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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)

The structure was elucidated in this paper
NCBI PubMed ID: 31756464
Publication DOI: 10.1016/j.ijbiomac.2019.11.143
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: yqtian

scu.edu.cn
Institutions: College of Biomass Science and Engineering, Sichuan University, Chengdu 610065, PR China, Key Laboratory of Leather Chemistry and Engineering (Sichuan University), Ministry of Education, Chengdu 610065, PR China

A novel exopolysaccharide (named mhEPS) with a molecular weight of 5.881 × 104 g/mol was isolated from Gracilibacillus sp. SCU50's high-salt fermentation broth by ethanol precipitation, anion-exchange and gel-filtration chromatography before being structurally characterized and functionally evaluated. mhEPS consists of mannose, galactose, glucose and fucose in a molar ratio of 90.81:5.76:2.22:1.21. The backbone of mhEPS was (1→3,6)-linked α-D-mannopyranose residues, branched by single α-D-mannopyranose units attached to the main chain at C-2 position of every residue. The water solubility index, water holding capacity and oil holding capacity of mhEPS were 93.53, 14.89 and 1023.34%, respectively. mhEPS showed to possess good emulsifying activity against all tested substrates, and it could potentially increase the high-salinity tolerance of strain SCU50. The lack of toxicity of mhEPS was also preliminarily determined. Due to the functional properties of mhEPS, it is a good candidate to develop as an active ingredient in food, cosmetics and detergents.

exopolysaccharide, Structural characterization, functional evaluation, Gracilibacillus sp.

Structure type: structural motif or average structure ; 58810
Location inside paper: p.1147, Fig.5
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164174,IEDB_76933,IEDB_857732,IEDB_857733,IEDB_857734,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_73,SB_77

Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, FTIR, genetic methods, SEM, emulsifying activity, HPSEC-RI-MALLS, WSI, WHC, OHC
Comments, role: One of the possible chemical structures of EPS. Published NMR chemical shifts of #6,6,3_aDManp (C4 and C5) and #6,6,6,2_aDManp (C4 and C5) that seemed erroneously interchanged in the published assignment were swapped by CSDB staff.

NCBI Taxonomy refs (TaxIDs): 2663022
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,2	aDManp	103.97	71.60	71.74	67.93	74.82	62.52
6,6,6	aDManp	102.06	79.93	71.89	67.5	68.21	68.43
3,6	SUG
3	aDManp	103.69	71.14	71.52	67.47	67.87	68.23
6,2,6	SUG
6,2	aDManp	103.69	71.74	71.52	67.47	67.87	68.23
6,6,6,6	aDManp
6,6,3	aDManp	103.97	71.60	71.74	67.93	74.82	62.52
6,6	aDManp	99.74	71.22	79.40	67.33	?	?
6	aDManp	102.06	79.93	71.89	67.5	68.21	68.43
	aDManp	99.74	71.22	79.40	67.33	?	?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,2	aDManp	5.20	4.11	3.88	3.80	3.78	3.77-3.79
6,6,6	aDManp	5.34	4.16	3.94	3.81	3.70	3.68-3.72
3,6	SUG
3	aDManp	5.08	4.26	3.99	3.84	3.73	3.75
6,2,6	SUG
6,2	aDManp	5.17	4.26	3.99	3.84	3.73	3.75
6,6,6,6	aDManp
6,6,3	aDManp	5.10	4.10	3.96	3.80	3.78	3.77-3.79
6,6	aDManp	5.14	4.07	4.00	3.82	?	?
6	aDManp	5.34	4.16	3.94	3.81	3.70	3.68-3.72
	aDManp	5.14	4.07	4.00	3.82	?	?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,6,2	aDManp	103.97/5.20	71.60/4.11	71.74/3.88	67.93/3.80	74.82/3.78	62.52/3.77-3.79
6,6,6	aDManp	102.06/5.34	79.93/4.16	71.89/3.94	67.5/3.81	68.21/3.70	68.43/3.68-3.72
3,6	SUG
3	aDManp	103.69/5.08	71.14/4.26	71.52/3.99	67.47/3.84	67.87/3.73	68.23/3.75
6,2,6	SUG
6,2	aDManp	103.69/5.17	71.74/4.26	71.52/3.99	67.47/3.84	67.87/3.73	68.23/3.75
6,6,6,6	aDManp
6,6,3	aDManp	103.97/5.10	71.60/4.10	71.74/3.96	67.93/3.80	74.82/3.78	62.52/3.77-3.79
6,6	aDManp	99.74/5.14	71.22/4.07	79.40/4.00	67.33/3.82	?/?	?/?
6	aDManp	102.06/5.34	79.93/4.16	71.89/3.94	67.5/3.81	68.21/3.70	68.43/3.68-3.72
	aDManp	99.74/5.14	71.22/4.07	79.40/4.00	67.33/3.82	?/?	?/?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,2	aDManp	5.20	4.11	3.88	3.80	3.78	3.77 3.79
6,6,6	aDManp	5.34	4.16	3.94	3.81	3.70	3.68 3.72
3,6	SUG
3	aDManp	5.08	4.26	3.99	3.84	3.73	3.75
6,2,6	SUG
6,2	aDManp	5.17	4.26	3.99	3.84	3.73	3.75
6,6,6,6	aDManp
6,6,3	aDManp	5.10	4.10	3.96	3.80	3.78	3.77 3.79
6,6	aDManp	5.14	4.07	4.00	3.82	?	?
6	aDManp	5.34	4.16	3.94	3.81	3.70	3.68 3.72
	aDManp	5.14	4.07	4.00	3.82	?	?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,2	aDManp	103.97	71.60	71.74	67.93	74.82	62.52
6,6,6	aDManp	102.06	79.93	71.89	67.5	68.21	68.43
3,6	SUG
3	aDManp	103.69	71.14	71.52	67.47	67.87	68.23
6,2,6	SUG
6,2	aDManp	103.69	71.74	71.52	67.47	67.87	68.23
6,6,6,6	aDManp
6,6,3	aDManp	103.97	71.60	71.74	67.93	74.82	62.52
6,6	aDManp	99.74	71.22	79.40	67.33	?	?
6	aDManp	102.06	79.93	71.89	67.5	68.21	68.43
	aDManp	99.74	71.22	79.40	67.33	?	?

