Recently discovered functions of glucosylceramides in plants and fungi

Cellular and Molecular Life Sciences

Volumn 60, Issue 5, 2003, Pages 919-941

  Warnecke, D ^a   Heinz, E ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Ceramide glucosyltransferase; Cerebroside; Glucosylceramide synthase; Glycosphingolipid; Glycosyl phosphoryl inositol ceramide; Host pathogen interaction; Pathogenicity; Saccharomyces cerevisiae; UDP glucose

Indexed keywords

3 KETOSPHINGANINE REDUCTASE; ACYLSPHINGOSINE DEACYLASE; GLUCOSYLCERAMIDE; GLUCOSYLTRANSFERASE; METHYLTRANSFERASE; OXYGENASE; SERINE PALMITOYLTRANSFERASE; SPHINGOSINE ACYLTRANSFERASE; UNCLASSIFIED DRUG;

CELL COMMUNICATION; CELL INTERACTION; COMPARATIVE STUDY; FATTY ACID DESATURATION; FUNGAL DEVELOPMENT; FUNGUS; GENETIC ANALYSIS; GENETICS; HOST PATHOGEN INTERACTION; LIPID DEGRADATION; LIPID METABOLISM; LIPOGENESIS; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ANALYSIS; YEAST;

ANIMALIA; EUKARYOTA; FUNGI; SACCHAROMYCES CEREVISIAE;

EID: 0038039171     PISSN: 1420682X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00018-003-2243-4     Document Type: Review

References (248)

1. Huwiler A., Koller T., Pfeilschifter J. and Sandhoff K. (2000) Physiology and pathophysiology of sphingolipid metabolism and signaling. Biochim. Biophys. Acta 1485: 63-99
2. Hannun Y. A., Loomis C. R., Merrill A. H. Jr and Bell R. M. (1986) Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets. J. Biol. Chem. 261: 12604-12609
3. Ohanian J. and Ohanian V. (2001) Sphingolipids in mammalian cell signalling. Cell. Mol. Life Sci. 58: 2053-2068
4. Tilly J. L. and Kolesnick R. N. (1999) Sphingolipid signaling in gonadal development and function. Chem. Phys. Lipids 102: 149-155
5. Senchenkov A., Litvak D. A. and Cabot M. C. (2001) Targeting ceramide metabolism - a strategy for overcoming drug resistance. J. Natl. Cancer Inst. 93: 347-357
6. Olivera A. and Spiegel S. (2001) Sphingosine kinase: a mediator of vital cellular functions. Prostaglandins 64: 123-134
7. Sietsma H., Veldman R. J. and Kok J. W. (2001) The involvement of sphingolipids in multidrug resistance. J. Membr. Biol. 181: 153-162
8. Blitterswijk W. J. van, Luit A. H. van der, Caan W, Verheij M. and Borst J. (2001) Sphingolipids related to apoptosis from the point of view of membrane structure and topology. Biochem. Soc. Trans. 29: 819-824
9. Hannun Y. A., Luberto C. and Argraves K. M. (2001) Enzymes of sphingolipid metabolism: from modular to integrative signaling. Biochemistry 40: 4893-4903
10. Radin N. S. (2001) Killing cancer cells by poly-drug elevation of ceramide levels: a hypothesis whose time has come? Eur. J. Biochem. 268: 193-204
11. Hakomori S. I. (2000) Cell adhesion/recognition and signal transduction through glycosphingolipid microdomain. Glycoconj. J. 17: 143-151
12. Guillas I., Pfefferli M. and Conzelmann A. (2000) Analysis of ceramides present in glycosylphosphatidylinositol anchored proteins of Saccharomyces cerevisiae. Methods Enzymol. 312: 506-515
13. Holthuis J. C., Pomorski T, Raggers R. J., Sprong H. and Van Meer G. (2001) The organizing potential of sphingolipids in intracellular membrane transport. Physiol. Rev. 81: 1689-1723
14. Olsen I. and Jantzen E. (2001) Sphingolipids in bacteria and fungi. Anaerobe 7: 103-112
15. Conzelmann A., Puoti A., Lester R. L. and Desponds C. (1992) Two different types of lipid moieties are present in glycophosphoinositol-anchored membrane proteins of Saccharomyces cerevisiae. EMBO J. 11: 457-466
16. Macher B. A. and Sweeley C. C. (1978) Glycosphingolipids: structure, biological source, and properties. Methods Enzytool. 50: 236-251
17. Hakomori S. (1981) Glycosphingolipids in cellular interaction, differentiation, and oncogenesis. Annu. Rev. Biochem. 50: 733-764
18. Schneiter R. (1999) Brave little yeast, please guide us to Thebes: sphingolipid function in S. cerevisiae. BioEssays 21: 1004-1010
19. Dickson R. C. and Lester R. L. (2002) Sphingolipid functions in Saccharomyces cerevisiae. Biochim. Biophys. Acta 1583: 13-25
20. Chung N. and Obeid L. M. (2000) Use of yeast as a model system for studies of sphingolipid metabolism and signaling. Methods Enzymol. 311: 319-331
21. Dunn T. M., Gable K., Monagban E. and Bacikova D. (2000) Selection of yeast mutants in sphingolipid metabolism. Methods Enzymol. 312: 317-330
22. Sakaki T., Zähringer U., Warnecke D. C., Fahl A., Knogge W and Heinz E. (2001) Sterol glycosides and cerebrosides accumulate in Pichia pastoris, Rhynchosporium secalis and other fungi under normal conditions or under heat shock and ethanol stress. Yeast 18: 679-695
23. Mullins E. D. and Kang S. (2001) Transformation: a tool for studying fungal pathogens of plants. Cell. Mol. Life Sci. 58: 2043-2052
24. Bölker M., Bohnert H. U., Braun K. H., Gorl J. and Kahmann R. (1995) Tagging pathogenicity genes in Ustilago maydis by restriction enzyme-mediated integration (REMI). Mol. Gen. Genet. 248: 547-552
25. Maier F. J. and Schäfer W. (1999) Mutagenesis via insertional-or restriction enzyme-mediated-integration (REMI) as a tool to tag pathogenicity related genes in plant pathogenic fungi. Biol. Chem 380: 855-864
26. Sweigard J. A., Carroll A. M., Farrall L., Chumley F. G. and Valent B. (1998) Magnaporthe grisea pathogenicity genes obtained through insertional mutagenesis. Mol. Plant Microbe Interact. 11: 404-412
27. Kempin S. A., Liljegren S. J., Block L. M., Rounsley S. D., Yanofsky M. F. and Lam E. (1997) Targeted disruption in Arabidopsis. Nature 389: 802-803
28. Puchta H. (2002) Gene replacement by homologous recombination in plants. Plant Mol. Biol. 48: 173-182
29. Bouche N. and Bouchez D. (2001) Arabidopsis gene knock-out: phenotypes wanted. Curr. Opin. Plant Biol. 4: 111-117
30. Thorneycroft D., Sherson S. M. and Smith S. M. (2001) Using gene knockouts to investigate plant metabolism. J. Exp. Bot. 52: 1593-1601
31. Arabidopsis Genome Initiative (2000) Analysis of the genome sequence of the flowering plant Arabidopsis thaliana. Nature 408: 796-815
