Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 24299820Publication DOI: 10.1016/j.carbpol.2013.09.085Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Ding K <dingkan
simm.ac.cn>
Institutions: Glycochemistry and Glycobiology Lab, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China, Department of Oncology, Taizhou Hospital, Wenzhou Medical College, Linhai, China, Department of Medicine, Zhejiang University, Hangzhou, China
The tumor growth and metastasis are angiogenesis dependent, thus blockade of angiogenesis is a promising approach for treatment of cancer. Herein we reported the structural and biological features of a novel water-soluble polysaccharide named GFPW from the fruit body of Grifola frondosa. Chemical and spectral analysis revealed that GFPW with an average molecular weight of 15.7 kDa, possessed a backbone consisting of α-1,6-linked galactopyranosyl residues, with branches attached to O-2 of α-1,3-linked fucose residues and α-terminal mannose. By the chlorosulfonic acid-pyridine method, we prepared a sulfated derivative of GFPW, SulGFPW, with a substitution degree of 0.33. According to the 13C NMR spectrum, the substitution position was deduced at C-2 and C-3. The angiogenesis assays in vitro showed that Sul-GFPW significantly inhibited endothelial cell proliferation in a dose- and time-dependent manner, and reduced endothelial cell migration and tube formation as well.
Galactan, Grifola frondosa, antiangiogenesis, human microvascular endothelial cell line-1 (HMEC-1)
Structure type: structural motif or average structure ; 15700
Location inside paper: GFPW, p. 636, Table 2
Trivial name: a water-soluble polysaccharide GFPW
Compound class: glycan, fucomannogalactan, heteropolysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_983930,SB_154,SB_163,SB_44,SB_67,SB_7,SB_72,SB_86
Methods: deacetylation, 13C NMR, 1H NMR, IR, partial acid hydrolysis, GC-MS, TLC, ESI-MS, GC, extraction, optical rotation measurement, acetylation, acetolysis, statistical analysis, methylation analysis, reduction with NaBH4, HMBC, DEPT, MTT, HSQC, TFA hydrolysis, HPGPG
Biological activity: Sulfated derivative of GFPW (Sul-GFPW) reduced the proliferation of human microvascular endothelial cell line-1 (HMEC-1) in a dose- and time-dependent manner. Sul-GFPW could also inhibit HMEC-1 migration as well as tube formation in vitro.
NCBI Taxonomy refs (TaxIDs): 5627Reference(s) to other database(s): GTC:G41832MU
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,6,6,6 aDGalp 99.18 71.37 69.92 70.07 69.16 68.05
6,6,6,2,3 aDManp 103.51 68.3 69.7 67.47 70.23 61.04
6,6,6,2 aLFucp 102.56 70.52 77.48 73.38 68.77 17.42
6,6,6 aDGalp 99.18 77.31 71.61 71.43 69.27 68.15
6,6 aDGalp 99.18 71.37 69.92 70.07 69.16 68.05
