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Journal of Lipid Research, Vol. 9, 168-175, March 1968
Copyright © 1968 by Lipid Research, Inc.

Biosynthesis of ßbeta;-glucuronides of retinol and of retinoic acid in vivo and in vitro

Kenneth Lippel and James Allen Olson

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

After the intraportal injection of retinol-6,7-¹⁴C to rats, the O-ether derivative of retinol, retinyl ßbeta;-glucosiduronate, appears in the bile. Both retinoyl ßbeta;-glucuronide and retinyl ßbeta;-glucosiduronate are also synthesized in vitro when washed rat liver microsomes are incubated with uridine diphosphoglucuronic acid (UDPGA) and either retinoic acid or retinol, respectively. The synthesis of retinoyl ßbeta;-glucuronide was also demonstrated in microsomes of the kidney and in particulate fractions of the intestinal mucosa. The glucuronides were characterized by their UV absorption spectra, by their quenching of UV light or fluorescence under it, by their thin-layer chromatographic behavior in two solvent systems, and by the identification of products released during their hydrolysis by ßbeta;-glucuronidase.

With retinoic acid as the substrate, the UDP glucuronyl transferase of rat liver microsomes had a pH optimum of 7.0, a temperature optimum of 38°C, and a marked dependence on the concentrations of both retinoic acid and UDPGA, but was unaffected by a number of possible inhibitors, protective agents, and competitive substrates. The conversion of retinal to retinoic acid and the synthesis of retinoyl ßbeta;-glucuronide from retinoic acid could not be detected in whole homogenates, cell fractions, or outer segments of the bovine retina.

Supplementary key words retinol • retinyl ßbeta;-glucosiduronate • retinoic acid • retinoyl ßbeta;-glucuronide • rat liver microsomes • glucuronyl transferase • uridine diphosphoglucuronic acid • bile • retina

Submitted on July 21, 1967
Accepted on October 24, 1967

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