32. Samson F., Brunaud V., Balzergue S., Dubreucq B., Lepiniec L., Pelletier G. et al. (2002) FLAGdb/FST: a database of mapped flanking insertion sites (FSTs) of Arabidopsis thaliana T-DNA transformants. Nucleic Acids Res. 30: 94-97
33. Li X., Song Y., Century K., Straight S., Ronald P., Dong X. et al. (2001) A fast neutron deletion mutagenesis-based reverse genetics system for plants. Plant J. 27: 235-242
34. Galbiati M., Moreno M. A., Nadzan G., Zourelidou M. and Dellaporta S. L. (2000) Large-scale T-DNA mutagenesis in Arabidopsis for functional genomic analysis. Funct. Integr. Genomics 1: 25-34
35. Sussman M. R., Amasino R. M., Young J. C., Krysan P. J. and Austin-Phillips S. (2000) The Arabidopsis knockout facility at the University of Wisconsin-Madison. Plant Physiol. 124: 1465-1467
36. Mourrain P., Beclin C. and Vaucheret H. (2000) Are gene silencing mutants good tools for reliable transgene expression or reliable silencing of endogenous genes in plants? Genet. Eng. (N. Y.) 22: 155-170
37. Fagard M. and Vaucheret H. (2000) (Trans)gene silencing in plants: how many mechanism? Annu. Rev. Plant Physiol. Plant Mol. Biol. 51: 167-194
38. Wesley S. V., Helliwell C. A., Smith N. A., Wang M. B., Rouse D. T., Liu Q. et al. (2001) Construct design for efficient, effective and high-throughput gene silencing in plants. Plant J. 27: 581-590
39. Lynch D. V. and Phinney A. J. (1995) The transbilayer distribution of glucosylceramide in plant plasma membrane. In: Plant Lipid Metabolism, pp. 239-241, Mazliak P. (ed.), Kluwer, Dordrecht
40. Lynch D. V. (1993) Sphingolipids. In: Lipid Metabolism in Plants, pp. 285-308, Moore T. S. (ed.), CRC, Boca Raton
41. Heinz E. (1996) Plant glycolipids: structure, isolation and analysis. In: Advances in Lipid Methodology - Three, pp. 211-332, Christie W. W. (ed.), Oily Press, Dundee
42. Uemura M., Joseph R. A. and Steponkus P. L. (1995) Cold acclimation in Arabidopsis thaliana. Plant Physiol. 109: 15-30
43. Kawaguchi M., Imai H., Naoe M, Yasui Y. and Ohnishi M. (2000) Cerebrosides in grapevine leaves: distinct composition of sphingoid bases among the grapevine species having different tolerances to freezing temperature. Biosci. Biotechnol. Biochem. 64: 1271-1273
44. Imai H., Ohnishi M., Hotsubo K., Kojima M and Ito S. (1997) Sphingoid base composition of cerebrosides from plant leaves. Biosci. Biotechnol. Biochem. 61: 351-353
45. Mano Y., Kawaminami K., Kojima M., Ohnishi M. and Ito S. (1999) Comparative composition of brown rice lipids (lipid fractions) of indica and japonica rices. Biosci. Biotechnol. Biochem. 63: 619-626
46. Imai H., Morimoto Y. and Tamura K. (2000) Sphingoid base composition of monoglucosylceramide in Brassicaceae. J. Plant Physiol. 157: 453-456
47. Whitaker B. D. (1996) Cerebrosides in mature-green and red-ripe bell pepper and tomato fruits. Phytochemistry 42: 627-632
48. Bohn M., Heinz E. and Lüthje S. (2001) Lipid composition and fluidity of plasma membranes isolated from corn (Zea mays L.) roots. Arch. Biochem. Biophys. 387: 35-40
49. Imai H., Yamamoto K., Shibahara A., Miyatani S. and Nakayama T. (2000) Determining double-bond positions in monoenoic 2-hydroxy fatty acids of glucosylceramides by gas chromatography-mass spectrometry. Lipids 35: 233-236
50. Imai H., Ohnishi M., Kinoshita M., Kojima M. and Ito S. (1995) Structure and distribution of cerebroside containing unsaturated hydroxy fatty acids in plant leaves. Biosci. Biotechnol. Biochem. 59: 1309-1313
51. Uemura M. and Steponkus P. L. (1994) A contrast of the plasma membrane lipid composition of oat and rye leaves in relation to freezing tolerance. Plant Physiol. 104: 479-496
52. Jung J. H., Lee C. O., Kim Y. C. and Kang S. S. (1996) New bioactive cerebrosides from Arisaema amurense. J. Nat. Prod. 59: 319-322
53. Kang S. S., Kim J. S., Xu Y. N. and Kim Y. H. (1999) Isolation of a new cerebroside from the root bark of Aralia elata. J. Nat. Prod. 62: 1059-1060
54. Kim S. Y., Choi Y. H., Huh H., Kim J., Kim Y. C. and Lee H. S. (1997) New antihepatotoxic cerebroside from Lycium chinense fruits. J. Nat. Prod. 60: 274-276
55. Yamauchi R., Aizawa K., Inakuma T. and Kato K. (2001) Analysis of molecular species of glycolipids in fruit pastes of red bell pepper (Capsicum annuum L.) by high-performance liquid chromatography-mass spectrometry. J. Agric. Food Chem. 49: 622-627
56. Cahoon E. B. and Lynch D. V (1991) Analysis of glucocerebrosides of rye (Secale cereale L. cv Puma) leaf and plasma membrane. Plant Physiol. 95: 58-68
57. Norberg E, Mansson J. E. and Liljenberg C. (1991) Characterization of glucosylceramide from plasma membranes of plant root cells. Biochim. Biophys. Acta 1066: 257-260
58. Sullards M. C., Lynch D. V, Merrill A. H. Jr and Adams J. (2000) Structure determination of soybean and wheat glucosylceramides by tandem mass spectrometry. J. Mass Spectrom. 35: 347-353
59. Dickson R. C. and Lester R. L. (1999) Yeast sphingolipids. Biochim. Biophys. Acta 1426: 347-357
60. Loureiro y Penha C. V., Todeschini A. R., Lopes-Bezerra L. M., Wait R., Jones C., Mattos K. A. et al. (2001) Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii. Eur. J. Biochem. 268: 4243-4250
61. Wagner H. and Fiegert E. (1969) Sphingolipids and glycolipids of fungi and higher plants. 3. Isolation of a cerebroside from Aspergillus niger (in German). Z. Naturforsch. B 24: 359
62. Brennan P. J. and Losel D. M. (1978) Physiology of fungal lipids: selected topics. Adv. Microb. Physiol. 17: 47-179
63. Wells G. B., Dickson R. C. and Lester R. L. (1996) Isolation and composition of inositolphosphorylceramide-type sphingolipids of hypbal forms of Candida albicans. J. Bacteriol. 178: 6223-6226
64. Matsubara T., Hayashi A., Banno Y., Morita T. and Nozawa Y. (1987) Cerebroside of the dimorphic human pathogen, Candida albicans. Chem. Phys. Lipids 43: 1-12
65. Wagner H. and Zofcsik W (1966) Sphingolipide und Glykolipide von Pilzen und höheren Pflanzen. Biochem. Z 346: 333-342
66. Wagner H. and Zofcsik W (1966) Über neue Sphingolipide der Hefe. Biochem. Z. 344: 314-316
