title: Characterization of human liver 3-O-beta-D-glucopyranuronosyl-cholesterol by mass spectrometry and nuclear magnetic resonance spectroscopy.
abstract: We have isolated an unusual acidic glycolipid which was detected in the lower phase of the Folch partition of the total lipid extract of human liver during a routine isolation of glycosphingolipids. With the solvent systems commonly used for thin-layer chromatography of glycosphingolipids, this glycolipid has a mobility similar to GbOse3Cer, one of the major glycosphingolipids in human liver. Free cholesterol was released from this glycolipid upon treatment with beta-glucuronidase. The electron impact mass spectrum of the permethylated derivative of this glycolipid showed an intense peak at m/e 369 which is consistent with the cholesterol part of the molecule. It also showed m/e 233 and 201 which are derived from the permethylated glucopyranuronosyl residue. The final proof of the structure was accomplished by high resolution NMR spectroscopy which revealed the presence of beta-linked glucopyranuronosyl residue and cholesterol. Thus, the structure of this acidic glycolipid was conclusively established to be 3-O-beta-D-glucopyranuronosyl-cholesterol.
mesh_terms: D002784:Cholesterol / Q000031:analogs & derivatives* / Q000032:analysis; D002855:Chromatography, Thin Layer / Q000379:methods; D005966:Glucuronidase / Q000378:metabolism; D006017:Glycolipids / Q000032:analysis; D006801:Humans; D006868:Hydrolysis; D008099:Liver / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods
chemical_list: D006017:Glycolipids; C035843:cholesterol glucuronide; D002784:Cholesterol; D005966:Glucuronidase