Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperNCBI PubMed ID: 25785351Publication DOI: 10.1021/jf505915tJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Yu R <tyrm
jnu.edu.cn>; Zhu J <tzhujh
jnu.edu.cn>; Song L <tsly
jnu.edu.cn>
Institutions: Biotechnological Institute of Chinese Materia Medica, Jinan University, Guangzhou, China, College of Chemistry and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang, China, College of Pharmacy, Department of Natural Medicinal Chemistry, Jinan University, Guangzhou, China, College of Pharmacy, Department of Pharmacology, Jinan University, Guangzhou, China
A novel polysaccharide (CMPA90-1; compound 1) was isolated from the cultured fruiting bodies of Cordyceps militaris. The chemical structure of compound 1 was elucidated by acid hydrolysis, periodate oxidation, Smith degradation, and methylation analysis, along with Fourier transform infrared spectroscopy, high-performance anion-exchange chromatography coupled with pulsed amperometric detection, gas chromatography-mass spectrometry, and one-dimensional [1H and 13C nuclear magnetic resonance (NMR)] and two-dimensional NMR (heteronuclear single-quantum coherence and heteronuclear multiple-bond correlation). Sulfation of compound 1 by the chlorosulfonic acid-pyridine (CSA-Pyr) method led to synthesis of its sulfated analogue (CMPA90-M1; compound 2). The ultrastructures of both compounds 1 and 2 were further characterized by scanning electron microscopy and atomic force microscopy. The results of antioxidant assays showed that compounds 1 and 2 exhibited free-radical-scavenging effects, ferrous-ion-chelating ability, and reducing power. Also, in the cytotoxicity assay, compounds 1 and 2 showed inhibitory activity against A549 cells, with IC50 values of 39.08 and 17.33 μg/mL, respectively
polysaccharide, Structural characterization, Antioxidant activity, antitumor activity, Cordyceps militaris, sulfated modification
Structure type: structural motif or average structure ; 9300
Location inside paper: Fig. 3, Table 3
Compound class: polysaccharide, arabinogalactomannan
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_1394182,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_742246,IEDB_918313,IEDB_983930,SB_7,SB_87
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, IR, GC-MS, acid hydrolysis, GC, Smith degradation, HPAEC-PAD, colorimetry, extraction, periodate oxidation, optical rotation measurement, acetylation, methylation analysis, reduction, column chromatography, gel permeation chromatography, dialysis, cytotoxicity assay, reducing sugar assays, precipitation, phenol-sulfuric acid assay, spectrophotometry, carbazole-sulfuric acid assay, radical scavenging assay, SEM, derivatization, evaporation, centrifugation, AFM
Biological activity: polysaccharide exhibits the capability of anti-proliferation in A549 cells, with the IC50 values of 39.08 μg/mL. Polysaccharide exhibits free radical-scavenging activity, ferrous ion-chelating ability and reducing power
NCBI Taxonomy refs (TaxIDs): 73501Reference(s) to other database(s): GTC:G81066SC
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,6,5 aLAraf 105.89 81.53 78.35 86.86 68.40
3,6,2 aLMan? 99.33 75.50 66.03 65.99 72.80 60.86
6,3 bLAra? 104.15 73.92 81.11 73.04 61.10
3,3,6,5,5 aLMan? 100.60 69.40 69.89 66.20 72.50 60.86
3,3,6 aLAraf 105.89 81.53 78.35 86.86 68.40
3,3 aDGal? 98.08 70.62 76.00 70.01 74.78 67.20
3,6,2,2 aLMan? 100.60 69.40 69.89 66.20 72.50 60.86
3,6 aLMan? 99.33 75.50 66.03 65.99 72.80 60.86