67. 3-unsaturation correlates with the yeast-mycelium phase transition. Glycobiology 11: 113-124
68. Barr K. and Lester R. L. (1984) Occurrence of novel antigenic phosphoinositol-containing sphingolipids in the pathogenic yeast Histoplasma capsulatum. Biochemistry 23: 5581-5588
69. Barr K., Laine R. A. and Lester R. L. (1984) Carbohydrate structures of three novel phosphoinositol-containing sphingolipids from the yeast Histoplasma capsulatum. Biochemistry 23: 5589-5596
70. 3glu]ceramide. J. Biol. Chem. 249: 3388-3394
71. 3-unsaturation in cerebrosides of Paracoccidioides brasiliensis and Aspergillus fumigatus. Biochemistry 38: 7294-7306
72. Levery S. B., Toledo M. S., Straus A. H. and Takahashi H. K. (1998) Structure elucidation of sphingolipids from the mycopathogen Paracoccidioides brasiliensis: an immunodominant beta-galactofuranose residue is carried by a novel glycosylinositol phosphorylceramide antigen. Biochemistry 37: 8764-8775
73. Smith S. W. and Lester R. L. (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
74. Steiner S., Smith S., Waechter C. J. and Lester R. L. (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
75. Toledo M. S., Levery S. B., Straus A. H. and Takahashi H. K. (2000) Dimorphic expression of cerebrosides in the mycopathogen Sporothrix schenckii. J. Lipid Res. 41: 797-806
76. Toledo M. S., Levery S. B., Glushka J., Straus A. H. and Takahashi H. K. (2001) Structure elucidation of sphingolipids from the mycopathogen Sporothrix schenckii: identification of novel glycosylinositol phosphorylceramides with core Manα1→61ns linkage. Biochem. Biophys. Res. Commun. 280: 19-24
77. Maciel D. M., Rodrigues M. L., Wait R, Villas Boas M. H., Tischler C. A. and Barreto Bergter E. (2002) Glycosphingolipids from Magnaporthe grisea cells: expression of a ceramide dihexoside presenting phytosphingosine as the long chain base. Arch. Biochem. Biophys. 405: 205-213
78. Leipelt M., Warnecke D., Zähringer U., Ott C., Müller F., Hube B. et al. (2001) Glucosylceramide synthases, a gene family responsible for the biosynthesis of glucosphingolipids in animals, plants, and fungi. J. Biol. Chem. 276: 33621-33629
79. Takakuwa N., Kinoshita M., Oda Y. and Ohnishi M. (2002) Existence of cerebroside in Saccharomyces kluyveri and its related species. FEMS Yeast Res. 1496: 1-6
80. Kawai G. and Ikeda Y. (1985) Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune. J. Lipid Res. 26: 338-343
81. Kawai G. (1989) Molecular species of cerebrosides in fruiting bodies of Lentinus edodes and their biological activity. Biochim. Biophys. Acta 1001: 185-190
82. Fujino Y. and Ohnishi M. (1977) Structure of cerebroside in Aspergillus oryzae. Biochim. Biophys Acta 486: 161-171
83. Karlsson K. A., Leffler H. and Samuelsson B. E. (1979) Characterization of cerebroside (monoglycosylceramide) from the sea anemone, Metridium senile: identification of the major long-chain base as an unusual dienic base with a methyl branch at a double bond. Biochim. Biophys. Acta 574: 79-93
84. Sawabe A., Morita M., Okamoto T. and Ouchi S. (1994) The location of double bonds in a cerebroside from edible fungi (mushroom) estimated by B/E linked scan fast atom bombardment mass spectrometry. Biol. Mass Spectrom. 23: 660-664
85. Weiss B. and Stiller R. L. (1972) Sphingolipids of mushrooms. Biochemistry 11: 4552-4557
86. Gao J. M., Hu L., Dong Z. J. and Liu J. K. (2001) New glycosphingolipid containing an unusual sphingoid base from the basidiomycete Polyporus ellisii. Lipids 36: 521-527
87. Zipser B., Bradford J. J. and Hollingsworth R. I. (1998) Structural analysis of leech galactocerebrosides using 1D and 2D NMR spectroscopy, gas chromatography-mass spectrometry, and FAB mass spectrometry. Carbohydr. Res. 308: 47-55
88. Zinser E. and Daum G. (1995) Isolation and biochemical characterization of organelles from the yeast, Saccharomyces cerevisiae. Yeast 11: 493-536
89. Rest M. E. van der, Kamminga A. H., Nakano A., Anraku Y., Poolman B. and Konings W. N. (1995) The plasma membrane of Saccharomyces cerevisiae: structure, function, and biogenesis. Microbiol. Rev. 59: 304-322
90. Patton J. L. and Lester R. L. (1991) The phosphoinositol sphingolipids of Saccharomyces cerevisiae are highly localized in the plasma membrane. J. Bacteriol. 173: 3101-3108
91. Borner G. H., Sherrier D. J., Stevens T. J., Arkin I. T. and Dupree P. (2002) Prediction of glycosylphosphatidylinositol-anchored proteins in Arabidopsis: a genomic analysis. Plant Physiol. 129: 486-499
92. Thompson G. A. Jr and Okuyama H. (2000) Lipid-linked proteins of plants. Prog. Lipid Res. 39: 19-39
93. Svetek J., Yadav M. P. and Nothnagel E. A. (1999) Presence of a glycosylphosphatidylinositol lipid anchor on rose arabinogalactan proteins. J. Biol. Chem. 274: 14724-14733
94. Oxley D. and Bacic A. (1999) Structure of the glycosylphosphatidylinositol anchor of an arabinogalactan protein from Pyrus communis suspension-cultured cells. Proc. Natl. Acad. Sci. USA 96: 14246-14251
95. Wertz P. W. and Downing D. T. (1983) Glucosylceramides of pig epidermis: structure determination. J. Lipid Res. 24: 1135-1139
96. Hamanaka S., Asagami C., Suzuki M., Inagaki F. and Suzuki A. (1989) Structure determination of glucosyl β1-N-(omega-O-linoleoyl)-acylsphingosines of human epidermis. J. Biochem. (Tokyo) 105: 684-690
97. Doering T., Proia R. L. and Sandhoff K. (1999) Accumulation of protein-bound epidermal glucosylceramides in β-glucocerebrosidase deficient type 2 Gaucher mice. FEBS Lett. 447: 167-170
98. Daum G., Tuller G., Nemec T., Hrastnik C., Balliano G., Cattel L. et al. (1999) Systematic analysis of yeast strains with possible defects in lipid metabolism. Yeast 15: 601-614
99. Hanada K. and Nishijima M. (2000) Selection of mammalian cell mutants in sphingolipid biosynthesis. Methods Enzymol. 312: 304-317
100. Mandon E. C., Ehses I., Rother J., Echten G. van and Sandhoff K. (1992) Subcellular localization and membrane topology of serine palmitoyltransferase, 3-dehydrosphinganine reductase, and sphinganine N-acyltransferase in mouse liver. J. Biol. Chem. 267: 11144-11148
