Identification of novel oxidized levuglandin D 2in marine red alga and mouse tissue

Yoshikazu Kanai, Sadahiko Hiroki, Hiroyuki Koshino, Keiichi Konoki, Yuko Cho, Mirriam Cayme, Yasuo Fukuyo, Mari Yotsu-Yamashita

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2245-2254
Number of pages10
JournalJournal of lipid research
Volume52
Issue number12
DOIs
Publication statusPublished - 2011 Dec

Keywords

  • Gracilaria
  • LC-MS/MS
  • NMR
  • Prostaglandins

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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