title: Microbial transformations of halolactones with p-menthane system.
abstract: Biologically active piperitone-derived racemic iodo-, bromo- and chlorolactones (1-3) were transformed with the use of microbial enzymatic systems. Four strains of filamentous fungi Absidia glauca AM254, Absidia cylindrospora AM336, Mortierella vinaceae AM149 and Nigrospora oryzae AM8 transformed halolactones (1-3) to four new halohydroxylactones (4-7). In all biotransformations the hydroxy group was incorporated in inactivated methine carbon atom at isopropyl substituent. In N. oryzae AM8 culture the bromolactone with additional hydroxy group in α-position, relative to CO bond in γ-lactone ring, was also formed as a product. The structures of new compounds were established on the basis of spectral data.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. Electronic address: marcelina.mazur@up.wroc.pl.
authors.forename: Marcelina
authors.initials: M
authors.lastname: Mazur
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. Electronic address: aleksandra.grudniewska@up.wroc.pl.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Grudniewska
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. Electronic address: czeslaw.wawrzenczyk@up.wroc.pl.
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D020095:Absidia / Q000145:classification / Q000378:metabolism*; D001711:Biotransformation; D000081005:Cyclohexane Monoterpenes; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D008697:Methane / Q000378:metabolism*; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism; D013729:Terpenes / Q000378:metabolism
chemical_list: D000081005:Cyclohexane Monoterpenes; D007783:Lactones; D039821:Monoterpenes; D013729:Terpenes; C496656:piperitone; D008697:Methane
keywords: Fungal transformation; Halolactones; Microbial hydroxylation; Piperytone derivatives; Terpenoid lactones