Lactones 43. New biologically active lactones: <i>β</i>
-cyclocitral derivatives

Mazur, Marcelina; Gładkowski, Witold; Podkowik, Magdalena; Bania, Jacek; Nawrot, J.; Białońska, Agata; Wawrzeńczyk, Czesław

doi:10.1002/ps.3557

Cited by 24 publications

(40 citation statements)

References 30 publications

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“…The metabolism of three β-cyclocitral-derived halolactones which exhibit antifeedant activity towards storage product pests [22] was investigated in fungal strains cultures. Preliminary screening procedure was carried out for iodolactone ( 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Three racemic lactones containing different halogen atoms: 1-iodomethyl-2,2,6-trimethyl-9-oxabicyclo [4.3.0]nonan-8-one ( 1 ), 1-bromomethyl-2,2,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one ( 2 ) and 1-chloromethyl-2,2,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one ( 3 ) were synthesized from β-cyclocitral in four steps chemical synthesis, according to the procedure described earlier [22]. …”

Section: Methodsmentioning

confidence: 99%

“…Parent compounds exhibit antifeedant activity [22] hence it is important to establish the possible metabolic pathway of those compounds in natural environment. Biotransformations of halolactones involving the hydroxylation reaction which entails the increase of their polarity is essential during their further biodegradation.…”

Section: Introductionmentioning

confidence: 99%

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Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

et al. 2017

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Three β-cyclocitral-derived halolactones, which exhibit antifeedant activity towards storage product pests, were subjected to microbial transformation processes. Among the thirty tested strains of filamentous fungi and yeast, the most effective biocatalysts were Absidia cylindrospora AM336, Mortierella isabellina AM212 and Mortierella vinaceae AM149. As a result of regio- and enantioselective hydroxylation four new oxygenated derivatives were obtained. Regardless of the biocatalyst applied, the δ-iodo- and δ-bromo-γ-lactones were hydroxylated in an inactivated position C-5 of cyclohexane ring. The analogous transformation of chlorolactone was observed in Mortierella isabellina AM212 culture but in the case of two other biocatalysts the hydroxy group was introduced at C-3 position. All obtained hydroxylactones were enantiomerically pure (ee = 100%) or enriched (ee = 50%). The highest enantioselectivity of hydroxylation was observed for M. isabellina AM212. The cytotoxic activity of halolactones was also examined by WST-1 assay wherein tested compounds did not exhibit significant effect on the viability of tumor HeLa and normal CHO-K1 cells.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

et al. 2017

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“…Up to the present day, many biologically active lactones, mostly with isoprenoid skeleton, have been synthesized by our research team. They exhibited antifeedant activity towards storage insect pests, [16][17][18][19][20] aphids, 21,22 lesser mealworm 23,24 or colorado potato beetle. 2,25 Some of the obtained lactones also inhibited the growth of pathogenic fungi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

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“…New lactones have also been estimated in terms of their antifeedant activity toward the granary weevil beetle ( Sitophilus granarius L.), the khapra beetle ( Trogoderma granarium Everts) and the confused flour beetle ( Tribolium confusum Du Val.) . These studies have shown the wide application possibilities of new lactones.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans‐γ‐Halo‐δ‐lactones

et al. 2018

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A new four‐step pathway for the synthesis of γ‐halo‐δ‐lactones is described from simple, commercially available substrates: aryl bromides and 3‐methyl crotonaldehyde. The halogenolactonization reaction of β,δ‐substituted, γ,δ‐unsaturated carboxylic acid 4 a–c is regio‐ and stereoselective and gives only the trans‐isomers of lactones 5 a–c, 6 a–c, and 7 a–c. The structures of all synthesized compounds were confirmed by using spectroscopic methods. For bromolactone, containing a naphthyl moiety in the structure, crystallographic analysis was also performed. The lactones were tested for their cytotoxic activity against L929 cell lines (mouse fibroblasts) and antibacterial activity against Escherichia coli strains ATCC 8739 and Staphylococcus aureus ATCC 65389. Compounds 5 a, 5 c, 7 a, and 7 b statistically significantly inhibited the metabolic activity of mouse fibroblasts L929. Compounds 5 b and 6 a were not cytotoxic towards L929 cells, but showed moderate bactericidal properties.

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Lactones 43. New biologically active lactones: β -cyclocitral derivatives

Abstract: Studies on the biological activity of synthesised lactones revealed high selectivity towards insect pests as well as bacterial strains. Only the halolactones exhibited significant antifeedant activity. In contrast, antibacterial activity was shown only by the lactone (8) without halogen.

Cited by 24 publications

References 30 publications

Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans‐γ‐Halo‐δ‐lactones

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