Y.G. Xia <yonggangxia
Key Laboratory of Basic and Application Research of Beiyao (Heilongjiang University of Chinese Medicine), Ministry of Education, 24 Heping Road, Harbin 150040, PR China
An unprecedent glucuronoxylogalactoglucomannan (GXG'G″M), ME-2 (Mw, 2.60 × 105 g/mol; O-acetyl % = 16.7 %), was isolated and purified from water extracts of Auricularia auricula-judae (black woody ear). Firstly, due to much higher O-acetyl contents, we prepared its fully deacetylated products (dME-2; Mw, 2.13 × 105 g/mol) for convenient structure survey. The repeating structure-unit of dME-2 was readily proposed based on Mw determination, monosaccharide compositions, methylation analysis, free-radical degradation and 1/2D NMR spectroscopy. The dME-2 was identified as a highly branched polysaccharide with an average of 10 branches per 10 sugar backbone units. The backbone was only repeating →3)-α-Manp-(1→ residues, substituted at the C-2, C-6 and C-2,6 positions. The side chains included β-GlcAp-(1→, β-Xylp-(1→, α-Manp-(1→, α-Galp-(1→ and β-Glcp-(1→. Secondly, the complex substituted positions of O-acetyl groups in ME-2 were determined to be at C-2, C-4, C-6 and C-4,6 in the backbone and at C-2 and C-2,3 in some side chains. Finally, the anti-inflammatory activity of ME-2 was preliminarily explored on LPS-stimulated THP-1 cells. The above date not only provided the first example for structural studies of GXG'G″M type polysaccharides, but also facilitated development and application of black woody ear polysaccharides as medicinal agents or functional dietary supplements.
Fig. 9A, table 2, dME-2
13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, MS/MS, de-O-acetylation, composition analysis, HPLC, cytokine analysis, ion-exchange chromatography, extraction, statistical analysis, reduction, HILIC-ESI-MS, cytotoxicity assay, DEPT-135, SEC-MALLS-VIS-RID, RPLC-QQQ-MS
the tentative structures of de-O-acetylated ME-2 (dMe-2); NMR temperature was not specified.
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,3,3,3,3,3,3,3,2 bDGlcpA 102.2 72.1 77.0 71.5 73.1 176.1
3,3,3,3,3,3,3,3,3 aDManp 101.9 77.5 77.8 69.0 72.9 60.5
3,3,3,3,3,3,3,3 aDManp 103.0 69.8 78.1 68.3 72.5 60.5
3,3,3,3,3,3,3,6 bDXylp 103.2 72.9 75.3 69.2 65.1
3,3,3,3,3,3,3 aDManp 100.0 69.8 77.5 69.6 73.2 64.9
3,3,3,3,3,3,6 bDXylp 103.2 72.9 75.3 69.2 65.1
3,3,3,3,3,3 aDManp 100.0 69.8 77.5 69.6 73.2 64.9
3,3,3,3,3 aDManp
3,3,3,3,2 bDGlcpA 102.2 72.1 77.0 71.5 73.1 176.1
3,3,3,3,6 aDManp 103.0 69.6 72.9 69.3 73.2 60.3
3,3,3,3 aDManp 100.1 77.5 77.9 69.1 72.9 65.1
3,3,3,2 bDGlcpA 102.2 72.1 77.0 71.5 73.1 176.1
3,3,3,6 aDGalp 102.2 70.8 ? ? 73.14 60.6
3,3,3 aDManp 100.1 77.5 77.9 69.1 72.9 65.1
3,3,6 bDXylp 103.2 72.9 75.3 69.2 65.1
3,3 aDManp 100.0 69.8 77.5 69.6 73.2 64.9
