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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 35621983
Publication DOI: 10.3390/md20050332
Journal NLM ID: 101213729
Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: R. Huang <huangriming

scau.edu.cn>
Institutions: Guangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Guangzhou, China, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China, Joint Laboratory of Guangdong Province and Hong Kong Region on Marine Bioresource Conservation and Exploitation, College of Marine Sciences, South China Agricultural University, Guangzhou, China, Department of Food Sciences, University of Otago, P.O. Box 56, Dunedin 9054, New Zealand, Food Science and Technology Program, Beijing Normal University-Hong Kong Baptist University-United International College, Zhuhai 519087, China

Marine fungi represent an important and sustainable resource, from which the search for novel biological substances for application in the pharmacy or food industry offers great potential. In our research, novel polysaccharide (AUM-1) was obtained from marine Aureobasidium melanogenum SCAU-266 were obtained and the molecular weight of AUM-1 was determined to be 8000 Da with 97.30% of glucose, 1.9% of mannose, and 0.08% galactose, owing to a potential backbone of α-D-Glcp-(1→2)-α-D-Manp-(1→4)-α-D-Glcp-(1→6)-(SO3-)-4-α-D-Glcp-(1→6)-1-β-D-Glcp-1→2)-α-D-Glcp-(1→6)-β-D-Glcp-1→6)-α-D-Glcp-1→4)-α-D-Glcp-6→1)-[α-D-Glcp-4]26→1)-α-D-Glcp and two side chains that consisted of α-D-Glcp-1 and α-D-Glcp-(1→6)-α-D-Glcp residues. The immunomodulatory effect of AUM-1 was identified. Then, the potential molecular mechanism by which AUM-1 may be connected to ferroptosis was indicated by metabonomics, and the expression of COX2, SLC7A11, GPX4, ACSL4, FTH1, and ROS were further verified. Thus, we first speculated that AUM-1 has a potential effect on the ferroptosis-related immunomodulatory property in RAW 264.7 cells by adjusting the expression of GPX4, regulated glutathione (oxidative), directly causing lipid peroxidation owing to the higher ROS level through the glutamate metabolism and TCA cycle. Thus, the ferroptosis related immunomodulatory effect of AUM-1 was obtained.

polysaccharide, Structural characterization, immunomodulatory, Aureobasidium melanogenum, ferroptosis

Structure type: cyclic polymer repeating unit ; 8000
Location inside paper: Fig. 2f, table 2
Trivial name: polysaccharide AUM-1
Contained glycoepitopes: IEDB_130701,IEDB_140628,IEDB_140629,IEDB_141806,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_158538,IEDB_420417,IEDB_420418,IEDB_420419,IEDB_420421,IEDB_857742,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, anion-exchange chromatography, Western blotting, FTIR, UV, statistical analysis, determination of NO production, cytokine production, HPGPC, BLAST, cultivation, immunomodulatory activity analysis, ROS measurement, immunofluorescence staining, metabolites analysis
Comments, role: NMR temperature was not specified; published erroneous NMR chemical shifts of C5 #4,6,6_aDGlcp (63.84) was removed by CSDB staff

