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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 36535356
Publication DOI: 10.1016/j.ijbiomac.2022.12.127
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: R. Huang <huangriming

scau.edu.cn>; X. Zhang <zhangxiaoyong

scau.edu.cn>
Institutions: Food Science and Technology Program, Beijing Normal University-Hong Kong Baptist University-United International College, Zhuhai 519087, China, Guangdong Provincial Key Laboratory of Nutraceuticals and Functional Foods, College of Food Science, South China Agricultural University, Guangzhou 510642, China, University Joint Laboratory of Guangdong Province, Hong Kong and Macao Region on Marine Bioresource Conservation and Exploitation, College of Marine Sciences, South China Agricultural University, Guangzhou, Guangdong 510642, China

Until now, relatively little is known about marine-derived fungal polysaccharides and their activities. Exopolysaccharide AVP141-A was isolated from the broth of marine-derived fungus Aspergillus versicolor SCAU141 and purified by Diethylaminoethyl-Sepharose Fast Flow and Sephadex G-100. The structural characteristics of AVP141-A was studied by chemical analysis together with high-performance gel permeation chromatography, ion chromatography, Fourier-transform infrared spectroscopy, gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. The results showed that AVP141-A with the molecular weight of 5.10 kDa was mainly composed of →4)-α-D-Glcp-(1→, branched by α-D-Glcp-(1→ and →6)-α-D-Glcp-(1→ at C-6 positions of the glucan backbone. In particular, sulfate ester (approximately 3.62 %) was found in AVP141-A, which was frequently considered to occur in marine-derived microbial polysaccharides rather than other microbial polysaccharides. Furthermore, AVP141-A significantly enhanced the activity of the inflammatory factors NO, COX-2 and TNF-α in RAW264.7 macrophages by activating the MAPK/p38 and NF-κB/p65 pathways. In addition, metabolomic analysis revealed that most of the pathways with significant changes in RAW264.7 macrophages treated with AVP141-A were amino acid-related pathways, and arginine was the characteristic metabolite. In conclusion, this study identified AVP141-A as a marine fungus-derived sulfated exopolysaccharide with potential for development as an immune activator.

marine-derived fungus, amino acid metabolism, RAW264.7 macrophages

Structure type: structural motif or average structure ; 5100
Location inside paper: table 2, Fig. 2G, AVP141-A
Trivial name: polysaccharide AVP141-A
Compound class: EPS

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, sugar analysis, Western blotting, FTIR, extraction, statistical analysis, cell viability assay, HPGPC, immunomodulatory activity analysis, immunofluorescence staining, metabolomics analysis, ROS, IC
Comments, role: possible chemical structure of AVP141-A; NMR temperature was not specified; total number of aDGlcp(1-4) residues ~ 12. Published erroneous NMR chemical shifts of C1 #4,4,6_aDGlcp (91.98) was removed by CSDB staff.

NCBI Taxonomy refs (TaxIDs): 46472
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,4,4,4,4,4,4	aDGlcp	99.97	73.30	70.30	77.52	72.94	60.75
4,4,4,4,4,4	aDGlcp
4,4,4,4,4,6	aDGlcp	98.84	72.99	72.83	69.70	72.97	60.78
4,4,4,4,4	aDGlcp	98.10	74.58	73.14	77.38	74.40	70.42
4,4,4,4	aDGlcp
4,4,4	aDGlcp
4,4,6,6	S
4,4,6	aDGlcp	?	71.56	72.79	71.87	71.40	69.45
4,4	aDGlcp	98.10	74.58	73.14	77.38	74.40	70.42
4	aDGlcp	99.97	73.30	70.30	77.52	72.94	60.75
	aDGlcp


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4,4,4,4,4,4	aDGlcp	5.41	3.62	3.73	3.57	3.86	3.75
4,4,4,4,4,4	aDGlcp
4,4,4,4,4,6	aDGlcp	5.00	3.57	3.76	3.45	3.79	3.87
4,4,4,4,4	aDGlcp	4.98	3.58	3.78	3.69	3.87	3.73
4,4,4,4	aDGlcp
4,4,4	aDGlcp
4,4,6,6	S
4,4,6	aDGlcp	5.25	3.59	3.76	3.67	3.88	3.77
4,4	aDGlcp	4.98	3.58	3.78	3.69	3.87	3.73
4	aDGlcp	5.41	3.62	3.73	3.57	3.86	3.75
	aDGlcp


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4,4,4,4,4,4,4	aDGlcp	99.97/5.41	73.30/3.62	70.30/3.73	77.52/3.57	72.94/3.86	60.75/3.75
4,4,4,4,4,4	aDGlcp
4,4,4,4,4,6	aDGlcp	98.84/5.00	72.99/3.57	72.83/3.76	69.70/3.45	72.97/3.79	60.78/3.87
4,4,4,4,4	aDGlcp	98.10/4.98	74.58/3.58	73.14/3.78	77.38/3.69	74.40/3.87	70.42/3.73
4,4,4,4	aDGlcp
4,4,4	aDGlcp
4,4,6,6	S
4,4,6	aDGlcp	?/5.25	71.56/3.59	72.79/3.76	71.87/3.67	71.40/3.88	69.45/3.77
4,4	aDGlcp	98.10/4.98	74.58/3.58	73.14/3.78	77.38/3.69	74.40/3.87	70.42/3.73
4	aDGlcp	99.97/5.41	73.30/3.62	70.30/3.73	77.52/3.57	72.94/3.86	60.75/3.75
	aDGlcp