101. Lynch D. V. (2000) Enzymes of sphingolipid metabolism in plants. Methods Enzymol. 311: 130-149
102. Hanada K., Hara T. and Nishijima M. (2000) Purification of the serine palmitoyltransferase complex responsible for sphingoid base synthesis by using affinity peptide chromatography techniques. J. Biol. Chem. 275: 8409-8415
103. Gable K., Han G., Monaghan E., Bacikova D., Natarajan M., Williams R. et al. (2002) Mutations in the yeast LCB1 and LCB2 genes, including those corresponding to the hereditary sensory neuropathy type 1 mutations, dominantly inactivate serine palmitoyltransferase. J. Biol. Chem. 277: 10194-10200
104. Buede R., Rinker-Schaffer C., Pinto W. J., Lester R. L and Dickson R. C. (1991) Cloning and characterization of LCB1, a Saccharomyces gene required for biosynthesis of the long-chain base component of sphingolipids. J. Bacteriol. 173: 4325-4332
105. Nagiec M. M., Baltisberger J. A., Wells G. B., Lester R. L. and Dickson R. C. (1994) The LCB2 gene of Saccharomyces and the related LCB1 gene encode subunits of serine palmitoyltransferase, the initial enzyme in sphingolipid synthesis. Proc. Natl. Acad. Sci. USA 91: 7899-7902
106. Zhao C., Beeler T. and Dunn T. (1994) Suppressors of the Ca(2+)-sensitive yeast mutant (csg2) identify genes involved in sphingolipid biosynthesis: cloning and characterization of SCS1, a gene required for serine palmitoyltransferase activity. J. Biol. Chem. 269: 21480-21488
107. Weiss B. and Stoffel W. (1997) Human and murine serinepalmitoyl-CoA transferase - cloning, expression and characterization of the key enzyme in sphingolipid synthesis. Eur. J. Biochem. 249: 239-247
108. Nagiec M. M., Lester R. L. and Dickson R. C. (1996) Sphingolipid synthesis: identification and characterization of mammalian cDNAs encoding the Lcb2 subunit of serine palmitoyltransferase. Gene 177: 237-241
109. Tamura K., Mitsuhashi N., Hara-Nishimura I. and Imai H. (2001) Characterization of an Arabidopsis cDNA encoding a subunit of serine palmitoyltransferase, the initial enzyme in sphingolipid biosynthesis. Plant Cell Physiol. 42: 1274-1281
110. Gable K., Slife H., Bacikova D., Monaghan E. and Dunn T. M. (2000) Tsc3p is an 80-amino acid protein associated with serine palmitoyltransferase and required for optimal enzyme activity. J. Biol. Chem. 275: 7597-7603
111. Beeler T, Bacikova D., Gable K., Hopkins L., Johnson C., Slife H. et al. (1998) The Saccharomyces cerevisiae TSC10/YBR265w gene encoding 3-ketosphinganine reductase is identified in a screen for temperature-sensitive suppressors of the Ca2+-sensitive csg2Δ mutant. J. Biol. Chem 273: 30688-30694
112. Haak D., Gable K., Beeler T. and Dunn T. (1997) Hydroxylation of Saccharomyces cerevisiae ceramides requires Sur2p and Scs7p. J. Biol. Chem. 272: 29704-29710
113. Grilley M. M., Stock S. D., Dickson R. C., Lester R. L. and Takemoto J. Y. (1998) Syringomycin action gene SYR2 is essential for sphingolipid 4-hydroxylation in Saccharomyces cerevisiae. J. Biol. Chem. 273: 11062-11068
114. Sperling P., Ternes P., Moll H., Franke S., Zähringer U. and Heinz E. (2001) Functional characterization of sphingolipid C4-hydroxylase genes from Arabidopsis thaliana. FEBS Lett. 494: 90-94
115. Dickson R. C. and Lester R. L. (1999) Metabolism and selected functions of sphingolipids in the yeast Saccharomyces cerevisiae. Biochim. Biophys. Acta 1438: 305-321
116. Ternes P., Franke S., Zähringer U., Sperling P. and Heinz E. (2002) Identification and characterization of a sphingolipid Δ4-desaturase family. J. Biol. Chem. 277: 25512-25518
117. Schorling S., Vallee B., Barz W. P., Riezman H. and Oesterhelt D. (2001) Lag1p and Lac1p are essential for the Acyl-CoA-dependent ceramide synthase reaction in Saccharomyces cerevisae. Mol. Biol. Cell 12: 3417-3427
118. Guillas I., Kirchman P. A., Chuard R., Pfefferli M., Jiang J. C., Jazwinski S. M. et al. (2001) C26-CoA-dependent ceramide synthesis of Saccharomyces cerevisiae is operated by Lag1p and Lac1p. EMBO J. 20: 2655-2665
119. Jiang J. C., Kirchman P. A., Zagulski M., Hunt J. and Jazwinski S. M. (1998) Homologs of the yeast longevity gene LAG1 in Caenorhabditis elegans and human. Genome Res. 8: 1259-1272
120. Pan H., Qin W. X., Huo K K., Wan D. F.,Yu Y., Xu Z. G. et al. (2001) Cloning, mapping, and characterization of a human homologue of the yeast longevity assurance gene LAG1. Genomics 77: 58-64
121. Lee S. J. (1991) Expression of growth/differentiation factor 1 in the nervous system: conservation of a bicistronic structure. Proc. Natl. Acad. Sci. USA 88: 4250-4254
122. Venkataraman K., Rinbeling C., Bodennec J., Riezman H., Allegood J. C., Sullards M. C. et al. (2002) Up-stream of growth and differentiation factor 1 (uog1), a mammalian homolog of the yeast longevity assurance gene 1 (LAGI), regulates N-stearoyl-sphinganine (C18-(dihydro)ceramide) synthesis in a fumonisin B1-independent manner in mammalian cells. J. Biol. Chem. 277: 35642-35649
123. Brandwagt B. F., Mesbah L. A., Takken F. L., Laurent P. L., Kneppers T. J., Hille J. et al. (2000) A longevity assurance gene homolog of tomato mediates resistance to Alternaria alternata f. sp. lycopersici toxins and fumonisin B1. Proc. Natl. Acad. Sci. USA 97: 4961-4966
124. Hirschberg K., Rodger J. and Futerman A. H. (1993) The long-chain sphingoid base of sphingolipids is acylated at the cytosolic surface of the endoplasmic reticulum in rat liver. Biochem. J. 290: 751-757
125. Kohlwein S. D., Eder S., Oh C. S., Martin C. E., Gable K., Bacikova D. et al. (2001) Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae. Mol. Cell Biol. 21: 109-125
126. Oh C. S., Toke D. A., Mandala S. and Martin C. E. (1997) ELO2 and ELO3, homologues of the Saccharomyces cerevisiae ELO1 gene, function in fatty acid elongation and are required for sphingolipid formation. J. Biol. Chem. 272: 17376-17384
127. Tvrdik P., Westerberg R., Silve S., Asadi A., Jakobsson A., Cannon B. et al. (2000) Role of a new mammalian gene family in the biosynthesis of very long chain fatty acids and sphingolipids. J. Cell Biol. 149: 707-718
