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Molecules 2016, 21(9), 1226; doi:10.3390/molecules21091226

Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents

1
Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
2
Bioprocess and Biomedical Engineering Division, Wroclaw University of Technology, Norwida 4/6, Wrocław 50-373, Poland
3
Department of Invertebrate Zoology, Nicolaus Copernicus University, Lwowska 1, Toruń 87-100, Poland
4
Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, Zielona Góra 65-516, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Tobias A. M. Gulder
Received: 18 July 2016 / Revised: 4 September 2016 / Accepted: 8 September 2016 / Published: 13 September 2016
(This article belongs to the Special Issue Biosynthesis of Natural Products)
View Full-Text   |   Download PDF [1598 KB, uploaded 13 September 2016]   |  

Abstract

A chemoenzymatic method was applied to obtain optically pure alkyl-substituted δ-lactones. First, chemical Baeyer–Villiger oxidation of dihydrojasmone (1) was carried out, affording two new alkyl-substituted δ-lactones: 3,4-dihydro-5-methyl-6-pentyl-2H-pyran-2-one (2) and 5-methyl-6-pentyl-1,13-dioxabicyclo[4.1.0]heptan-2-one (3). In the next step, fungal strains were investigated as biocatalysts to enantioselective conversion of δ-lactones (2) and (3). The fungal cultures: Fusarium culmorum AM10, Fusarium equiseti AM15 and Beauveria bassiana AM278 catalyzed the stereoselective hydration of the double bond of lactone (2) (ee = 20%–99%) while Didymosphaeria igniaria KCh6670 proved to be the best biocatalyst for the reduction of carbonyl group in the epoxylactone (3) (ee = 99%). In both cases, chiral oxyderivatives were obtained in low to high yields (7%–91%). The synthetic lactones (2), (3) and its derivatives (4), (5) were tested for their antifeedant activity towards larvae and adults of lesser mealworm (Alphitobius diaperinus Panzer) and peach potato aphid (Myzus persicae [Sulzer]) and some of them were active towards studied insects. View Full-Text
Keywords: dihydrojasmone; alkyl-substituted δ-lactones; oxyfunctionalization; Baeyer–Villiger oxidation dihydrojasmone; alkyl-substituted δ-lactones; oxyfunctionalization; Baeyer–Villiger oxidation
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Gliszczyńska, A.; Semba, D.; Szczepanik, M.; Dancewicz, K.; Gabryś, B. Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents. Molecules 2016, 21, 1226.

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