Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
The structure was elucidated in this paperNCBI PubMed ID: 25683410Publication DOI: 10.1016/j.foodchem.2012.01.046Journal NLM ID: 7702639Publisher: Elsevier Applied Science Publishers
Correspondence: mghasemlou
ut.ac.ir
Institutions: Department of Food Science, Engineering and Technology, Faculty of Agricultural Engineering and Technology, University of Tehran, Iran, Shahrood University of Technology, Faculty of Agriculture, School of Agricultural Engineering, Shahrood, Iran, Chemistry and Chemical Engineering Research Center of Iran, Tehran, Iran
Kefiran, a water-soluble heteropolysaccharide with molecular weight of 1350000 Da and a specific optical rotation of +64° (c 1.0, H2O), was isolated from kefir grains grown in cheese whey and further purified through DEAE-Sepharose XK26. Response surface methodology was employed to optimise the culture conditions for kefiran production from kefir grains to be lactose concentration 67 g/l, yeast extract 13 g/l, pH 5.7 and temperature 24 °C. Intrinsic viscosity was 5.84 dl/g using the Huggins extrapolation and 5.53 dl/g using the Kramer extrapolation. Monosaccharide analysis revealed that kefiran is composed of glucose (Glc) and galactose (Gal) in a relative molar ratio of 1.0:1.1. Its structural features were elucidated by a combination of FT-IR, methylation and GC-MS analysis, periodate oxidation-Smith degradation, partial acid hydrolysis and NMR spectroscopy ( 1H, 13C and HMBC). The data obtained indicated that kefiran possessed a backbone of (1→6)-linked Glc, (1→3)-linked Gal, (1→4)-linked Gal, (1→4)-linked Glc and (1→2,6)-linked Gal, with a branch attached to O-2 of Gal residues and terminated with Glc residues.
exopolysaccharide, structural analysis, kefiran, cheese whey, response surface methodology
Structure type: polymer chemical repeating unit ; 1350000
Location inside paper: Fig.3, table 4
Trivial name: kefiran
Compound class: EPS, O-polysaccharide, galactoglucan
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_153218,IEDB_190606,IEDB_241101,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, IR, acid hydrolysis, GC, Smith degradation, GPC, UV, ion-exchange chromatography, viscosity measurement, extraction, optical rotation measurement, acetylation, reduction, protein detection, HMBC, ethanol precipitation, phenol-sulphuric acid assay
NCBI Taxonomy refs (TaxIDs): 267818Reference(s) to other database(s): GTC:G44179ZJ
Show glycosyltransferases
NMR conditions: in D2O at 300(C) K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,4,6 bDGlcp 105.4 75.6 78.1 71.7 77.8 71.6
4,3,4,2 bDGlcp 105.4 76.3 78.7 71.8 78.9 63.7
4,3,4 bDGalp 105.4 82.2 75.3 71.6 76.9 72.8
4,3 aDGalp 99.0 71.7 74.2 82.7 73.3 63.3
4 bDGalp 105.4 72.0 81.3 68.0 77.3 63.8
bDGlcp 105.4 75.5 77.8 82.1 77.5 63.4
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,4,6 | bDGlcp | 105.4 | 75.6 | 78.1 | 71.7 | 77.8 | 71.6 |
| 4,3,4,2 | bDGlcp | 105.4 | 76.3 | 78.7 | 71.8 | 78.9 | 63.7 |
| 4,3,4 | bDGalp | 105.4 | 82.2 | 75.3 | 71.6 | 76.9 | 72.8 |
| 4,3 | aDGalp | 99.0 | 71.7 | 74.2 | 82.7 | 73.3 | 63.3 |
| 4 | bDGalp | 105.4 | 72.0 | 81.3 | 68.0 | 77.3 | 63.8 |
| | bDGlcp | 105.4 | 75.5 | 77.8 | 82.1 | 77.5 | 63.4 |
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 31047067Publication DOI: 10.1016/j.carbpol.2019.03.104Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: He L <kite006
126.com>
