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Synthesis and Antifeedant Activity of Racemic and Optically Active Hydroxy Lactones with the p-Menthane System.

Grudniewska A, Kłobucki M, Dancewicz K, Szczepanik M, Gabryś B, Wawrzeńczyk C - PLoS ONE (2015)

Bottom Line: The structures of the compounds were confirmed spectroscopically.All hydroxy lactones deterred the settling of M. persicae.Among chewing insects, the highest sensitivity showed A. diaperinus adults.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.

ABSTRACT
Two racemic and two enantiomeric pairs of new δ-hydroxy-γ-lactones based on the p-menthane system were prepared from racemic and optically active cis- and trans-piperitols. The Johnson-Claisen rearrangement of the piperitols, epoxidation of the γδ-unsaturated esters, and acidic lactonization of the epoxy esters were described. The structures of the compounds were confirmed spectroscopically. The antifeedant activities of the hydroxy lactones and racemic piperitone were evaluated against three insect pests: lesser mealworm, Alphitobius diaperinus (Panzer); Colorado potato beetle, Leptinotarsa decemlineata (Say); and peach-potato aphid, Myzus persicae (Sulz.). The chemical transformation of piperitone by the introduction of a lactone moiety and a hydroxy group changed its antifeedant properties. Behavioral bioassays showed that the feeding deterrent activity depended on the insect species and the structure of the compounds. All hydroxy lactones deterred the settling of M. persicae. Among chewing insects, the highest sensitivity showed A. diaperinus adults.

No MeSH data available.


Related in: MedlinePlus

Synthesis of hydroxy lactones 11a-c.
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pone.0131028.g002: Synthesis of hydroxy lactones 11a-c.

Mentions: Two racemic and two enantiomerically enriched pairs of new δ-hydroxy-γ-lactones, 6a-c and 11a-c, with the p-menthane system were synthesized from cis- and trans-piperitols, 1a-c (Fig 1) and 7a-c (Fig 2), respectively, which were prepared from (±)-piperitone [28]. Enantiomerically enriched cis- (1a,b) and trans-piperitols (7a,b) were obtained from racemic piperitols (1c and 7c, respectively) via their enzymatic esterification with vinyl propionate in the presence of lipase Amano PS [28]. Racemic and optically active γ,δ-unsaturated esters (2a-c and 8a-c) were obtained via the Johnson-Claisen- rearrangement of the corresponding allylic alcohols, as described earlier [13].


Synthesis and Antifeedant Activity of Racemic and Optically Active Hydroxy Lactones with the p-Menthane System.

Grudniewska A, Kłobucki M, Dancewicz K, Szczepanik M, Gabryś B, Wawrzeńczyk C - PLoS ONE (2015)

Synthesis of hydroxy lactones 11a-c.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4488555&req=5

pone.0131028.g002: Synthesis of hydroxy lactones 11a-c.
Mentions: Two racemic and two enantiomerically enriched pairs of new δ-hydroxy-γ-lactones, 6a-c and 11a-c, with the p-menthane system were synthesized from cis- and trans-piperitols, 1a-c (Fig 1) and 7a-c (Fig 2), respectively, which were prepared from (±)-piperitone [28]. Enantiomerically enriched cis- (1a,b) and trans-piperitols (7a,b) were obtained from racemic piperitols (1c and 7c, respectively) via their enzymatic esterification with vinyl propionate in the presence of lipase Amano PS [28]. Racemic and optically active γ,δ-unsaturated esters (2a-c and 8a-c) were obtained via the Johnson-Claisen- rearrangement of the corresponding allylic alcohols, as described earlier [13].

Bottom Line: The structures of the compounds were confirmed spectroscopically.All hydroxy lactones deterred the settling of M. persicae.Among chewing insects, the highest sensitivity showed A. diaperinus adults.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.

ABSTRACT
Two racemic and two enantiomeric pairs of new δ-hydroxy-γ-lactones based on the p-menthane system were prepared from racemic and optically active cis- and trans-piperitols. The Johnson-Claisen rearrangement of the piperitols, epoxidation of the γδ-unsaturated esters, and acidic lactonization of the epoxy esters were described. The structures of the compounds were confirmed spectroscopically. The antifeedant activities of the hydroxy lactones and racemic piperitone were evaluated against three insect pests: lesser mealworm, Alphitobius diaperinus (Panzer); Colorado potato beetle, Leptinotarsa decemlineata (Say); and peach-potato aphid, Myzus persicae (Sulz.). The chemical transformation of piperitone by the introduction of a lactone moiety and a hydroxy group changed its antifeedant properties. Behavioral bioassays showed that the feeding deterrent activity depended on the insect species and the structure of the compounds. All hydroxy lactones deterred the settling of M. persicae. Among chewing insects, the highest sensitivity showed A. diaperinus adults.

No MeSH data available.


Related in: MedlinePlus