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Lee JS, Cho JY, Hong EK
Study on macrophage activation and structural characteristics of purified polysaccharides from the liquid culture broth of Hericium erinaceus
Carbohydrate Polymers 78(1) (2009)
162-168
|
b-D-Manp-(1-3)-b-D-Manp-(1-3)-20%b-D-Manp-(1-6)-+
|
-2)-b-D-Manp-(1- |
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Hericium erinaceus
(NCBI TaxID 91752,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.carbpol.2009.04.036Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: ekhong
kangwon.ac.kr
Institutions: Department of Bioengineering and Technology, Kangwon National University, Chuncheon, South Korea, School of Bioscience and Biotechnology, Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon, South Korea
Recently, a number of bioactive molecules, including antitumor agents, have been identified in various higher basidiomycetes mushrooms. Polysaccharides are the best known and most potent mushroom derived substances that display immuno-pharmacological properties. In this study, the water soluble crude polysaccharide HEB-P, which was obtained from the liquid culture broth of Hericium erinaceus by ethanol precipitation, was fractionated by DEAE cellulose and Sepharose CL-6B column chromatography. This fractionation process resulted in two polysaccharide fractions that were termed HEB-NP Fr I and HEB-AP Fr I. Of the fractions, HEB-AP Fr I was able to upregulate the functional events mediated by activated macrophages, such as production of nitric oxide (NO) and expression of cytokines (IL-1β and TNF-α). Its structural characteristics were investigated by a combination of chemical and instrumental analyses, including methylation, reductive cleavage, acetylation, Fourier transform infrared spectroscopy (FT-IR), and gas chromatography-mass spectrometry (GC-MS). Results indicate that HEB-AP Fr I was a low molecular mass polysaccharide with a laminarin-like triple helix conformation of the β-1,3-branched-β-1,2-mannan.
Hericium erinaceus, immunostimulating polysaccharide, laminarin-like triple helix, macrophage activation
Structure type: structural motif or average structure ; 46000
Location inside paper: Table 3, HEB-AP Fr I
Compound class: O-polysaccharide, mannan
Contained glycoepitopes: IEDB_115576,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_137485,IEDB_140116,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_1539315,IEDB_173895,IEDB_76920,IEDB_858578,IEDB_983930,SB_44,SB_72
Methods: methylation, gel filtration, IR, GC-MS, ELISA, acid hydrolysis, HPLC, UV, extraction, RT-PCR, reduction, CC, cell growth, determination of NO production, cell viability assay, ethanol precipitation, Bradford method, evaporation, Congo Red assay, phenol–sulfuric acid assay, macrophage production, glucose assay, Elson–Morgan method, Blumenkrantz method
Biological activity: HEB-AP Fr I very effectively upregulates cytokine expression (TNF-a and IL-1b) and NO release indicating that it was able to induce the functional activation of macrophages
Related record ID(s): 44122
NCBI Taxonomy refs (TaxIDs): 91752Reference(s) to other database(s): GTC:G53199UW
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There is only one chemically distinct structure:
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Lee JS, Cho JY, Hong EK
Study on macrophage activation and structural characteristics of purified polysaccharides from the liquid culture broth of Hericium erinaceus
Carbohydrate Polymers 78(1) (2009)
162-168
Alcaligenes faecalis var. myxogenes
(Ancestor NCBI TaxID 511,
species name lookup)
Laminaria digitata
(NCBI TaxID 80365,
species name lookup)
Taxonomic group: bacteria, algae / Proteobacteria, Ochrophyta
(Phylum: Proteobacteria, Ochrophyta)
Publication DOI: 10.1016/j.carbpol.2009.04.036Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: ekhong
kangwon.ac.kr
Institutions: Department of Bioengineering and Technology, Kangwon National University, Chuncheon, South Korea, School of Bioscience and Biotechnology, Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon, South Korea
Recently, a number of bioactive molecules, including antitumor agents, have been identified in various higher basidiomycetes mushrooms. Polysaccharides are the best known and most potent mushroom derived substances that display immuno-pharmacological properties. In this study, the water soluble crude polysaccharide HEB-P, which was obtained from the liquid culture broth of Hericium erinaceus by ethanol precipitation, was fractionated by DEAE cellulose and Sepharose CL-6B column chromatography. This fractionation process resulted in two polysaccharide fractions that were termed HEB-NP Fr I and HEB-AP Fr I. Of the fractions, HEB-AP Fr I was able to upregulate the functional events mediated by activated macrophages, such as production of nitric oxide (NO) and expression of cytokines (IL-1β and TNF-α). Its structural characteristics were investigated by a combination of chemical and instrumental analyses, including methylation, reductive cleavage, acetylation, Fourier transform infrared spectroscopy (FT-IR), and gas chromatography-mass spectrometry (GC-MS). Results indicate that HEB-AP Fr I was a low molecular mass polysaccharide with a laminarin-like triple helix conformation of the β-1,3-branched-β-1,2-mannan.