Institutions: Institute of Biochemistry, College of Life Sciences, Zhejiang University, Hangzhou, China, Key Laboratory of State Forest Food Resources Utilization and Quality Control, Zhejiang Provincial Key Laboratory of Forest Food, Zhejiang Academy of Forestry, Hangzhou, China, Department of Processing, Marine Fisheries Research Institute of Zhejiang, Zhoushan, China, Department of Food Science, Rutgers University, New Brunswick, NJ, USA
The fine structure and chain conformation of a heteropolysaccharide (PCIPS3) from mycelium of Paecilomyces cicadae were investigated via the analysis of HPLC, IR, methylation, NMR spectroscopy and multiangle light scattering. It was determined to be a 22300 g/mol heteropolysaccharide primarily composed of glucose, galactose and mannose in a molar ratio of 23.8:2.1:1.0. The PCIPS3 backbone consisted of 1,4-linked α-D-Glcp and 1,4-linked 6-O-Me-α-D-Glcp residues, which were occasionally interrupted by branched β-Galf residues through 1,6-linkage. Moreover, the α (0.60) from Mark-Houwink-Sakurada (MHS) equation suggested that PCIPS3 adopted a flexible chain conformation in 0.1 mol/L NaNO3 at 25 °C. The worm-like chains model parameters for PCIPS3 were estimated as following: ML = 437 nm-1, q = 0.46 nm and 0.79 nm, which were further evidenced by AFM. Furthermore, PCIPS3 showed excellent scavenging capacities of 2,2-diphenyl-1-picrylhydrazyl radical, superoxide radical, hydroxyl radical, ORAC radical and moderate immunomodulatory activity.
structural elucidation, biological activity, heteropolysaccharide, AFM, Paecilomyces cicadae
Structure type: structural motif or average structure ; 22300
Location inside paper: p. 276, Fig. 4, p. 276, Table 3
Compound class: polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_140629,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153217,IEDB_190606,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, IR, GC-MS, acid hydrolysis, viscosity measurement, extraction, acetylation, methylation analysis, SEC, reduction, CC, cell growth, dialysis, antioxidant activities, cell viability assay, precipitation, phenol-sulphuric acid assay, derivatization, Bradford method, AFM, photometry, HPLC-UV, immunomodulatory activity analysis
Biological activity: polysaccharide showed excellent scavenging capacities of DPPH radical (IC50=0.28 mg/mL), superoxide radical (IC50=0.46 mg/mL), hydroxyl radical (IC50=0.32 mg/mL) and ORAC radical (1623.44 μmol Trolox/g). In addition, it exhibited a moderate immunomodulatory activity by enhancing the secretion of major inflammatory cytokines in macrophages such as TNF-α, IL-1β, IL-6
Comments, role: the published 13C NMR spectrum in DSS was shifted 1.6 ppm upfield by CSDB staff, to accord to a TMS reference
NCBI Taxonomy refs (TaxIDs): 218633
Show glycosyltransferases
NMR conditions: in D2O / DSS at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,4 aDGlcp 100.90 72.79 74.59 78.09 72.44 61.68
6,6 Me 55.25
6 aDGlcp 99.82 72.74 74.66 78.09 72.25 67.20
bDGalf 108.24 82.61 77.64 82.61 76.84 67.20
5,4 aDGlcp 101.04 72.74 74.00 70.58 74.14 62.30
5 aDManp 103.82 ? 71.21 77.67 74.28 63.90
5,2 aDGlcp 101.04 72.74 74.00 70.58 74.14 62.30
5 bDGalp 105.53 78.06 72.42 71.24 75.76 ?
5,6 aDGlcp 101.04 72.74 74.00 70.58 74.14 62.30
5 bDGlcp 96.95 75.00 76.87 70.58 75.78 67.25
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,4 aDGlcp 5.40 3.64 3.97 3.66 3.85 3.85
6,6 Me 3.23
6 aDGlcp 4.97 3.59 4.03 3.66 3.91 3.68
bDGalf 5.19 4.15 4.11 4.13 3.96 3.68
5,4 aDGlcp 5.40 3.57 3.70 3.43 3.75 3.77-3.86
5 aDManp 5.05 4.13 4.08 3.85 3.77 3.68-3.73
5,2 aDGlcp 5.40 3.57 3.70 3.43 3.75 3.77-3.86
5 bDGalp 4.64 3.68 3.79 3.97 3.73 ?
