Found 8 structures.
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1. Compound ID: 18003
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a-Gal-(1-6)-a-Gal-(1-6)-a-Gal-(1-6)-b-Gal-(1-6)-b-Gal-(1-1)-CER |
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Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 7054
Tani Y, Funatsu T, Ashida H, Ito M, Itonori S, Sugita M, Yamamoto K "Novel neogala-series glycosphingolipids with terminal mannose and glucose residues from Hirsutella rhossiliensis, an aureobasidin A-resistant ascomycete fungus" -
Glycobiology 20(4) (2010) 433-441
Hirsutella rhossiliensis, a nematophagous fungus belonging to the Ascomycota, is resistant to aureobasidin A (AbA). In this fungus, the biosynthetic pathway leading to mannosylinositolphosphoceramides, which is inhibited by AbA, was not detected. Instead, this fungus contains neutral complex glycosphingolipids (GSLs) and monoglycosylceramides. Except for monoglycosylceramides, neutral GSLs share a neogala-series core structure, Galβ1-6Galβ1-Cer. Among the GSLs of H. rhossiliensis, three novel GSLs with terminal Man and Glc residues on the sugar chain were elucidated. We analyzed GSL structure using compositional sugar, fatty acid, and sphingoid analyses, methylation analysis, matrix-assisted laser desorption ionization time-of-flight/mass spectrometry (MALDI-TOF MS), and (1)H nuclear magnetic resonance spectroscopy (NMR). The following structures were determined: Manα1-3Galβ1-6Galβ1-6Galβ1-Cer; Glcα1-2Galβ1-6Galβ1-6Galβ1-Cer; and Manα1-3Galβ1-6(Glcα1-4)Galβ1-6Galβ1-Cer. In the ceramides, the fatty acids were predominantly saturated h24:0-acids and the sphingoids were predominately t18:0- or t18:1-sphingoids. In contrast, the ceramides of Glcβ1-Cer contained d18:2- and d19:2-sphingoids. These findings indicate the presence of a novel biosynthetic pathway of neogala-series GSLs in fungi.
glycosphingolipid, Aureobasidin A, Ascomycota, Hirsutella rhossiliensis, neogalatriaosylceramide
NCBI PubMed ID: 20007186Publication DOI: 10.1093/glycob/cwp190Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: yasu-t@lif.kyoto-u.ac.jp
Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Shiga 525-8577, and Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
Methods: 1H NMR, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, enzymatic digestion, mild alkaline hydrolysis, methylation analysis
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2. Compound ID: 18117
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a-D-Galp-(1-6)-a-D-Galp-(1-6)-a-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1-1)-CER |
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Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 7090
Hada N, Oka J, Hakamata K, Yamamoto K, Takeda T "Synthesis of neutral glycosphingolipids from Zygomycetes" -
Carbohydrate Research 343(13) (2008) 2315-2324
Novel neutral glycosphingolipids (NGSLs) containing Gal-α1→6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different from those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis α-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethanesulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids.
1, Mucor hiemalis, α-Galactosylation, 2-cis-Glycoside, Di-tert-butylsilylene group, Zygomycetes species
NCBI PubMed ID: 18534568Publication DOI: 10.1016/j.carres.2008.04.019Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: takeda-td@kyoritsu-ph.ac.jp (Tadahiro Takeda)
Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Kyoritsu University of Pharmacy, Tokyo, Japan
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MALDI-TOF MS
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3. Compound ID: 18118
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a-D-Galp-(1-6)-a-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1-1)-CER |
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Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 7090
Hada N, Oka J, Hakamata K, Yamamoto K, Takeda T "Synthesis of neutral glycosphingolipids from Zygomycetes" -
Carbohydrate Research 343(13) (2008) 2315-2324
Novel neutral glycosphingolipids (NGSLs) containing Gal-α1→6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different from those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis α-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethanesulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids.
1, Mucor hiemalis, α-Galactosylation, 2-cis-Glycoside, Di-tert-butylsilylene group, Zygomycetes species
NCBI PubMed ID: 18534568Publication DOI: 10.1016/j.carres.2008.04.019Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: takeda-td@kyoritsu-ph.ac.jp (Tadahiro Takeda)
Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Kyoritsu University of Pharmacy, Tokyo, Japan
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MALDI-TOF MS
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4. Compound ID: 18119
Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 7090
Hada N, Oka J, Hakamata K, Yamamoto K, Takeda T "Synthesis of neutral glycosphingolipids from Zygomycetes" -
Carbohydrate Research 343(13) (2008) 2315-2324
Novel neutral glycosphingolipids (NGSLs) containing Gal-α1→6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different from those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis α-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethanesulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids.
