Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei, China, School of Pharmacy, College of Medicine, National Taiwan University, Taipei, China, National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, China
A xylosyl 1,3-galactofucan (AMPS-III) was isolated and identified as a novel anti-inflammatory agent from an edible fungus, Armillaria mellea. The characteristics chemical structure of AMPS-III including the linkages of compositional monosaccharides and structure of the repeat unit were depicted and elucidated by proton, carbon and two-dimensional nuclear magnetic resonance techniques. AMPS-III was chemically proposed to have a partial 4-O-xylosylated 1,3-linked α-D-galactosyl-interlaced α-L-fucan composed of a pentadecasaccharide repeat unit with a molecular mass approximately 13 kDa. AMPS-III significantly suppressed the release of tumor necrosis factor-α (TNF-α) and cytokine monocyte chemotactic protein-1 (MCP-1) in RAW264.7 macrophages and EAhy926 following LPS and TNF-α induction. The results provide helpful evidences for application of AMPS-III as anti-inflammatory food supplements.
p. 590, scheme, table 2, AMPS-III
13C NMR, 1H NMR, HPSEC, statistical analysis, TOCSY, cytokine production, phenol-sulfuric acid assay, DQF-COSY, HMBC, centrifugation, NOESY, HSQC, TFA hydrolysis
AMPS-III showed significant inhibition and production of TNF-α was reduced down to 32.66% following LPS stimulation (100%)
anomeric and absolute configurations of xylose are messed in the article; 13C NMR chemical shifts are contradictory (possibly, erroneous NMR assignment)
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,3,3,3,3,3,3,3,3 aLFucp 99.2 69.7 68.2 70.9 70.2 17.1
3,3,3,3,3,3,3,3,3,2 Me 57.4
3,3,3,3,3,3,3,3,3,4 ?LXylp 99.2 70.2 73.5 71.1 67.9
3,3,3,3,3,3,3,3,3 aDGalp 103.4 80.9 70.9 71.1 75.0 62.4
3,3,3,3,3,3,3,3 aLFucp 99.2 69.7 68.2 70.9 70.2 17.1
3,3,3,3,3,3,3,2 Me 57.4
3,3,3,3,3,3,3 aDGalp 103.4 80.9 70.8 71.1 77.0 62.4
3,3,3,3,3,3 aLFucp 99.2 69.7 67.9 70.9 70.2 16.89
3,3,3,3,3,4 ?LXylp 99.2 70.2 73.5 71.1 67.9
3,3,3,3,3 aDGalp 103.4 68.5 70.8 71.1 75.0 62.4
3,3,3,3 aLFucp 99.2 69.7 67.9 70.9 70.2 16.94
3,3,3,2 Me 57.4
3,3,3,4 ?LXylp 99.2 70.2 73.5 71.1 67.9
3,3,3 aDGalp 103.4 80.9 70.9 71.1 75.0 62.4
3,3 aLFucp 99.2 69.7 67.9 70.9 70.2 17.0
3,2 Ac 174.7 21.6-21.7
3,4 ?LXylp 99.2 70.2 73.5 71.1 67.9