5,6 aDGlcp 5.40 3.57 3.70 3.43 3.75 3.77-3.86
5 bDGlcp 4.66 3.28 3.55 3.52 3.68 3.77-4.00
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,4 aDGlcp 100.90/5.40 72.79/3.64 74.59/3.97 78.09/3.66 72.44/3.85 61.68/3.85
6,6 Me 55.25/3.23
6 aDGlcp 99.82/4.97 72.74/3.59 74.66/4.03 78.09/3.66 72.25/3.91 67.20/3.68
bDGalf 108.24/5.19 82.61/4.15 77.64/4.11 82.61/4.13 76.84/3.96 67.20/3.68
5,4 aDGlcp 101.04/5.40 72.74/3.57 74.00/3.70 70.58/3.43 74.14/3.75 62.30/3.77-3.86
5 aDManp 103.82/5.05 ?/4.13 71.21/4.08 77.67/3.85 74.28/3.77 63.90/3.68-3.73
5,2 aDGlcp 101.04/5.40 72.74/3.57 74.00/3.70 70.58/3.43 74.14/3.75 62.30/3.77-3.86
5 bDGalp 105.53/4.64 78.06/3.68 72.42/3.79 71.24/3.97 75.76/3.73 ?/?
5,6 aDGlcp 101.04/5.40 72.74/3.57 74.00/3.70 70.58/3.43 74.14/3.75 62.30/3.77-3.86
5 bDGlcp 96.95/4.66 75.00/3.28 76.87/3.55 70.58/3.52 75.78/3.68 67.25/3.77-4.00
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,4 | aDGlcp | 5.40 | 3.64 | 3.97 | 3.66 | 3.85 | 3.85 |
| 6,6 | Me | 3.23 | |
| 6 | aDGlcp | 4.97 | 3.59 | 4.03 | 3.66 | 3.91 | 3.68 |
| | bDGalf | 5.19 | 4.15 | 4.11 | 4.13 | 3.96 | 3.68 |
| 5,4 | aDGlcp | 5.40 | 3.57 | 3.70 | 3.43 | 3.75 | 3.77
3.86 |
| 5 | aDManp | 5.05 | 4.13 | 4.08 | 3.85 | 3.77 | 3.68
3.73 |
| 5,2 | aDGlcp | 5.40 | 3.57 | 3.70 | 3.43 | 3.75 | 3.77
3.86 |
| 5 | bDGalp | 4.64 | 3.68 | 3.79 | 3.97 | 3.73 | ? |
| 5,6 | aDGlcp | 5.40 | 3.57 | 3.70 | 3.43 | 3.75 | 3.77
3.86 |
| 5 | bDGlcp | 4.66 | 3.28 | 3.55 | 3.52 | 3.68 | 3.77
4.00 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,4 | aDGlcp | 100.90 | 72.79 | 74.59 | 78.09 | 72.44 | 61.68 |
| 6,6 | Me | 55.25 | |
| 6 | aDGlcp | 99.82 | 72.74 | 74.66 | 78.09 | 72.25 | 67.20 |
| | bDGalf | 108.24 | 82.61 | 77.64 | 82.61 | 76.84 | 67.20 |
| 5,4 | aDGlcp | 101.04 | 72.74 | 74.00 | 70.58 | 74.14 | 62.30 |
| 5 | aDManp | 103.82 | ? | 71.21 | 77.67 | 74.28 | 63.90 |
| 5,2 | aDGlcp | 101.04 | 72.74 | 74.00 | 70.58 | 74.14 | 62.30 |
| 5 | bDGalp | 105.53 | 78.06 | 72.42 | 71.24 | 75.76 | ? |
| 5,6 | aDGlcp | 101.04 | 72.74 | 74.00 | 70.58 | 74.14 | 62.30 |
| 5 | bDGlcp | 96.95 | 75.00 | 76.87 | 70.58 | 75.78 | 67.25 |
|
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The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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