Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota) Organ / tissue: mycelium Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 ]
The structure was elucidated in this paper Publication DOI: 10.1093/glycob/cwm122 Journal NLM ID: 9104124 Publisher: IRL Press at Oxford University Press
Correspondence: Thierry Fontaine <tfontain
pasteur.fr>
Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France, Unité de Résonance Magnétique Nucléaire des Biomolécules, CNRS URA 2185 Institut Pasteur, Paris, France, Unité de Glycobiologie Structurale et Fonctionnelle, UMR 8576 CNRS, Université des Sciences et Technologies de Lille, Villeneuve d’Ascq, France
Fungal glycosylinositolphosphoceramides (GIPCs) are involved in cell growth and fungal–host interactions. In this study, six GIPCs from the mycelium of the human pathogen Aspergillus fumigatus were purified and characterized using Q-TOF mass spectrometry and 1H, 13C, and 31P NMR. All structures have the same inositolphosphoceramide moiety with the presence of a C18:0-phytosphingosine conjugated to a 2-hydroxylated saturated fatty acid (2-hydroxy-lignoceric acid). The carbohydrate moiety defines two types of GIPC. The first, a mannosylated zwitterionic glycosphingolipid contains a glucosamine residue linked in α1-2 to an inositol ring that has been described in only two other fungal pathogens. The second type of GIPC presents an α-Manp-(1→3)-α-Manp-(1→2)-IPC common core. A galactofuranose residue is found in four GIPC structures, mainly at the terminal position via a β1-2 linkage. Interestingly, this galactofuranose residue could be substituted by a choline–phosphate group, as observed only in the GIPC of Acremonium sp., a plant pathogen.
NMR, galactofuranose, glycosphingolipid, Aspergillus fumigatus, glycosylinositolphosphoceramide
Structure type: oligomer
Location inside paper: p.90, p.91, table VI, p.92, table VIII, fraction GSL-C1
Compound class: glycosphingolipid, glycosylinositolphosphoceramide
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_137472,IEDB_1394182,IEDB_141793,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_190606,IEDB_983930,SB_197,SB_198,SB_44,SB_67,SB_72,SB_73
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, 31P NMR, GLC, composition analysis, ion-exchange chromatography, extraction, HF treatment, 15N NMR, HPTLC, N-acetylation, nESI-QTOF-MS
Related record ID(s): 41793, 42003, 42004, 42005, 42006, 42007, 42009, 42010
NCBI Taxonomy refs (TaxIDs): 746128
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 323 K
[as TSV] 13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2 l?2HOLig
1,0,2,3,2 b?Galf 108.47 83.60 79.93 87.07 73.72 65.72
1,0,2,3 a?Manp 101.72 76.81 72.77 70.79 76.29 63.74-64.17
1,0,2,6 a?Manp 102.57 73.20 73.72 70.07 76.51 64.17
1,0,2 a?Manp 103.83 72.43 82.02 68.27 74.31 68.27
1,0 xLmyoIno 78.92 80.70 73.43 75.15 78.49 75.42
1 P
xXphSphC18
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2 l?2HOLig
1,0,2,3,2 b?Galf 4.877 3.777 3.800 3.933 3.518 3.360-3.392
1,0,2,3 a?Manp 4.989 3.933 3.604 3.325 3.565 3.451-3.599
1,0,2,6 a?Manp 4.640 3.642 3.506 3.366 3.380 3.445-3.602
1,0,2 a?Manp 4.982 3.924 3.621 3.632 4.021 3.486-3.702
1,0 xLmyoIno 3.706 3.949 3.208 3.337 2.936 3.480
1 P
xXphSphC18
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2 l?2HOLig
1,0,2,3,2 b?Galf 108.47/4.877 83.60/3.777 79.93/3.800 87.07/3.933 73.72/3.518 65.72/3.360-3.392
1,0,2,3 a?Manp 101.72/4.989 76.81/3.933 72.77/3.604 70.79/3.325 76.29/3.565 63.74-64.17/3.451-3.599
1,0,2,6 a?Manp 102.57/4.640 73.20/3.642 73.72/3.506 70.07/3.366 76.51/3.380 64.17/3.445-3.602
1,0,2 a?Manp 103.83/4.982 72.43/3.924 82.02/3.621 68.27/3.632 74.31/4.021 68.27/3.486-3.702
1,0 xLmyoIno 78.92/3.706 80.70/3.949 73.43/3.208 75.15/3.337 78.49/2.936 75.42/3.480
1 P
xXphSphC18
1 H NMR data:Linkage Residue H1 H2 H3 H4 H5 H6 2 l?2HOLig 1,0,2,3,2 b?Galf 4.877 3.777 3.800 3.933 3.518 3.360 1,0,2,3 a?Manp 4.989 3.933 3.604 3.325 3.565 3.451 1,0,2,6 a?Manp 4.640 3.642 3.506 3.366 3.380 3.445 1,0,2 a?Manp 4.982 3.924 3.621 3.632 4.021 3.486 1,0 xLmyoIno 3.706 3.949 3.208 3.337 2.936 3.480 1 P xXphSphC18
13 C NMR data:Linkage Residue C1 C2 C3 C4 C5 C6 2
l?2HOLig 1,0,2,3,2
b?Galf108.47 83.60 79.93 87.07 73.72 65.72 1,0,2,3
a?Manp101.72 76.81 72.77 70.79 76.29 63.74 1,0,2,6
a?Manp102.57 73.20 73.72 70.07 76.51 64.17 1,0,2
a?Manp103.83 72.43 82.02 68.27 74.31 68.27 1,0
xLmyoIno78.92 80.70 73.43 75.15 78.49 75.42 1
P
xXphSphC18
There are 16 chemically distinct structures. Please, select:
l?2HOLig?(1-2)[bDGalf(1-2)aDManp(1-3)[aDManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aDManp(1-3)[aDManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aDManp(1-3)[aLManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aDManp(1-3)[aLManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aLManp(1-3)[aDManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aLManp(1-3)[aDManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aLManp(1-3)[aLManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bDGalf(1-2)aLManp(1-3)[aLManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aDManp(1-3)[aDManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aDManp(1-3)[aDManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aDManp(1-3)[aLManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aDManp(1-3)[aLManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aLManp(1-3)[aDManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aLManp(1-3)[aDManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aLManp(1-3)[aLManp(1-6)]aDManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
l?2HOLig?(1-2)[bLGalf(1-2)aLManp(1-3)[aLManp(1-6)]aLManp(1-2)xLmyoIno?(1-P-1)]xXphSphC18? // 2HOLig = 2-hydroxylignoceric acid C24:0; phSphC18 = phytosphingosine C18
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