title: 13,14-Dihydroxy-retinol, a new bioactive retinol metabolite.
abstract: Deprivation of vitamin A (retinol) leads to reduced potential of B cell proliferation and nearly complete block of T cell activation in vitro. Retinol, which is thought to function as a pro-hormone, is enzymatically converted into intracellular messenger molecules. Thus, 14-hydroxy-retro-retinol (14-HRR) is an intracellular messenger molecule linked to activation and growth regulation of lymphocytes; whereas, anhydroretinol, another natural retro-retinoid, is an antagonist of 14-HRR effects. In this article, we describe the isolation, structure determination, synthesis, and biological properties of a new intracellular retinol derivative, 13,14-dihydroxy-retinol (DHR), which also supports the viability of retinol-deprived lymphocytes. DHR is found in numerous cell lines representing a large cross-section of tissues and animals from insects to mammals. In T lymphocytes the production of DHR and 14-HRR is up-regulated by phorbol ester. DHR is converted to 14-HRR by mild acid treatment, but not by cells; therefore DHR is not a biosynthetic intermediate in the conversion of retinol to 14-HRR. DHR is a distinct end point of retinol metabolism. Although it is linked to cell proliferation, its biological role remains to be determined.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: F
authors.initials: F
authors.lastname: Derguini
authors.forename: K
authors.initials: K
authors.lastname: Nakanishi
authors.forename: U
authors.initials: U
authors.lastname: Hämmerling
authors.forename: R
authors.initials: R
authors.lastname: Chua
authors.forename: T
authors.initials: T
authors.lastname: Eppinger
authors.forename: E
authors.initials: E
authors.lastname: Levi
authors.forename: J
authors.initials: J
authors.lastname: Buck
mesh_terms: D002460:Cell Line; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D014801:Vitamin A / Q000378:metabolism*
chemical_list: D014801:Vitamin A