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

Gniłka, Radosław; Majchrzak, Wojciech; Wawrzeńczyk, Czesław

doi:10.1016/j.phytol.2015.05.006

Cited by 7 publications

(2 citation statements)

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“…In both cases the basic limitation is the presence of carbonyl or hydroxy function already in the defined place in a substrate molecule. In literature we can find numerous examples of enantioselective hydroxylation of inactivated position in steroid skeleton [ 6 , 14 , 30 , 31 ] and terpenes [ 13 , 32 ]. Nevertheless, the regio- and stereoselective incorporation of hydroxy function into smaller non-functionalized molecules is still a challenge [ 33 ].…”

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%