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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 B, table IV, fig.5, table III
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_144983,IEDB_145668,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_190606,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%); some NMR signals are tentative

Related record ID(s): 41805, 42033, 42034, 42035, 43707, 43709, 43710
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	104.95	74.59	77.41	73.35	67.02
0,2,6,4,3,6	a?Manp	101.52	71.82	72.44	68.63	74.62	62.82
0,2,6,4,3	a?Manp	104.86	72.00	72.60	67.84	73.24	67.03
0,2,6,4	a?Manp	101.10	79.90	79.15	67.81	75.18	62.33
0,2,6	b?Galp	105.41	72.71	73.95	78.92	76.76	61.97
0,2	a?Manp	103.49	72.04	72.38	68.35	73.68	70.55
0	xLmyoIno	74.45	82.18	72.25	71.11	76.67	74.51
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,6,4,2	b?Xylp	4.391	3.309	3.438	3.634	3.286-3.998
0,2,6,4,3,6	a?Manp	4.930	4.032	3.888	3.677	3.658	3.774-3.910
0,2,6,4,3	a?Manp	5.145	4.091	3.852	3.876	4.099	3.660-4.088
0,2,6,4	a?Manp	5.011	4.081	4.042	3.857	4.087	3.772-3.800
0,2,6	b?Galp	4.503	3.619	3.765	4.103	3.802	3.851-3.851
0,2	a?Manp	5.127	4.118	3.870	3.799	4.188	3.910-4.196
0	xLmyoIno	3.662	4.134	3.584	3.651	3.292	3.712
	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	104.95/4.391	74.59/3.309	77.41/3.438	73.35/3.634	67.02/3.286-3.998
0,2,6,4,3,6	a?Manp	101.52/4.930	71.82/4.032	72.44/3.888	68.63/3.677	74.62/3.658	62.82/3.774-3.910
0,2,6,4,3	a?Manp	104.86/5.145	72.00/4.091	72.60/3.852	67.84/3.876	73.24/4.099	67.03/3.660-4.088
0,2,6,4	a?Manp	101.10/5.011	79.90/4.081	79.15/4.042	67.81/3.857	75.18/4.087	62.33/3.772-3.800
0,2,6	b?Galp	105.41/4.503	72.71/3.619	73.95/3.765	78.92/4.103	76.76/3.802	61.97/3.851-3.851
0,2	a?Manp	103.49/5.127	72.04/4.118	72.38/3.870	68.35/3.799	73.68/4.188	70.55/3.910-4.196
0	xLmyoIno	74.45/3.662	82.18/4.134	72.25/3.584	71.11/3.651	76.67/3.292	74.51/3.712
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,6,4,2	b?Xylp	4.391	3.309	3.438	3.634	3.286 3.998
0,2,6,4,3,6	a?Manp	4.930	4.032	3.888	3.677	3.658	3.774 3.910
0,2,6,4,3	a?Manp	5.145	4.091	3.852	3.876	4.099	3.660 4.088
0,2,6,4	a?Manp	5.011	4.081	4.042	3.857	4.087	3.772 3.800
0,2,6	b?Galp	4.503	3.619	3.765	4.103	3.802	3.851 3.851
0,2	a?Manp	5.127	4.118	3.870	3.799	4.188	3.910 4.196
0	xLmyoIno	3.662	4.134	3.584	3.651	3.292	3.712
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,6,4,2	b?Xylp	104.95	74.59	77.41	73.35	67.02
0,2,6,4,3,6	a?Manp	101.52	71.82	72.44	68.63	74.62	62.82
0,2,6,4,3	a?Manp	104.86	72.00	72.60	67.84	73.24	67.03
0,2,6,4	a?Manp	101.10	79.90	79.15	67.81	75.18	62.33
0,2,6	b?Galp	105.41	72.71	73.95	78.92	76.76	61.97
0,2	a?Manp	103.49	72.04	72.38	68.35	73.68	70.55
0	xLmyoIno	74.45	82.18	72.25	71.11	76.67	74.51
	P

There are 64 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](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