文章基本信息

标题：Identification of novel oxidized levuglandin D2 in marine red alga and mouse tissue
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作者：Yoshikazu Kanai ; Sadahiko Hiroki ; Hiroyuki Koshino 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：2011
卷号：52
期号：12
页码：2245-2254
DOI：10.1194/jlr.M017053
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：In animals, the product of cyclooxygenase reacting with arachidonic acid, prostaglandin(PG)H₂, can undergo spontaneous rearrangement and nonenzymatic ring cleavage to form levuglandin(LG)E₂ and LGD₂. These LGs and their isomers are highly reactive γ-ketoaldehydes that form covalent adducts with proteins, DNA, and phosphatidylethanolamine in cells. Here, we isolated a novel oxidized LGD₂ (ox-LGD₂) from the red alga Gracilaria edulis and determined its planar structure. Additionally, ox-LGD₂ was identified in some tissues of mice and in the lysate of phorbol-12-myristate-13-acetate (PMA)-treated THP-1 cells incubated with arachidonic acid using LC-MS/MS. These results suggest that ox-LGD₂ is a common oxidized metabolite of LGD₂. In the planar structure of ox-LGD₂, H8 and H12 of LGD₂ were dehydrogenated and the C9 aldehyde was oxidized to a carboxylic acid, which formed a lactone ring with the hydrated ketone at C11. These structural differences imply that ox-LGD₂ is less reactive with amines than LGs. Therefore, ox-LGD₂ might be considered a detoxification metabolite of LGD₂.
关键词：prostaglandins ; Gracilaria ; LC-MS/MS ; NMR