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Vol. 29, Issue 5, 652-655, May 2001

13-Hydroxy- and 13-Oxooctadecadienoic acids: Novel Substrates for Human UDP-Glucuronosyltransferases

Anthony R. Jude, Joanna M. Little, Arthur W. Bull, Izabela Podgorski, and Anna Radominska-Pandya

Department of Chemistry, University of Arkansas at Little Rock, Arkansas (A.R.J.); Department of Biochemistry and Molecular Biology, University of Arkansas for Medical Sciences, Little Rock, Arkansas (J.M.L., A.R.-P.); and Department of Chemistry, Oakland University, Rochester, Minnesota (A.W.B., I.P.)

Although there are numerous studies of glucuronidation of endogenous compounds, information on the glucuronidation of fatty acids is lacking. In the present studies, both linoleic acid (LA) and its biologically active oxidized derivatives, 13-hydroxyoctadecadienoic acid (13-HODE) and 13-oxooctadecadienoic acid (13-OXO), have been shown to be effective substrates for human liver UDP-glucuronosyltransferases (UGT) and recombinant UGT2B7. LA (carboxyl glucuronide) and 13-OXO (carboxyl glucuronide, unproven) were actively glucuronidated by human liver microsomes (HLM) and human recombinant UGT2B7 with similar activities, in the range of 2 nmol/mg · min. The hydroxyl derivative of LA, 13-HODE, was glucuronidated at both the hydroxyl and carboxyl functions with carboxyl glucuronidation predominating (ratio of COOH/OH, 2:1). For all substrates, the Km for formation of the carboxyl-linked glucuronide was in the range of 100 to 200 µM while that for the hydroxyl-linked glucuronide was somewhat lower (>100 µM). This is the first demonstration of glucuronidation of LA and its oxidized derivatives, 13-HODE and 13-OXO, by HLM and recombinant UGT2B7.

Copyright © 2001 by The American Society for Pharmacology and Experimental Therapeutics


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Copyright © 2001 by the American Society for Pharmacology and Experimental Therapeutics.