Hericium erinaceus, immunostimulating polysaccharide, laminarin-like triple helix, macrophage activation
Structure type: homopolymer
Location inside paper: Fig.6, A, curdlan, laminarin
Trivial name: glucan, β-1,3-glucan, curdlan, curdlan-type polysaccharide 13140, paramylon, curdlan, laminarin, β-glucan, curdlan, β-(1,3)-glucan, β-(1,3)-glucan, curdlan, curdlan, β-1,3-glucan, paramylon, reserve polysaccharide, b-glucan, β-1,3-D-glucan, laminaran, botryosphaeran, laminaran type β-D-glucan, latiglucan I, pachymaran, Curdlan, zymosan A, β-glucan, curdlan, laminarin, zymosan, zymosan, glucan particles, zymosan, β-(1-3)-glucan, β-(1,3)-glucan, β-(1,3)glucan, pachymaran, D-glucan (DPn)540, pachyman, laminaran, curdlan, zymosan, zymosan, β-(1,3)-glucan, zymosan A, zymosan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, pachyman, β-(1,3)-glucan, curdlan, callose, a water-insoluble β-(1→3)-glucan, fermentum β-polysaccharide, water-insoluble glucan, alkali-soluble β-glucan (PeA3), alkali-soluble polysaccharide (PCAP), callose, laminarin
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, lipophosphoglycan, glycoprotein, LPG, glucan, polysaccharide, glycoside, β-glucan, β3-glucan, cell wall glucan
Contained glycoepitopes: IEDB_1397514,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_2278476,IEDB_2278477,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: methylation, gel filtration, IR, GC-MS, ELISA, acid hydrolysis, HPLC, UV, extraction, RT-PCR, reduction, CC, cell growth, determination of NO production, cell viability assay, ethanol precipitation, Bradford method, evaporation, Congo Red assay, phenol–sulfuric acid assay, macrophage production, glucose assay, Elson–Morgan method, Blumenkrantz method
Related record ID(s): 44121
NCBI Taxonomy refs (TaxIDs): 511,
80365Reference(s) to other database(s): GTC:G51056AN, GlycomeDB:
157, CCSD:
50049, CBank-STR:4225, CA-RN: 51052-65-4, GenDB:FJ3380871.1
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Turner SH, Cherniak R
Glucuronoxylomannan of Cryptococcus neoformans serotype B: structural analysis by gas-liquid chromatography-mass spectrometry and 13C-nuclear magnetic resonance spectroscopy
Carbohydrate Research 211(1) (1991)
103-116
|
b-D-Xylp-(1-2)-+
|
b-D-Xylp-(1-2)-+ |
| |
b-D-GlcpA-(1-2)-+ | |
| | |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-
|
b-D-Xylp-(1-4)-+ |
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Cryptococcus neoformans B
(later renamed to: Cryptococcus gattii VGI B)
(NCBI TaxID 37769,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: capsuleAssociated disease: infection due to Cryptococcus neoformans [ICD11:
XN3EH 
];
infection due to Cryptococcus gattii [ICD11:
XN0LE ]
The structure was elucidated in this paperNCBI PubMed ID: 1773425Publication DOI: 10.1016/0008-6215(91)84149-9Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Laboratory of Microbial and Biochemical Sciences, Georgia State University, Atlanta, USA
The major extracellular polysaccharide (glucuronoxylomannan, GXM) from six strains of Cryptococcus neoformans serotype B was characterized by gas-liquid chromatography (g.l.c.), g.l.c.-mass spectrometry (g.l.c.-m.s.), and nuclear magnetic resonance (n.m.r.) spectroscopy. Ultrasonic irradiation (u.i.) was used to reduce the mol.wt. of native GXM from 975000 to 115000 without apparent change in its composition (GXM-S). The Xylp:Manp:GlcpA molar ratio of the GXM and GXM-S from the six strains of C. neoformans serotype B is approximately 3.5:3.0:0.6. GXM-S was O-deacetylated (GXM-D) by treatment with NH4OH. The 13C-n.m.r. analysis of GXM-D gave spectra that served as characteristic fingerprints of the structure and also facilitated the assignment of the anomeric carbon resonances to specific structural moieties present in GXM-D. The GXM-D from each serotype B strain was found to be similar by 13C-n.m.r. spectroscopy. The structure contains a linear (1→3)-α-d-Manp backbone substituted with 2-O-β-GlcpA and 2-O-β-Xylp. β-Xylp is also O-4 linked to the Manp substituted with GlcpA. In addition, a model for the disposition of the Xylp and GlcpA side chain substituents along the mannopyranan backbone is proposed, based upon results from the combination of g.l.c.-m.s. and 13C-n.m.r. spectroscopy.
