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

Autori
Marcelina Mazur ; Witold Gładkowski ; Višnja Gaurina-Srček ; Kristina Radošević ; Gabriela Maciejewska ; Czesław Wawrzeńczyk

Izvornik
PLoS One (1932-6203) 12 (2017), 8; E0183429-e0183429

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
halolactones ; hydroxylation ; cytotoxicity

Sažetak
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, theδ-iodo- andδ-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.

Izvorni jezik
Engleski

Znanstvena područja
Biotehnologija

POVEZANOST RADA