title: Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions.
abstract: Nicotiana tabacum cell suspensions, 2 g wet wt/ml, rapidly took up 1 mM isonitrosoacetophenone (INAP), a plant-derived stress metabolite with anti-oxidative and anti-fungal properties, producing 4'-hexopyranosyloxy-3'-methoxyisonitrosoacetophenone in 54 % yield over 18 h. Unconverted INAP was at 33 μM. UPLC-MS/MS analyses with MassFragment software were used for metabolite identification. INAP had been hydroxylated at its meta- and para-positions as well as undergoing subsequent methoxylation and glycosylation. INAP is thus recognized by the enzymatic machinery of the phenylpropanoid pathway and is converted to a molecule with a substitution pattern similar to ferulic acid.
authors.affiliation: Department of Biochemistry, University of Johannesburg, Auckland Park, Johannesburg 2006, South Africa. ntaka.madala@gmail.com
authors.forename: Ntakadzeni E
authors.initials: NE
authors.lastname: Madala
authors.forename: P A
authors.initials: PA
authors.lastname: Steenkamp
authors.forename: L A
authors.initials: LA
authors.lastname: Piater
authors.forename: I A
authors.initials: IA
authors.lastname: Dubery
mesh_terms: D001711:Biotransformation; D002478:Cells, Cultured; D002853:Chromatography, Liquid; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000378:metabolism; D053719:Tandem Mass Spectrometry; D014026:Nicotiana / Q000378:metabolism*
chemical_list: C057115:isonitrosoacetophenone; D010658:Phenylglyoxal