3 aDGalp 103.4 80.9 70.8 66.5 75.0 62.4
aLFucp 99.2 69.7 67.9 70.9 70.2 17.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,3,3,3,3,3,3,3,3 aLFucp 4.92 3.74 3.78 3.81 4.10 1.03
3,3,3,3,3,3,3,3,3,2 Me 3.33
3,3,3,3,3,3,3,3,3,4 ?LXylp 4.94 4.10 3.53 3.49 3.57-3.81
3,3,3,3,3,3,3,3,3 aDGalp 4.96 3.45 3.92 3.96 3.66 3.65-3.78
3,3,3,3,3,3,3,3 aLFucp 4.92 3.74 3.78 3.81 4.10 1.03
3,3,3,3,3,3,3,2 Me 3.33
3,3,3,3,3,3,3 aDGalp 4.99 3.45 3.78 3.78 4.12 3.65-3.78
3,3,3,3,3,3 aLFucp 4.88 3.74 3.57 3.81 4.10 1.13
3,3,3,3,3,4 ?LXylp 4.94 4.10 3.53 3.49 3.57-3.81
3,3,3,3,3 aDGalp 5.00 3.89 3.92 3.75 3.66 3.65-3.78
3,3,3,3 aLFucp 4.88 3.74 3.57 3.81 4.10 1.13
3,3,3,2 Me 3.33
3,3,3,4 ?LXylp 4.94 4.10 3.53 3.49 3.57-3.81
3,3,3 aDGalp 4.96 3.45 3.92 3.96 3.66 3.65-3.78
3,3 aLFucp 4.88 3.74 3.57 3.81 4.10 1.13
3,2 Ac - 2.05-2.10
3,4 ?LXylp 4.94 4.10 3.53 3.49 3.57-3.81
3 aDGalp 4.88 3.45 3.92 4.20 3.66 3.65-3.78
aLFucp 4.88 3.74 3.57 3.81 4.10 1.13
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,3,3,3,3,3,3,3,3 aLFucp 99.2/4.92 69.7/3.74 68.2/3.78 70.9/3.81 70.2/4.10 17.1/1.03
3,3,3,3,3,3,3,3,3,2 Me 57.4/3.33
3,3,3,3,3,3,3,3,3,4 ?LXylp 99.2/4.94 70.2/4.10 73.5/3.53 71.1/3.49 67.9/3.57-3.81
3,3,3,3,3,3,3,3,3 aDGalp 103.4/4.96 80.9/3.45 70.9/3.92 71.1/3.96 75.0/3.66 62.4/3.65-3.78
3,3,3,3,3,3,3,3 aLFucp 99.2/4.92 69.7/3.74 68.2/3.78 70.9/3.81 70.2/4.10 17.1/1.03
3,3,3,3,3,3,3,2 Me 57.4/3.33
3,3,3,3,3,3,3 aDGalp 103.4/4.99 80.9/3.45 70.8/3.78 71.1/3.78 77.0/4.12 62.4/3.65-3.78
3,3,3,3,3,3 aLFucp 99.2/4.88 69.7/3.74 67.9/3.57 70.9/3.81 70.2/4.10 16.89/1.13
3,3,3,3,3,4 ?LXylp 99.2/4.94 70.2/4.10 73.5/3.53 71.1/3.49 67.9/3.57-3.81
3,3,3,3,3 aDGalp 103.4/5.00 68.5/3.89 70.8/3.92 71.1/3.75 75.0/3.66 62.4/3.65-3.78
3,3,3,3 aLFucp 99.2/4.88 69.7/3.74 67.9/3.57 70.9/3.81 70.2/4.10 16.94/1.13
3,3,3,2 Me 57.4/3.33
3,3,3,4 ?LXylp 99.2/4.94 70.2/4.10 73.5/3.53 71.1/3.49 67.9/3.57-3.81
3,3,3 aDGalp 103.4/4.96 80.9/3.45 70.9/3.92 71.1/3.96 75.0/3.66 62.4/3.65-3.78
3,3 aLFucp 99.2/4.88 69.7/3.74 67.9/3.57 70.9/3.81 70.2/4.10 17.0/1.13
3,2 Ac 21.6-21.7/2.05-2.10
3,4 ?LXylp 99.2/4.94 70.2/4.10 73.5/3.53 71.1/3.49 67.9/3.57-3.81
3 aDGalp 103.4/4.88 80.9/3.45 70.8/3.92 66.5/4.20 75.0/3.66 62.4/3.65-3.78
aLFucp 99.2/4.88 69.7/3.74 67.9/3.57 70.9/3.81 70.2/4.10 17.0/1.13
report error
Found 1 record.
Displayed record 1
ntu.edu.tw>; Lu MK <mklu