Identification of a new all-trans-retinol metabolite produced through a new retinol metabolic pathway

Biochemistry
X JiaH F DeLuca

Abstract

In vitro incubation of all-trans-retinol (atROL) with kidney homogenate from vitamin A-deficient and retinoic acid-supplemented (VAD-RAS) female rats produces a new retinol metabolite. Reverse-phase (RP) and normal-phase (NP) high-performance liquid chromatography (HPLC) analysis showed that this metabolite coelutes with the unknown all-trans-retinol (atROL) metabolite previously found in the day 10 conceptus and kidneys of vitamin A-deficient rats maintained on all-trans-retinoic acid (VAD-RA) and given 2 microg of [3H]atROL. Normal-phase (NP) HPLC purification of the metabolite collected from a RP HPLC column further separated the radiolabeled material into two components. The two isolated compounds have identical or very similar spectroscopic properties. Their nuclear magnetic resonance (1H NMR) and mass spectra (MS) indicated that they are isomers. Spectroscopic studies of the metabolites and their derivatives showed that they are nine-carbon fragments resulting from an oxidative cleavage of the side chain of atROL. The cleavage occurs at C-9, and the product is then oxidized to a keto group. The primary hydroxy group from atROL is preserved in the metabolite. A sulfide bridge is formed between C-11 and C-14, which interrup...Continue Reading

References

Oct 1, 1975·The Journal of Nutrition·Y I TakahashiD S Goodman
Jan 1, 1986·Annual Review of Nutrition·M H Stipanuk
Sep 1, 1970·The Journal of Nutrition·T SudaY Tanaka
Jul 28, 1995·The Journal of Biological Chemistry·S B KurlandskyW S Blaner
Jan 1, 1993·Proceedings of the National Academy of Sciences of the United States of America·G AllenbyP Chambon

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Citations

Jun 11, 2002·Annual Review of Nutrition·Margaret Clagett-Dame, Hector F DeLuca
Sep 15, 2001·Archives of Biochemistry and Biophysics·E A Werner, H F DeLuca

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