Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 29628263Publication DOI: 10.1016/j.carbpol.2018.02.077Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Li H <lihongyan1447
163.com>; Xue C <xuechanghuouc
163.com>
Institutions: College of Food Science and Engineering, Ocean University of China, Qingdao, China
A neutral water soluble polysaccharide (HPA) was isolated from the marine fungus Hansfordia sinuosae. Monosaccharide composition analysis indicated that HPA was mainly composed of mannose with minor amounts of galactose and glucose. The molecular weight of HPA was approximately 22.5 kDa as analyzed by HPGPC. Structure analysis of HPA with methylation and 1D, 2D NMR indicated that HPA was composed of [α-D-Manp(1→], [→2)-α-D-Manp(1→], [→3)-α-D-Manp(1→] and [→2,6)-α-D-Manp(1→] with [α-D-Manp(1→] linked to C-6 position of [→2,6)-α-D-Manp(1→]. The antitumor effect of HPA was evaluated in vitro. HPA showed remarkable inhibitory effect on human cervical carcinoma HeLa cells and human breast carcinoma MCF-7 cells. When cells were incubated with HPA at 400 μg/mL for 48 h, the inhibition rate on HeLa and MCF-7 cells was 79.5% and 73.8%, respectively. Furthermore, for HeLa cells, HPA could increase intracellular ROS levels, induce cells apoptosis, decrease mitochondrial membrane potential, and elevate the expression of caspase-3. The results suggested that HPA could be explored as a potential antitumor agent.
structure, extracellular polysaccharide, apoptosis, antitumor activity, Hansfordia sinuosae
Structure type: polymer chemical repeating unit ; 22500
Location inside paper: Fig. 2, HPA, table 2
Compound class: mannan, EPC
Contained glycoepitopes: IEDB_130701,IEDB_134620,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153756,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164480,IEDB_174840,IEDB_241100,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, GC-MS, ROESY, TOCSY, methylation analysis, dialysis, anticancer activity assay, HPGPC, phenol-sulfuric acid assay, HMBC, carbazole-sulfuric acid assay, ethanol precipitation, HMQC, COSY, TFA hydrolysis
Biological activity: the inhibition ratio on HeLa and MCF-7 cells for 48 h was 79.5% and 73.8%; with the concentration 0, 25, 50, and 100 μg/mL, the apoptosis ratio of HeLa cells was 7.2%, 9.3%, 15.1, and 50.8%; decreases the mitochondrial membrane potential; could promote the generation of ROS in HeLa cells at the high concentration; invokes caspase-3 activity in dose-dependent manner
NCBI Taxonomy refs (TaxIDs): 1217297Reference(s) to other database(s): GTC:G75835TJ
Show glycosyltransferases
NMR conditions: in D2O at 296 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,2,2,2,2 aDManp 101.3 79.3 71.1 67.7 74.1 61.9
3,2,2,2,2,6 aDManp 103.0 71.9 71.1 67.7 74.1 61.9
3,2,2,2,2 aDManp 99.0 79.5 71.1 67.7 74.1 67.7
3,2,2,2 aDManp 101.3 79.3 71.1 67.7 74.1 61.9
3,2,2,6 aDManp 103.0 71.9 71.1 67.7 74.1 61.9
3,2,2 aDManp 99.0 79.5 71.1 67.7 74.1 67.7
3,2 aDManp 101.3 79.3 71.1 67.7 74.1 61.9
3,6 aDManp 103.0 71.9 71.1 67.7 74.1 61.9
