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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Associated disease: pityriasis versicolor [ICD11: 1F2D.0

, ICD11: XN43L

]; infection due to Malassezia furfur [ICD11: XN25C

]

The structure was elucidated in this paper
NCBI PubMed ID: 19389777
Publication DOI: 10.1099/mic.0.029967-0
Journal NLM ID: 0376646
Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: nshibata

tohoku-pharm.ac.jp
Institutions: Department of Infection and Host Defense, Tohoku Pharmaceutical University, Aoba-ku, Sendai, Japan

Lipophilic yeasts of the genus Malassezia are associated with several skin diseases, such as pityriasis versicolor, Malassezia folliculitis, seborrhoeic dermatitis and atopic dermatitis, and are also increasingly associated with catheter-related fungaemia. The cell wall components of pathogenic micro-organisms behave as an antigen and/or ligand of the innate immune response. Live cells of Malassezia furfur and Malassezia pachydermatis did not react with an anti-α-1,2-mannoside antibody. However, they showed a strong hydrophobicity and reactivity with an anti-β-1,3-glucan antibody compared to those of C. albicans. The cell wall polysaccharides of M. furfur and M. pachydermatis were isolated and their structures analysed by (1)H and (13)C NMR experiments. Both polysaccharides were shown to be β-1,6-linked linear galactofuranosyl polymers with a small amount of mannan. The presence of galactomannan on cells of Malassezia species has not been described previously. The galactomannan did not react with an anti-Aspergillus fumigatus monoclonal antibody which has specificity for β-1,5-linked galactofuranosyl residues. An anti-M. furfur antibody strongly reacted with the galactomannans of M. furfur and M. pachydermatis, but did not react with the galactomannans of Trichophyton rubrum, A. fumigatus or Fonsecaea pedrosoi. The characteristics of the anti-M. furfur antibody suggest that there is potential for diagnosis of Malassezia infections by antigen detection.

galactofuranose, HMBC, TOCSY, NOESY, HSQC, mannopyranose, DEPT

Structure type: structural motif or average structure
Location inside paper: p.3425, fig.4
Aglycon: protein
Compound class: cell wall polysaccharide, N-glycan
Contained glycoepitopes: IEDB_130701,IEDB_135813,IEDB_136095,IEDB_136104,IEDB_137340,IEDB_137472,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_149176,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, ELISA, composition analysis, GPC, ion-exchange chromatography, cell surface hydrophobicity, immunization, flow cytometry analysis
Comments, role: Malassezia furfur NBRC 0656 (=CBS 1878), Malassezia pachydermatis NBRC 10064 (=CBS 1879). One of the possible structures; in which a core mannan has a comb-like structure (with multiple -6)aDManp(1- residues); attachment of Galf side chain to one of mannose residues is undetermined

NCBI Taxonomy refs (TaxIDs): 55194, 77020
Show glycosyltransferases

There are 36 chemically distinct structures. Please, select:

CC(=O)N[C@H]1C(NC(=O)CC(N)C(=O)O)O[C@H](CO)[C@@H](O)[C@@H]1OC1O[C@H](CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CO[C@@H]3O[C@@H]([C@H](O)CO[C@@H]4O[C@@H]([C@H](O)CO[C@@H]5O[C@@H]([C@H](O)CO[C@@H]6O[C@@H]([C@H](O)CO[C@@H]7O[C@@H]([C@H](O)CO[C@@H]8O[C@@H]([C@H](O)CO)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at bDGalf: large unit count (29) was reduced to 5