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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: mycelium

The structure was elucidated in this paper
NCBI PubMed ID: 29767770
Publication DOI: 10.1093/mmy/myx167
Journal NLM ID: 9815835
Publisher: Oxford: Oxford University Press
Correspondence: eliana.bergter

micro.ufrj.br
Institutions: Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro, Brazil, Laboratório de Tecido Conjuntivo, Hospital Universitário Clementino Fraga Filho and Instituto de Bioquímica Médica Leopoldo de Meis, Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro, Brazil, Instituto Biomédico, Universidade Federal Fluminense (UFF), Niterói, Brazil, Hospital Universitário Clementino Fraga Filho, Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro, Brazil, Instituto Biomédico, UNIRIO, Rio de Janeiro, Brazil, Departamento de Microbiologia Geral, Instituto de Microbiologia da Universidade Federal do Rio de Janeiro (UFRJ), Rio de Janeiro, Brazil

A peptidogalactomannan (PGM) from Fusarium oxysporum was structurally characterized by a combination of chemical and spectroscopic methods, including one and two-dimensional nuclear magnetic resonance (1D and 2D NMR). The galactomannan component consists of a main chain containing (1→6)-linked β-D-galactofuranose residues with side chains containing (1→2)-linked α-D-Glcp, (1→2)-linked β-D-Manp (1→2) and β-D-Manp terminal nonreducing end units and differs from that of Aspergillus fumigatus and Cladosporium resinae that present a main chain containing (1→6)-linked α-D-Manp residues presenting β-D-Galf as side chains of 3-4 units that are (1→5)-interlinked. The importance of the carbohydrate moiety of the F. oxysporum PGM was demonstrated. Periodate oxidation abolished much of the PGM antigenic activity. A strong decrease in reactivity was also observed with de-O-glycosylated PGM. In addition, de-O-glycosylated PGM was not able to inhibit F. oxysporum phagocytosis, suggesting that macrophages recognize and internalize F. oxysporum via PGM. F. oxysporum PGM triggered TNF-α release by macrophages. Chemical removal of O-linked oligosaccharides from PGM led to a significant increase of TNF-α cytokine levels, suggesting that their removal could exposure another PGM motifs able to induce a higher secretion of TNF-α levels. Interestingly, F. oxysporum conidia, intact and de-O-linked PGM were not able to induce IL-10 cytokine release. The difference in patient serum reativity using a PGM from F. oxysporum characterized in the present study as compared with a PGM from C. resinae, that presents the same epitopes recognized by serum from patients with aspergillosis, could be considered a potential diagnostic antigen and should be tested with more sera.

macrophage activation, Peptidogalactomannan, Fusarium oxysporum, potential diagnostic antigen

Structure type: structural motif or average structure
Location inside paper: Table 1, Table 2, Fig. 4
Compound class: polysaccharide, glucogalactomannan
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136095,IEDB_137472,IEDB_137485,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, GC-MS, ELISA, acid hydrolysis, Smith degradation, GPC, alkaline hydrolysis, extraction, acetylation, methylation analysis, reduction, dialysis, cytokine production, cell viability assay, precipitation, phenol-sulfuric acid assay, carbazole-sulfuric acid assay, evaporation, centrifugation, Folin phenol reagent method, phagocytic assay
Biological activity: polysaccharide inhibited the phagocytosis of conidia and stimulated of TNF-α and IL-10 cytokine production

NCBI Taxonomy refs (TaxIDs): 5507
Show glycosyltransferases

NMR conditions: in D2O at 323 K

¹H NMR data: present in publication

¹³C NMR data: present in publication

There is only one chemically distinct structure:

*OC[C@@H](O)[C@@H]1O[C@@H](*)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: fruiting bodies

The structure was elucidated in this paper
NCBI PubMed ID: 34973775
Publication DOI: 10.1016/j.carbpol.2021.118960
Journal NLM ID: 8307156
Publisher: Elsevier
Correspondence: Y.M. Lu <ymlu

ahu.edu.cn>; Y. Chen <chenyan91030

yahoo.com>
Institutions: School of Life Sciences, Anhui University, Hefei, Anhui, PR China, Key Laboratory of Ecological Engineering and Biotechnology of Anhui Province and Anhui Key Laboratory of Modern Biomanufacturing, Hefei, Anhui, PR China

