Aglycon diversity of brain sterylglucosides: Structure determination of cholesteryl- and sitosterylglucoside

Hisako Akiyama, Kazuki Nakajima, Yoshiyuki Itoh, Tomoko Sayano, Yoko Ohashi, Yoshiki Yamaguchi, Peter Greimel, Yoshio Hirabayashi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

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)/galactosylcerami-des, 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.

Original languageEnglish
Pages (from-to)2061-2072
Number of pages12
JournalJournal of Lipid Research
Volume57
Issue number11
DOIs
Publication statusPublished - 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Endocrinology
  • Cell Biology

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