NMR, GLC-MS, Cryptococcus neoformans, Glucuronoxylomannan
Structure type: suggested polymer biological repeating unit
Location inside paper: p.114, GXM-D, table III, fig.3
Trivial name: glucuronoxylomannan (GXM), glucuronoxylomannan
Compound class: CPS, EPS, O-polysaccharide, O-antigen, cell wall polysaccharide, polysaccharide, glucuronoxylomannan, capsule polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, deacetylation, acid hydrolysis, GLC, GPC, ion-exchange chromatography, extraction, acetylation, reduction, ethanol precipitation, sonication, Blumenkrantz method, HETCOR
Comments, role: chemical repeating unit frame was shifted for compatibility with structures elucidated by MS [Eukaryotic Cell 2007, 6: 1464-1473]; published erroneous 13C NMR chemical shifts of #_aDManp C2 (72.12) and #3_aDManp C2 (72.12) were removed by the CSDB staff (the published spectrum indicated the presence of aDManp unsubstituted at C2). The published 13C NMR spectrum in DSS was shifted 1.6 ppm upfield by CSDB staff to accord to a TMS reference.
Related record ID(s): 40816, 42130, 43808, 43816, 43822, 43825, 43917, 44110, 44281, 44286, 44351
NCBI Taxonomy refs (TaxIDs): 37769Reference(s) to other database(s): GTC:G42955PN
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NMR conditions: in D2O / DSS; pH 7.6 at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,2 bDGlcpA 102.39 73.73 75.55 72.73 77.70 178.37
3,3,4 bDXylp 105.10 73.75 76.73 70.36 66.20
3,3 aDManp 101.75 ? ? ? ? ?
3,2 bDXylp 105.95-106.09 73.75 76.73 70.36 66.20
3 aDManp 102.36-102.95 ? 79.60 ? ? 61.83
2 bDXylp 105.95-106.09 73.75 76.73 70.36 66.20
aDManp 102.36-102.95 ? 79.60 ? ? 61.83
1H NMR data: present in publication
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,2 | bDGlcpA | 102.39 | 73.73 | 75.55 | 72.73 | 77.70 | 178.37 |
| 3,3,4 | bDXylp | 105.10 | 73.75 | 76.73 | 70.36 | 66.20 | |
| 3,3 | aDManp | 101.75 | ? | ? | ? | ? | ? |
| 3,2 | bDXylp | 105.95
106.09 | 73.75 | 76.73 | 70.36 | 66.20 | |
| 3 | aDManp | 102.36
102.95 | ? | 79.60 | ? | ? | 61.83 |
| 2 | bDXylp | 105.95
106.09 | 73.75 | 76.73 | 70.36 | 66.20 | |
| | aDManp | 102.36
102.95 | ? | 79.60 | ? | ? | 61.83 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.39,"l":"1","c":[0,0,225]},{"s":73.73,"l":"2","c":[0,0,225]},{"s":75.55,"l":"3","c":[0,0,225]},{"s":72.73,"l":"4","c":[0,0,225]},{"s":77.7,"l":"5","c":[0,0,225]},{"s":178.37,"l":"6","c":[0,0,225]},{"s":105.1,"l":"1","c":[230,0,30]},{"s":73.75,"l":"2","c":[230,0,30]},{"s":76.73,"l":"3","c":[230,0,30]},{"s":70.36,"l":"4","c":[230,0,30]},{"s":66.2,"l":"5","c":[230,0,30]},{"s":101.75,"l":"1","c":[0,165,0]},{"s":106.02,"l":"1","c":[120,0,225]},{"s":73.75,"l":"2","c":[120,0,225]},{"s":76.73,"l":"3","c":[120,0,225]},{"s":70.36,"l":"4","c":[120,0,225]},{"s":66.2,"l":"5","c":[120,0,225]},{"s":102.66,"l":"1","c":[0,192,255]},{"s":79.6,"l":"3","c":[0,192,255]},{"s":61.83,"l":"6","c":[0,192,255]},{"s":106.02,"l":"1","c":[220,0,180]},{"s":73.75,"l":"2","c":[220,0,180]},{"s":76.73,"l":"3","c":[220,0,180]},{"s":70.36,"l":"4","c":[220,0,180]},{"s":66.2,"l":"5","c":[220,0,180]},{"s":102.66,"l":"1","c":[100,160,0]},{"s":79.6,"l":"3","c":[100,160,0]},{"s":61.83,"l":"6","c":[100,160,0]}])
