title: In vitro and in vivo metabolism of the radiolytic compound 2-dodecylcyclobutanone.
abstract: Our knowledge about the metabolism of alkylcyclobutanones (2-ACBs) is limited, and the lack of literature on the metabolism of 2-ACBs causes consumers to doubt the safety of irradiated foods. The objectives of this study were to evaluate the metabolism of 2-dodecylcyclobutanone (2-DCB) and identify any possible metabolite. The 2-DCB was mixed with rat S9 (postmitochondrial supernatant fraction) and beta-nicotinamide adenine dinucleotide phosphate (NADPH) in phosphate buffer (pH 7.4) and incubated for 2 h at 37 degrees C. Then, the incubation mixture was mixed with sodium sulfate and extracted with n-hexane by using a Soxhlet apparatus. The hexane extract was concentrated under nitrogen and injected into the gas chromatography-mass spectrometry (GC-MS) machine running in selective ion monitoring mode (SIM) to measure 2-DCB concentration. The hexane extract from the in vitro and in vivo studies was also derivatized with a silylation reagent and injected into a GC-MS running in full scan mode. The average percentage of 2-DCB recovered from the test incubations was 23%, compared with 50% from the controls. The GC-MS chromatograms of the derivatized samples showed a unique peak in the in vitro test incubations and in the hexane extract of the rat feces that were given 2-DCB. This peak was later identified as 2-doecylcyclobutanol.
authors.affiliation: Food Science Inst., Dept. of Animal Sciences and Industry, 208 Call Hall, Kansas State Univ., Manhattan, KS 66506, USA.
authors.forename: Faraj
authors.initials: F
authors.lastname: Hijaz
authors.forename: Tej B
authors.initials: TB
authors.lastname: Shrestha
authors.forename: Stefan H
authors.initials: SH
authors.lastname: Bossman
authors.forename: Faris
authors.initials: F
authors.lastname: Hussain
authors.forename: J Scott
authors.initials: JS
authors.lastname: Smith
mesh_terms: D053000:Analytic Sample Preparation Methods; D000818:Animals; D001711:Biotransformation; D003503:Cyclobutanes / Q000032:analysis / Q000737:chemistry / Q000378:metabolism* / Q000493:pharmacokinetics*; D003600:Cytosol / Q000201:enzymology; D005243:Feces / Q000737:chemistry; D005260:Female; D005514:Food Irradiation / Q000009:adverse effects; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000201:enzymology; D009249:NADP / Q000378:metabolism; D051381:Rats; D017207:Rats, Sprague-Dawley; D013055:Spectrophotometry, Infrared; D014556:Urine / Q000737:chemistry
chemical_list: C553088:2-dodecylcyclobutanol; D003503:Cyclobutanes; D009249:NADP; C063381:2-dodecylcyclobutanone