Glycolipids: Distribution and Biological Function

Klaus Brandenburg, Research Center Borstel, Borstel, Germany
Otto Holst, Research Center Borstel, Borstel, Germany

Published online: May 2005

DOI: 10.1038/npg.els.0003912

Glycolipids are amphiphilic components of cell membranes, composed of a hydrophilic polar sugar headgroup (backbone) and a hydrophobic apolar lipid moiety anchoring the molecule in the membrane. According to their detailed chemical structure, in particular of the sugar part, these compounds may fulfil a variety of biological functions important for many processes in life.

Keywords: glycolipids; storage diseases; membrane anchors; membrane domains; lipid rafts; storage diseases; lipopolysaccharide; mycobacteria

Figure 1. Chemical structures of (a) glucosyldiacylglycerol, (b) galactosylceramide, (c) ganglioside GM1, and (d) lipid part of bacterial deep rough mutant lipopolysaccharide from Escherichia coli.
Figure 2. Macroscopic current increase in an asymmetric planar phospholipid/lipopolysaccharide membrane after addition of 0.1% whole human serum as a result of the incorporation of complement C9 monomers. Bathing solution consisted of Hepes buffer including 0.1 mol L–1  KCl.
Figure 3. Structure of the backbone of glycopeptidolipids of M. avium. R=oligosaccharide residues that determine the serospecificity; R¢=H or  CH3; x=13–15, y=7–11.
Figure 4. Chemical structure of phenolic glycolipid from M. leprae. R=long-chain fatty acyl residue.
Figure 5. (a–c) Structures of glycosyl diacylglycerols from plants and (d) the structure of a novel galactolipid from oat seeds.
Figure 6. Chemical structure of a phytoglycolipid.
Figure 7. Chemical structure of a plant sterylglycoside.
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 References
    Aspinall GO, Chatterjee D and Brennan PJ (1995) The variable surface glycolipids of mycobacteria: structures, synthesis of epitopes, and biological properties. Advances in Carbohydrate Chemistry and Biochemistry 51: 169–242.
    Brennan PJ and Nikaido H (1995) The envelope of mycobacteria. Annual Review of Biochemistry 64: 29–63.
    Chatterjee D and Khoo K-H (1998) Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects. Glycobiology 8: 113–120.
    Chen C-S, Bach G and Pagano RE (1998) Abnormal transport along the lysosomal pathway in mucolipidosis, type IV disease. Proceedings of the National Academy of Sciences of the USA 95: 6373–6378.
    Daffé M and Draper P (1998) The envelope layers of mycobacteria with reference to their pathogenicity. Advances in Microbial Physiology 39: 131–203.
    Dykstra M, Cherukuri A, Sohn HW, Tzeng S-J and Pierce SK (2003) Location is everything: lipid rafts and immune cell signaling. Annual Reviews in Immunology 21: 457–481.
    Fattorusso E and Mangoni A (1997) Marine glycolipids. Fortschritte der Chemie Organischer Naturstoffe 72: 215–301.
    Gornati R, Bembi B, Tong X, Boscolo R and Berra B (1998) Total glycolipid and glucosylceramide content in serum and urine of patients with Gaucher's disease type 3 before and after enzyme replacement therapy. Clinica Chimica Acta 271: 151–161.
    Hamberg M, Liepinsh E, Otting G and Griffith W (1998) Isolation and structure of a new galactolipid from oat seeds. Lipids 33: 355–363.
    book Heinz E (1996) "Plant glycolipids: structure, isolation and analysis". In: Christie WW (ed.) Lipid Methodology – Three, pp. 211–332. Dundee: The Oily Press
    Huijbregts RPH, de Kroon AIPM and de Kruijff B (2000) Topology and transport of membrane lipids in bacteria. Biochimica et Biophysica Acta 1469: 43–61.
