CSDB: Search results

Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Associated disease: cryptococcosis [ICD11: 1F27

, ICD11: XN0LE

, ICD11: XN3EH

]; cryptococcal meningitis [ICD11: 1D01.10

, ICD11: XN3EH

]; infection due to Cryptococcus neoformans [ICD11: XN3EH

]

Publication DOI: 10.1016/S1572-5995(06)80045-1
Publisher: New York: Elsevier
Editors: Atta-ur-Rahman
Correspondence: Barreto-Bergter E <eliana.bergter

micro.ufrj.br>
Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil

During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

biosynthesis, structure, glycosphingolipids, fungi

Structure type: oligomer
Location inside paper: p. 1037, table 2, GIPC D
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_191,SB_195,SB_196,SB_197,SB_198,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
Comments, role: review; acapsular Cap67 mutant of C. neoformans; LIP is 2-hydroxy C24, 2,3-dihydroxy C24, C25 and C26 for the GIPC from the acapsular mutant. D-configuration of aManp and bGalp was assumed by CSDB staff.

Related record ID(s): 41830, 42058, 42059
NCBI Taxonomy refs (TaxIDs): 5207
Show glycosyltransferases

There are 2 chemically distinct structures. Please, select:

[2*]N[C@@H](COP(=O)(O)O[1*]O[C@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O[C@H]4O[C@H](CO[C@H]5O[C@H](CO[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H]3O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O)[C@@H](O)[C@H](O)CCCCCCCCCCCCCC

SVG MW SMILES 3D mol Ionize

R1 = INO
R2 = LIP