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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)

NCBI PubMed ID: 28097754
Publication DOI: 10.1002/anie.201610680
Journal NLM ID: 0370543
Publisher: Weinheim: Wiley-VCH
Correspondence: byu

sioc.ac.cn; molinaro

unina.it
Institutions: Department of Plant and Environmental Sciences, University of Copenhagen, 1871, Frederiksberg, Denmark, Department of Chemical Sciences, University of Naples 'Federico II', Via Cintia 4, 80126, Napoli, Italy, State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China

The unique α-(1→7)-bradyrhizoside linkages are constructed for the first time via judicious choice of the glycosylation partners and conditions, thus tetra- and penta-bradyrhizosides relevant to the peculiar O-antigen of Bradyrhizobium are synthesized, which are shown to adopt the defined right-handed helical conformations and to be unable to induce innate immune responses in plants.

conformation, carbohydrates, Oligosaccharides, glycosylation, Bradyrhizobium

Structure type: homopolymer
Location inside paper: p.2092, fig.1
Compound class: O-antigen

Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, MD simulations, glycosylation, molecular mechanics, generation of reactive oxygen species (ROS)
3D data: 3D data

NCBI Taxonomy refs (TaxIDs): 288000
Show glycosyltransferases

There are 2 chemically distinct structures. Please, select:

*O[C@@H]1C[C@H]2O[C@H](*)[C@H](O)[C@@H](O)[C@]2(O)[C@H](O)[C@@]1(C)O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: fruiting body

The structure was elucidated in this paper
NCBI PubMed ID: 22572124
Publication DOI: 10.1016/j.carres.2012.03.043
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Islam SS <sirajul_1999

yahoo.com>
Institutions: Department of Chemistry and Chemical Technology, Vidyasagar University, Midnapore, India, Division of Plant Biology, Bose Institute, Kolkata, India, Department of Biotechnology, Indian Institute of Technology (IIT) Kharagpur, Kharagpur, India

A water soluble heteroglycan, isolated from the alkaline extract of the fruit bodies of the somatic hybrid mushroom (PfloVv1aFB), raised through protoplast fusion between the strains of Pleorutus florida and Volverilla volvacea, was found to consist of (1→3)-, (1→6)-, (1→3,4)-linked, and terminal β-D-Glcp along with (1→2,6)-α-D-Galp and terminal α-D-Manp in a relative proportion of approximately 1:1:1:1:1:1. This polysaccharide exhibited strong immunostimulating activity of macrophages as well as splenocytes and thymocytes. Structural investigation was carried out using sugar analysis, methylation analysis; periodate oxidation study, and NMR experiments (1H, 13C, DEPT-135, DQF-COSY, TOCSY, NOESY, ROESY, HMQC, and HMBC). On the basis of the above mentioned experiments, the structure of the repeating unit of the polysaccharide was established as: /structure/

structure, immunostimulation, NMR experiments, heteroglycan, Somatic hybrid mushroom (PfloVv1aFB)

Structure type: polymer chemical repeating unit ; 192000
Location inside paper: Table 1
Compound class: O-polysaccharide, galactoglucomannan
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_153543,IEDB_190606,IEDB_241101,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72

Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, gel chromatography, optical rotation measurement, generation of reactive oxygen species (ROS), cytokine production, DEPT, MTT, alkaline extraction, splenocyte proliferation assay, thymocyte proliferation assay
Biological activity: stimulation of mice splenocytes, thymocytes and peritoneal macrophages proliferation
Comments, role: organism: hybrid PfloVv1aFB

NCBI Taxonomy refs (TaxIDs): 188765, 36659
Reference(s) to other database(s): GTC:G57739RO
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,3	bDGlcp	103.0	73.5	76.0	69.6	75.3	69.2
3,2,4	bDGlcp	102.8	73.5	76.3	70.0	76.0	61.1
3,2	bDGlcp	103.4	73.3	84.5	76.6	75.3	61.1
3,6	aDManp	102.0	70.8	71.9	68.6	74.2	61.6
3	aDGalp	99.8	77.3	70.0	69.9	70.8	67.2
	bDGlcp	103.4	73.3	84.8	70.0	76.0	61.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,3	bDGlcp	4.52	3.31	3.47	3.40	3.46	3.86-4.20
3,2,4	bDGlcp	4.50	3.31	3.49	3.46	3.47	3.83-3.91
3,2	bDGlcp	4.50	3.51	3.71	3.38	3.62	3.72-3.91
3,6	aDManp	4.98	3.86	3.83	3.59	3.69	3.71-3.90
3	aDGalp	5.12	3.95	4.01	4.05	4.09	3.68-3.69
	bDGlcp	4.52	3.49	3.72	3.47	3.62	3.73-3.89