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize

R1 = SUG
Warning = sub-repeat ending at aDManp: unknown unit count was assumed to be 3

Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)

The structure was elucidated in this paper
NCBI PubMed ID: 32289411
Publication DOI: 10.1016/j.ijbiomac.2020.04.062
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: pengbiyu

scu.edu.cn; yqtian

A novel exopolysaccharide, designated hsEPS, was successfully prepared from the high-salt-fermented broth of a novel species Halomonas saliphila LCB169T by ethanol precipitation, anion-exchange and gel-filtration chromatography, and its structure was well-characterized by means of chemical and spectral analyses. Results showed that hsEPS was primarily composed of mannose and glucose with a relative weight-average molecular weight of 5.133 × 104 g/mol. It was deduced that the major backbone contained (1→2)-linked α-D-Manp and (1→6)-linked α-D-Manp with branches substituted at C-2 by T-α-D-Manp and at C-6 by the fragment of T-α-D-Manp-(1→2)-α-D-Manp-(1→. A sheet-like structure was observed under high magnification. The water solubility index, water holding capacity, oil holding capacity and foaming capacity of hsEPS were 98.0, 19.3, 1386.7 and 82.2%, respectively. It also exhibited outstanding emulsifying activity against all tested edible oils. Together, the resulted data indicated that hsEPS might serve as an active ingredient in food, cosmetics and detergents.

structure, exopolysaccharide, halophiles, Functional properties, Halomonas saliphila

Structure type: structural motif or average structure ; 51330
Location inside paper: p.378, Fig.4, table 3
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_76933,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, FTIR, HPAEC-PAD, SEM, HPSEC-RI-MALLS, WSI, WHC, OHC
Comments, role: Putative structure of hsEPS produced by H. saliphila LCB169T

NCBI Taxonomy refs (TaxIDs): 1848458
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,2,6,2,2	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2,6,2,6	aDManp	103.69	71.58	71.87	68.41	74.82	62.52
2,6,2,6,2	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2,6,2,6	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2,2,2	aDManp	103.69	71.58	71.87	68.41	74.82	62.52
2,6,2,2	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2,6,6,6	SUG
2,6,6	bDGlcp	104.52	74.58	77.11	69.65	74.42	67.71
2,6	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2	aDManp	103.60	71.14	70.36	67.94	74.68	68.6
	aDManp