    IUPAC/IUBMB (International Union of Pure and Applied Chemistry and International Union of Biochemistry and Molecular Biology) (1996) On biochemical nomenclature of glycolipids. Advances in Carbohydrate Chemistry and Biochemistry 55: 311–326.
    Nikaido H and Vaara M (1985) Molecular basis of bacterial outer membrane permeability. Microbiological Reviews 49: 1–32.
    Ridaura-Sanz C (1994) The pathologist's approach to the diagnosis of metabolic disease. Pathology in Research and Practice 190: 1109–1122.
    Rose AL, Farmer PM and Mitra N (1999) Clinical, pathologic, and neurochemical studies of an unusual case of neuronal storage disease with lamellar cytoplasmic inclusions: a new genetic disorder? Journal of Child Neurology 14: 123–129.
    book Scriver CR, Beaudet AL, Sly WS, Valle D (eds); Childs B, Kinzler KW and Vogelsteing B (assoc. eds) (2001) The Metabolic and Molecular Basis of Inherited Disease, 8th edn. New York: McGraw-Hill.
    Seydel U, Oikawa M, Fukase K, Kusumoto S and Brandenburg K (2000) Intrinsic conformation of lipid A is responsible for agonistic and antagonistic activity. European Journal of Biochemistry 267: 3032–3039.
    Simons K and Ehehalt R (2002) Cholesterol, lipid rafts, and disease. Journal of Clinical Investigation 110: 597–603.
    Triantafilou M, Miyake K, Golenbock DT and Triantafilou K (2002) Mediators of innate immune recognition of bacteria concentrate in lipid rafts and facilitate lipopolysaccharide-induced cell activation. Journal of Cell Science 115: 2603–2611.
    Welby M, Poquet Y and Tocanne J-F (1996) The spatial distribution of phospholipids and glycolipids in the membrane of the bacterium Micrococcus luteus varies during the cell cycle. FEBS Letters 384: 107–111.
    Yuan C, Furlong J, Burgos P and Johnston LJ (2002) The size of lipid rafts: an atomic force microscopy study of ganglioside GM1 domains in sphingomyelin/DOPC/cholesterol membranes. Biophysical Journal 82: 2526–2535.
 Further Reading
    book Gabius H-J and Gabius S (1997) Glycosciences, Status and Perspectives. London: Chapman and Hall.
    Jolly RD and Walkley SU (1997) Lysosomal storage diseases of animals: an essay in comparative pathology. Veterinary Pathology 34: 527–548.
    McConville MJ and Menon AK (2000) Recent developments in the cell biology and biochemistry of glycosylphosphatidylinositols. Molecular Membrane Biology 17: 1–16.
    Morrison DC (1996) Proceedings of the symposium ‘Antibiotic-mediated endotoxin release – contribution to pathogenesis in Gram-negative sepsis’. Journal of Endotoxin Research 3: 171–282.
    Münstermann M, Wiese A, Brandenburg K et al. (1999) Complement activation by bacterial surface glycolipids: a study with planar bilayer membranes. Journal of Membrane Biology 167: 223–232.
    Nikaido H (1993) Transport across the bacterial outer membrane. Journal of Bioenergetics and Biomembranes 25: 581–589.
    Rietschel ET, Brade H, Holst O et al. (1996) Bacterial endotoxin: chemical constitution, biological recognition, host response, and immunological detoxification. Current Topics in Microbiology and Immunology 216: 39–81.
    Tocanne JF, Dupou-Cezanne L and Lopez A (1994) Lateral diffusion of lipids in model and natural membranes. Progress in Lipid Research 33: 203–237.
    Wiese A, Brandenburg K, Ulmer AJ, Seydel U and Müller-Loennies S (1999) The dual role of lipopolysaccharide as effector and target molecule. Biological Chemistry 380: 767–784.

Related Sub-Topics:

Lipids: Structure, Function, Metabolism
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Article Title: Glycolipids: Distribution and Biological Function
 
How to Cite close
Brandenburg, Klaus, and Holst, Otto(May 2005) Glycolipids: Distribution and Biological Function. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1038/npg.els.0003912]