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ID 111621
Title Alternative
脂質過酸化反応において金属触媒による2-アルケナールの酸化は、遺伝毒性を有する4-オキソ-2-アルケナールを生成する
Metal-catalyzed formation of 4-oxo-2-alkenals
Author
Nuka, Erika Tokushima University
Tomono, Susumu University of Shizuoka
Ishisaka, Akari University of Hyogo
Kato, Yoji University of Hyogo
Miyoshi, Noriyuki University of Shizuoka
Keywords
Lipid peroxidation
DNA adducts
LC-MS/MS
4-oxo-2-alkenals
transition metals
Content Type
Thesis or Dissertation
Description
Lipid peroxidation products react with cellular molecules, such as DNA bases, to form covalent adducts, which are associated with aging and disease processes. Since lipid peroxidation is a complex process and occurs in multiple stages, there might be yet unknown reaction pathways. Here, we analyzed comprehensively 2’-deoxyguanosine (dG) adducts with oxidized arachidonic acid using liquid chromatography-tandem mass spectrometry and found the formation of 7-(2-oxo-hexyl)-etheno-dG as one of the major unidentified adducts. The formation of this adduct was reproduced in the reaction of dG with 2-octenal and predominantly with 4-oxo-2-octenal (OOE). We also found that other 2-alkenals (with five or more carbons) generate corresponding 4-oxo-2-alkenal-type adducts. Importantly, it was found that transition metals enhanced the oxidation of C4-position of 2-octenal, leading to the formation of OOE-dG adduct. These findings demonstrated a new pathway for the formation of 4-oxo-2-alkenals during lipid peroxidation and might provide a mechanism for metal-catalyzed genotoxicity.
Journal Title
Bioscience, Biotechnology, and Biochemistry
ISSN
09168451
13476947
NCID
AA10824164
Publisher
Taylor & Francis|Japan Society for Bioscience, Biotechnology, and Agrochemistry
Volume
80
Issue
10
Start Page
2007
End Page
2013
Published Date
2016-06-07
Remark
内容要旨・審査要旨・論文本文の公開
本論文は, 著者Erika Nukaの学位論文として提出され, 学位審査・授与の対象となっている。
This is an Accepted Manuscript of an article published by Taylor & Francis in Bioscience, Biotechnology, and Biochemistry on 07/06/2016, available online: http://www.tandfonline.com/10.1080/09168451.2016.1191334.
Rights
© 2016 Japan Society for Bioscience, Biotechnology, and Agrochemistry
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
ETD
MEXT report number
甲第3147号
Diploma Number
甲栄第256号
Granted Date
2018-03-23
Degree Name
Doctor of Nutritional Science
Grantor
Tokushima University
departments
Medical Sciences