title: A Macrosphelide as the Unexpected Product of a Pleurotus ostreatus Strain-Mediated Biotransformation of Halolactones Containing the gem-Dimethylcyclohexane Ring. Part 1.
abstract: The aim of the study was to obtain new compounds during biotransformation of two halocompounds, the δ-bromo and δ-iodo-γ-bicyclolactones 1 and 2. Unexpectedly Pleurotus ostreatus produced together with the hydroxylactone, 2-hydroxy-4,4-dimethyl-9-oxabicyclo[4.3.0]nonane-8-one (3), its own metabolite (3S,9S,15S)-(6E,12E)-3,9,15-trimethyl-4,10,16-trioxacyclohexa-deca-6,12-diene-1,5,8,11,14-pentaone (4). The method presented here, in which this macrosphelide 4 was obtained by biotransformation, has not been previously described in the literature. To the best of our knowledge, this compound has been prepared only by chemical synthesis to date. This is the first report on the possibility of the biosynthesis of this compound by the Pleurotus ostreatus strain. The conditions and factors, like temperature, salts, organic solvents, affecting the production of this macrosphelide by Pleurotus ostreatus strain were examined. The highest yield of macroshphelide production was noticed for halolactones, as well with iodide, bromide, iron and copper (2+) ions as inductors.
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc&#322;aw, Poland. katarzyna.winska@up.wroc.pl.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Wińska
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc&#322;aw, Poland. wanda_m19@o2.pl.
authors.forename: Wanda
authors.initials: W
authors.lastname: Mączka
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc&#322;aw, Poland. magrab@onet.pl.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Grabarczyk
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, 930-0194 Toyama, Japan. ksugimo@pha.u-toyama.ac.jp.
authors.forename: Kenji
authors.initials: K
authors.lastname: Sugimoto
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, 930-0194 Toyama, Japan. matsuya@pha.u-toyama.ac.jp.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc&#322;aw, Poland. antjasz@o2.pl.
authors.forename: Antoni
authors.initials: A
authors.lastname: Szumny
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroc&#322;aw, Poland. miroslaw.aniol@up.wroc.pl.
authors.forename: Mirosław
authors.initials: M
authors.lastname: Anioł
mesh_terms: D001711:Biotransformation; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000378:metabolism*; D006868:Hydrolysis; D007783:Lactones / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D020076:Pleurotus / Q000378:metabolism*
chemical_list: D006571:Heterocyclic Compounds; D007783:Lactones
keywords: Pleurotus ostreatus; biotransformation; hydrolytic dehalogenation; macrosphelide