Glycerol-, inositol-, and reducing end hexose-containing oligosaccharides in human urine

Abstract

Key words: Urinary oligosaccharides, inositol-oligosaccharides, glycerol-oligosaccharidesTen previously unreported oligosaccharides have been purified from the urines of human subjects using a combination of gel filtration, ion exchange, and thin-layer chromatographies. Their structures were determined by direct probe mass spectrometry, methylation analysis, and proton NMR spectroscopy of the permethylated oligosao. charide alditols.On the basis of composition, the oligosaccharides could be divided into three groups~ Five oligosaccharides containing glycerol were characterized as glucosyl~l-l'glycerol; glucosyl/31-1'glycerol; galactosyl/31-1'glycerol; glucosyl-l-l'(fucosyl-l-2')glycerol and/or fucosyl-l-l'(glucosyl-l-2')glycerol; and glucosyl-l-t'(galactosyl-l-2')glycerol or galactosyl-l-l'(glucosyl-l-2')glycerol. Four inositol-containing oligosaccharides were charao. terized as galactosyl/~l (fucosylc~l)inositol, N-acetylgalactosaminylo~l (fucosyk~l)inositol, fucosyl~l-2galactosyl/31 (N-acetylgalactosaminylcd)inositol and fucosylc~l-2galac-tosyl/31-4-N-acelylglucosaminyl~l(N-acelylgalactosaminyk~1)inositol. Finally, galactosylo~l-3(fucosylc~l-2)galactosyl~l-6galactosylo~l-4(fucosyloll-3)glucose, an oligosaccharide with glucose at its reducing end, was tentatively identified. The significance, and possible origins of the carbohydrate structures are discussed.Oligosaccharides of human urine are reflective of normal and abnormal biosynthetic and degradation processes of tissue glycoconjugates. Lu ndblad eta/. have reported extensively on these human urinary oligosaccharides and have found structures which are related to blood groups A, B, and O oligosaccharides, from both secretor and non-

Oligosaccharides and Complex Carbohydrates: A New Paradigm for Cranberry Bioactivity

“…The presence of multiple types of oligosaccharides in mammalian urine from both dietary and other sources indicates that the kidneys are able to filter this class of compounds from blood into the urine [168][169][170][171][172][173][174][175][176][177][178][179][180][181]. Early studies using gel filtration, ion-exchange, and paper chromatography, combined with hydrolysis and chemical derivatization, characterized trisaccharides and oligosaccharides from healthy adult urine [168][169][170]. Studies of adult human urine have indicated the presence of high oligosaccharide concentrations associated with various endogenous disease states and have reported the presence of oligosaccharides in the urine of normal, healthy adults [171,172].…”