The spectrum also has 11 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Müller BM, Kraus J, Franz G
Chemical structure and biological activity of water-soluble polysaccharides from Cassia angustifolia leaves
Planta Medica 55(6) (1989)
536-539
|
/Variants 2/-+
|
-4)-a-D-GalpA-(1-2)-a-L-Rhap-(1-
/Variants 0/ is:
50%L-Araf-(1-5)-
OR (exclusively)
50%L-Araf-(1-3)-
/Variants 1/ is:
50%L-Araf-(1-5)-
OR (exclusively)
50%L-Araf-(1-3)-
/Variants 2/ is:
D-Galp-(1-3)-+
|
/Variants 0/-L-Araf-(1-6)-75%D-Galp-(1-4)-
OR (exclusively)
D-Galp-(1-6)-+
|
/Variants 1/-L-Araf-(1-3)-25%D-Galp-(1-4)- |
Show graphically |
Cassia angustifolia
(later renamed to: Senna alexandrina)
(NCBI TaxID 72402,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperNCBI PubMed ID: 2616672Publication DOI: 10.1055/s-2006-962088Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Departement of Pharmacy, University of Regensburg, Regensburg, Germany
The water-soluble polysaccharides from Cassia angustifolia L. leaves were isolated and fractionated. The acidic polysaccharide fraction was separated into two subfractions S1 and S2 consisting of L-rhamnose, L-arabinose, D-galactose, and D-galacturonic acid. Further fractionation of the predominant S1 by GPC gave two fractions S1A and S1B with an average molecular weight of 2000000 and 150000 Da, respectively. Methylation analysis of S1A showed the presence of 1,4-linked galacturonic acid (31.0%), 1,2-linked rhamnose (14.5%), 1,2,4-linked rhamnose (15.8%), 1,3,6-linked galactose (15.3%), smaller amounts of 1,3-linked arabinose, 1,5-linked arabinose, and terminal galactose and arabinose residues. Mild acid hydrolysis of S1A indicated that the backbone consists of 1,4-linked galacturonic acid and 1,2-linked rhamnose residues in the ratio of 1:1. Every second rhamnose is connected via C-4 to arabinogalactan sidechains. The antitumor activity of the polysaccharide fractions was tested against the solid Sarcoma-180 in CD1 mice. Only S1A exhibited a significant antitumor activity with an inhibition rate of 51%.
acidic polysaccharide, heteropolysaccharide, antitumor activity, Cassia angustifolia
Structure type: structural motif or average structure ; 2000000
Location inside paper: p. 538, Fig. 1
Compound class: polysaccharide, arabinorhamnogalactan
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_134624,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_225177,IEDB_742246,IEDB_742248,IEDB_885823,IEDB_918313,IEDB_918314,SB_163,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
Methods: methylation, GC-MS, acid hydrolysis, GPC, extraction, acetylation, uronic acid degradation, methylation analysis, reduction, CC, dialysis, antitumor activity assay, centrifugation, ion exchange chromatography, Blumenkrantz method
Biological activity: polysaccharide has no direct cytotoxic activity against Sarcoma-180 cells. The possible action of polysaccharide against Sarcoma-180 should be initiated through a stimulation of the hosts immune system
NCBI Taxonomy refs (TaxIDs): 72402
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There is only one chemically distinct structure:
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