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4,4,4,4,4,4	aDGlcp	5.41	3.62	3.73	3.57	3.86	3.75
4,4,4,4,4,4	aDGlcp
4,4,4,4,4,6	aDGlcp	5.00	3.57	3.76	3.45	3.79	3.87
4,4,4,4,4	aDGlcp	4.98	3.58	3.78	3.69	3.87	3.73
4,4,4,4	aDGlcp
4,4,4	aDGlcp
4,4,6,6	S
4,4,6	aDGlcp	5.25	3.59	3.76	3.67	3.88	3.77
4,4	aDGlcp	4.98	3.58	3.78	3.69	3.87	3.73
4	aDGlcp	5.41	3.62	3.73	3.57	3.86	3.75
	aDGlcp

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
4,4,4,4,4,4,4	aDGlcp	99.97	73.30	70.30	77.52	72.94	60.75
4,4,4,4,4,4	aDGlcp
4,4,4,4,4,6	aDGlcp	98.84	72.99	72.83	69.70	72.97	60.78
4,4,4,4,4	aDGlcp	98.10	74.58	73.14	77.38	74.40	70.42
4,4,4,4	aDGlcp
4,4,4	aDGlcp
4,4,6,6	S
4,4,6	aDGlcp	?	71.56	72.79	71.87	71.40	69.45
4,4	aDGlcp	98.10	74.58	73.14	77.38	74.40	70.42
4	aDGlcp	99.97	73.30	70.30	77.52	72.94	60.75
	aDGlcp

The spectrum also has 1 signal at unknown position (not plotted).

SMILES errors: -4)/aDGlcp(1-4)/n=?//aDGlcp(1-4)[aDGlcp(1-6)]aDGlcp(1-4)/n=4//aDGlcp(1-4)/n=?//aDGlcp(1-4)[S-6)aDGlcp(1-6)]aDGlcp(1-4)/n=2//aDGlcp(1-4)/n=?/aDGlcp(1-:
SMILES error: could not calculate brutto descriptors of a molecule from SMILES [*]O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H](CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)O[C@H](O[C@@H]8[C@@H](CO)O[C@H](O[C@@H]9[C@@H](CO[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%10O)O[C@H](O[C@@H]%10[C@@H](CO)O[C@H](O[C@@H]%11[C@@H](CO[C@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@H](O[C@@H]%12[C@@H](CO)O[C@H](O[C@@H]%13[C@@H](CO)O[C@H](O[C@@H]%14[C@@H](CO)O[C@H](O[C@@H]%15[C@@H](CO)O[C@H](O[C@@H]%16[C@@H](CO[C@H]%17O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]%17O)O[C@H](O[C@@H]%17[C@@H](CO)O[C@H](O[C@@H]%18[C@@H](CO[C@H]%19O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]%19O)O[C@H](O[C@@H]%19[C@@H](CO)O[C@H](O[C@@H]%20[C@@H](CO)O[C@H](O[C@@H]%21[C@@H](CO)O[C@H](O[C@@H]%22[C@@H](CO)O[C@H]([*])[C@H](O)[C@H]%22O)[C@H](O)[C@H]%21O)[C@H](O)[C@H]%20O)[C@H](O)[C@H]%19O)[C@H](O)[C@H]%18O)[C@H](O)[C@H]%17O)[C@H](O)[C@H]%16O)[C@H](O)[C@H]%15O)[C@H](O)[C@H]%14O)[C@H](O)[C@H]%13O)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
Invalid SMILES [*]O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H](CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)O[C@H](O[C@@H]8[C@@H](CO)O[C@H](O[C@@H]9[C@@H](CO[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%10O)O[C@H](O[C@@H]%10[C@@H](CO)O[C@H](O[C@@H]%11[C@@H](CO[C@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@H](O[C@@H]%12[C@@H](CO)O[C@H](O[C@@H]%13[C@@H](CO)O[C@H](O[C@@H]%14[C@@H](CO)O[C@H](O[C@@H]%15[C@@H](CO)O[C@H](O[C@@H]%16[C@@H](CO[C@H]%17O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]%17O)O[C@H](O[C@@H]%17[C@@H](CO)O[C@H](O[C@@H]%18[C@@H](CO[C@H]%19O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]%19O)O[C@H](O[C@@H]%19[C@@H](CO)O[C@H](O[C@@H] [C@@H](CO)O[C@H](O[C@@H]%21[C@@H](CO)O[C@H](O[C@@H]"[C@@H](CO)O[C@H]([*])[C@H](O)[C@H]"O)[C@H](O)[C@H]%21O)[C@H](O)[C@H] O)[C@H](O)[C@H]%19O)[C@H](O)[C@H]%18O)[C@H](O)[C@H]%17O)[C@H](O)[C@H]%16O)[C@H](O)[C@H]%15O)[C@H](O)[C@H]%14O)[C@H](O)[C@H]%13O)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O