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Background Studies carried out during the 1990's demonstrated the presence of fungal glycoinositol phosphorylceramides (GIPCs) with unique structures, some of them showed reactivity with sera of patients with histoplasmosis, paracoccidioidomycosis or aspergillosis. It was also observed that fungal GIPCs were able to inhibit T lymphocyte proliferation "in vitro", and studies regarding the importance of these molecules to fungal survival showed that many species of fungi are vulnerable to inhibitors of sphingolipid biosynthesis. Results In this paper, we describe a detailed characterization of an IgG2a monoclonal antibody (mAb), termed MEST-3, directed to the Paracoccidioides brasiliensis glycolipid antigen Pb-2 (Manp α1→3Manp α1→2IPC). mAb MEST-3 also recognizes GIPCs bearing the same structure in other fungi. Studies performed on fungal cultures clearly showed the strong inhibitory activity of MEST-3 on differentiation and colony formation of Paracoccidioides brasiliensis, Histoplasma capsulatum and Sporothrix schenckii. Similar inhibitory results were observed when these fungi where incubated with a different mAb, which recognizes GIPCs bearing terminal residues of β-D-galactofuranose linked to mannose (mAb MEST-1). On the other hand, mAb MEST-2 specifically directed to fungal glucosylceramide (GlcCer) was able to promote only a weak inhibition on fungal differentiation and colony formation. Conclusions These results strongly suggest that mAbs directed to specific glycosphingolipids are able to interfere on fungal growth and differentiation. Thus, studies on surface distribution of GIPCs in yeast and mycelium forms of fungi may yield valuable information regarding the relevance of glycosphingolipids in processes of fungal growth, morphological transition and infectivity.

monoclonal antibodies, Paracoccidioides brasiliensis, monoclonal antibody MEST-3, glycosylinositol

NCBI PubMed ID: 20156351
Publication DOI: 10.1186/1471-2180-10-47
Journal NLM ID: 100966981
Publisher: Biomed Central
Correspondence: takahashi.bioq@epm.br
Institutions: Division of Glycoconjugate Immunochemistry, Department of Biochemistry, Universidade Federal de São Paulo/Escola Paulista de Medicina, Rua Botucatu 862, São Paulo, SP, Brazil
Methods: ELISA, serological methods, genetic methods, UV, extraction, periodate oxidation, HPTLC, binding assays, immunofluorescence analyses, dialysis, fungal differentiation

Twelve different species of neutral monohexosyl ceramides (CMHs) and two species of neutral monohexosyl ceramides were isolated from mycelium and yeast forms of Paracoccidioides brasiliensis, respectively, by a combination of ion-exchange chromatography, HPLC, and HPTLC. The glucosylceramides did not react with sera from patients with paracoccidioidomycosis (PCM). Carbohydrate analysis indicated that CMHs contain glucose. Analysis of 1H-NMR and mass spectrometry data suggest that the structure of the CMHs is Glcp beta 1-->Cer (mycelium forms present 12 different ceramides and yeast forms present 2 different ceramides). The composition of the lipid moieties was analyzed by negative fast atom bombardment mass spectrometry. No glycosphingolipid other than glucosylceramide was detected in P. brasiliensis.

glycosphingolipids, Paracoccidioides brasiliensis, glucosylceramide, Fast atom bombardment mass spectrometry

NCBI PubMed ID: 9196542
Journal NLM ID: 8112917
Publisher: SP, Brasil: Associação Brasileira de Divulgação Científica
Institutions: Departamento de Bioquímica, Escola Paulistade Medicina, Universidade Federal de São Paulo, São Paulo, Brasil, Perkin Elmer-Applied Biosystems Division, Foster City, USA, Pacific Northwest Research Foundation, University of Washington, Seattle, USA, Department of Pathobiology and Microbiology, University of Washington, Seattle, USA
Methods: 1H NMR, NMR-2D, FAB-MS, NMR-1D, HPLC, extraction, acetylation, HPTLC, column chromatography

A cerebroside fraction prepared from the mycelia of Schizophyllum commune was further fractionated into five components (I-V) by reverse-phase high-performance liquid chromatography. Fruiting-inducing activity was found in I-IV but not in V. By gas-liquid chromatography-mass spectrometry and nuclear magnetic resonance analyses it was shown that these fractions contained: I, a mixture of N-2'-hydroxypentadecanoyl-1-O-glucosyl-nonadecasphingadienine and N-2'-hydroxyhexadecanoyl-1-O-glucosyl-sphingadienine; II, (4E,8E)-N-D-2'-hydroxyhexadecanoyl-1-O-beta-D-glucopyr anosyl-9-methyl-4,8-sphingadienine (Kawai and Ikeda. 1983. Biochim. Biophys. Acta. 754: 243-248); III, N-2'-hydroxyheptadecanoyl-1-O-glucosyl-nonadecasphingadienine; IV, N-2'-hydroxyoctadecanoyl-1-O-glucosyl-nonadecasphinadienine; V, (4E,8E)-N-2'-hydroxytetracosanoyl-1-O-beta-glucopyrano syl-9-methyl-4,8- sphingadienine. The only structural difference observed between biologically active and inactive cerebrosides was the chain length of acyl moiety; the cerebroside having an acyl chain of 24 carbon atoms was inactive.

mass spectrometry, gas-liquid chromatography, reverse-phase HPLC, fruiting-inducing activity, nuclear magnetic resonance spectrometry

NCBI PubMed ID: 4039347
Publication DOI: 10.1016/0009-3084(87)90012-0
Journal NLM ID: 0376606
Publisher: ASBMB
Institutions: Noda Institute for Scientific Research, Noda, Japan, Nodai Research Institute, The Tokyo University of Agriculture, Tokyo, Japan
Methods: 1H NMR, GLC-MS, TLC, GLC, HPLC, extraction

Glucosylceramide and galactosylceramide were detected in three Aspergillus species: Aspergillus oryzae, Aspergillus sojae and Aspergillus. awamori, using borate-coated TLC. The cerebrosides from A. oryzae were further purified by ion exchange and iatrobeads column chromatographies with or without borate, and determined the composition of sugar, fatty acid and sphingoid base by GC/MS, MALDI-TOF/MS and 1H-NMR. We identified them as β-glucosylceramide and β-galactosylceramide. The ceramide moiety of both cerebrosides consisted mainly of 2-hydroxystearic acid and either 9-methyl-octadeca-4, 8-sphingadienine or octadeca-4, 8-sphingadienine. To our knowledge, this is the first study to provide evidence for the presence of β-galactosylceramide in A. oryzae.

glycosphingolipid, galactosylceramide, cerebroside, Aspergillus oryzae, filamentous fungus

NCBI PubMed ID: 25129050
Publication DOI: 10.1007/s10529-014-1631-1
Journal NLM ID: 8008051
Publisher: Kluwer Academic Publishers
Correspondence: Ashida H
Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Japan, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan, Gekkeikan Sake Co. Ltd, Research Institute, Kyoto, Japan, Faculty of Biology-Oriented Science and Technology, Kinki University, Kinokawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoichi, Japan
Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, methanolysis, ion-exchange chromatography, extraction, methylation analysis

NCBI PubMed ID: 8158158
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Institutions: Department of Phytochemistry, China Pharmaceutical University, Nanjing, China