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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: mycelia, culture filtrate

The structure was elucidated in this paper
NCBI PubMed ID: 35725172
Publication DOI: 10.1016/j.carbpol.2022.119677
Journal NLM ID: 8307156
Publisher: Elsevier
Correspondence: Z. Zhao <zhaozh429

nenu.edu.cn>; Y. Zhou <zhouyf383

nenu.edu.cn>
Institutions: Engineering Research Center of Glycoconjugates of Ministry of Education, Jilin Provincial Key Laboratory of Chemistry and Biology of Changbai Mountain Natural Drugs, School of Life Sciences, Northeast Normal University, Changchun 130024, China, Department of Biochemistry, Molecular Biology and Biophysics, University of Minnesota, 6-155 Jackson Hall, 321 Church Street, Minneapolis, MN 55455, USA

Polysaccharides from fungi have many bioactivities. Previous studies showed that galactomannans from Penicillium oxalicum antagonize galectin-8-mediated activity. Here, two intracellular and two extracellular galactomannans were purified and their structures were comparatively characterized by NMR, partial acid hydrolysis and methylation. All four of them were identified to be galactomannans with similar mannan backbones having 1,2-/1,6-linkages (~3:1) and various amounts of galactofuranan side chains. The interaction of those polysaccharides with galectin-8 was assessed by hemagglutination and biolayer interferometry. These results show that side chains are important for the interaction, and the more the side chains, the stronger the interaction. But the side chains alone did not show act on galectin-8, which indicated that the cooperation between backbone and side chains is another necessary factor for this interaction. Our findings provide important information about structure-activity relationships and the galactofuranose-containing galactomannans might be as potential therapeutic of galectin-8 related diseases.

polysaccharide, structure-activity relationship, Galactomannan, Penicillium, galectin-8

Structure type: structural motif or average structure ; 39500-94600
Location inside paper: Fig. 4, table 3, PC-IPS,PC-EPS,PD-IPS,PD-EPS
Trivial name: galactomannan
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_147453,IEDB_149137,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_885812,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, methylation, partial acid hydrolysis, GC-MS, sugar analysis, HPLC, HPSEC-MALLS-RID analysis, NMR-2
Comments, role: Putative structure of the repeating unit of galactomannans. The four galactomannans had the different amount of side chains.

NCBI Taxonomy refs (TaxIDs): 5076, 36651
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,2,6,2,2,2	aDManp	97.17	68.91	69.31	65.16	71.64	64.36
2,2,6,2,2	aDManp	99.57-99.76	77.47-77.60	68.81	65.87	72.19	60.01
2,2,6,2	aDManp
2,2,6	aDManp
2,3,5,5	bDGalf	106.48	80.28	75.29	81.85	70.13	61.53
2,3,5	bDGalf	105.95-106.08	79.92-80.31	75.35-75.77	81.38-81.85	74.73	61.69
2	aDManp	100.63	77.62	81.82	65.54	71.93	60.01
2,3	bDGalf
2,6	bDGalf
2,2	aDManp
	aDManp


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,2,6,2,2,2	aDManp	5.06	3.97	3.78	3.78	3.63	3.57-4.02
2,2,6,2,2	aDManp	5.14-5.21	3.97-4.06	3.87	3.63	3.72	3.70-3.83
2,2,6,2	aDManp
2,2,6	aDManp
2,3,5,5	bDGalf	4.99	4.06	3.97	4.02	3.69	3.74-3.75
2,3,5	bDGalf	5.13-5.22	3.91-4.09	4.01-4.05	4.01-4.06	3.90-3.91	3.61-3.66
2	aDManp	5.03	3.91	3.94	3.93	3.53	3.74-3.83
2,3	bDGalf
2,6	bDGalf
2,2	aDManp
	aDManp


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,2,6,2,2,2	aDManp	97.17/5.06	68.91/3.97	69.31/3.78	65.16/3.78	71.64/3.63	64.36/3.57-4.02
2,2,6,2,2	aDManp	99.57-99.76/5.14-5.21	77.47-77.60/3.97-4.06	68.81/3.87	65.87/3.63	72.19/3.72	60.01/3.70-3.83
2,2,6,2	aDManp
2,2,6	aDManp
2,3,5,5	bDGalf	106.48/4.99	80.28/4.06	75.29/3.97	81.85/4.02	70.13/3.69	61.53/3.74-3.75
2,3,5	bDGalf	105.95-106.08/5.13-5.22	79.92-80.31/3.91-4.09	75.35-75.77/4.01-4.05	81.38-81.85/4.01-4.06	74.73/3.90-3.91	61.69/3.61-3.66
2	aDManp	100.63/5.03	77.62/3.91	81.82/3.94	65.54/3.93	71.93/3.53	60.01/3.74-3.83
2,3	bDGalf
2,6	bDGalf
2,2	aDManp
	aDManp

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,2,6,2,2,2	aDManp	5.06	3.97	3.78	3.78	3.63	3.57 4.02
2,2,6,2,2	aDManp	5.14 5.21	3.97 4.06	3.87	3.63	3.72	3.70 3.83
2,2,6,2	aDManp
2,2,6	aDManp
2,3,5,5	bDGalf	4.99	4.06	3.97	4.02	3.69	3.74 3.75
2,3,5	bDGalf	5.13 5.22	3.91 4.09	4.01 4.05	4.01 4.06	3.90 3.91	3.61 3.66
2	aDManp	5.03	3.91	3.94	3.93	3.53	3.74 3.83
2,3	bDGalf
2,6	bDGalf
2,2	aDManp
	aDManp

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,2,6,2,2,2	aDManp	97.17	68.91	69.31	65.16	71.64	64.36
2,2,6,2,2	aDManp	99.57 99.76	77.47 77.60	68.81	65.87	72.19	60.01
2,2,6,2	aDManp
2,2,6	aDManp
2,3,5,5	bDGalf	106.48	80.28	75.29	81.85	70.13	61.53
2,3,5	bDGalf	105.95 106.08	79.92 80.31	75.35 75.77	81.38 81.85	74.73	61.69
2	aDManp	100.63	77.62	81.82	65.54	71.93	60.01
2,3	bDGalf
2,6	bDGalf
2,2	aDManp
	aDManp

There is only one chemically distinct structure:

OC[C@@H](O)[C@@H]1O[C@@H](O[C@H](CO)[C@@H]2O[C@@H](O[C@H](CO)[C@@H]3O[C@@H](O[C@H](CO)[C@@H]4O[C@@H](O[C@@H]5[C@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@@H]([C@@H](CO)O[C@@H]8O[C@@H]([C@@H](CO)O[C@@H]9O[C@@H]([C@@H](CO)O[C@@H]%10O[C@@H]([C@H](O)CO)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H]6O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@@H]([C@@H](CO)O[C@@H]8O[C@@H]([C@@H](CO)O[C@@H]9O[C@@H]([C@@H](CO)O[C@@H]%10O[C@@H]([C@H](O)CO)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H]6O[C@H]6O[C@H](CO[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H](CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O)[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]6[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]6O)O[C@H](CO)[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