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Barreto-Bergter E, Sassaki GL, de Souza LM
Structural analysis of fungal cerebrosides
Frontiers in Microbiology 2 (2011)
1-11
|
/Variants 0/-+
|
b-D-Galp-(1-1)-S,R-9b1SphdC19
/Variants 0/ is:
2HOSte-(1-2)-
OR (exclusively)
2HOPam-(1-2)-
OR (exclusively)
2HOC18={t3}-(1-2)- |
Show graphically |
Aspergillus fumigatus
(NCBI TaxID 746128,
species name lookup)
Hansenula anomala
(later renamed to: Wickerhamomyces anomalus)
(NCBI TaxID 4927,
species name lookup)
Neurospora crassa
(NCBI TaxID 5141,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
NCBI PubMed ID: 22164155Publication DOI: 10.3389/fmicb.2011.00239Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: eliana.bergter
micro.ufrj.br
Institutions: Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Departamento de Bioquímica e Biologia Celular, Universidade Federal do Paraná, Curitiba, Brazil
Of the ceramide monohexosides (CMHs), gluco- and galactosyl-ceramides are the main neutral glycosphingolipids expressed in fungal cells. Their structural determination is greatly dependent on the use of mass spectrometric techniques, including fast atom bombardment-mass spectrometry, electrospray ionization, and energy collision-induced dissociation mass spectrometry. Nuclear magnetic resonance has also been used successfully. Such a combination of techniques, combined with classical analytical separation, such as high-performance thin layer chromatography and column chromatography, has led to the structural elucidation of a great number of fungal CMHs. The structure of fungal CMH is conserved among fungal species and consists of a glucose or galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to hydroxylated fatty acids, most commonly having 16 or 18 carbon atoms and unsaturation between C-3 and C-4. Along with their unique structural characteristics, fungal CMHs have a peculiar subcellular distribution and striking biological properties. Fungal cerebrosides were also characterized as antigenic molecules directly or indirectly involved in cell growth or differentiation in Schizophyllum commune, Cryptococcus neoformans, Pseudallescheria boydii, Candida albicans, Aspergillus nidulans, Aspergillus fumigatus, and Colletotrichum gloeosporioides. Besides classical techniques for cerebroside (CMH) analysis, we now describe new approaches, combining conventional thin layer chromatography and mass spectrometry, as well as emerging technologies for subcellular localization and distribution of glycosphingolipids by secondary ion mass spectrometry and imaging matrix-assisted laser desorption ionization time-of-flight.
NMR spectroscopy, mass spectrometry, Structural characterization, cerebrosides, pathogenic fungi
Structure type: monomer
Location inside paper: p.8, fig.8
Trivial name: galactosylceramide
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_1,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, GC-MS, TLC, ESI-MS, NMR-1D, extraction, CID-MS, HPTLC, SIMS, HPTLC immunostaining, MALDI
Related record ID(s): 42250, 42251, 42252, 42253, 42254, 42255, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43403, 43417, 43418, 43419, 43420, 43679, 43680
NCBI Taxonomy refs (TaxIDs): 746128,
4927,
5141
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There is only one chemically distinct structure:
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Barreto-Bergter E, Sassaki GL, de Souza LM
Structural analysis of fungal cerebrosides
Frontiers in Microbiology 2 (2011)
1-11
|
/Variants 0/-+
|
b-D-Glcp-(1-1)-S,R-9b1SphdC19
/Variants 0/ is:
2HOSte-(1-2)-
OR (exclusively)
2HOPam-(1-2)- |
Show graphically |
Pseudallescheria boydii
(later renamed to: Scedosporium boydii)
(NCBI TaxID 5597,
species name lookup)
Colletotrichum gloeosporioides
(NCBI TaxID 474922,
species name lookup)
Scedosporium apiospermum
(NCBI TaxID 563466,
species name lookup)
Fusarium oxysporum
(NCBI TaxID 5507,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Pseudallescheria boydii [ICD11:
XN6BV ]
NCBI PubMed ID: 22164155Publication DOI: 10.3389/fmicb.2011.00239Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: eliana.bergter
micro.ufrj.br
Institutions: Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Departamento de Bioquímica e Biologia Celular, Universidade Federal do Paraná, Curitiba, Brazil
Of the ceramide monohexosides (CMHs), gluco- and galactosyl-ceramides are the main neutral glycosphingolipids expressed in fungal cells. Their structural determination is greatly dependent on the use of mass spectrometric techniques, including fast atom bombardment-mass spectrometry, electrospray ionization, and energy collision-induced dissociation mass spectrometry. Nuclear magnetic resonance has also been used successfully. Such a combination of techniques, combined with classical analytical separation, such as high-performance thin layer chromatography and column chromatography, has led to the structural elucidation of a great number of fungal CMHs. The structure of fungal CMH is conserved among fungal species and consists of a glucose or galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to hydroxylated fatty acids, most commonly having 16 or 18 carbon atoms and unsaturation between C-3 and C-4. Along with their unique structural characteristics, fungal CMHs have a peculiar subcellular distribution and striking biological properties. Fungal cerebrosides were also characterized as antigenic molecules directly or indirectly involved in cell growth or differentiation in Schizophyllum commune, Cryptococcus neoformans, Pseudallescheria boydii, Candida albicans, Aspergillus nidulans, Aspergillus fumigatus, and Colletotrichum gloeosporioides. Besides classical techniques for cerebroside (CMH) analysis, we now describe new approaches, combining conventional thin layer chromatography and mass spectrometry, as well as emerging technologies for subcellular localization and distribution of glycosphingolipids by secondary ion mass spectrometry and imaging matrix-assisted laser desorption ionization time-of-flight.
NMR spectroscopy, mass spectrometry, Structural characterization, cerebrosides, pathogenic fungi
Structure type: monomer ; 726 [M-H]-, 754 [M-H]-, 756 [M+H]+
Location inside paper: fig.3, fig.4
Trivial name: glucoceramide
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, GC-MS, TLC, ESI-MS, NMR-1D, extraction, CID-MS, HPTLC, SIMS, HPTLC immunostaining, MALDI
Related record ID(s): 42250, 42251, 42252, 42253, 42254, 42255, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43402, 43417, 43418, 43419, 43420, 43679, 43680
NCBI Taxonomy refs (TaxIDs): 5597,
474922,
563466,
5507
Show glycosyltransferases
There is only one chemically distinct structure:
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