Characterization of neutral and acidic glycosphingolipids from the lectin-producing mushroom, Polyporus squamosus

Glycobiology

Volumn 17, Issue 7, 2007, Pages 754-766

  Arigi, Emma ^a   Singh, Suddham ^a   Kahlili, Ardalan H ^b   Winter, Harry C ^c   Goldstein, Irwin J ^c   Levery, Steven B ^a  

^a University of New Hampshire   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

^c UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

Basidiomycete; Electrospray ionization; Glycolipid; Mass spectrometry; NMR spectroscopy

Indexed keywords

CERAMIDE; GLUCOSYLCERAMIDE; GLYCOSPHINGOLIPID; GLYCOSYLINOSITOL PHOSPHORYLCERAMIDE; LECTIN; MONOHEXOSYLCERAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; ELECTROSPRAY MASS SPECTROMETRY; FRACTIONATION; GAS CHROMATOGRAPHY; GLYCOBIOLOGY; LIPID ANALYSIS; LIPID COMPOSITION; METHYLATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYPORUS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN INTERACTION;

ACIDIC GLYCOSPHINGOLIPIDS; AGARICALES; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOSPHINGOLIPIDS; GLYCOSYLATION; INOSITOL; LECTINS; LIPIDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHYLATION; MODELS, CHEMICAL; NEUTRAL GLYCOSPHINGOLIPIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANIMALIA; BASIDIOMYCOTA; FUNGI; POLYPORUS SQUAMOSUS;

EID: 34447313948     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwm035     Document Type: Article

References (48)