In our continuous exploration for bioactive polysaccharides, a novel polysaccharide FMP-2 was isolated and purified from the fruiting bodies of Morchella esculenta by alkali-assisted extraction. FMP-2 had an average molecular weight of 1.09 × 10^6 Da and contained mannose, glucuronic acid, glucose, galactose, and arabinose in a molar ratio of 4.10:0.22:1.00:5.75:0.44. The backbone of FMP-2 mainly consisted of 1,2-α-D-Galp, 1,6-α-D-Galp, and 1,4-α-D-Manp, with branches of 1,4,6-α-D-Manp and 1,2,6-α-D-Galp. FMP-2 can stimulate phagocytosis and promote the secretion of NO, ROS, and cytokines like IL-6, IL-1β, and TNF-α in RAW264.7 cells ranging from 25 to 400 μg/mL. FMP-2 had great repairing effect on the immune injury of zebrafish induced by chloramphenicol. The phagocytosis ability of zebrafish macrophages and the proliferation of neutrophils can be greatly enhanced by polysaccharide FMP-2 with concentrations from 50 to 200 μg/mL. These findings suggest that FMP-2 might be used as a potential immunomodulator in the food and pharmaceutical industries.

polysaccharide, immunomodulatory activity, Structural characterization, Morchella esculenta, alkali-assisted extraction

Structure type: structural motif or average structure
Location inside paper: Fig. 4, table 2, FMP-2
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_131186,IEDB_134624,IEDB_135818,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_140630,IEDB_141794,IEDB_141836,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_163,SB_192,SB_44,SB_67,SB_7,SB_72

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, FTIR, HPLC, UV, cytokine analysis, statistical analysis, determination of NO production, cell viability assay, immunomodulatory activity analysis, ROS measurement, hot water extraction, alkaline extraction, phagocytic assay
Comments, role: possible structure of polysaccharide FMP-2; published NMR chemical shifts of C1 #6,6,4,4_aDManp (109.46) suggestedly erroneous

NCBI Taxonomy refs (TaxIDs): 39407
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,4,4,4,4,2	aDGalp	101.27	81.37	70.50	71.30	72.34	65.45
6,6,4	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
6	aDGalp	101.27	71.30	70.15	71.50	71.36	65.20
6,6,4,4,4,4,2,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,4,4,2,6	aDManp	108.19	71.21	72.70	69.13	71.36	60.88
6,6,4,4,4,4,2,2,2	aDGalp	98.01	79.76	72.34	71.36	70.32	62.54
6,6,4,4,4,4,2,2	aDGalp	98.01	79.76	72.34	71.36	70.32	62.54
6,6,4,4,4,4	aDGalp	101.27	81.37	70.50	71.30	72.34	65.45
6,6,4,4,4	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
6,6,4,4	aDManp	?	70.50	71.21	76.14	73.32	65.45
6,6	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
	aDGalp	101.27	71.30	70.15	71.50	71.36	65.20
6,6,4,4,4,4,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,4,4,6	aDManp	108.19	71.21	72.70	69.13	71.36	60.88
6,6,4,4,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,6	aDGlcpA


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,4,4,4,4,2	aDGalp	5.24	4.21	3.90	3.70	3.86	4.02
6,6,4	aDManp	5.41	3.80	3.95	3.69	4.17	3.75-3.91
6	aDGalp	5.24	3.75	4.08	3.86	3.68	3.75
6,6,4,4,4,4,2,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70-3.75
6,6,4,4,4,4,2,6	aDManp	5.41	4.18	3.75	3.46	3.71	3.85-3.91
6,6,4,4,4,4,2,2,2	aDGalp	5.24	4.07	3.86	3.69	4.00	3.77
6,6,4,4,4,4,2,2	aDGalp	5.24	4.07	3.86	3.69	4.00	3.77
6,6,4,4,4,4	aDGalp	5.24	4.21	3.90	3.70	3.86	4.02
6,6,4,4,4	aDManp	5.41	3.80	3.95	3.69	4.17	3.75-3.91
6,6,4,4	aDManp	5.24	3.92	4.16	3.74	4.00	3.75-3.85
6,6	aDManp	5.41	3.80	3.95	3.69	4.17	3.75-3.91
	aDGalp	5.24	3.75	4.08	3.86	3.68	3.75
6,6,4,4,4,4,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70-3.75
6,6,4,4,4,4,6	aDManp	5.41	4.18	3.75	3.46	3.71	3.85-3.91
6,6,4,4,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70-3.75
6,6,4,4,6	aDGlcpA


