (Basel, Switzerland) · 2018Article
- Biocatalytic Oxidation Reactions: A Chemist's Perspective.Angewandte Chemie (International ed. in English) · 2018Review
- Gold-catalyzed stereoselective cycloisomerization of allenoic acids for two types of common natural γ-butyrolactones.Nature communications · 2018Article
- Microbial synthesis of a useful optically active (+)-isomer of lactone with bicyclo[4.3.0]nonane structure.Scientific reports · 2018Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
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.
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