1, Mucor hiemalis, α-Galactosylation, 2-cis-Glycoside, Di-tert-butylsilylene group, Zygomycetes species
NCBI PubMed ID: 18534568Publication DOI: 10.1016/j.carres.2008.04.019Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: takeda-td@kyoritsu-ph.ac.jp (Tadahiro Takeda)
Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Kyoritsu University of Pharmacy, Tokyo, Japan
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MALDI-TOF MS
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5. Compound ID: 20151
Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 8025
Tani Y, Nakamura K, Sawa R, Nishio M, Saito S, Ito M, Itonori S, Mihara H "Novel neogala-series glycosphingolipids with a terminal glucose residue from the fungus Mariannaea elegans" -
Bioscience, Biotechnology, and Biochemistry 77(4) (2013) 754-759
Glycosphingolipids (GSLs) are essential membrane components of eukaryotic cells. Recently, a new type of fungal neogala-series GSL was identified in aureobasidin A-resistant fungi. In this study, we analyzed GSLs from four pathogenic fungal strains belonging to the order Hypocreales, and found that Mariannaea elegans contained both acidic GSLs and neutral GSLs with mono- and di-saccharides. The structures of the neutral GSLs of M. elegans were determined by compositional sugar, fatty acid, and sphingoid analyses by GC/MS, MALDI time-of-flight/MS, and 1H NMR. The ceramide moiety of Glcβ1-Cer consisted mainly of the 2-hydroxylated C18:0-fatty acid 9-methyl-octadeca-4-sphinganine or 9-methyl-octadeca-4,8-sphingadienine. In contrast, the ceramides of Galβ1-6Galβ1-Cer and Glc1-6Galβ1-Cer consisted mainly of saturated 2-hydroxylated C24:0-fatty acids and C18:0-phytosphingosine. To our knowledge, Glc1-6Galβ1-Cer is a novel GSL in fungi, and M. elegans is the first example of an aureobasidin A-sensitive fungus that possesses fungal neogala series GSLs.
Hypocreales, Aureobasidin A, fungal neogala-series glycosphingolipids, glycosylinositolphosphoceramides
NCBI PubMed ID: 23563544Publication DOI: 10.1271/bbb.120879Journal NLM ID: 9205717Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Correspondence: mihara@fc.ritsumei.ac.jp
Institutions: Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Ritsumeikan Global Innovation Research Organization, Ritsumeikan University, Shiga, Japan, Department of Bioinformatics, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Shiga, Japan
Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, alkaline hydrolysis, ion-exchange chromatography, extraction, methylation analysis, CC
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6. Compound ID: 20152
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LIP-(1-2)-+
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a-D-Gal-(1-6)-a-D-Gal-(1-6)-b-D-Gal-(1-6)-b-D-Gal-(1-1)-phSph |
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Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 8025
Tani Y, Nakamura K, Sawa R, Nishio M, Saito S, Ito M, Itonori S, Mihara H "Novel neogala-series glycosphingolipids with a terminal glucose residue from the fungus Mariannaea elegans" -
Bioscience, Biotechnology, and Biochemistry 77(4) (2013) 754-759
Glycosphingolipids (GSLs) are essential membrane components of eukaryotic cells. Recently, a new type of fungal neogala-series GSL was identified in aureobasidin A-resistant fungi. In this study, we analyzed GSLs from four pathogenic fungal strains belonging to the order Hypocreales, and found that Mariannaea elegans contained both acidic GSLs and neutral GSLs with mono- and di-saccharides. The structures of the neutral GSLs of M. elegans were determined by compositional sugar, fatty acid, and sphingoid analyses by GC/MS, MALDI time-of-flight/MS, and 1H NMR. The ceramide moiety of Glcβ1-Cer consisted mainly of the 2-hydroxylated C18:0-fatty acid 9-methyl-octadeca-4-sphinganine or 9-methyl-octadeca-4,8-sphingadienine. In contrast, the ceramides of Galβ1-6Galβ1-Cer and Glc1-6Galβ1-Cer consisted mainly of saturated 2-hydroxylated C24:0-fatty acids and C18:0-phytosphingosine. To our knowledge, Glc1-6Galβ1-Cer is a novel GSL in fungi, and M. elegans is the first example of an aureobasidin A-sensitive fungus that possesses fungal neogala series GSLs.
