Identification of novel oxidized levuglandin D2 in marine red alga and mouse tissue[S]
| Autor: | Yoshikazu Kanai, Sadahiko Hiroki, Hiroyuki Koshino, Keiichi Konoki, Yuko Cho, Mirriam Cayme, Yasuo Fukuyo, Mari Yotsu-Yamashita |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: | |
| Zdroj: | Journal of Lipid Research, Vol 52, Iss 12, Pp 2245-2254 (2011) |
| Druh dokumentu: | article |
| ISSN: | 0022-2275 56014740 |
| DOI: | 10.1194/jlr.M017053 |
| Popis: | 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. |
| Databáze: | Directory of Open Access Journals |
| Externí odkaz: |
|