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,2,3	bDGlcp	103.0/4.52	73.5/3.31	76.0/3.47	69.6/3.40	75.3/3.46	69.2/3.86-4.20
3,2,4	bDGlcp	102.8/4.50	73.5/3.31	76.3/3.49	70.0/3.46	76.0/3.47	61.1/3.83-3.91
3,2	bDGlcp	103.4/4.50	73.3/3.51	84.5/3.71	76.6/3.38	75.3/3.62	61.1/3.72-3.91
3,6	aDManp	102.0/4.98	70.8/3.86	71.9/3.83	68.6/3.59	74.2/3.69	61.6/3.71-3.90
3	aDGalp	99.8/5.12	77.3/3.95	70.0/4.01	69.9/4.05	70.8/4.09	67.2/3.68-3.69
	bDGlcp	103.4/4.52	73.3/3.49	84.8/3.72	70.0/3.47	76.0/3.62	61.1/3.73-3.89

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,3	bDGlcp	4.52	3.31	3.47	3.40	3.46	3.86 4.20
3,2,4	bDGlcp	4.50	3.31	3.49	3.46	3.47	3.83 3.91
3,2	bDGlcp	4.50	3.51	3.71	3.38	3.62	3.72 3.91
3,6	aDManp	4.98	3.86	3.83	3.59	3.69	3.71 3.90
3	aDGalp	5.12	3.95	4.01	4.05	4.09	3.68 3.69
	bDGlcp	4.52	3.49	3.72	3.47	3.62	3.73 3.89

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,3	bDGlcp	103.0	73.5	76.0	69.6	75.3	69.2
3,2,4	bDGlcp	102.8	73.5	76.3	70.0	76.0	61.1
3,2	bDGlcp	103.4	73.3	84.5	76.6	75.3	61.1
3,6	aDManp	102.0	70.8	71.9	68.6	74.2	61.6
3	aDGalp	99.8	77.3	70.0	69.9	70.8	67.2
	bDGlcp	103.4	73.3	84.8	70.0	76.0	61.1

There is only one chemically distinct structure:

*OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O[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](O)[C@H](*)O[C@H](CO)[C@H]3O)O[C@H](CO)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Pleurotus florida blue variant

(previously named: Pleurotus ostreatus var. florida; later renamed to: Pleurotus sp. Florida; Pleurotus sp. Florida blue variant)
(NCBI TaxID 188765, species name lookup)

Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: fruiting body

The structure was elucidated in this paper
NCBI PubMed ID: 22322111
Publication DOI: 10.1016/j.ijbiomac.2012.01.031
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: Islam SS <sirajul_1999

Two different glucans (PS-I and PS-II) were isolated from the alkaline extract of the fruiting bodies of an edible mushroom, Pleurotus florida blue variant and the PS-I showed macrophage, splenocyte and thymocyte activations. On the basis of sugar analysis, methylation analysis, periodate oxidation, and NMR studies (1H, 13C, DEPT-135, DQF-COSY, TOCSY, NOESY, ROESY, HMQC and HMBC), the structure of the repeating unit of these polysaccharides were established.

structure, NMR spectroscopy, mushroom polysaccharide, Immunoactivation, Pleurotus florida blue variant

Structure type: homopolymer ; 202000
Location inside paper: Table 1, Table 2, p.596, PS-I
Trivial name: 1-6-β-glucan
Compound class: O-polysaccharide, cell wall polysaccharide, D-glucan
Contained glycoepitopes: IEDB_135614,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, NMR-2D, GLC, paper chromatography, extraction, gel chromatography, optical rotation measurement, generation of reactive oxygen species (ROS), cytokine production, DEPT, MTT, splenocyte proliferation assay, thymocyte proliferation assay
Biological activity: stimulation of mouse splenocytes, thymocytes and peritoneal macrophages proliferation
Comments, role: water soluble glucan

Related record ID(s): 43795
NCBI Taxonomy refs (TaxIDs): 188765
Reference(s) to other database(s): GTC:G26777BZ
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
	bDGlcp	103.4	73.4	75.9	69.9	75.3	69.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
	bDGlcp	4.51	3.31	3.48	3.46	3.61	3.84-4.19