1. Adams J, Ann Q. 1993. Structure determination of sphingolipids by mass spectrometry. Mass Spectrom Rev. 12:51-85.
2. Aoki K, Uchiyama R, Itonori S, Sugita S, Che F-S, Isogai A, Hada N, Takeda T, Kumagai H. et al. 2004. Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramide in filamentous fungi and their induction of cell death of cultured rice cells. Biochem J. 378: 461-472.
3. n. Anal Chem. 77:6250-6262.
4. Barr K, Laine RA, Lester RL. 1984. Carbohydrate structures of three novel phosphoinositol-containing sphingolipids from the yeast Histoplasma capsulatum. Biochemistry. 23:5589-5596.
5. Barr K, Lester RL. 1984. Occurrence of novel antigenic phosphoinositol-containing sphingolipids in the pathogenic yeast capsulatum. Biochemistry. 23:5581-5588.
6. Barreto-Bergter E, Pinto MR, Rodrigues ML. 2004. Structure and biological functions of fungal cerebrosides. An Acad Bras Cienc. 76:67-84.
7. Bennion B, Park C, Fuller M, Lindsey R, Momany M, Jennemann R, Levery SB. 2003. Glycosphingolipids of the model fungus Aspergillus nidulans characterization of GIPCs with oligo-α-mannose-type glycans. J Lipid Res. 44:2073-2088.
8. Boulianne RP, Liu Y, Aebi M, Lu BC, Kues U. 2000. Fruiting body development in Coprinus cinereus: Regulated expression of two galectins secreted by a non-classical pathway. Microbiology. 146:1841-1853.
9. Ciucanu I, Costello CE. 2003. Elimination of oxidative degradation during the per-O-methylation of carbohydrates. J Am Chem Soc. 125:16213-16219.
10. Ciucanu I, Kerek F. 1984. A simple and rapid method for the permethylation of carbohydrates. Carbohydr Res. 131:209-217.
11. Cooper DN, Boulianne RP, Charlton S, Farrell EM, Sucher A, Lu BC. 1997. Fungal galectins, sequence and specificity of two isolectins from Coprinus cinereus. J Biol Chem. 272:1514-1521.
12. Costello CE, Vath JE. 1990. Tandem mass spectrometry of glycolipids. Methods Enzymol. 193:738-768.
13. Dabrowski J, Hanfland P, Egge H. 1980. Structural analysis of glycosphingolipids by high-resolution 1H nuclear magnetic resonance spectroscopy. Biochemistry. 19:5652-5658.
14. Dickson RC, Lester RL. 2002. Sphingolipid functions in Saccharomyces cerevisiae. Biochim Biophys Acta. 1583:13-25.
15. Gagneux P, Varki A. 1999. Evolutionary considerations in relating oligosaccharide diversity to biological function. Glycobiology. 9:747-755.
16. Heise N, Gutierrez ALS, Mattos KA, Jones C, Wait R, Previato JO, Mendonca-Previato L. 2002. Molecular analysis of a novel family of complex glycoinositolphosphoryl ceramides from Cryptococcus neoformans: Structural differences between encapsulated and acapsular yeast forms. Glycobiology. 12:409-420.
17. Hellerqvist CG. 1990. Linkage analysis using the Lindberg method. Methods Enzymol. 193:554-573.
18. Hsu F-F, Turk J. 2001. Structural determination of glycosphingolipids as lithiated adducts by electrospray ionization mass spectrometry using lowenergy collisional-activated dissociation on a triple stage quadrupole instrument. J Am Soc Mass Spectrom. 12:61-79.
19. Jansson P-E, Kenne L, Liedgren H, Lindberg B, Lönngren J. 1976. A practical guide to methylation analysis of carbohydrates. Chem Commun Univ Stockholm 1-75.
20. Jennemann R, Bauer BL, Bertalnffy H, Geyer R, Gschwind RM, Selmer T, Wiegandt H. 1999. Novel glycoinositolphosphosphingolipids, basidiolipids, from Agaricus. Eur J Biochem. 259:331-338.
21. Jennemann R, Geyer R, Sandhoff R, Gschwind RM, Levery SB, Gröne H-J, Wiegandt H. 2001. Glycoinositolphosphosphingolipids (basidiolipids) of higher mushrooms. Eur J Biochem. 268:1190-1205.
22. Koerner TA, Prestegard JH, Yu RK. 1987. Oligosaccharide structure by two-dimensional proton nuclear magnetic resonance spectroscopy. Methods Enzymol. 138:38-59.
23. Laine RA, Young ND, Gerber JN, Sweeley CC. 1974. Identification of 2-hydroxy fatty acids in complex mixtures of fatty acid methyl esters by mass chromatography. Biomed Mass Spectrom. 1:10-14.
24. Leipelt M, Warnecke D, Zahringer U, Ott C, Muller F, Hube B, Heinz E. 2001. Glucosylceramide synthases, a gene family responsible for the biosynthesis of glucosphingolipids in animals, plants, and fungi. J Biol Chem. 276: 33621-33629.
25. Lester RL, Dickson RC. 1993. Sphingolipids with inositolphosphate-containing head groups. Adv Lipid Res. 26:253-274.
26. Levery SB. 2005. Glycosphingolipid structural analysis and glycosphingolipidomics. Methods Enzymol. 405:300-369.