128. Gaigg B., Neergaard T. B., Schneiter R., Hansen J. K., Faergeman N. J., Jensen N. A. et al. (2001) Depletion of acyl-coenzyme A-binding protein affects sphingolipid synthesis and causes vesicle accumulation and membrane defects in Saccharomyces cerevisiae. Mol. Biol. Cell 12: 1147-1160
129. Beaudoin F., Gable K., Sayanova O., Dunn T. and Napier J. A. (2002) A Saccharomyces cerevisiae gene required for heterologous fatty acid elongase activity encodes a microsomal β-keto-reductase. J. Biol. Chem. 277: 11481-11488
130. Han G., Gable K., Kohlwein S. D., Beaudoin F., Napier J. A. and Dunn T. M. (2002) The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase. J. Biol. Chem. 277: 35440-35449
131. Millar A. A., Clemens S., Zachgo S., Giblin E. M., Taylor D. C. and Kunst L. (1999) CUT1, an Arabidopsis gene required for cuticular wax biosynthesis and pollen fertility, encodes a very-long-chain fatty acid condensing enzyme. Plant Cell 11: 825-838
132. Mao C, Xu R., Bielawska A., Szulc Z. M. and Obeid L. M. (2000) Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide. J. Biol. Chem. 275: 31369-31378
133. Mao C., Xu R., Bielawska A. and Obeid L. M. (2000) Cloning of an alkaline ceramidase from Saccharomyces cerevisiae: an enzyme with reverse (CoA-independent) ceramide synthase activity. J. Biol. Chem. 275: 6876-6884
134. El Bawnh S, Roddy P., Qian T., Bielawska A., Lemasters J. J. and Hannun Y. A. (2000) Molecular cloning and characterization of a human mitochondrial ceramidase. J. Biol. Chem. 275: 21508-21513
135. Bernardo K., Hurwitz R., Zenk T, Desnick R. J., Ferlinz K., Schuchman E. H. et al. (1995) Purification, characterization, and biosynthesis of human acid ceramidase. J. Biol. Chem. 270: 11098-11102
136. Mao C., Xu R., Szulc Z. M., Bielawska A., Galadari S. H. and Obeid L. M. (2001) Cloning and characterization of a novel human alkaline ceramidase: a mammalian enzyme that hydrolyzes phytoceramide. J. Biol. Chem. 276: 26577-26588
137. Mitsutake S., Tani M., Okino N., Mori K., Ichinose S., Omori A. et al (2001) Purification, characterization, molecular cloning, and subcellular distribution of neutral ceramidase of rat kidney. J. Biol. Chem. 276: 26249-26259
138. Mitchell A. G. and Martin C. E. (1997) Fahlp, a Saccharomyces cerevisiae cytochrome b5 fusion protein, and its Arabidopsis thaliana homolog that lacks the cytochrome b5 domain both function in the alpha-hydroxylation of sphingolipid-associated very long chain fatty acids. J. Biol. Chem. 272: 28281-28288
139. Kaya K., Ramesha C. S. and Thompson G. A. Jr (1984) On the formation of α-hydroxy fatty acids: evidence for a direct hydroxylation of nonhydroxy fatty acid-containing sphingolipids. J. Biol. Chem. 259: 3548-3553
140. Michel C., Echten-Deckert G. van, Rother J., Sandhoff K., Wang E. and Merrill A. H. Jr (1997) Characterization of ceramide synthesis: a dihydroceramide desaturase introduces the 4,5-trans-double bond of sphingosine at the level of dihydroceramide. J. Biol. Chem. 272: 22432-22437
141. Michel C. and Echten-Deckert G. van (1997) Conversion of dihydroceramide to ceramide occurs at the cytosolic face of the endoplasmic reticulum. FEBS Lett. 416: 153-155
142. Endo K., Akiyama T., Kobayashi S. and Okada M. (1996) Degenerative spermatocyte, a novel gene encoding a transmembrane protein required for the initiation of meiosis in Drosophila spermatogenesis. Mol. Gen. Genet. 253: 157-165
143. Endo K., Matsuda Y. and Kobayashi S. (1997) Mdes, a mouse homolog of the Drosophila degenerative spermatocyte gene is expressed during mouse spermatogenesis. Dev. Growth Differ. 39: 399-403
144. Cadena D. L., Kurten R. C. and Gill G. N. (1997) The product of the MLD gene is a member of the membrane fatty acid desaturase family: overexpression of MLD inhibits EGF receptor biosynthesis. Biochemistry 36: 6960-6967
145. Sperling R, Zähringer U. and Heinz E. (1998) A sphingolipid desaturase from higher plants: identification of a new cytochrome b5 fusion protein. J. Biol. Chem. 273: 28590-28596
146. 8-sphingolipid desaturase from Borago officinalis. Arch. Biochem. Biophys. 388: 293-298
147. 8-sphingolipid desaturases from higher plants. Biochem Soc. Trans. 28: 638-641
148. Ichikawa S., Sakiyama H., Suzuki G., Hidari K. I. and Hirabayashi Y. (1996) Expression cloning of a cDNA for human ceramide glucosyltransferase that catalyzes the first glycosylation step of glycosphingolipid synthesis. Proc. Natl. Acad. Sci. USA 93: 4638-4643
149. Marks D. L., Wu K., Paul P., Kamisaka Y., Watanabe R. and Pagano R. E. (1999) Oligomerization and topology of the Golgi membrane protein glucosylceramide synthase. J. Biol. Chem. 274: 451-456
150. Futerman A. H. and Pagano R. E. (1991) Determination of the intracellular sites and topology of glucosylceramide synthesis in rat liver. Biochem. J. 280: 295-302
151. Jeckel D., Karrenbauer A., Burger K. N., Meer G. van and Wieland F. (1992) Glucosylceramide is synthesized at the cytosolic surface of various Golgi subfractions. J. Cell Biol. 117: 259-267
152. Campbell J. A., Davies G. J., Bulone V. and Henrissat B. (1997) A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities. Biochem. J. 326: 929-939
153. Kapitonov D. and Yu R. K. (1999) Conserved domains of glycosyltransferases. Glycobiology 9: 961-978
154. Marks D. L., Dominguez M., Wu K. and Pagano R. E. (2001) Identification of active site residues in glucosylceramide synthase: a nucleotide-binding catalytic motif conserved with processive β-glycosyltransferases. J. Biol. Chem. 276: 26492-26498
155. Cantatore J. L., Murphy S. M. and Lynch D. V. (2000) Compartmentation and topology of glucosylceramide synthesis. Biochem. Soc. Trans. 28: 748-750
156. Basu S., Kaufman B. and Roseman S. (1968) Enzymatic synthesis of ceramide-glucose and ceramide-lactose by glycosyltransferases from embryonic chicken brain. J. Biol. Chem. 243: 5802-5804
157. Marks D. L., Paul P., Kamisaka Y. and Pagano R. E. (2000) Methods for studying glucosylceramide synthase. Methods Enzymol. 311: 50-59