3,2 bDGlcpA 102.2 72.1 77.0 71.5 73.1 176.1
3,6 bDGlcp 103.3 72.3 76.2 69.3 75.3 61.1
3 aDManp 100.1 77.5 77.9 69.1 72.9 65.1
aDManp 103.0 69.8 78.1 68.3 72.5 60.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,3,3,3,3,3,3,3,2 bDGlcpA 4.40 3.31 3.57 3.50 3.22 -
3,3,3,3,3,3,3,3,3 aDManp 5.12 4.18 3.81 3.86 3.97 3.64-3.82
3,3,3,3,3,3,3,3 aDManp 5.00 4.16 3.85 3.75 4.00 3.64-3.82
3,3,3,3,3,3,3,6 bDXylp 4.35 3.20 3.36 3.51 3.21-3.86
3,3,3,3,3,3,3 aDManp 5.15 4.16 3.88 3.66 3.72 3.62.-3.73
3,3,3,3,3,3,6 bDXylp 4.35 3.20 3.36 3.51 3.21-3.86
3,3,3,3,3,3 aDManp 5.15 4.16 3.88 3.66 3.72 3.62.-3.73
3,3,3,3,3 aDManp
3,3,3,3,2 bDGlcpA 4.40 3.31 3.57 3.50 3.22 -
3,3,3,3,6 aDManp 5.04 4.14 3.92 3.53 3.72 3.62-3.79
3,3,3,3 aDManp 5.17 4.18 3.94 3.73 3.81 3.50-3.70
3,3,3,2 bDGlcpA 4.40 3.31 3.57 3.50 3.22 -
3,3,3,6 aDGalp 5.33 3.60 ? ? 3.86 3.55-3.65
3,3,3 aDManp 5.17 4.18 3.94 3.73 3.81 3.50-3.70
3,3,6 bDXylp 4.35 3.20 3.36 3.51 3.21-3.86
3,3 aDManp 5.15 4.16 3.88 3.66 3.72 3.62.-3.73
3,2 bDGlcpA 4.40 3.31 3.57 3.50 3.22 -
3,6 bDGlcp 4.37 3.28 3.49 3.23 3.38 3.65-3.83
3 aDManp 5.17 4.18 3.94 3.73 3.81 3.50-3.70
aDManp 5.00 4.16 3.85 3.75 4.00 3.64-3.82
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,3,3,3,3,3,3,3,2 bDGlcpA 102.2/4.40 72.1/3.31 77.0/3.57 71.5/3.50 73.1/3.22
3,3,3,3,3,3,3,3,3 aDManp 101.9/5.12 77.5/4.18 77.8/3.81 69.0/3.86 72.9/3.97 60.5/3.64-3.82
3,3,3,3,3,3,3,3 aDManp 103.0/5.00 69.8/4.16 78.1/3.85 68.3/3.75 72.5/4.00 60.5/3.64-3.82
3,3,3,3,3,3,3,6 bDXylp 103.2/4.35 72.9/3.20 75.3/3.36 69.2/3.51 65.1/3.21-3.86
3,3,3,3,3,3,3 aDManp 100.0/5.15 69.8/4.16 77.5/3.88 69.6/3.66 73.2/3.72 64.9/3.62.-3.73
3,3,3,3,3,3,6 bDXylp 103.2/4.35 72.9/3.20 75.3/3.36 69.2/3.51 65.1/3.21-3.86
3,3,3,3,3,3 aDManp 100.0/5.15 69.8/4.16 77.5/3.88 69.6/3.66 73.2/3.72 64.9/3.62.-3.73
3,3,3,3,3 aDManp
3,3,3,3,2 bDGlcpA 102.2/4.40 72.1/3.31 77.0/3.57 71.5/3.50 73.1/3.22
3,3,3,3,6 aDManp 103.0/5.04 69.6/4.14 72.9/3.92 69.3/3.53 73.2/3.72 60.3/3.62-3.79
3,3,3,3 aDManp 100.1/5.17 77.5/4.18 77.9/3.94 69.1/3.73 72.9/3.81 65.1/3.50-3.70
3,3,3,2 bDGlcpA 102.2/4.40 72.1/3.31 77.0/3.57 71.5/3.50 73.1/3.22
3,3,3,6 aDGalp 102.2/5.33 70.8/3.60 ?/? ?/? 73.14/3.86 60.6/3.55-3.65
3,3,3 aDManp 100.1/5.17 77.5/4.18 77.9/3.94 69.1/3.73 72.9/3.81 65.1/3.50-3.70
3,3,6 bDXylp 103.2/4.35 72.9/3.20 75.3/3.36 69.2/3.51 65.1/3.21-3.86
3,3 aDManp 100.0/5.15 69.8/4.16 77.5/3.88 69.6/3.66 73.2/3.72 64.9/3.62.-3.73
3,2 bDGlcpA 102.2/4.40 72.1/3.31 77.0/3.57 71.5/3.50 73.1/3.22
3,6 bDGlcp 103.3/4.37 72.3/3.28 76.2/3.49 69.3/3.23 75.3/3.38 61.1/3.65-3.83
3 aDManp 100.1/5.17 77.5/4.18 77.9/3.94 69.1/3.73 72.9/3.81 65.1/3.50-3.70
aDManp 103.0/5.00 69.8/4.16 78.1/3.85 68.3/3.75 72.5/4.00 60.5/3.64-3.82
report error
Found 2 records.
Displayed records from 1 to 2
163.com>