NCBI Taxonomy refs (TaxIDs): 46634
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,4	aDGlcp	101.69	71.96	72.22	79.68	71.08	60.86
4,4,4,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,4,4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,4,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2,6,6,4,2	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,6,6,2,6,6,4	aDManp	101.52	76.30	68.95	65.20	71.77	60.04
4,6,6,2,6,6,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,6,6,2,6,6	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2,6,4	S
4,6,6,2,6	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2	bDGlcp	98.72	70.70	73.40	70.40	71.33	71.40
4,6,6	aDGlcp	102.88	77.20	71.33	73.94	?	62.32
4,6	bDGlcp	98.72	70.70	73.40	70.40	71.33	71.40
4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
6,4,4	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
6	aDGlcp
	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,4	aDGlcp	5.41	3.62	3.73	3.68	3.93	3.69
4,4,4,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,4,4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,4,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2,6,6,4,2	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,6,6,2,6,6,4	aDManp	4.97	3.89	3.92	3.79	3.64	3.75
4,6,6,2,6,6,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,6,6,2,6,6	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2,6,4	S
4,6,6,2,6	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2	bDGlcp	4.97	3.56	4.61	3.51	3.94	3.64
4,6,6	aDGlcp	5.26	3.60	3.72	3.29	3.62	3.92
4,6	bDGlcp	4.97	3.56	4.61	3.51	3.94	3.64
4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
6,4,4	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
6	aDGlcp
	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,4	aDGlcp	101.69/5.41	71.96/3.62	72.22/3.73	79.68/3.68	71.08/3.93	60.86/3.69
4,4,4,6	aDGlcp	102.72/5.38	71.94/3.60	74.03/3.70	70.61/3.95	71.68/3.97	62.30/3.60
4,4,4	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71
4,4,6	aDGlcp	102.72/5.38	71.94/3.60	74.03/3.70	70.61/3.95	71.68/3.97	62.30/3.60
4,4	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71
4,6,6,2,6,6,4,2	aDGlcp	102.72/5.38	71.94/3.60	74.03/3.70	70.61/3.95	71.68/3.97	62.30/3.60
4,6,6,2,6,6,4	aDManp	101.52/4.97	76.30/3.89	68.95/3.92	65.20/3.79	71.77/3.64	60.04/3.75
4,6,6,2,6,6,6	aDGlcp	102.72/5.38	71.94/3.60	74.03/3.70	70.61/3.95	71.68/3.97	62.30/3.60
4,6,6,2,6,6	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71
4,6,6,2,6,4	S
4,6,6,2,6	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71
4,6,6,2	bDGlcp	98.72/4.97	70.70/3.56	73.40/4.61	70.40/3.51	71.33/3.94	71.40/3.64
4,6,6	aDGlcp	102.88/5.26	77.20/3.60	71.33/3.72	73.94/3.29	?/3.62	62.32/3.92
4,6	bDGlcp	98.72/4.97	70.70/3.56	73.40/4.61	70.40/3.51	71.33/3.94	71.40/3.64
4	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71
6,4,4	aDGlcp	102.72/5.38	71.94/3.60	74.03/3.70	70.61/3.95	71.68/3.97	62.30/3.60
6	aDGlcp
	aDGlcp	101.01/4.99	75.73/3.57	74.02/3.65	76.01/3.68	74.60/3.85	68.47/3.71

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,4	aDGlcp	5.41	3.62	3.73	3.68	3.93	3.69
4,4,4,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,4,4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,4,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2,6,6,4,2	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,6,6,2,6,6,4	aDManp	4.97	3.89	3.92	3.79	3.64	3.75
4,6,6,2,6,6,6	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
4,6,6,2,6,6	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2,6,4	S
4,6,6,2,6	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
4,6,6,2	bDGlcp	4.97	3.56	4.61	3.51	3.94	3.64
4,6,6	aDGlcp	5.26	3.60	3.72	3.29	3.62	3.92
4,6	bDGlcp	4.97	3.56	4.61	3.51	3.94	3.64
4	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71
6,4,4	aDGlcp	5.38	3.60	3.70	3.95	3.97	3.60
6	aDGlcp
	aDGlcp	4.99	3.57	3.65	3.68	3.85	3.71

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,4	aDGlcp	101.69	71.96	72.22	79.68	71.08	60.86
4,4,4,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,4,4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,4,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2,6,6,4,2	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,6,6,2,6,6,4	aDManp	101.52	76.30	68.95	65.20	71.77	60.04
4,6,6,2,6,6,6	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
4,6,6,2,6,6	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2,6,4	S
4,6,6,2,6	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
4,6,6,2	bDGlcp	98.72	70.70	73.40	70.40	71.33	71.40
4,6,6	aDGlcp	102.88	77.20	71.33	73.94	?	62.32
4,6	bDGlcp	98.72	70.70	73.40	70.40	71.33	71.40
4	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47
6,4,4	aDGlcp	102.72	71.94	74.03	70.61	71.68	62.30
6	aDGlcp
	aDGlcp	101.01	75.73	74.02	76.01	74.60	68.47

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

There is only one chemically distinct structure:

[*]O[C@@H]1[C@@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](O[C@@H]2[C@@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O[C@H](O[C@@H]3[C@@H](CO[C@@H]4O[C@H](CO[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@H](CO[C@H]6O[C@H](CO[C@H]7O[C@H](CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H](OS(=O)(=O)O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)O[C@H](O[C@@H]4[C@@H](CO[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]9O[C@H](CO)[C@@H](O[C@H]%10O[C@H](CO)[C@@H](O[C@H]%11O[C@H](CO)[C@@H](O)[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)O[C@H]([*])[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at aDGlcp: large unit count (25) was reduced to 5