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Journal of Lipid Research, Vol. 9, 580-586, September 1968
Copyright © 1968 by Lipid Research, Inc.

Origin of some derivatives of retinoic acid found in rat bile

Kenneth Lippel and James Allen Olson

Department of Biochemistry, University of Florida College of Medicine, Gainesville, Florida 32601

After the intraportal injection of retinoic acid-15-14C into rats, all-trans methyl retinoate, a cis isomer of methyl retinoate, retinoyl ßbeta;-glucurono-ggr-lactone, retinoic acid, and retinoyl ßbeta;-glucuronide were isolated from methanol extracts of rat bile by chromatography on anion-exchange resin and silicic acid columns and characterized on thin-layer plates of Silica Gel G. On the other hand, when bile was extracted with n-butanol or analyzed directly by thin-layer chromatography, only retinoyl ßbeta;-glucuronide and a very small amount of retinoic acid could be detected. Butanol extracts of the liver and the intestine, however, still contained a small radioactive nonpolar fraction. When retinoyl ßbeta;-glucuronide was incubated with an anion-exchange resin in the presence of methanol, several nonpolar products appeared. Apparently the methyl retinoate, retinoyl ßbeta;-glucurono-ggr-lactone, and most of the retinoic acid previously found in bile after retinoic acid administration are produced from retinoyl ßbeta;-glucuronide during the isolation procedure.

Supplementary key words retinoic acid • retinoyl ßbeta;-glucuronide • methyl esters of retinoic acid • retinoyl ßbeta;-glucurono-ggr-lactone • rat bile • chromatographic artifacts

Submitted on January 2, 1968
Accepted on April 29, 1968


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