27. Levery SB, Hakomori S. 1987. Microscale methylation analysis of glycolipids using capillary gas chromatography-chemical ionization mass fragmentography with selected ion monitoring. Methods Enzymol. 138:13-25.
28. Levery SB, Momany M, Lindsey R, Toledo MS, Shayman JA, Fuller M, Brooks K, Doong RL, Straus AH, Takahashi HK. 2002. Disruption of the glucosylceramide biosynthesis pathway in Aspergillus nidulans and Aspergillus fumigatus by inhibitors of UDP-Glc: Ceramide glucosyltransferase strongly affects spore germination, cell cycle, and hyphal growth. FEBS Lett. 525:59-64.
29. + adduct ions. Rapid Commun Mass Spectrom. 14:551-563.
30. Levery SB, Toledo MS, Straus AH, Takahashi HK. 1998. Structure elucidation of sphingolipids from the mycopathogen Paracoccidioides brasiliensis: An immunodominant β-galactofuranose residue is carried by a novel glycosylinositol phosphorylceramide antigen. Biochemistry. 37:8764-8775.
31. + adduct ions. Rapid Commun Mass Spectrom. 15:2240-2258.
32. Loureiro Y, Penha CV, Todeschini AR, Lopes-Bezerra LM, Wait R, Jones C, Mattos KA, Heise N, Mendonca-Previato L, Previato JO. 2001. Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii. Eur J Biochem. 268:4243-4250.
33. Mayberry WR. 1981. Dihydroxy and monohydroxy fatty acids in Legionella pneumophila. J Bacteriol. 147:373-381.
34. Mo H, Winter HC, Goldstein IJ. 2000. Purification and characterization of a Neu5Acalpha2-6Galbeta1-4Glc/GlcNAc-specific lectin from the fruiting body of the polypore mushroom Polyporus squamosus. J Biol Chem. 275:10623-10629.
35. Park C, Bennion B, Francois IE, Ferket KK, Cammue BP, Thevissen K, Levery SB. 2005. Characterization of neutral glycolipids of the model filamentous fungus, Neurospora crassa: Altered expression in plant defensin-resistant mutants. J Lipid Res. 46:759-768.
36. Singh BN, Costello CE, Beach DH. 1991. Structures of glycophosphosphingolipids of Tritrichomonas foetus: A novel glycophosphosphingolipid. Arch Biochem Biophys. 286:409-418.
37. Smith SW, Lester RL. 1974. Inositol phosphorylceramide, a novel substance and the chief member of a major group of yeast sphingolipids containing a single inositol phosphate. J Biol Chem. 249:3395-3405.
38. Steiner S, Smith SW, Waechter CJ, Lester RL. 1969. Isolation and partial characterization of a major inositol-containing lipid in baker's yeast, mannosyl-diinositol, diphosphoryl-ceramide. Proc Natl Acad Sci USA. 64:1042-1048.
39. Thorpe SR, Sweeley CC. 1967. Chemistry and metabolism of sphingolipids. On the biosynthesis of phytosphingosine by yeast. Biochemistry. 6: 887-897.
40. Toledo MS, Levery SB, Glushka J, Straus AH, Takahashi HK. 2001. Structure elucidation of sphingolipids from the mycopathogen Sporothrix schenckii: Identification of novel glycosylinositol phosphorylceramides with core Manα1->6Ins linkage. Biochem Biophys Res Commun. 280: 19-24.
41. 3-unsaturation in cerebrosides of Paracoccidioides brasiliensis and Aspergillus fumigatus. Biochemistry. 38:7294-7306.
42. Toledo MS, Levery SB, Straus AH, Takahashi HK. 2000. Dimorphic expression of cerebrosides in the mycopathogen Sporothrix schenckii J Lipid Res. 41:797-806.
43. Toledo MS, Levery SB, Straus AH, Takahashi HK. 2001. Sphingolipids of the mycopathogen Sporothrix schenckii: Identification of a glycosylinositol phosphorylceramide novel core GlcNH2 α1->2Ins motif. FEBS Lett. 493:50-56.
44. 3-unsaturation correlates with the yeast-mycelium phase transition. Glycobiology. 11:113-124.
45. Vyas AA, Patel HV, Fromholt SE, Heffer-Lauc M, Vyas KA, Dang J, Schachner M, Schnaar RL. 2002. Gangliosides are functional nerve cell ligands for myelin-associated glycoprotein MAG, an inhibitor of nerve regeneration. Proc Natl Acad Sci USA. 99:8412-8417.
46. Walser PJ, Haebel PW, Kunzler M, Sargent D, Kues U, Aebi M, Ban N. 2004. Structure and functional analysis of the fungal galectin CGL2. Structure (Camb). 12:689-702.
47. Warnecke D, Heinz E. 2003. Recently discovered functions of glucosylceramides in plants and fungi. Cell Mol Life Sci. 60:919-941.
48. Zhang B, Palcic MM, Mo H, Goldstein IJ, Hindsgaul O. 2001. Rapid determination of the binding affinity and specificity of the mushroom Polyporus squamosus lectin using frontal affinity chromatography coupled to electrospray mass spectrometry. Glycobiology. 11:141-147.