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Honda K, Hitora Y, Tsukamoto S
Akanthomins A-C, aphidicolin analogs from a fungus Akanthomyces sp., that inhibit cell cycle
Phytochemistry 216 (2023)
113885
|
b-D-Glcp4Me-(1-9)-Subst
Subst = 9-hydroxyeugenetin = SMILES O{9}CC(OC1=CC(OC)=C(C){5}C(O)=C12)=CC2=O |
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Akanthomyces sp. 18F18403
(Ancestor NCBI TaxID 150366,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 37806468Publication DOI: 10.1016/j.phytochem.2023.113885Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Y. Hitora <hitora
kumamoto-u.ac.jp>; S. Tsukamoto <sachiko
kumamoto-u.ac.jp>
Institutions: Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto, 862-0973, Japan
Natural products that inhibit cell cycle progression may have potential as anticancer agents. In this study, cell cycle inhibition of microbial culture extracts was screened by fluorescent images using HeLa/Fucci2 cells. The culture extract of a fungus, Akanthomyces sp., inhibited the cell cycle progression at the S/G2/M phases, and bioassay-guided fractionation of the extract afforded three previously undescribed aphidicolin derivatives, namely akanthomins A-C, and an undescribed chromone glycoside, specifically 9-hydroxyeugenetin 9-O-β-d-(4-O-methyl)glucopyranoside, in addition to aphidicolin. The chemical structures of these compounds were elucidated by spectroscopic analysis and chemical derivatization. Using a flow cytometer, akanthomin A and aphidicolin were found to inhibit cell cycle progression at the S phase.
pharmaceutical, fungus, cordycipitaceae, Akanthomyces sp., Aphidicolin derivative, cell cycle inhibitor
Structure type: monomer
C
19H
24O
10Location inside paper: Fig. 1, table 2, compound 5
Trivial name: chromone glycoside, 9-hydroxyeugenetin 9-O-β-d-(4-O-methyl)glucopyranoside
Methods: 13C NMR, 1H NMR, UV, extraction, optical rotation measurement, RP-HPLC, HR-ESI-MS, cytotoxicity assay, MPLC, cultivation, ECD, fluorescent microscopy, cell cycle analysis
Comments, role: NMR temperature was not specified
NCBI Taxonomy refs (TaxIDs): 150366
Show glycosyltransferases
NMR conditions: in DMSO‑d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13
9,4 Me 59.6
9 bDGlcp 102.3 73.5 76.3 79.3 75.7 60.5
Subst - 166.4 107.3 181.9 104.6 157.5 107.6 163.1 90.1 155.6 65.5 7.2 56.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
9,4 Me 3.42
9 bDGlcp 4.31 3.07 3.37 2.95 3.17 3.49-3.61
Subst - - 6.54 - - - - - - 6.63 - 4.50-4.70 1.95 3.06
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14
9,4 Me 59.6/3.42
9 bDGlcp 102.3/4.31 73.5/3.07 76.3/3.37 79.3/2.95 75.7/3.17 60.5/3.49-3.61
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 |
|---|
| 9,4 | Me | 3.42 | |
| 9 | bDGlcp | 4.31 | 3.07 | 3.37 | 2.95 | 3.17 | 3.49
3.61 | |
| | Subst |
|
| 6.54 |
|
|
|
|
|
| 6.63 |
| 4.50
4.70 | 1.95 | 3.06 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 |
|---|
| 9,4 | Me | 59.6 | |
| 9 | bDGlcp | 102.3 | 73.5 | 76.3 | 79.3 | 75.7 | 60.5 | |
| | Subst |
| 166.4 | 107.3 | 181.9 | 104.6 | 157.5 | 107.6 | 163.1 | 90.1 | 155.6 | 65.5 | 7.2 | 56.3 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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da Silva Milhorini S, de Lima Bellan D, Zavadinack M, Simas FF, Smiderle FR, de Santana-Filho AP, Sassaki GL, Iacomini M