158. Shayman J. A. and Abe A. (2000) Glucosylceramide synthase: assay and properties. Methods Enzymol. 311: 42-49
159. Ichikawa S. and Hirabayashi Y. (2000) Genetic approaches for studies of glycolipid synthetic enzymes. Methods Enzymol. 311: 303-318
160. Lynch D. V., Criss A. K., Lehoczky J. L. and Bui V. T. (1997) Ceramide glucosylation in bean hypocotyl microsomes: evidence that steryl glucoside serves as glucose donor. Arch. Biochem. Biophys. 340: 311-316
161. Nakayama M., Kojima M., Ohnishi M. and Ito S. (1995) Enzymatic formation of plant cerebroside: properties of UDP-glucose:ceramide glucosyltransferase in radish seedlings. Biosci. Biotechnol. Biochem. 59: 1882-1886
162. Peng L., Kawagoe Y., Hogan P. and Delmer D. (2002) Sitosterol-β-glucoside as primer for cellulose synthesis in plants. Science 295: 147-150
163. Read S. M. and Bacic T. (2002) Plant biology: prime time for cellulose. Science 295: 59-60
164. Brown D. J. and DuPont F. M. (1989) Lipid composition of plasma membranes and endomembranes prepared from roots of barley (Hordeum vulgare L.). Plant Physiol. 90: 955-961
165. Verhoek B., Haas R., Wrage K., Linscheid M. and Heinz E. (1983) Lipids and enzymatic activities in vacuolar membranes isolated from oat primary leaves. Z. Naturforsch. 38: 770-777
166. 2-fixation mechanisms. Bot. Acta 103: 32-38
167. Yoshida S. and Uemura M. (1986) Lipid composition of plasma membranes and tonoplasts isolated from etiolated seedlings of mung bean (Vigna radiata L.). Plant Physiol. 82: 807-812
168. Venkataraman K. and Futerman A. H. (2001) Comparison of the metabolism of L-erythro- and L-threo-sphinganines and ceramides in cultured cells and in subcellular fractions. Biochim. Biophys. Acta 1530: 219-226
169. Yaoita Y., Kohata R., Kakuda R., Machida K. and Kikuchi M. (2002) Ceramide constituents from five mushrooms. Chem. Pharm. Bull. (Tokyo) 50: 681-684
170. Brunner F., Wirtz W., Rose J. K., Darvill A. G., Govers F., Scheel D. et al. (2002) A β-glucosidase/xylosidase from the phytopathogenic oomycete, Phytophthora infestans. Phytochemistry 59: 689-696
171. Ichikawa S., Nakajo N., Sakiyama H. and Hirabayashi Y. (1994) A mouse
172. Yamashita T., Wada R., Sasaki T., Deng C., Bierfreund U., Sandhoff K. et al. (1999) A vital role for glycosphingolipid synthesis during development and differentiation. Proc. Natl. Acad. Sci. USA 96: 9142-9147
173. Takizawa M., Nomura T., Wakisaka E., Yoshizuka N., Aoki J., Arai H. et al. (1999) cDNA cloning and expression of human lactosylceramide synthase. Biochim. Biophys. Acta 1438: 301-304
174. Nomura T., Takizawa M., Aoki J., Arai H., Inoue K., Wakisaka E. et al. (1998) Purification, cDNA cloning, and expression of UDP-Gal:glucosylceramide β-1,4-galactosyltransferase from rat brain. J. Biol. Chem. 273: 13570-13577
175. Schulte S. and Stoffel W. (1993) Ceramide UDPgalactosyltransferase from myelinating rat brain: purification, cloning, and expression. Proc. Natl. Acad. Sci. USA 90: 10265-10269
176. Bosio A., Binczek E. and Stoffel W. (1996) Functional breakdown of the lipid bilayer of the myelin membrane in central and peripheral nervous system by disrupted galactocerebroside synthesis. Proc. Natl. Acad. Sci. USA 93: 13280-13285
177. Coetzee T., Fujita N., Dupree J., Shi R., Blight A., Suzuki K. et al. (1996) Myelination in the absence of galactocerebroside and sulfatide: normal structure with abnormal function and regional instability. Cell 86: 209-219
178. Fujimoto H., Tadano-Aritomi K., Tokumasu A., Ito K., Hikita T., Suzuki K. et al. (2000) Requirement of seminolipid in spermatogenesis revealed by UDP-galactose: ceramide galactosyltransferase-deficient mice. J. Biol. Chem. 275: 22623-22626
179. Bijl P van der., Strous G. J., Lopes-Cardozo M., Thomas-Oates J. and Meer G. van (1996) Synthesis of non-hydroxygalactosylceramides and galactosyldiglycerides by hydroxyceramide galactosyltransferase. Biochem. J. 317: 589-597
180. Sprong H., Kruithof B., Leijendekker R., Slot J. W., Meer G. van and Sluijs P. van der (1998) UDP-galactose:ceramide galactosyltransferase is a class I integral membrane protein of the endoplasmic reticulum. J. Biol. Chem. 273: 25880-25888
181. Babia T., Veldman R. J., Hoekstra D. and Kok J. W. (1998) Modulation of carcinoembryonic antigen release by glucosylceramide - implications for HT29 cell differentiation. Eur. J. Biochem. 258: 233-242
182. Deng W., Li R., Guerrera M., Liu Y. and Ladisch S. (2002) Transfection of glucosylceramide synthase antisense inhibits mouse melanoma formation. Glycobiology 12: 145-152
183. Di Sano F., Di Bartolomeo S., Fazi B., Fiorentini C., Matarrese P., Spinedi A. et al. (2002) Antisense to glucosylceramide synthase in human neuroepithelioma affects cell growth but not apoptosis. Cell Death Differ. 9: 693-695
184. Liu Y. Y., Han T. Y., Giuliano A. E., Hansen N. and Cabot M. C. (2000) Uncoupling ceramide glycosylation by transfection of glucosylceramide synthase antisense reverses adriamycin resistance. J. Biol. Chem. 275: 7138-7143
185. Lavie Y., Cao H., Bursten S. L., Giuliano A. E. and Cabot M. C. (1996) Accumulation of glucosylceramides in multidrug-resistant cancer cells. J. Biol. Chem. 271: 19530-19536
186. Morjani H., Aouali N., Belhoussine R., Veldman R. J., Levade T. and Manfait M. (2001) Elevation of glucosylceramide in multidrug-resistant cancer cells and accumulation in cytoplasmic droplets. Int. J. Cancer 94: 157-165
187. Lucci A., Cho W. I., Han T. Y., Giuliano A. E., Morton D. L. and Cabot M. C. (1998) Glucosylceramide: a marker for multiple-drug resistant cancers. Anticancer Res. 18: 475-480
188. Veldman R. J., Klappe K., Hinrichs J., Hummel I., Schaaf G. van der, Sietsma H. et al. (2002) Altered sphingolipid metabolism in multidrug-resistant ovarian cancer cells is due to uncoupling of glycolipid biosynthesis in the Golgi apparatus. FASEB J. 16: 1111-1113
189. Liu Y. Y., Han T. Y., Giuliano A. E. and Cabot M. C. (2001) Ceramide glycosylation potentiates cellular multidrug resistance. FASEB J. 15: 719-730