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
	bDGlcp	103.4/4.51	73.4/3.31	75.9/3.48	69.9/3.46	75.3/3.61	69.2/3.84-4.19

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
	bDGlcp	4.51	3.31	3.48	3.46	3.61	3.84 4.19

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
	bDGlcp	103.4	73.4	75.9	69.9	75.3	69.2

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize

Pleurotus florida blue variant

(previously named: Pleurotus ostreatus var. florida; later renamed to: Pleurotus sp. Florida; Pleurotus sp. Florida blue variant)
(NCBI TaxID 188765, species name lookup)

structure, NMR spectroscopy, mushroom polysaccharide, Immunoactivation, Pleurotus florida blue variant

Structure type: polymer chemical repeating unit ; 176000
Location inside paper: Table 1, Table 3, p.596, PS-II
Trivial name: (1-3,4)-glucan, pleurotan
Compound class: O-polysaccharide, cell wall polysaccharide, D-glucan
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_153755,IEDB_158555,IEDB_423115,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, NMR-2D, GLC, paper chromatography, extraction, gel chromatography, optical rotation measurement, generation of reactive oxygen species (ROS), cytokine production, DEPT, MTT, splenocyte proliferation assay, thymocyte proliferation assay
Comments, role: water insoluble glucan

Related record ID(s): 43794
NCBI Taxonomy refs (TaxIDs): 188765
Reference(s) to other database(s): GTC:G21016AK
Show glycosyltransferases

NMR conditions: in DMSO-d6 at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3	bDGlcp	103.7	73.7	86.9	69.2	76.9	61.7
3,3,4	aDGlcp	100.6	72.8	74.5	70.8	73.2	61.0
3,3	bDGlcp	103.7	73.2	86.5	77.5	76.8	61.7
3	bDGlcp	103.7	73.7	86.9	69.2	76.9	61.7
	aDGlcp	100.3	71.7	83.6	70.3	73.6	60.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3	bDGlcp	4.50	3.55	3.52	3.29	3.21	3.73-4.26
3,3,4	aDGlcp	5.21	3.38	3.35	3.45	3.84	3.55-3.86
3,3	bDGlcp	4.56	3.35	3.54	3.32	3.27	3.73-4.25
3	bDGlcp	4.50	3.55	3.52	3.29	3.21	3.73-4.26
	aDGlcp	5.11	3.45	3.66	3.25	3.62	3.87-4.15


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,3	bDGlcp	103.7/4.50	73.7/3.55	86.9/3.52	69.2/3.29	76.9/3.21	61.7/3.73-4.26
3,3,4	aDGlcp	100.6/5.21	72.8/3.38	74.5/3.35	70.8/3.45	73.2/3.84	61.0/3.55-3.86
3,3	bDGlcp	103.7/4.56	73.2/3.35	86.5/3.54	77.5/3.32	76.8/3.27	61.7/3.73-4.25
3	bDGlcp	103.7/4.50	73.7/3.55	86.9/3.52	69.2/3.29	76.9/3.21	61.7/3.73-4.26
	aDGlcp	100.3/5.11	71.7/3.45	83.6/3.66	70.3/3.25	73.6/3.62	60.9/3.87-4.15

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,3	bDGlcp	4.50	3.55	3.52	3.29	3.21	3.73 4.26
3,3,4	aDGlcp	5.21	3.38	3.35	3.45	3.84	3.55 3.86
3,3	bDGlcp	4.56	3.35	3.54	3.32	3.27	3.73 4.25
3	bDGlcp	4.50	3.55	3.52	3.29	3.21	3.73 4.26
	aDGlcp	5.11	3.45	3.66	3.25	3.62	3.87 4.15

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,3	bDGlcp	103.7	73.7	86.9	69.2	76.9	61.7
3,3,4	aDGlcp	100.6	72.8	74.5	70.8	73.2	61.0
3,3	bDGlcp	103.7	73.2	86.5	77.5	76.8	61.7
3	bDGlcp	103.7	73.7	86.9	69.2	76.9	61.7
	aDGlcp	100.3	71.7	83.6	70.3	73.6	60.9

There is only one chemically distinct structure:

*O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3[C@@H](O)[C@H](O[C@@H]4[C@@H](O)[C@@H](*)O[C@H](CO)[C@H]4O)O[C@H](CO)[C@H]3O)O[C@H](CO)[C@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize