Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 7196285Publication DOI: 10.1016/S0008-6215(00)85986-8Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Faculty of Science of Living, Osaka City University, Osaka, Japan, Konan Women's University, Kobe, Japan, Chemotherapy Division, National Cancer Center Research Institute, Tokyo, Japan, Research and Development Division, Meito Sangyo Co. Ltd., Nagoya, Japan
Antitumor activities of two (1→6)-branched (1→3)-β-D-glucans, isolated from the fruiting body of Auricularia auricula-judae ("kikurage", an edible mushroom), and other branched polysaccharides containing a backbone chain of (1→3)-α-d-glucosidic or (1→3)-α-d-mannosidic linkages [and their corresponding (1→3)-d-glycans, derived by mild, Smith degradation] were compared. Among these polysaccharides, a water-soluble, branched (1→3)-β-D-glucan (glucan I) of A. auricula-judae exhibited potent, inhibitory activity against implanted Sarcoma 180 solid tumor in mice. The alkali-insoluble, branched (1→3)-β-D-glucan (glucan II), a major constituent of the fruiting body, showed essentially no inhibitory activity. When the latter glucan, having numerous branches attached, was modified by controlled, periodate oxidation, borohydride reduction, and mild, acid hydrolysis, the resulting, water-soluble, degraded glucan, having covalently linked polyhydroxy groups attached at O-6 of the (1→3)-linked d-glucosyl residues, exhibited potent antitumor activity. Further investigations using the glucan-polyalcohol indicated that the attachment of the polyhydroxy groups to the (1→3)-β-D-glucan backbone may enhance the antitumor potency of the glucan. On the other hand, partial introduction of carboxymethyl groups into glucan II (d.s., 0.47-0.86), which altered the insolubility property, failed to enhance the antitumor activity. The interrelation between the antitumor activity and the structure of the branched (1→3)-β-D-glucan is discussed, on the basis of methylation and 13C-NMR studies of the periodate-modified glucans.
polysaccharide, β-glucan, antitumor activity, Auricularia auricula-judae
Structure type: homopolymer
Location inside paper: Fig.2, C, CSD-50-SA
Trivial name: glucan, β-1,3-glucan, curdlan, curdlan-type polysaccharide 13140, paramylon, curdlan, laminarin, β-glucan, curdlan, β-(1,3)-glucan, β-(1,3)-glucan, curdlan, curdlan, β-1,3-glucan, paramylon, reserve polysaccharide, b-glucan, β-1,3-D-glucan, laminaran, botryosphaeran, laminaran type β-D-glucan, latiglucan I, pachymaran, Curdlan, zymosan A, β-glucan, curdlan, laminarin, zymosan, zymosan, glucan particles, zymosan, β-(1-3)-glucan, β-(1,3)-glucan, β-(1,3)glucan, pachymaran, D-glucan (DPn)540, pachyman, laminaran, curdlan, zymosan, zymosan, β-(1,3)-glucan, zymosan A, zymosan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, β-1,3-glucan, curdlan, pachyman, β-(1,3)-glucan, curdlan, callose, a water-insoluble β-(1→3)-glucan, fermentum β-polysaccharide, water-insoluble glucan, alkali-soluble β-glucan (PeA3), alkali-soluble polysaccharide (PCAP), callose, laminarin
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, lipophosphoglycan, glycoprotein, LPG, glucan, polysaccharide, glycoside, β-glucan, β3-glucan, cell wall glucan
Contained glycoepitopes: IEDB_1397514,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_161166,IEDB_2278476,IEDB_2278477,IEDB_558869,IEDB_857743,IEDB_983931,SB_192
Methods: 13C NMR, methylation, periodate oxidation, acid hydrolysis, GLC, paper chromatography, HPLC, enzymatic digestion, extraction, antitumor activity assay, carboxymethylation, evaporation
Biological activity: intraperitoneal administration of the glucan inhibites the growth of Sarcoma 180 solid tumor implanted in mice
Related record ID(s): 43950, 43951, 43952
NCBI Taxonomy refs (TaxIDs): 29892Reference(s) to other database(s): GTC:G51056AN, GlycomeDB:
157, CCSD:
50049, CBank-STR:4225, CA-RN: 51052-65-4, GenDB:FJ3380871.1
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 328(C) K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
bDGlcp 102.91 72.75 86.15 68.32 76.15 60.81
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| | bDGlcp | 102.91 | 72.75 | 86.15 | 68.32 | 76.15 | 60.81 |
|
There is only one chemically distinct structure:
Found 
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