Reference - Detail
| RRC ID | 18625 |
|---|---|
| Author | Kanai Y, Hiroki S, Koshino H, Konoki K, Cho Y, Cayme M, Fukuyo Y, Yotsu-Yamashita M. |
| Title | Identification of novel oxidized levuglandin D2 in marine red alga and mouse tissue. |
| Journal | J Lipid Res |
| Abstract |
In animals, the product of cyclooxygenase reacting with arachidonic acid, prostaglandin(PG)H(2), can undergo spontaneous rearrangement and nonenzymatic ring cleavage to form levuglandin(LG)E(2) and LGD(2). 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 LGD(2) (ox-LGD(2)) from the red alga Gracilaria edulis and determined its planar structure. Additionally, ox-LGD(2) 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-LGD(2) is a common oxidized metabolite of LGD(2). In the planar structure of ox-LGD(2), H8 and H12 of LGD(2) 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-LGD(2) is less reactive with amines than LGs. Therefore, ox-LGD(2) might be considered a detoxification metabolite of LGD(2). |
| Volume | 52(12) |
| Pages | 2245-2254 |
| Published | 2011-12-1 |
| DOI | 10.1194/jlr.M017053 |
| PII | S0022-2275(20)40828-4 |
| PMID | 21893678 |
| PMC | PMC3220291 |
| MeSH | Animals Aquatic Organisms / chemistry* Arachidonic Acid / pharmacology Butylated Hydroxytoluene / pharmacology Cell Extracts Cell Line, Tumor Chromatography, Liquid Cysteine / chemistry Gracilaria / chemistry* Humans Male Mice Oxidation-Reduction Prostaglandin D2 / analogs & derivatives* Prostaglandin D2 / analysis Prostaglandin D2 / chemistry Prostaglandin D2 / metabolism Prostaglandins / analysis* Prostaglandins / chemistry Prostaglandins / metabolism Spectrum Analysis Sulfhydryl Compounds / metabolism Tandem Mass Spectrometry Tetradecanoylphorbol Acetate / analogs & derivatives Tetradecanoylphorbol Acetate / pharmacology |
| IF | 4.483 |
| Times Cited | 5 |
| WOS Category | BIOCHEMISTRY & MOLECULAR BIOLOGY |
| Resource | |
| Human and Animal Cells | THP-1(RCB1189) |