190. Lavie Y., Cao H., Volner A., Lucci A., Han T. Y., Geffen V. et al. (1997) Agents that reverse multidrug resistance, tamoxifen, verapamil, and cyclosporin A, block glycosphingolipid metabolism by inhibiting ceramide glycosylation in human cancer cells. J. Biol. Chem. 272: 1682-1687
191. Olshefski R. S. and Ladisch S. (2001) Glucosylceramide synthase inhibition enhances vincristine-induced cytotoxicity. Int. J. Cancer 93: 131-138
192. Sietsma H., Veldman R. J., Kolk D., Ausema B., Nijhof W., Kamps W. et al. (2000) 1-Phenyl-2-decanoylamino-3-morpholino-1-propanol chemosensitizes neuroblastoma cells for taxol and vincristine. Clin. Cancer Res. 6: 942-948
193. Liu Y. Y., Hun T. Y., Giuliano A. E., Ichikawa S., Hirabayashi Y. and Cabot M. C. (1999) Glycosylation of ceramide potentiates cellular resistance to tumor necrosis factor-alpha-induced apoptosis. Exp. Cell Res. 252: 464-470
194. Tepper A. D., Diks S. H., Blitterswijk W. J. van and Borst J. (2000) Glucosylceramide synthase does not attenuate the ceramide pool accumulating during apoptosis induced by CD95 or anti-cancer regimens. J. Biol. Chem. 275: 34810-34817
195. Komori H., Ichikawa S., Hirahayashi Y. and Ito M. (1999) Regulation of intracellular ceramide content in B16 melanoma cells: biological implications of ceramide glycosylation. J. Biol. Chem. 274: 8981-8987
196. Komori H., Ichikawa S., Hirabayashi Y. and Ito M. (2000) Regulation of UDP-glucose:ceramide glucosyltransferase-1 by ceramide. FEBS Lett. 475: 243-250
197. Korkotian E., Schwarz A., Pelled D., Schwarzmann G., Segal M. and Futerman A. H. (1999) Elevation of intracellular glucosylceramide levels results in an increase in endoplasmic reticulum density and in functional calcium stores in cultured neurons. J. Biol. Chem. 274: 21673-21678
198. Mizukami H., Mi Y., Wada R., Kono M., Yamashita T., Liu Y. et al. (2002) Systemic inflammation in glucocerebrosidase-deficient mice with minimal glucosylceramide storage. J. Clin. Invest. 109: 1215-1221
199. Zhao H. and Grahowski G. A. (2002) Gaucher disease: perspectives on a prototype lysosomal disease. Cell. Mol. Life Sci. 59: 694-707
200. Sprong H., Degroote S., Claessens T., Drunen J. van, Oorschot V., Westerink B. H. et al. (2001) Glycosphingolipids are required for sorting melanosomal proteins in the Golgi complex. J. Cell Biol. 155: 369-380
201. Brodersen P., Petersen M., Pike H. M., Olszak B., Skov S., Odum N. et al. (2002) Knockout of Arabidopsis accelerated-cell-death11 encoding a sphingosine transfer protein causes activation of programmed cell death and defense. Genes Dev. 16: 490-502
202. Ng C. K., Carr K., McAinsh M. R., Powell B. and Hetherington A. M. (2001) Drought-induced guard cell signal transduction involves sphingosine-1-phosphate. Nature 410: 596-599
203. Lynch D. V. and Steponkus P. L. (1987) Plasma membrane lipid alterations associated with cold acclimation of winter rye seedlings (Scale cereale L. cv Puma). Plant Physiol. 83: 761-767
204. Bohn M. (1999) Der Einfluß einer Kältehärtung im Vergleich zu einer Hormonbehandlung (Abscisinsäure) auf das Lipid-muster von Plasma- und Chloroplastenmembranen des Winterweizens (Triticum aestivum L.). PhD thesis, University of Hamburg, Hamburg
205. Steponkus P. L. (1984) Role of the plasma membrane in freezing injury and cold acclimation. Annu. Rev. Plant Physiol. 35: 543-584
206. Yoshida S. and Uemura M. (1990) Responses of the plasma membrane to cold acclimation and freezing stress. In: The Plant Plasma Membrane, pp. 293-319, Moller I. (ed.), Springer, Berlin
207. Yoshida S., Washio K., Kenrick J. and Orr G. (1988) Thermotropic properties of lipids extracted from plasma membrane and tonoplast isolated from chilling-sensitive mung bean (Vigna radiata [L.] Wilczek). Plant Cell Physiol. 29: 1411-1416
208. Webb M. S., Irving T. C. and Steponkus P. L. (1997) Cerebrosides alter the lyotropic and thermotropic phase transitions of DOPE:DOPC and DOPE:DOPC:sterol mixtures. Biochim. Biophys. Acta 1326: 225-235
209. Lynch D. V., Caffrey M., Hogan J. L. and Steponkus P. L. (1992) Calorimetric and X-ray diffraction studies of rye glucocerebtoside mesomorphism. Biophys. J. 61: 1289-1300
210. Koga J., Yamauchi T., Shimura M., Ogawa N., Oshima K., Umemura K. et al. (1998) Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J. Biol. Chem. 273: 31985-31991
211. Umemura K., Ogawa N., Yamauchi T., Iwata M., Shimura M. and Yoga J. (2000) Cerebroside elicitors found in diverse phytopathogens activate defense responses in rice plants. Plant Cell Physiol. 41: 676-683
212. Umemura K., Ogawa N., Koga J., Iwata M. and Usami H. (2002) Elicitor activity of cerebroside, a sphingolipid elicitor, in cell suspension cultures of rice. Plant Cell Physiol. 43: 778-784
213. Abul-Milh M., Foster D. B. and Lingwood C. A. (2001) In vitro binding of Helicobacter pylori to monohexosylceramides. Glycoconj. J. 18: 253-260
214. Kawai G. and Ikeda Y. (1983) Chemistry and functional moiety of a fruiting-inducing cerebroside in Schizophyllum commune. Biochim. Biophys. Acta 754: 243-248
215. Kawai G., Ohnishi M., Fujino Y. and Ikeda Y. (1986) Stimulatory effect of certain plant sphingolipids on fruiting of Schizophyllum commune. J. Biol. Chem. 261: 779-784
216. Mizushina Y., Hanashima L., Yamaguchi T., Takemura M., Sugawara F., Saneyoshi M. et al. (1998) A mushroom fruiting body-inducing substance inhibits activities of replicative DNA polymerases. Biochem. Biophys. Res. Commun. 249: 17-22
217. Stock S. D., Hama H., Radding J. A., Young D. A. and Takemoto J. Y. (2000) Syringomycin E inhibition of Saccharomyces cerevisiae: requirement for biosynthesis of sphingolipids with very-long-chain fatty acids and mannose- and phosphoinositol-containing head groups. Antimicrob. Agents Chemother. 44: 1174-1180
218. Thevissen K., Cammue B. P., Lemaire K., Winderickx J., Dickson R. C., Lester R. L. et al. (2000) A gene encoding a sphingolipid biosynthesis enzyme determines the sensitivity of Saccharomyces cerevisiae to an antifungal plant defensin from dahlia (Dahlia merckii). Proc. Natl. Acad. Sci. USA 97: 9531-9536
