Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems

Grudniewska, Aleksandra; Wawrzeńczyk, Czesław

doi:10.3390/molecules18032778

Cited by 11 publications

(6 citation statements)

References 22 publications

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“…Several bicyclic γ-lactones of this group, such as mintlactone, isomintlactone, and wine lactone, are well known as flavoring ingredients [ 1 – 6 ]. Synthetic lactones with the p -menthane system, in addition to interesting odoriferous attributes [ 7 – 9 ], exhibit valuable biological activities such as antifungal [ 10 ] and antifeedant properties [ 11 – 16 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…The choice of these microorganisms as biocatalysts was due to literature information. We have found that the fungi of genus Absidia were able to biohydroxylte lactones (Grudniewska and Wawrze nczyk, 2013), steroids (Brzezowska et al, 1996) and triterpenoids (Guo et al, 2010). So, we expected to obtain hydroxy thujones as products of microbial transformations.…”

Section: Introductionmentioning

confidence: 97%

Microbial transformations of (−)-α- and (+)-β-thujone by fungi of Absidia species

Gniłka

Majchrzak

Wawrzeńczyk

2015

Phytochemistry Letters

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“…The hydroxylation potential of filamentous fungi has been applied by the pharmaceutical industry to develop products such as hydroxylated flavonoids [ 20 , 21 ] and steroid compounds [ 22 , 23 , 24 ]. There are also documented examples of bicyclic γ-lactone hydroxylation catalysed by filamentous fungi [ 3 , 25 ]. In our research we selected three fungal strains ( Fusarium culmorum AM10, Armillaria mellea AM296, Trametes versicolor AM536) with the ability for selective hydroxylation of tetramethyl-γ-lactone ( 1 ).…”

Section: Introductionmentioning

confidence: 99%

Microbial Asymmetric Functionalization of β-Cyclocitral-Derived Tetramethyl-Substituted γ-Lactone

et al. 2019

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Searching for the new anticancer compounds we prepared three new β-cyclocitral-derived hydroxyl-γ-lactones by microbial hydroxylation of tetramethyl-substituted bicyclic γ-lactone. The substrate was transformed by the enzymatic system of filamentous fungi. Three out of fifteen strains were selected as effective biocatalysts (Fusarium culmorum AM10, Armillaria mellea AM296, Trametes versicolor AM536). The hydroxylation processes were not only regioselective but also stereoselective. The hydroxylation products of each secondary carbon atom in the cyclohexane ring were obtained by the application of the selected fungal strains. The Fusarium culmorum AM10 introduced the hydroxy function at C-3 and C-4, Armillaria mellea AM296 incorporated the hydroxy function at C-3 and C-5 and Trametes versicolor AM536 transformed the substrate to the mixture of C-3, C-4 and C-5 hydroxylactones. The hydroxylactones obtained were enantiomericaly enriched (ee values in the range 17–99%). The in vitro antiproliferative activities of the functionalization products were also evaluated. Regardless of the hydroxy substituent location all tested lactones exhibited similar, significant activity towards selected cancer cell lines (IC50 in the range 22.8–33.9 µg/mL).

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Lactones 41. Synthesis and Microbial Hydroxylation of Unsaturated Terpenoid Lactones with p-Menthane Ring Systems

Cited by 11 publications

References 22 publications

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

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

Microbial transformations of (−)-α- and (+)-β-thujone by fungi of Absidia species

Microbial Asymmetric Functionalization of β-Cyclocitral-Derived Tetramethyl-Substituted γ-Lactone

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