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Structure type: monomer ; 780.1-806.1 [M+Na]+
Compound class: glycolipid
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141181,IEDB_141794,IEDB_151528,IEDB_187036,IEDB_190606,SB_7

• Article ID: 5341
  Ben-Menachem G, Kubler-Kielb J, Coxon B, Yergey A, Schneerson R "A newly discovered cholesteryl galactoside from Borrelia burgdorferi" - Proceedings of the National Academy of Sciences of the USA 100(13) (2003) 7913-7918
  

  Two major glycolipids, which comprise ≈36% of the total lipid mass from Borrelia burgdorferi, the etiological agent of Lyme disease, were investigated. We determined the fatty acid type, sugar identity, anomeric configuration, and substituent type and position. The structures were identified as cholesteryl 6-O-acyl-β-d-galactopyranoside (B. burgdorferi glycolipid 1, BbGL-I), and 1,2-di-O-acyl-3-O-α-d-galactopyranosyl-sn-glycerol (BbGL-II). The major fatty acids were palmitate and oleate. The structures were corroborated by gas-liquid chromatography MS, matrix-assisted laser desorption/ionization time-of-flight spectroscopy, fast atom bombardment MS, detailed NMR spectrometry, and metabolic labeling. This is a previously undescribed demonstration of a cholesteryl galactoside in bacteria. Lipopolysaccharide was not detected in B. burgdorferi. The two glycolipids have several properties suggesting they may function as lipopolysaccharide: both are main components of the bacterial membrane, surface exposed, and have a three-domain structure. BbGL-I elicited specific antibodies in mice and rabbits, and BbGL-II elicited antibodies that reacted with both glycolipids.

  glycolipid, Borrelia burgdorferi, Lyme disease, galactoside

  NCBI PubMed ID: 12799465
  Publication DOI: 10.1073/pnas.1232451100
  Journal NLM ID: 7505876
  Publisher: National Academy of Sciences
  Correspondence: Ben-Menachem G
  Institutions: Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, USA, Laboratory of Cellular and Molecular Biophysics, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, USA
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, deacetylation, NMR-2D, FAB-MS, TLC, MALDI-TOF MS, biological assays, radiolabeling, enzymatic digestion, extraction, affinity chromatography, acetylation, methylation analysis, reduction, hydrolysis, CC, cell growth, derivatization, evaporation, centrifugation
  
   
  
  Borrelia burgdorferi B31 ATCC 35210, Borrelia burgdorferi BL303, Borrelia burgdorferi N40
  CSDB ID 45777 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_241118,IEDB_983931,SB_192

• Article ID: 5342
  Hirai Y, Haque M, Yoshida T, Yokota K, Yasuda T, Oguma K "Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis" - Journal of Bacteriology 177(18) (1995) 5327-5333
  

  A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-α-D-glucopyranoside and cholesteryl-6-O-tetrade-canoyl-α-D-glucopyranoside, and the plausible structure of the third one was identified as cholesteryl-6-O-phosphatidyl-α-D-glucopyranoside. Cholesteryl glucosides are very rare in animals and bacteria. Furthermore, those in H. pylori had an α-glycosidic linkage, which is rather unusual for natural glycosides, and a phosphate-linked cholesteryl glycoside like the cholesteryl-6-O-phosphatidyl-α-D-glucopyranoside has not been reported previously. As the cholesterol glucosides were detected in strains obtained from diverse geographical locations, the presence of cholesteryl glucosides in H. pylori is a very unique and a characteristic feature of the species. These findings add a new facet to the physiology and biochemistry, especially the cholesterol and glucose metabolism, of H. pylori. Furthermore, the cholesteryl glucosides of H. pylori showed hemolytic activities.

  Helicobacter pylori, cholesteryl glycosides

  NCBI PubMed ID: 7665522
  Publication DOI: 10.1128/jb.177.18.5327-5333.1995
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Institutions: Department of Bacteriology, Institute of Cellular and Molecular Biology, Okayama University Medical School, Okayama, Japan, Department of Cell Chemistry, Institute of Cellular and Molecular Biology, Okayama University Medical School, Okayama, Japan, Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Okayama University, Okayama, Japan
  Methods: 1H NMR, NMR-2D, FAB-MS, TLC, acid hydrolysis, GLC, biological assays, methanolysis, alkaline hydrolysis, enzymatic digestion, extraction, optical rotation measurement, CC, cell growth, derivatization, orcinol-sulfuric acid assay
  
   
  
  Helicobacter pylori NCTC 11638
  CSDB ID 45781 (all data & tools)