Hypocreales, Aureobasidin A, fungal neogala-series glycosphingolipids, glycosylinositolphosphoceramides
NCBI PubMed ID: 23563544Publication DOI: 10.1271/bbb.120879Journal NLM ID: 9205717Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Correspondence: mihara@fc.ritsumei.ac.jp
Institutions: Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Ritsumeikan Global Innovation Research Organization, Ritsumeikan University, Shiga, Japan, Department of Bioinformatics, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Shiga, Japan
Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, alkaline hydrolysis, ion-exchange chromatography, extraction, methylation analysis, CC
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7. Compound ID: 20153
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LIP-(1-2)-+
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a-D-Gal-(1-6)-a-D-Gal-(1-6)-a-D-Gal-(1-6)-b-D-Gal-(1-6)-b-D-Gal-(1-1)-phSph |
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Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_742248,SB_1,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 8025
Tani Y, Nakamura K, Sawa R, Nishio M, Saito S, Ito M, Itonori S, Mihara H "Novel neogala-series glycosphingolipids with a terminal glucose residue from the fungus Mariannaea elegans" -
Bioscience, Biotechnology, and Biochemistry 77(4) (2013) 754-759
Glycosphingolipids (GSLs) are essential membrane components of eukaryotic cells. Recently, a new type of fungal neogala-series GSL was identified in aureobasidin A-resistant fungi. In this study, we analyzed GSLs from four pathogenic fungal strains belonging to the order Hypocreales, and found that Mariannaea elegans contained both acidic GSLs and neutral GSLs with mono- and di-saccharides. The structures of the neutral GSLs of M. elegans were determined by compositional sugar, fatty acid, and sphingoid analyses by GC/MS, MALDI time-of-flight/MS, and 1H NMR. The ceramide moiety of Glcβ1-Cer consisted mainly of the 2-hydroxylated C18:0-fatty acid 9-methyl-octadeca-4-sphinganine or 9-methyl-octadeca-4,8-sphingadienine. In contrast, the ceramides of Galβ1-6Galβ1-Cer and Glc1-6Galβ1-Cer consisted mainly of saturated 2-hydroxylated C24:0-fatty acids and C18:0-phytosphingosine. To our knowledge, Glc1-6Galβ1-Cer is a novel GSL in fungi, and M. elegans is the first example of an aureobasidin A-sensitive fungus that possesses fungal neogala series GSLs.
Hypocreales, Aureobasidin A, fungal neogala-series glycosphingolipids, glycosylinositolphosphoceramides
NCBI PubMed ID: 23563544Publication DOI: 10.1271/bbb.120879Journal NLM ID: 9205717Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Correspondence: mihara@fc.ritsumei.ac.jp
Institutions: Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Ritsumeikan Global Innovation Research Organization, Ritsumeikan University, Shiga, Japan, Department of Bioinformatics, College of Life Sciences, Ritsumeikan University, Shiga, Japan, Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Shiga, Japan
Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, alkaline hydrolysis, ion-exchange chromatography, extraction, methylation analysis, CC
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8. Compound ID: 21589
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b-D-GlcpNAc-(1-2)-a-D-Manp-(1-3)-+
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a-D-Manp-(1-6)-+ |
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a-D-Manp-(1-3)-a-D-Manp-(1-6)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc-(1-1)-PhNO2
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b-D-GlcpNAc-(1-4)-+ |
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Structure type: oligomer
Compound class: mannan
Contained glycoepitopes: IEDB_123886,IEDB_130701,IEDB_135813,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141828,IEDB_144983,IEDB_151079,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_153220,IEDB_164174,IEDB_187201,IEDB_429156,IEDB_548907,IEDB_857734,IEDB_983930,SB_197,SB_198,SB_33,SB_44,SB_67,SB_72,SB_73,SB_74,SB_77,SB_85
The structure is contained in the following publication(s):
- Article ID: 8715
Yamanoi T, Oda Y, Katsuraya K, Inazu T, Yamamoto K "Complete NMR assignment of a bisecting hybrid-type oligosaccharide transferred by Mucor hiemalis endo-β-N-acetylglucosaminidase" -
Carbohydrate Research 427 (2016) 60-65
This study describes the complete nuclear magnetic resonance (NMR) spectral assignment of a bisecting hybrid-type oligosaccharide 1, transferred by Mucor hiemalis endo-β-N-acetylglucosaminidase (Endo-M). Through 1H- and 13C-NMR, DQF-COSY, HSQC, HMBC, TOCSY, and NOESY experiments, we determine the structure of the glycoside linkage formed by the Endo-M transglycosylation, i.e., the connection between GlcNAc and GlcNAc in oligosaccharide 1.
bisecting hybrid-type oligosaccharide, endo-M, endo-β-N-acetylglucosaminidase, NMR spectral assignment, transglycosylation product
NCBI PubMed ID: 27131291Publication DOI: 10.1016/j.carres.2016.03.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Yamanoi T
Institutions: Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama, Japan, Technology Joint Management Office, Tokai University, Hiratsuka, Kanagawa, Japan, Department of Human Ecology, Wayo Women’s University, Chiba, Japan, Department of Applied Chemistry, School of Engineering, Institute of Glycoscience, Tokai University, Hiratsuka, Kanagawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Ishikawa, Japan
Methods: 13C NMR, 1H NMR, TOCSY, DQF-COSY, HMBC, COSY, NOESY, HSQC
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