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,4,4,4,4,2	aDGalp	101.27/5.24	81.37/4.21	70.50/3.90	71.30/3.70	72.34/3.86	65.45/4.02
6,6,4	aDManp	99.70/5.41	72.97/3.80	73.32/3.95	77.03/3.69	71.21/4.17	60.88/3.75-3.91
6	aDGalp	101.27/5.24	71.30/3.75	70.15/4.08	71.50/3.86	71.36/3.68	65.20/3.75
6,6,4,4,4,4,2,6	aDGlcp	99.32/4.98	73.32/4.00	74.61/4.25	70.32/3.96	72.70/3.84	62.70/3.70-3.75
6,6,4,4,4,4,2,6	aDManp	108.19/5.41	71.21/4.18	72.70/3.75	69.13/3.46	71.36/3.71	60.88/3.85-3.91
6,6,4,4,4,4,2,2,2	aDGalp	98.01/5.24	79.76/4.07	72.34/3.86	71.36/3.69	70.32/4.00	62.54/3.77
6,6,4,4,4,4,2,2	aDGalp	98.01/5.24	79.76/4.07	72.34/3.86	71.36/3.69	70.32/4.00	62.54/3.77
6,6,4,4,4,4	aDGalp	101.27/5.24	81.37/4.21	70.50/3.90	71.30/3.70	72.34/3.86	65.45/4.02
6,6,4,4,4	aDManp	99.70/5.41	72.97/3.80	73.32/3.95	77.03/3.69	71.21/4.17	60.88/3.75-3.91
6,6,4,4	aDManp	?/5.24	70.50/3.92	71.21/4.16	76.14/3.74	73.32/4.00	65.45/3.75-3.85
6,6	aDManp	99.70/5.41	72.97/3.80	73.32/3.95	77.03/3.69	71.21/4.17	60.88/3.75-3.91
	aDGalp	101.27/5.24	71.30/3.75	70.15/4.08	71.50/3.86	71.36/3.68	65.20/3.75
6,6,4,4,4,4,6	aDGlcp	99.32/4.98	73.32/4.00	74.61/4.25	70.32/3.96	72.70/3.84	62.70/3.70-3.75
6,6,4,4,4,4,6	aDManp	108.19/5.41	71.21/4.18	72.70/3.75	69.13/3.46	71.36/3.71	60.88/3.85-3.91
6,6,4,4,6	aDGlcp	99.32/4.98	73.32/4.00	74.61/4.25	70.32/3.96	72.70/3.84	62.70/3.70-3.75
6,6,4,4,6	aDGlcpA

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,4,4,4,4,2	aDGalp	5.24	4.21	3.90	3.70	3.86	4.02
6,6,4	aDManp	5.41	3.80	3.95	3.69	4.17	3.75 3.91
6	aDGalp	5.24	3.75	4.08	3.86	3.68	3.75
6,6,4,4,4,4,2,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70 3.75
6,6,4,4,4,4,2,6	aDManp	5.41	4.18	3.75	3.46	3.71	3.85 3.91
6,6,4,4,4,4,2,2,2	aDGalp	5.24	4.07	3.86	3.69	4.00	3.77
6,6,4,4,4,4,2,2	aDGalp	5.24	4.07	3.86	3.69	4.00	3.77
6,6,4,4,4,4	aDGalp	5.24	4.21	3.90	3.70	3.86	4.02
6,6,4,4,4	aDManp	5.41	3.80	3.95	3.69	4.17	3.75 3.91
6,6,4,4	aDManp	5.24	3.92	4.16	3.74	4.00	3.75 3.85
6,6	aDManp	5.41	3.80	3.95	3.69	4.17	3.75 3.91
	aDGalp	5.24	3.75	4.08	3.86	3.68	3.75
6,6,4,4,4,4,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70 3.75
6,6,4,4,4,4,6	aDManp	5.41	4.18	3.75	3.46	3.71	3.85 3.91
6,6,4,4,6	aDGlcp	4.98	4.00	4.25	3.96	3.84	3.70 3.75
6,6,4,4,6	aDGlcpA

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,4,4,4,4,2	aDGalp	101.27	81.37	70.50	71.30	72.34	65.45
6,6,4	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
6	aDGalp	101.27	71.30	70.15	71.50	71.36	65.20
6,6,4,4,4,4,2,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,4,4,2,6	aDManp	108.19	71.21	72.70	69.13	71.36	60.88
6,6,4,4,4,4,2,2,2	aDGalp	98.01	79.76	72.34	71.36	70.32	62.54
6,6,4,4,4,4,2,2	aDGalp	98.01	79.76	72.34	71.36	70.32	62.54
6,6,4,4,4,4	aDGalp	101.27	81.37	70.50	71.30	72.34	65.45
6,6,4,4,4	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
6,6,4,4	aDManp	?	70.50	71.21	76.14	73.32	65.45
6,6	aDManp	99.70	72.97	73.32	77.03	71.21	60.88
	aDGalp	101.27	71.30	70.15	71.50	71.36	65.20
6,6,4,4,4,4,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,4,4,6	aDManp	108.19	71.21	72.70	69.13	71.36	60.88
6,6,4,4,6	aDGlcp	99.32	73.32	74.61	70.32	72.70	62.70
6,6,4,4,6	aDGlcpA

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

*O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](OC[C@H]6O[C@H](OC[C@H]7O[C@H](OC[C@H]8O[C@H](*)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@@H](O)[C@H]7O)[C@H](O)[C@@H](O)[C@H]6O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize