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Biosci Biotechnol Biochem. 2015;79(7):1044-9. doi: 10.1080/09168451.2015.1012149. Epub 2015 May 26.

15-Deoxy-Δ¹²,¹⁴-prostaglandin J₂ as an electrophilic mediator.

Author information

1
a Laboratory of Food and Biodynamics, Graduate School of Bioagricultural Sciences , Nagoya University , Nagoya , Japan.

Erratum in

  • Erratum. [Biosci Biotechnol Biochem. 2015]

Abstract

Lipid-derived electrophilic molecules are endogenously generated and are causally involved in many pathophysiological effects. Prostaglandin D2, a major cyclooxygenase product in a variety of tissues and cells, readily undergoes dehydration to yield the J-series PGs such as 15-deoxy-Δ(12,14)-PGJ2 (15d-PGJ2). Because of the electrophilic α,β-unsaturated ketone moiety present in its cyclopentenone ring, 15d-PGJ2 acts as an endogenous electrophile. 15d-PGJ2 can covalently react via the Michael addition reaction with critical cellular nucleophiles, such as the free cysteine residues of proteins that play a key role in the regulation of the intracellular signaling pathways. Covalent modification of cellular proteins by 15d-PGJ2 may be one of the most important mechanisms by which 15d-PGJ2 induces many biological responses involved in the pathophysiological effects associated with inflammation. This current review is intended to provide a comprehensive summary of 15d-PGJ2 as an endogenous electrophilic mediator of biological activities.

KEYWORDS:

electrophile; lipid mediator; prostaglandin; protein modification

PMID:
26011133
DOI:
10.1080/09168451.2015.1012149
[Indexed for MEDLINE]

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