Lactones 27 [1]: Transformations of γ-lactones fused to a dimethylcyclohexane ring in Absidia cylindrospora cultures

Gładkowski, Witold; Grabarczyk, Małgorzata; Wińska, Katarzyna; Białońska, Agata; Ciunik, Zbigniew; Wawrzeńczyk, Czesław

doi:10.1016/j.molcatb.2006.01.023

Cited by 10 publications

(5 citation statements)

References 32 publications

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“…The ability of Absidia cylindrospora for catalyzing hydroxylation reactions, various dehalogenation reactions or epoxydation of double bond is well documented. Regardless of the biocatalyst the hydroxy group is commonly incorporated at a tertiary carbon atom [ 20 , 21 , 34 ] or into alkyl substituents [ 7 , 35 ]. For unsaturated lactones the formation of epoxy products can be observed [ 20 ].…”

Section: Resultsmentioning

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%

“…More examples of hydroxylation can be found for Absidia genus [ 10 – 12 ]. Different Absidia strains are able to transform biologically active compounds [ 13 , 14 ], including those with steroid skeleton [ 15 , 16 ] or lactone ring [ 17 – 21 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…Our previous biotransformation of unsaturated lactones with A . cylindrospora AM336 afforded hydroxylactones with pseudoaxially oriented hydroxy groups in the allylic position [22,23].…”

Section: Resultsmentioning

confidence: 99%

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

Grudniewska

Wawrzeńczyk

2013

Molecules

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“…Our team has been conducting studies dealing with transformations of different kinds of lactones for a long time. Previously unsaturated lactones with one, two or three methyl groups attached to the cyclohexane ring were subjected to biotransformation [ 22 , 23 , 24 ]. During these biotransformations, hydroxylation in allylic position or epoxidation of double bond was observed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups

et al. 2017

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The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum racemosum strain hydroxylated both substrates in an allylic position. Using the Absidia cylindrospora and Penicillium vermiculatum strains led to the obtained epoxylactones. The structures of all lactones were established on the basis of spectroscopic data.

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Lactones 27 [1]: Transformations of γ-lactones fused to a dimethylcyclohexane ring in Absidia cylindrospora cultures

Cited by 10 publications

References 32 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

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

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups

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