Aglycon diversity of brain sterylglucosides: structure determination of cholesteryl- and sitosterylglucoside[S]
| Autor: | Tomoko Sayano, Kazuki Nakajima, Hisako Akiyama, Yoshiyuki Itoh, Yoshiki Yamaguchi, Yoshio Hirabayashi, Peter Greimel, Yoko Ohashi |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
glycolipids Magnetic Resonance Spectroscopy Stereochemistry Galactosylceramides matrix-assisted laser desorption/ionization-tandem mass spectrometry QD415-436 Glucosylceramides Biochemistry Mice 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Endocrinology Glycolipid Biosynthesis Animals Humans brain lipids sterols glucosylceramide Research Articles mass spectrometry Brain Chemistry Gaucher Disease Chemistry cholesterol Cell Biology Nuclear magnetic resonance spectroscopy Sitosterols Glucosylceramidase 030104 developmental biology Glucocerebrosidase 030217 neurology & neurosurgery Function (biology) |
| Zdroj: | Journal of Lipid Research, Vol 57, Iss 11, Pp 2061-2072 (2016) |
| ISSN: | 0022-2275 |
| Popis: | To date, sterylglucosides have been reported to be present in various fungi, plants, and animals. In bacteria, such as Helicobacter pylori, proton NMR spectral analysis of isolated 1-O-cholesteryl-β-d-glucopyranoside (GlcChol) demonstrated the presence of an α-glucosidic linkage. By contrast, in animals, no detailed structural analysis of GlcChol has been reported, in part because animal-derived samples contain a high abundance of glucosylceramides (GlcCers)/galactosylceramides, which exhibit highly similar chromatographic behavior to GlcChol. A key step in vertebrate GlcChol biosynthesis is the transglucosylation reaction catalyzed by glucocerebrosidase (GBA)1 or GBA2, utilizing GlcCer as a glucose donor. These steps are expected to produce a β-glucosidic linkage. Impaired GBA1 and GBA2 function is associated with neurological disorders, such as cerebellar ataxia, spastic paraplegia, and Parkinson’s disease. Utilizing a novel three-step chromatographic procedure, we prepared highly enriched GlcChol from embryonic chicken brain, allowing complete structural confirmation of the β-glucosidic linkage by 1H-NMR analysis. Unexpectedly, during purification, two additional sterylglucoside fractions were isolated. NMR and GC/MS analyses confirmed that the plant-type sitosterylglucoside in vertebrate brain is present throughout embryonic development. The aglycon structure of the remaining sterylglucoside (GSX-2) remains elusive due to its low abundance. Together, our results uncovered unexpected aglycon heterogeneity of sterylglucosides in vertebrate brain. |
| Databáze: | OpenAIRE |
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