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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 D, table IV, fig.5, table III
Aglycon: (->1) ceramide
Compound class: glycolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_1394182,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: 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%); some NMR signals are tentative

Related record ID(s): 41805, 42033, 42034, 42035, 43707, 43708, 43709
NCBI Taxonomy refs (TaxIDs): 40410
Show glycosyltransferases

NMR conditions: at 303 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,6,4,2	b?Xylp	104.90	74.51	77.37	73.3	66.94
0,2,6,4,3,6,6,2	a?Manp	104.13	71.86	73.01	68.71	75.10	?
0,2,6,4,3,6,6	a?Manp	100.08	80.63	72.06	68.75	?	?
0,2,6,4,3,6	a?Manp	103.67	71.77	72.65	68.33	?	?
0,2,6,4,3	a?Manp	104.91	72.00	72.62	67.82	73.25	67.03
0,2,6,4	a?Manp	101.17	79.88	79.31	67.74	74.95	?
0,2,6	b?Galp	105.37	72.70	73.95	78.97	76.71	?
0,2	a?Manp	103.44	71.92	72.21	68.30	73.51	70.80
0	xLmyoIno	?	82.19	72.23	?	76.59	?
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,6,4,2	b?Xylp	4.391	3.307	3.440	3.645	3.289-3.992
0,2,6,4,3,6,6,2	a?Manp	5.045	4.079	3.850	3.657	4.091	?
0,2,6,4,3,6,6	a?Manp	5.161	4.018	3.970	3.636	?	?
0,2,6,4,3,6	a?Manp	4.900	4.036	3.876	3.872	?	?
0,2,6,4,3	a?Manp	5.135	4.089	3.847	3.898	4.101	3.655-4.093
0,2,6,4	a?Manp	5.009	4.073	4.038	3.860	?	?
0,2,6	b?Galp	4.503	3.612	3.760	4.097	3.800	?
0,2	a?Manp	5.122	4.116	3.867	3.794	4.192	3.902-4.196
0	xLmyoIno	?	4.132	3.581	3.670	3.289	?
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,2,6,4,2	b?Xylp	104.90/4.391	74.51/3.307	77.37/3.440	73.3/3.645	66.94/3.289-3.992
0,2,6,4,3,6,6,2	a?Manp	104.13/5.045	71.86/4.079	73.01/3.850	68.71/3.657	75.10/4.091	?/?
0,2,6,4,3,6,6	a?Manp	100.08/5.161	80.63/4.018	72.06/3.970	68.75/3.636	?/?	?/?
0,2,6,4,3,6	a?Manp	103.67/4.900	71.77/4.036	72.65/3.876	68.33/3.872	?/?	?/?
0,2,6,4,3	a?Manp	104.91/5.135	72.00/4.089	72.62/3.847	67.82/3.898	73.25/4.101	67.03/3.655-4.093
0,2,6,4	a?Manp	101.17/5.009	79.88/4.073	79.31/4.038	67.74/3.860	74.95/?	?/?
0,2,6	b?Galp	105.37/4.503	72.70/3.612	73.95/3.760	78.97/4.097	76.71/3.800	?/?
0,2	a?Manp	103.44/5.122	71.92/4.116	72.21/3.867	68.30/3.794	73.51/4.192	70.80/3.902-4.196
0	xLmyoIno	?/?	82.19/4.132	72.23/3.581	?/3.670	76.59/3.289	?/?
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,6,4,2	b?Xylp	4.391	3.307	3.440	3.645	3.289 3.992
0,2,6,4,3,6,6,2	a?Manp	5.045	4.079	3.850	3.657	4.091	?
0,2,6,4,3,6,6	a?Manp	5.161	4.018	3.970	3.636	?	?
0,2,6,4,3,6	a?Manp	4.900	4.036	3.876	3.872	?	?
0,2,6,4,3	a?Manp	5.135	4.089	3.847	3.898	4.101	3.655 4.093
0,2,6,4	a?Manp	5.009	4.073	4.038	3.860	?	?
0,2,6	b?Galp	4.503	3.612	3.760	4.097	3.800	?
0,2	a?Manp	5.122	4.116	3.867	3.794	4.192	3.902 4.196
0	xLmyoIno	?	4.132	3.581	3.670	3.289	?
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,6,4,2	b?Xylp	104.90	74.51	77.37	73.3	66.94
0,2,6,4,3,6,6,2	a?Manp	104.13	71.86	73.01	68.71	75.10	?
0,2,6,4,3,6,6	a?Manp	100.08	80.63	72.06	68.75	?	?
0,2,6,4,3,6	a?Manp	103.67	71.77	72.65	68.33	?	?
0,2,6,4,3	a?Manp	104.91	72.00	72.62	67.82	73.25	67.03
0,2,6,4	a?Manp	101.17	79.88	79.31	67.74	74.95	?
0,2,6	b?Galp	105.37	72.70	73.95	78.97	76.71	?
0,2	a?Manp	103.44	71.92	72.21	68.30	73.51	70.80
0	xLmyoIno	?	82.19	72.23	?	76.59	?
	P

The spectrum also has 10 signals at unknown positions (not plotted).

There are 256 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]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