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,2,6,2,2	aDManp	5.33	4.16	4.07	3.79	3.93	3.68-3.80
2,6,2,6,2,6	aDManp	5.18	4.11	3.92	3.69	3.83	3.70-3.95
2,6,2,6,2	aDManp	5.13	4.06	3.81	3.70	3.84	3.73-3.91
2,6,2,6	aDManp	5.33	4.16	4.07	3.79	3.93	3.68-3.80
2,6,2,2,2	aDManp	5.09	4.11	3.92	3.69	3.83	3.70-3.95
2,6,2,2	aDManp	5.33	4.16	4.07	3.79	3.93	3.68-3.80
2,6,2	aDManp	5.13	4.06	3.81	3.70	3.84	3.73-3.91
2,6,6,6	SUG
2,6,6	bDGlcp	4.56	3.37	3.53	3.68	3.79	3.61-3.99
2,6	aDManp	5.16	4.08	3.81	3.70	3.84	3.73-3.91
2	aDManp	5.08	4.26	3.90	3.78	3.96	3.76-3.83
	aDManp


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,6,2,6,2,2	aDManp	102.06/5.33	79.94/4.16	71.52/4.07	67.88/3.79	74.70/3.93	62.61/3.68-3.80
2,6,2,6,2,6	aDManp	103.69/5.18	71.58/4.11	71.87/3.92	68.41/3.69	74.82/3.83	62.52/3.70-3.95
2,6,2,6,2	aDManp	99.73/5.13	80.21/4.06	71.73/3.81	68.36/3.70	74.89/3.84	68.44/3.73-3.91
2,6,2,6	aDManp	102.06/5.33	79.94/4.16	71.52/4.07	67.88/3.79	74.70/3.93	62.61/3.68-3.80
2,6,2,2,2	aDManp	103.69/5.09	71.58/4.11	71.87/3.92	68.41/3.69	74.82/3.83	62.52/3.70-3.95
2,6,2,2	aDManp	102.06/5.33	79.94/4.16	71.52/4.07	67.88/3.79	74.70/3.93	62.61/3.68-3.80
2,6,2	aDManp	99.73/5.13	80.21/4.06	71.73/3.81	68.36/3.70	74.89/3.84	68.44/3.73-3.91
2,6,6,6	SUG
2,6,6	bDGlcp	104.52/4.56	74.58/3.37	77.11/3.53	69.65/3.68	74.42/3.79	67.71/3.61-3.99
2,6	aDManp	99.73/5.16	80.21/4.08	71.73/3.81	68.36/3.70	74.89/3.84	68.44/3.73-3.91
2	aDManp	103.60/5.08	71.14/4.26	70.36/3.90	67.94/3.78	74.68/3.96	68.6/3.76-3.83
	aDManp

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,2,6,2,2	aDManp	5.33	4.16	4.07	3.79	3.93	3.68 3.80
2,6,2,6,2,6	aDManp	5.18	4.11	3.92	3.69	3.83	3.70 3.95
2,6,2,6,2	aDManp	5.13	4.06	3.81	3.70	3.84	3.73 3.91
2,6,2,6	aDManp	5.33	4.16	4.07	3.79	3.93	3.68 3.80
2,6,2,2,2	aDManp	5.09	4.11	3.92	3.69	3.83	3.70 3.95
2,6,2,2	aDManp	5.33	4.16	4.07	3.79	3.93	3.68 3.80
2,6,2	aDManp	5.13	4.06	3.81	3.70	3.84	3.73 3.91
2,6,6,6	SUG
2,6,6	bDGlcp	4.56	3.37	3.53	3.68	3.79	3.61 3.99
2,6	aDManp	5.16	4.08	3.81	3.70	3.84	3.73 3.91
2	aDManp	5.08	4.26	3.90	3.78	3.96	3.76 3.83
	aDManp

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,2,6,2,2	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2,6,2,6	aDManp	103.69	71.58	71.87	68.41	74.82	62.52
2,6,2,6,2	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2,6,2,6	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2,2,2	aDManp	103.69	71.58	71.87	68.41	74.82	62.52
2,6,2,2	aDManp	102.06	79.94	71.52	67.88	74.70	62.61
2,6,2	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2,6,6,6	SUG
2,6,6	bDGlcp	104.52	74.58	77.11	69.65	74.42	67.71
2,6	aDManp	99.73	80.21	71.73	68.36	74.89	68.44
2	aDManp	103.60	71.14	70.36	67.94	74.68	68.6
	aDManp

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

SVG MW SMILES 3D mol Ionize

R1 = SUG
Warning = sub-repeat ending at aDManp: unknown unit count was assumed to be 3