3 aDManp 99.0 79.5 71.1 67.7 74.1 67.7
aDManp 103.0 71.2 78.6 67.7 74.1 61.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,2,2,2,2 aDManp 5.30 4.12 3.90 3.66 3.78 3.76-3.90
3,2,2,2,2,6 aDManp 5.05 4.23 3.94 3.66 3.78 3.76-3.90
3,2,2,2,2 aDManp 5.12 4.12 3.90 3.66 3.78 3.74
3,2,2,2 aDManp 5.30 4.12 3.90 3.66 3.78 3.76-3.90
3,2,2,6 aDManp 5.05 4.23 3.94 3.66 3.78 3.76-3.90
3,2,2 aDManp 5.12 4.12 3.90 3.66 3.78 3.74
3,2 aDManp 5.30 4.12 3.90 3.66 3.78 3.76-3.90
3,6 aDManp 5.05 4.23 3.94 3.66 3.78 3.76-3.90
3 aDManp 5.10 4.12 3.90 3.66 3.78 3.74
aDManp 5.15 4.08 3.96 3.66 3.78 3.76-3.90
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,2,2,2,2 aDManp 101.3/5.30 79.3/4.12 71.1/3.90 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3,2,2,2,2,6 aDManp 103.0/5.05 71.9/4.23 71.1/3.94 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3,2,2,2,2 aDManp 99.0/5.12 79.5/4.12 71.1/3.90 67.7/3.66 74.1/3.78 67.7/3.74
3,2,2,2 aDManp 101.3/5.30 79.3/4.12 71.1/3.90 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3,2,2,6 aDManp 103.0/5.05 71.9/4.23 71.1/3.94 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3,2,2 aDManp 99.0/5.12 79.5/4.12 71.1/3.90 67.7/3.66 74.1/3.78 67.7/3.74
3,2 aDManp 101.3/5.30 79.3/4.12 71.1/3.90 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3,6 aDManp 103.0/5.05 71.9/4.23 71.1/3.94 67.7/3.66 74.1/3.78 61.9/3.76-3.90
3 aDManp 99.0/5.10 79.5/4.12 71.1/3.90 67.7/3.66 74.1/3.78 67.7/3.74
aDManp 103.0/5.15 71.2/4.08 78.6/3.96 67.7/3.66 74.1/3.78 61.9/3.76-3.90
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,2,2,2,2 | aDManp | 5.30 | 4.12 | 3.90 | 3.66 | 3.78 | 3.76
3.90 |
| 3,2,2,2,2,6 | aDManp | 5.05 | 4.23 | 3.94 | 3.66 | 3.78 | 3.76
3.90 |
| 3,2,2,2,2 | aDManp | 5.12 | 4.12 | 3.90 | 3.66 | 3.78 | 3.74 |
| 3,2,2,2 | aDManp | 5.30 | 4.12 | 3.90 | 3.66 | 3.78 | 3.76
3.90 |
| 3,2,2,6 | aDManp | 5.05 | 4.23 | 3.94 | 3.66 | 3.78 | 3.76
3.90 |
| 3,2,2 | aDManp | 5.12 | 4.12 | 3.90 | 3.66 | 3.78 | 3.74 |
| 3,2 | aDManp | 5.30 | 4.12 | 3.90 | 3.66 | 3.78 | 3.76
3.90 |
| 3,6 | aDManp | 5.05 | 4.23 | 3.94 | 3.66 | 3.78 | 3.76
3.90 |
| 3 | aDManp | 5.10 | 4.12 | 3.90 | 3.66 | 3.78 | 3.74 |
| | aDManp | 5.15 | 4.08 | 3.96 | 3.66 | 3.78 | 3.76
3.90 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,2,2,2,2 | aDManp | 101.3 | 79.3 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3,2,2,2,2,6 | aDManp | 103.0 | 71.9 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3,2,2,2,2 | aDManp | 99.0 | 79.5 | 71.1 | 67.7 | 74.1 | 67.7 |
| 3,2,2,2 | aDManp | 101.3 | 79.3 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3,2,2,6 | aDManp | 103.0 | 71.9 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3,2,2 | aDManp | 99.0 | 79.5 | 71.1 | 67.7 | 74.1 | 67.7 |
| 3,2 | aDManp | 101.3 | 79.3 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3,6 | aDManp | 103.0 | 71.9 | 71.1 | 67.7 | 74.1 | 61.9 |
| 3 | aDManp | 99.0 | 79.5 | 71.1 | 67.7 | 74.1 | 67.7 |
| | aDManp | 103.0 | 71.2 | 78.6 | 67.7 | 74.1 | 61.9 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
(later renamed to: Ascotricha sinuosa)