6,2,3 aDManp 103.51 68.3 69.7 67.47 70.23 61.04
6,2 aLFucp 102.56 70.52 77.48 73.38 68.77 17.42
6 aDGalp 99.18 77.31 71.61 71.43 69.27 68.15
aDGalp 99.18 71.37 69.92 70.07 69.16 68.05
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,6,6,6 aDGalp 5.07 3.72 3.91 4.08 4.11 3.72-3.95
6,6,6,2,3 aDManp 5.11 4.22 4.09 3.91 4.06 3.81-3.93
6,6,6,2 aLFucp 5.17 3.98 3.91 3.96 4.27 1.15
6,6,6 aDGalp 5.07 4.04 4.03 3.90 4.11 3.72-3.95
6,6 aDGalp 5.07 3.72 3.91 4.08 4.11 3.72-3.95
6,2,3 aDManp 5.11 4.22 4.09 3.91 4.06 3.81-3.93
6,2 aLFucp 5.17 3.98 3.91 3.96 4.27 1.15
6 aDGalp 5.07 4.04 4.03 3.90 4.11 3.72-3.95
aDGalp 5.07 3.72 3.91 4.08 4.11 3.72-3.95
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,6,6,6 aDGalp 99.18/5.07 71.37/3.72 69.92/3.91 70.07/4.08 69.16/4.11 68.05/3.72-3.95
6,6,6,2,3 aDManp 103.51/5.11 68.3/4.22 69.7/4.09 67.47/3.91 70.23/4.06 61.04/3.81-3.93
6,6,6,2 aLFucp 102.56/5.17 70.52/3.98 77.48/3.91 73.38/3.96 68.77/4.27 17.42/1.15
6,6,6 aDGalp 99.18/5.07 77.31/4.04 71.61/4.03 71.43/3.90 69.27/4.11 68.15/3.72-3.95
6,6 aDGalp 99.18/5.07 71.37/3.72 69.92/3.91 70.07/4.08 69.16/4.11 68.05/3.72-3.95
6,2,3 aDManp 103.51/5.11 68.3/4.22 69.7/4.09 67.47/3.91 70.23/4.06 61.04/3.81-3.93
6,2 aLFucp 102.56/5.17 70.52/3.98 77.48/3.91 73.38/3.96 68.77/4.27 17.42/1.15
6 aDGalp 99.18/5.07 77.31/4.04 71.61/4.03 71.43/3.90 69.27/4.11 68.15/3.72-3.95
aDGalp 99.18/5.07 71.37/3.72 69.92/3.91 70.07/4.08 69.16/4.11 68.05/3.72-3.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,6,6,6 | aDGalp | 5.07 | 3.72 | 3.91 | 4.08 | 4.11 | 3.72
3.95 |
| 6,6,6,2,3 | aDManp | 5.11 | 4.22 | 4.09 | 3.91 | 4.06 | 3.81
3.93 |
| 6,6,6,2 | aLFucp | 5.17 | 3.98 | 3.91 | 3.96 | 4.27 | 1.15 |
| 6,6,6 | aDGalp | 5.07 | 4.04 | 4.03 | 3.90 | 4.11 | 3.72
3.95 |
| 6,6 | aDGalp | 5.07 | 3.72 | 3.91 | 4.08 | 4.11 | 3.72
3.95 |
| 6,2,3 | aDManp | 5.11 | 4.22 | 4.09 | 3.91 | 4.06 | 3.81
3.93 |
| 6,2 | aLFucp | 5.17 | 3.98 | 3.91 | 3.96 | 4.27 | 1.15 |
| 6 | aDGalp | 5.07 | 4.04 | 4.03 | 3.90 | 4.11 | 3.72
3.95 |
| | aDGalp | 5.07 | 3.72 | 3.91 | 4.08 | 4.11 | 3.72
3.95 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,6,6,6 | aDGalp | 99.18 | 71.37 | 69.92 | 70.07 | 69.16 | 68.05 |
| 6,6,6,2,3 | aDManp | 103.51 | 68.3 | 69.7 | 67.47 | 70.23 | 61.04 |
| 6,6,6,2 | aLFucp | 102.56 | 70.52 | 77.48 | 73.38 | 68.77 | 17.42 |
| 6,6,6 | aDGalp | 99.18 | 77.31 | 71.61 | 71.43 | 69.27 | 68.15 |
| 6,6 | aDGalp | 99.18 | 71.37 | 69.92 | 70.07 | 69.16 | 68.05 |
| 6,2,3 | aDManp | 103.51 | 68.3 | 69.7 | 67.47 | 70.23 | 61.04 |
| 6,2 | aLFucp | 102.56 | 70.52 | 77.48 | 73.38 | 68.77 | 17.42 |
| 6 | aDGalp | 99.18 | 77.31 | 71.61 | 71.43 | 69.27 | 68.15 |
| | aDGalp | 99.18 | 71.37 | 69.92 | 70.07 | 69.16 | 68.05 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
