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1. (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: 12799465Publication DOI: 10.1073/pnas.1232451100Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: Ben-Menachem G
nih.gov>
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
The publication contains the following compound(s):
- Compound ID: 13444
|
/Variants 0/-a-D-Galp-(1-3)-Subst
/Variants 0/ is:
Pam-(1-6)-
OR (exclusively)
Ole-(1-6)-
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
; 809.87-835.87 [M+Na]+
Compound class: glycolipid, glycoside
- Compound ID: 13445
|
/Variants 0/-a-D-Galp2Ac3Ac4Ac-(1-3)-Subst
/Variants 0/ is:
Pam-(1-6)-
OR (exclusively)
Ole-(1-6)-
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
; 935.7-961.7 [M+Na]+
Compound class: glycolipid, glycoside
- Compound ID: 13446
|
/Variants 0/-+
|
a-D-Galp-(1-1)-D-Gro-(2-1)-Pam
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
Ole-(1-3)- |
Show graphically |
Structure type: monomer
; 780.1-806.1 [M+Na]+
Compound class: glycolipid
- Compound ID: 13447
|
/Variants 0/-+
|
a-D-Galp2Ac3Ac4Ac6Ac-(1-1)-D-Gro-(2-1)-Pam
/Variants 0/ is:
Pam-(1-3)-
OR (exclusively)
Ole-(1-3)- |
Show graphically |
Structure type: monomer
Compound class: glycolipid
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2. (Article ID: 5344)
Stübs G, Fingerle V, Wilske B, Göbel UB, Zähringer U, Schumann RR, Schröder NW
Acylated cholesteryl galactosides are specific antigens of borrelia causing lyme disease and frequently induce antibodies in late stages of disease
Journal of Biological Chemistry 284(20) (2019)
13326-13334
Borrelia burgdorferi sensu lato is the causative agent of Lyme disease (LD), an infectious disease occurring in North America, Europe, and Asia in different clinical stages. B. burgdorferi sensu lato encompasses at least 12 species, with B. burgdorferi sensu stricto, B. garinii, and B. afzelii being of highest clinical importance. Immunologic testing for LD as well as recent vaccination strategies exclusively refer to proteinaceous antigens. However, B. burgdorferi sensu stricto exhibits glycolipid antigens, including 6-O-acylated cholesteryl β-D-galactopyranoside (ACGal), and first the data indicated that this compound may act as an immunogen. Here we investigated whether B. garinii and B. afzelii also possess this antigen, and whether antibodies directed against these compounds are abundant among patients suffering from different stages of LD. Gas-liquid chromatography/mass spectroscopy and NMR spectroscopy showed that both B. garinii and B. afzelii exhibit ACGal in high quantities. In contrast, B. hermsii causing relapsing fever features 6-O-acylated cholesteryl β-D-glucopyranoside (ACGlc). Sera derived from patients diagnosed for LD contained antibodies against ACGal, with 80% of patients suffering from late stage disease exhibiting this feature. Antibodies reacted with ACGal from all three B. burgdorferi species tested, but not with ACGlc from B. hermsii. These data show that ACGal is present in all clinically important B. burgdorferi species, and that specific antibodies against this compound are frequently found during LD. ACGal may thus be an interesting tool for improving diagnostics as well as for novel vaccination strategies.
glycolipid, Borrelia burgdorferi, Lyme disease, galactoside
NCBI PubMed ID: 19307181Publication DOI: 10.1074/jbc.M809575200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: nicolas.schroeder

charite.de
Institutions: Division of Immunochemistry, Research Center Borstel, Borstel, Germany, Institute for Microbiology and Hygiene, Charité Medical Center, Berlin, Germany, Bavarian Health and Food Safety Authority, Oberschleissheim, Germany, Max von Pettenkofer-Institute for Medical Microbiology and Hygiene, Ludwig-Maximilian University, Munich, Germany, Institute for Neuropathology, Charité Medical Center, Berlin, Germany
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, DNA sequencing, TLC, GLC, biological assays, serological methods, immunoblotting, CC, cell growth, sonication, DEPT, centrifugation
The publication contains the following compound(s):
- Compound ID: 13454
|
/Variants 0/-b-D-Galp-(1-3)-Subst
/Variants 0/ is:
Ste-(1-6)-
OR (exclusively)
Pam-(1-6)-
OR (exclusively)
Ole-(1-6)-
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
Compound class: glycolipid, glycoside
- Compound ID: 13455
|
/Variants 0/-b-D-Glcp-(1-3)-Subst
/Variants 0/ is:
Ste-(1-6)-
OR (exclusively)
Pam-(1-6)-
OR (exclusively)
Ole-(1-6)-
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
Compound class: glycolipid, glycoside
- Compound ID: 13456
|
/Variants 1/-+
|
/Variants 0/-D-Gro-(3-1)-b-D-Galp
/Variants 0/ is:
Ste-(1-2)-
OR (exclusively)
Pam-(1-2)-
OR (exclusively)
Ole-(1-2)-
OR (exclusively)
Lin-(1-2)-
/Variants 1/ is:
Ste-(1-1)-
OR (exclusively)
Pam-(1-1)-
OR (exclusively)
Ole-(1-1)-
OR (exclusively)
Lin-(1-1)- |
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Structure type: monomer
Compound class: glycolipid, glycoside
- Compound ID: 13457
|
b-D-Glcp-(1-3)-Subst
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
Trivial name: cholesterol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside
- Compound ID: 13458
|
b-D-Galp-(1-3)-Subst
Subst = cholesterol = SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C |
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Structure type: monomer
Compound class: glycoside
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