Antimelanoma effect of a fucoxylomannan isolated from Ganoderma lucidum fruiting bodies
Carbohydrate Polymers 294 (2022)
119823
|
a-L-Fucp-(1-2)-b-D-Xylp-(1-6)-+
|
-4)-a-D-Manp-(1-4)-a-D-Manp-(1- |
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Ganoderma lucidum
(NCBI TaxID 5315,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
The structure was elucidated in this paperNCBI PubMed ID: 35868772Publication DOI: 10.1016/j.carbpol.2022.119823Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: M. Iacomini <iacomini
ufpr.br>
Institutions: Department of Biochemistry and Molecular Biology, Federal University of Paraná, CEP 81531-980 Curitiba, PR, Brazil, Department of Cell Biology, Federal University of Paraná, Curitiba, PR, Brazil, Faculdades Pequeno Príncipe, CEP 80230-020 Curitiba, PR, Brazil, Instituto de Pesquisa Pelé Pequeno Príncipe, CEP 80240-020 Curitiba, PR, Brazil
A fucoxylomannan (FXM) was isolated from the mushroom Ganoderma lucidum through alkaline extraction followed by dialysis, freeze-thawing, and fractionation by Fehling's solution. The main chain of FXM presented α-D-Manp-(1→4)-linked units, and some of them were branched at O-6 position by α-L-Fucp-(1→2)-β-D-Xylp groups. Its Mw was 35.9 kDa. FXM was tested on melanoma B16-F10 cells and it showed cell viability and cell density reduction, as well as antiproliferative effect, through cell cycle arrest. Additionally, the anchorage-independent clonogenic capacity of such cells was significantly reduced by FXM, decreasing the number of cells by colony and the colonies area. No effect on viability neither in proliferation of non-tumoral Balb c/3T3 fibroblasts was observed. These results indicate that FXM is a promising anti-proliferative compound impairing pivotal tumorigenic mechanisms, eliciting this polysaccharide to be further explored as an antimelanoma drug.
heteropolysaccharide, antitumor activity, Ganoderma lucidum, antimelanoma, fucoxylomannan
Structure type: polymer chemical repeating unit ; 35900
Location inside paper: table 2, Fig. 5, FXM fraction
Trivial name: fucoxylomannan (FXM)
Contained glycoepitopes: IEDB_114701,IEDB_130701,IEDB_136045,IEDB_140116,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_152206,IEDB_152214,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_76933,IEDB_983930,SB_44,SB_67,SB_72,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, GLC, HPSEC, extraction, acetylation, statistical analysis, partial hydrolysis, flow cytometry analysis, cell viability assay, cytotoxicity assay, antitumor activity assay, DEPT-135, soft agar assay, cell cycle analysis
Biological activity: Melanoma cell density was reduced by 14.5 % and 16.0 % when exposed to FXM (at 500 and 1000 μg⋅mL-1 FXM, respectively. Melanoma cells treated with 500 μg⋅mL-1 FXM resulted in 22.9 % less cells in S phase, and decreased their clonogenic capacity by 60.8 % and strikingly decreased the colony area by 86.4 % when compared to non-treated cells.
Comments, role: the presumed structure of the FXM fraction; published erroneous NMR 13C chemical shifts of C5 #6_bDXylp (experiment: 73.2 ref. to DSS) was removed by CSDB staff.
Related record ID(s): 51746
NCBI Taxonomy refs (TaxIDs): 5315
Show glycosyltransferases
NMR conditions: in D2O / DSS at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4 aDManp 100.3 69.3 72.5 78.7 70.4 61.2
6,2 aLFucp 102.6 70.4 73.3 73.3 67.8 16.5
6 bDXylp 102.3 79.1 77.2 70.2 ?
