title: Identification of octenal-related dA and dC adducts formed by reactions with a hemin-ω-6-fat peroxidation model system.
abstract: Deoxynucleosides were reacted in a lipid peroxidation model system, emulsified hemin-ethyl linoleate, and the adducts thus produced were analyzed by HPLC. Substantial amounts of stable adducts were detected in the dA- and dC-reaction mixtures. The structures of the major dA and dC adducts, other than the known 4-oxo-2-nonenal adducts, were determined to be etheno-type adducts, with a C₆ side chain bearing an α-hydroxyl-group. These results suggested that the substance involved in adduct formation is 2,3-epoxyoctanal. This compound showed mutagenicity in Salmonella strains TA 100 and TA 104 without the S-9 mix. In addition, based on the structure of a minor dC adduct, another possibly involved mutagen, 4-oxo-2-octenal, was proposed. These mutagens may be formed during storage and cooking of food, or during digestion, and may be involved in human cancers.
authors.affiliation: Department of Environmental Oncology, Institute of Industrial Ecological Sciences, University of Occupational and Environmental Health , 1-1 Iseigaoka, Yahatanishi-ku, Kitakyushu 807-8555, Japan.
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Kawai
authors.forename: Yuya
authors.initials: Y
authors.lastname: Kawasaki
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Kubota
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Kimura
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Sawa
authors.forename: Tomonari
authors.initials: T
authors.lastname: Matsuda
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kasai
mesh_terms: D000447:Aldehydes / Q000032:analysis / Q000737:chemistry* / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts / Q000032:analysis*; D003839:Deoxyadenosines / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry; D043371:Fatty Acids, Omega-6 / Q000737:chemistry*; D006427:Hemin / Q000737:chemistry* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009152:Mutagenicity Tests; D012475:Salmonella / Q000187:drug effects
chemical_list: C403894:4-oxo-2-nonenal; D000447:Aldehydes; D018736:DNA Adducts; D003839:Deoxyadenosines; D043371:Fatty Acids, Omega-6; D003841:Deoxycytidine; D006427:Hemin; C058118:2'-deoxyadenosine; C031639:caprylic aldehyde