219. Luberto C., Toffaletti D. L., Wills E. A., Tucker S. C., Casadevall A., Perfect J. R. et al. (2001) Roles for inositol-phosphoryl ceramide synthase 1 (IPC1) in pathogenesis of C. neoformans. Genes Dev. 15: 201-212
220. Cheng J., Park T. S., Fischl A. S. and Ye X. S. (2001) Cell cycle progression and cell polarity require sphingolipid biosynthesis in Aspergillas nidulans. Mol. Cell. Biol. 21: 6198-6209
221. Hamer J. E. and Talbot N. J. (1998) Infection-related development in the rice blast fungus Magnaporthe grisea. Curr. Opin. Microbiol. 1: 693-697
222. Howard R. J. and Valent B. (1996) Breaking and entering: host penetration by the fungal rice blast pathogen Magnaporthe grisea. Annu. Rev. Microbiol. 50: 491-512
223. Levery S., Momany M., Lindsey R., Toledo M., Shayman J., Fuller M. et al. (2002) Disruption of the glucosylceramide biosynthetic 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
224. Brade L., Vielhaber G., Heinz E. and Brade H. (2000) In vitro characterization of anti-glucosylceramide rabbit antisera. Glycobiology 10: 629-636
225. Rodrigues M. L., Travassos L. R., Miranda K. R., Franzen A. J., Rozental S., Souza W. de et al. (2000) Human antibodies against a purified glucosylceramide from Cryptococcus neoformans inhibit cell budding and fungal growth. Infect. Immun. 68: 7049-7060
226. Toledo M. S., Suzuki E., Levery S. B., Straus A. H. and Takahashi H. K. (2001) Characterization of monoclonal antibody MEST-2 specific to glucosylceramide of fungi and plants. Glycobiology 11: 105-112
227. Pinto M. R., Rodrigues M. L., Travassos L. R., Haido R. M., Wait R. and Barreto-Bergter E. (2002) Characterization of glucosylceramides in Pseudallescheria boydii and their involvement in fungal differentiation. Glycobiology 12: 251-260
228. Boas M. H., Egge H., Pohlentz G., Hartmann R. and Bergter E. B. (1994) Structural determination of N-2′-hydroxyoctadecenoyl-1-O-β-D-glucopyranosyl-9-methyl-4, 8-sphingadienine from species of Aspergillus. Chem. Phys. Lipids 70: 11-19
229. + adduct ions. Rapid Commun. Mass Spectrom. 14: 551-563
230. Mineki S., Iida M. and Tsutsumi T. (1994) A new cerebroside of the n-alkane-assimilating yeast Candida deformans. J. Ferment. Bioeng. 78: 327-330
231. Duarte R. S., Polycarpo C. R., Wait R., Hartmann R. and Bergter E. B. (1998) Structural characterization of neutral glycosphingolipids from Fusarium species. Biochim. Biophys. Acta 1390: 186-196
232. Ballio A., Casinovi C. G., Framondino M., Marino G., Nota G. and Santurbano B. (1979) A new cerebroside from Fusicoccum amygdali Del. Biochim. Biophys. Acta 573: 51-60
233. Ng K. H. and Laneelle M. A. (1977) Lipids of the yeast Hansenula anomala. Biochimie 59: 97-104
234. Sitrin R. D., Chan G., Dingerdissen J., DeBrosse C., Mehta R., Roberts G. et al. (1988) Isolation and structure determination of Pachybasium cerebrosides which potentiate the antifungal activity of aculeacin. J. Antibiot. (Tokyo) 41: 469-480
235. Gao J.-M., Hu L., Dong Z.-J. and Liu J.-K. (2001) New glycosphingolipid containing an unsual sphingoid base from the basidiomycete Polyporus ellisii. Lipids 36: 521-527
236. Qi J., Ojika M. and Sakagami Y. (2001) Neuritogenic cerebrosides from an edible Chinese mushroom. 2. Structures of two additional termitomycesphins and activity enhancement of an inactive cerebroside by hydroxylation. Bioorg. Med. Chem. 9: 2171-2177
237. Renault S., Shukla A., Giblin M., MacKenzie S. A. and Devine M. D. (1997) Plasma membrane lipid composition and herbicide effects on lipoxygenase activity do not contribute to differential membrane responses in herbicide-resistant and -susceptible wild oat (Avena fatua L.) biotypes. J. Agric. Food Chem. 45: 3269-3275
238. Sandstrom R. P. and Cleland R. E. (1989) Comparison of the lipid composition of oat root and coleoptile plasma membranes: lack of short-term change in response to auxin. Plant Physiol. 90: 1207-1213
239. Rochester C. P., Kjellbom P., Andersson B. and Larsson C. (1987) Lipid composition of plasma membranes isolated from light-grown barley (Hordeum vulgare) leaves: identification of cerebroside as a major component. Arch. Biochem. Biophys. 255: 385-391
240. Palta J. P., Whitaker B. D. and Weiss L. S. (1993) Plasma membrane lipids associated with genetic variability in freezing tolerance and cold acclimation of Solanum species. Plant Physiol. 103: 793-803
241. Zhang G., Slaski J. J., Archambault D. J. and Taylor G. J. (1997) Alteration of plasma membrane lipids in aluminium-resistant and aluminium-sensitive wheat genotypes in response to aluminium stress. Physiol. Plant. 99: 302-308
242. Quartacci M. F., Cosi E. and Navari-Izzo F. (2001) Lipids and NADPH-dependent superoxide production in plasma membrane vesicles from roots of wheat grown under copper deficiency or excess. J. Exp. Bot. 52: 77-84
243. Berglund A., Quartacci M., Calucci L., Navari-Izzo F., Pinzino C. and Liljenberg C. (2002) Alterations of wheat root plasma membrane lipid composition induced by copper stress result in changed physicochemical properties of plasma membrane lipid vesicles. Biochim. Biophys. Acta 1564: 466
244. Trinel P. A., Maes E., Zanetta J. P., Delplace F., Coddeville B., Jouault T. et al. (2002) Candida albicans phospholipomannan, a new member of the fungal mannoseinositolphosphoceramide family. J. Biol. Chem. 277: 37260-37271
245. Jennemann R., Geyer R., Sandhoff R., Gschwind R. M., Levery S. B., Grone H. J. et al. (2001) Glycoinositolphosphosphingolipids (basidiolipids) of higher mushrooms. Eur. J. Biochem. 268: 1190-1205
246. Toledo M. S., Levery S. B., Straus A. H. and Takahashi H. K. (2001) Sphingolipids of the mycopathogen Sporothrix schenckii: identification of a glycosylinositol phosphorylceramide with novel core GlcNH(2)α1→2Ins motif. FEBS Lett. 493: 50-56
247. Chester M. A. (1998) IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature of glycolipids - recommendations 1997. Eur. J. Biochem. 257: 293-298
248. Wertz P. W., Swartzendruber D. C., Madison K. C. and Downing D. T. (1987) Composition and morphology of epidermal cyst lipids. J. Invest. Dermatol. 89: 419-425