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Specific role of an alpha,beta-unsaturated carbonyl group in gamma-glutamylcysteine synthetase induction by prostaglandin A2.

The effects of prostaglandins (PGs) on cellular glutathione (GSH) status in L-1210 cells were examined. PGA2 and J2, which have an alpha,beta-unsaturated carbonyl group in the cyclopentane ring, elevated the GSH content, but PGB2, D2, E2 and F2 alpha did not show the effect. When L-1210 cells were incubated with various 2-cyclopentenone derivatives, 4-hydroxy-2-cyclopentenone and some of related compounds elevated cellular GSH levels. Subsequent study with cell-free extract of cultured L-1210 cells revealed that PGA2 and 4-hydroxy-2-cyclopentenone induced gamma-glutamycysteine synthetase activity at the transcriptional level. This induction was also found in other cultured mammalian cells such as HeLa S3, NIH/3T3 and porcine aorta endothelial cells. When L-1210 cells were incubated with PGA2 in the presence of 4-hydroxy-2-cyclopentenone and its analogues, they inhibited the accumulation of PGA2 in cell nuclei. Our findings thus suggest that an alpha,beta-unsaturated carbonyl moiety is responsible for enhancing the biosynthesis of gamma-glutamylcysteine synthetase in cultured cells.