3 aDGal? 98.08 70.62 76.00 70.01 74.78 67.20
6,3,3 aLMan? 100.60 69.40 69.89 66.20 72.50 60.86
6 bLAra? 104.15 73.92 81.11 73.04 61.10
aDGal? 98.08 70.62 76.00 70.01 74.78 67.20
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,6,5 aLAraf 5.04 4.01 4.05 4.12 3.85
3,6,2 aLMan? 5.10 4.10 3.85 3.59 3.61 3.85
6,3 bLAra? 5.12 4.10 3.74 3.68 3.80
3,3,6,5,5 aLMan? 5.07 4.00 3.87 3.95 3.72 3.68
3,3,6 aLAraf 5.04 4.01 4.05 4.12 3.85
3,3 aDGal? 4.98 3.48 4.05 3.95 4.17 3.75
3,6,2,2 aLMan? 5.07 4.00 3.87 3.95 3.72 3.68
3,6 aLMan? 5.10 4.10 3.85 3.59 3.61 3.85
3 aDGal? 4.98 3.48 4.05 3.95 4.17 3.75
6,3,3 aLMan? 5.07 4.00 3.87 3.95 3.72 3.68
6 bLAra? 5.12 4.10 3.74 3.68 3.80
aDGal? 4.98 3.48 4.05 3.95 4.17 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,6,5 aLAraf 105.89/5.04 81.53/4.01 78.35/4.05 86.86/4.12 68.40/3.85
3,6,2 aLMan? 99.33/5.10 75.50/4.10 66.03/3.85 65.99/3.59 72.80/3.61 60.86/3.85
6,3 bLAra? 104.15/5.12 73.92/4.10 81.11/3.74 73.04/3.68 61.10/3.80
3,3,6,5,5 aLMan? 100.60/5.07 69.40/4.00 69.89/3.87 66.20/3.95 72.50/3.72 60.86/3.68
3,3,6 aLAraf 105.89/5.04 81.53/4.01 78.35/4.05 86.86/4.12 68.40/3.85
3,3 aDGal? 98.08/4.98 70.62/3.48 76.00/4.05 70.01/3.95 74.78/4.17 67.20/3.75
3,6,2,2 aLMan? 100.60/5.07 69.40/4.00 69.89/3.87 66.20/3.95 72.50/3.72 60.86/3.68
3,6 aLMan? 99.33/5.10 75.50/4.10 66.03/3.85 65.99/3.59 72.80/3.61 60.86/3.85
3 aDGal? 98.08/4.98 70.62/3.48 76.00/4.05 70.01/3.95 74.78/4.17 67.20/3.75
6,3,3 aLMan? 100.60/5.07 69.40/4.00 69.89/3.87 66.20/3.95 72.50/3.72 60.86/3.68
6 bLAra? 104.15/5.12 73.92/4.10 81.11/3.74 73.04/3.68 61.10/3.80
aDGal? 98.08/4.98 70.62/3.48 76.00/4.05 70.01/3.95 74.78/4.17 67.20/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,6,5 | aLAraf | 5.04 | 4.01 | 4.05 | 4.12 | 3.85 | |
| 3,6,2 | aLMan? | 5.10 | 4.10 | 3.85 | 3.59 | 3.61 | 3.85 |
| 6,3 | bLAra? | 5.12 | 4.10 | 3.74 | 3.68 | 3.80 | |
| 3,3,6,5,5 | aLMan? | 5.07 | 4.00 | 3.87 | 3.95 | 3.72 | 3.68 |
| 3,3,6 | aLAraf | 5.04 | 4.01 | 4.05 | 4.12 | 3.85 | |
| 3,3 | aDGal? | 4.98 | 3.48 | 4.05 | 3.95 | 4.17 | 3.75 |
| 3,6,2,2 | aLMan? | 5.07 | 4.00 | 3.87 | 3.95 | 3.72 | 3.68 |
| 3,6 | aLMan? | 5.10 | 4.10 | 3.85 | 3.59 | 3.61 | 3.85 |
| 3 | aDGal? | 4.98 | 3.48 | 4.05 | 3.95 | 4.17 | 3.75 |
| 6,3,3 | aLMan? | 5.07 | 4.00 | 3.87 | 3.95 | 3.72 | 3.68 |
| 6 | bLAra? | 5.12 | 4.10 | 3.74 | 3.68 | 3.80 | |
| | aDGal? | 4.98 | 3.48 | 4.05 | 3.95 | 4.17 | 3.75 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,6,5 | aLAraf | 105.89 | 81.53 | 78.35 | 86.86 | 68.40 | |
| 3,6,2 | aLMan? | 99.33 | 75.50 | 66.03 | 65.99 | 72.80 | 60.86 |
| 6,3 | bLAra? | 104.15 | 73.92 | 81.11 | 73.04 | 61.10 | |
| 3,3,6,5,5 | aLMan? | 100.60 | 69.40 | 69.89 | 66.20 | 72.50 | 60.86 |
| 3,3,6 | aLAraf | 105.89 | 81.53 | 78.35 | 86.86 | 68.40 | |
| 3,3 | aDGal? | 98.08 | 70.62 | 76.00 | 70.01 | 74.78 | 67.20 |
| 3,6,2,2 | aLMan? | 100.60 | 69.40 | 69.89 | 66.20 | 72.50 | 60.86 |
| 3,6 | aLMan? | 99.33 | 75.50 | 66.03 | 65.99 | 72.80 | 60.86 |
| 3 | aDGal? | 98.08 | 70.62 | 76.00 | 70.01 | 74.78 | 67.20 |
| 6,3,3 | aLMan? | 100.60 | 69.40 | 69.89 | 66.20 | 72.50 | 60.86 |
| 6 | bLAra? | 104.15 | 73.92 | 81.11 | 73.04 | 61.10 | |
| | aDGal? | 98.08 | 70.62 | 76.00 | 70.01 | 74.78 | 67.20 |
|
There are too many chemically distinct structures (~16384), so only one is shown:
-3)[aLManp(1-5)aLAraf(1-5)aLAraf(1-5)aLAraf(1-5)aLAraf(1-6)]aDGalp(1-3)[aLManp(1-2)aLManp(1-2)aLManp(1-2)aLManp(1-2)aLManp(1-6)]aDGalp(1-3)[aLManp(1-3)bLArap(1-3)bLArap(1-3)bLArap(1-3)bLArap(1-6)]aDGalp(1-
report error
Found 1 record.
Displayed record 1
