Chemical synthesis and growth-promoting activity of all-trans-retinyl beta-D-glucuronide.
All-trans-retinol reacts with methyl (2,3,4-tri-O-acetyl-1-bromo-1-deoxy-beta-D-glucopyran)uronate in the presence of Ag2CO3 to give the triacetate methyl ester of retinyl beta-glucuronide. Hydrolysis of this ester with sodium methylate in methanol gives retinyl beta-D-glucuronide in about 15% yield. The water-soluble retinyl beta-D-glucuronide was characterized by u.v.-visible, n.m.r. and mass spectra, by elemental analysis and by its susceptibility to hydrolysis by bacterial beta-glucuronidase. Retinyl beta-glucuronide, when administered intraperitoneally in saline (0.9% NaCl), supports well the growth of vitamin A-deficient rats.
Barua
A B
AB
Department of Biochemistry and Biophysics, Iowa State University, Ames 50011.
Olson
J A
JA
D000818:Animals; D001835:Body Weight / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D005966:Glucuronidase; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D013053:Spectrophotometry; D014212:Tretinoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
C026787:retinoyl glucuronide; D014212:Tretinoin; D005966:Glucuronidase