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Journal of Lipid Research, Vol. 9, 501-508, July 1968
Copyright © 1968 by Lipid Research, Inc.

Oxidative decarboxylation of retinoic acid in microsomes of rat liver and kidney

Anita B. Roberts and Hector F. Deluca

Department of Biochemistry, University of Wisconsin, College of Agriculture and Life Sciences, Madison, Wisconsin 53706

Liver and kidney microsomes have been found to catalyze a rapid decarboxylation of retinoic acid in vitro. The reaction requires NADPH and Fe2+, and is further stimulated by the presence of pyrophosphate. Thiamine pyrophosphate contained sufficient iron as an impurity to provide strong enhancement of the reaction in the absence of added iron. The decarboxylation could also be shown to occur nonenzymatically in the presence of ascorbate, Fe2+, and boiled microsomes, but there was little autoxidation resulting in decarboxylation. The reaction was strongly inhibited by chelating agents, N,N'-diphenyl-p-phenylene diamine, phenazine methosulfate, and ferricyanide, and resembled lipid peroxidation in both its cofactor requirements and response to inhibitors.

The product of the reaction appeared to lack only the C-15 of the original retinoic acid molecule. It was not retained by diethylaminoethyl cellulose, was more polar than retinoic acid upon silicic acid chromatography, had a lower UV absorption maximum (295 mµ) than the starting product, and seemed to have an aldehyde group at C-14.

The physiological significance of the decarboxylation remains to be assessed, but its rapidity makes it important to in vitro work on retinoic acid.

Supplementary key words retinoic acid • decarboxylation • peroxidation • rat • microsomes • inhibition • chelation • iron

Submitted on October 5, 1967
Accepted on March 26, 1968


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