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Mass spectrometric identification of N ‐phenyllinoleamide metabolites in mouse peritoneal macrophages
Author(s) -
Bioque G.,
Abián J.,
Bulbena O.,
RosellóCatafau J.,
Gelpí E.
Publication year - 1995
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290090907
Subject(s) - chemistry , linoleic acid , lipoxygenase , metabolism , biochemistry , metabolite , fatty acid , lipid metabolism , enzyme
N ‐Phenyllinoleamide ( N PLA), the anilide of linoleic acid, has been regarded as a marker of the case oils associated with toxic oil syndrome, but the mechanisms of toxic injury remain enigmatic. Experimental data have related an increased systemic toxic effect of heated linoleic anilides to chemical structural modifications that might also be possible by in vivo metabolism; however, little is known about their metabolism. Taking into account that N PLA is a derivative of linoleic acid, a fatty acid that can be metabolized by lipoxygenase activity to a vast array of derivatives possessing biological activity, the objective has been to elucidate the oxidative metabolism of N PLA by mouse peritoneal macrophages, a cellular model with high lipoxygenase activity. Cells were incubated with 0.1 mM N PLA spiked with N ‐phenyl[1‐ 14 C]linoleamide. The metabolites were separated by high‐performance liquid chromatography and individually collected prior to GC/MS analysis. Identification of trihydroxy‐, monohydroxy‐ and epoxy‐derivatives of N PLA, suggests that this xenobiotic can be metabolized via the same oxidative processes as for linoleic acid. Furthermore, identification of the non‐amidated monohydroxylated and trihydroxylated derivatives of linoleic acid arising from N PLA suggests an amidase‐like activity with release of aniline and the free fatty acid. These results provide information about possible biological structures arising from N PLA, and open the way to evaluate the biological significance of these metabolites in the inflammatory reactions associated with toxic oil syndrome.