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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: cell culture
Associated disease: infection due to Cryptococcus neoformans [ICD11: XN3EH

]

The structure was elucidated in this paper
NCBI PubMed ID: 12122022
Publication DOI: 10.1093/glycob/cwf053
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: luciamp

biof.ufrj.br
Institutions: Laboratory for Molecular Structure, NIBSC, Herts, UK, Centro de Ciências da Saúde, Bloco G, Instituto de Biofísica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brasil, Kennedy Institute for Rheumatology Division, Faculty of Medicine, Imperial College of Science, Technology and Medicine, London, UK

Complex glycoinositolphosphoryl ceramides (GIPCs) have been purified from a pathogenic encapsulated wild-type (WT) strain of Cryptococcus neoformans var. neoformans and from an acapsular mutant (Cap67). The structures of the GIPCs were determined by a combination of tandem mass spectrometry, nuclear magnetic resonance spectroscopy, methylation analysis, gas chromatography-mass spectrometry, and chemical degradation. The main GIPC from the WT strain had the structure Manp(α1-3)[Xylp(β1-2)] Manp(α1-4)Galp(β1-6)Manp(α1-2)Ins-1-phosphoryl ceramide (GIPC A), whereas the compounds from the acapsular mutant were more heterogeneous in their glycan chains, and variants with Manp(α1-6) (GIPC B), Manp(α1-6) Manp(α1-6) (GIPC C), and Manp(α1-2)Manp(α1-6)Manp(α1-6) (GIPC D) substituents linked to the nonreducing terminal mannose residue found in the WT GIPC A were abundant. The ceramide moieties of C. neoformans GIPCs were composed of a C18 phytosphingosine long-chain base mainly N-acylated with 2-hydroxy-tetracosanoic acid in the WT GIPC while in the acapsular Cap67 mutant GIPCs, as well as 2-hydroxy-tetracosanoic acid, the unusual 2,3-dihydroxy-tetracosanoic acid was characterized. In addition, structural analysis revealed that the amount of GIPC in the WT cells was fourfold less of that in the acapsular mutant.

NMR spectroscopy, mass spectrometry, C. neoformans, glycophosphosphingolipids

Structure type: oligomer
Location inside paper: GIPC C, table IV
Aglycon: (->1) ceramide
Compound class: glycolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_136044,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_76933,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_197,SB_198,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, ESI-MS/MS, GC, Smith degradation, MALDI-TOF MS, NMR-1D, methanolysis, GPC, extraction, HPTLC, N-acetylation, methylation analysis, CC, ESI-QTOF-MS, ammonolysis
Comments, role: mutant strain ceramide consists of C18 phytosphingosine N-acylated with C24:0 2-OH (48%), C24:0 2,3-diOH (37%) and C25:0 2,3-diOH (15%)

Related record ID(s): 41805, 42033, 42034, 42035, 43707, 43708, 43710
NCBI Taxonomy refs (TaxIDs): 40410
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There are 128 chemically distinct structures. Please, select:

O=P(O)(O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O[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](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

SVG MW SMILES 3D mol Ionize