aDManp 100.2 69.5 72.5 78.7 70.4 65.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4 aDManp 5.28 3.81 3.80 4.00 4.24 3.88
6,2 aLFucp 5.02 4.27 4.01 4.00 4.25 1.26
6 bDXylp 4.48 3.44 3.68 3.68 3.97
aDManp 5.30 3.81 3.82 4.01 4.25 3.29-3.97
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4 aDManp 100.3/5.28 69.3/3.81 72.5/3.80 78.7/4.00 70.4/4.24 61.2/3.88
6,2 aLFucp 102.6/5.02 70.4/4.27 73.3/4.01 73.3/4.00 67.8/4.25 16.5/1.26
6 bDXylp 102.3/4.48 79.1/3.44 77.2/3.68 70.2/3.68 ?/3.97
aDManp 100.2/5.30 69.5/3.81 72.5/3.82 78.7/4.01 70.4/4.25 65.7/3.29-3.97
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4 | aDManp | 5.28 | 3.81 | 3.80 | 4.00 | 4.24 | 3.88 |
| 6,2 | aLFucp | 5.02 | 4.27 | 4.01 | 4.00 | 4.25 | 1.26 |
| 6 | bDXylp | 4.48 | 3.44 | 3.68 | 3.68 | 3.97 | |
| | aDManp | 5.30 | 3.81 | 3.82 | 4.01 | 4.25 | 3.29
3.97 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4 | aDManp | 100.3 | 69.3 | 72.5 | 78.7 | 70.4 | 61.2 |
| 6,2 | aLFucp | 102.6 | 70.4 | 73.3 | 73.3 | 67.8 | 16.5 |
| 6 | bDXylp | 102.3 | 79.1 | 77.2 | 70.2 | ? | |
| | aDManp | 100.2 | 69.5 | 72.5 | 78.7 | 70.4 | 65.7 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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da Silva Milhorini S, de Lima Bellan D, Zavadinack M, Simas FF, Smiderle FR, de Santana-Filho AP, Sassaki GL, Iacomini M
Antimelanoma effect of a fucoxylomannan isolated from Ganoderma lucidum fruiting bodies
Carbohydrate Polymers 294 (2022)
119823
Boletus speciosus Frost
(NCBI TaxID 374761,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting bodies
NCBI PubMed ID: 35868772Publication DOI: 10.1016/j.carbpol.2022.119823Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: M. Iacomini <iacomini
ufpr.br>
Institutions: Department of Biochemistry and Molecular Biology, Federal University of Paraná, CEP 81531-980 Curitiba, PR, Brazil, Department of Cell Biology, Federal University of Paraná, Curitiba, PR, Brazil, Faculdades Pequeno Príncipe, CEP 80230-020 Curitiba, PR, Brazil, Instituto de Pesquisa Pelé Pequeno Príncipe, CEP 80240-020 Curitiba, PR, Brazil
A fucoxylomannan (FXM) was isolated from the mushroom Ganoderma lucidum through alkaline extraction followed by dialysis, freeze-thawing, and fractionation by Fehling's solution. The main chain of FXM presented α-D-Manp-(1→4)-linked units, and some of them were branched at O-6 position by α-L-Fucp-(1→2)-β-D-Xylp groups. Its Mw was 35.9 kDa. FXM was tested on melanoma B16-F10 cells and it showed cell viability and cell density reduction, as well as antiproliferative effect, through cell cycle arrest. Additionally, the anchorage-independent clonogenic capacity of such cells was significantly reduced by FXM, decreasing the number of cells by colony and the colonies area. No effect on viability neither in proliferation of non-tumoral Balb c/3T3 fibroblasts was observed. These results indicate that FXM is a promising anti-proliferative compound impairing pivotal tumorigenic mechanisms, eliciting this polysaccharide to be further explored as an antimelanoma drug.
heteropolysaccharide, antitumor activity, Ganoderma lucidum, antimelanoma, fucoxylomannan
Structure type: polymer chemical repeating unit
Location inside paper: p. 119823-7
Trivial name: polysaccharide BSF‑A
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_1394182,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_983930,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, GLC, HPSEC, extraction, acetylation, statistical analysis, partial hydrolysis, flow cytometry analysis, cell viability assay, cytotoxicity assay, antitumor activity assay, DEPT-135, soft agar assay, cell cycle analysis
Biological activity: BSF‑A had anticancer activities that affected cell apoptosis in the human laryngeal carciona Hep‑2 cell line proliferation in concentrations from 25 to 400 μg⋅mL-1 while not affecting human hepatoma HepG2 cancer cell line. Additionally, 40 mg⋅kg-1 of the same polysaccharide reduced in vivo S180 tumor growth in Kunming mice.
Comments, role: structure from Hou Y et al., (2014) Mol Med Rep 9(4), 1337–1344, DOI:10.3892/mmr.2014.1976.
Related record ID(s): 51612
NCBI Taxonomy refs (TaxIDs): 374761
Show glycosyltransferases
There is only one chemically distinct structure:
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