A low molecular weight polysaccharides of HEP-1, with molecular weights of 1.67 × 104 Da and composition of →6)-β-D-Glcp-(1→, →3)-β-D-Glcp-(1→, β-D-Glcp-(1→ and →3,6)-β-D-Glcp-(1→, was isolated and characterized from the fruiting body of Hericium erinaceus. The results indicated that HEP-1 showed potential effects against T2DM-induced imbalance of glucose and lipid metabolism by promoting the serum glucose uptake by hepatic glycogen synthesis via activating the IRS/PI3K/AKT signaling pathway, and inhibiting fatty acid synthesis and reducing hepatic lipid accumulation via activating the AMPK/SREBP-1c signaling pathways. Besides, HEP-1 promoted the production of beneficial bacteria in the gut, and increased the beneficial metabolites in liver through the gut-liver axis, consequently, resisting the occurrence of T2DM.

Hericium erinaceus, gut microbiota, metabonomics, T2DM

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,3	bDGlcp
6,6	bDGlcp	103.00	73.06	84.23	69.62	75.53	68.85
6,3,3	bDGlcp
6,3	bDGlcp	103.00	73.32	84.23	69.62	76.00	60.72
6	bDGlcp	103.00	73.06	84.23	69.62	75.53	68.85
6,6,6	bDGlcp	103.00	72.84	75.66	69.57	75.43	60.70
	bDGlcp	103.00	73.05	75.58	69.48	74.90	68.85


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,3	bDGlcp
6,6	bDGlcp	4.48	3.46	3.69	3.34	3.45	4.15
6,3,3	bDGlcp
6,3	bDGlcp	4.68	3.28	3.69	3.34	3.46	3.67
6	bDGlcp	4.48	3.46	3.69	3.34	3.45	4.15
6,6,6	bDGlcp	4.48	3.47	3.68	3.34	3.44	3.84
	bDGlcp	4.46	3.26	3.44	3.41	3.57	3.80


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,3	bDGlcp
6,6	bDGlcp	103.00/4.48	73.06/3.46	84.23/3.69	69.62/3.34	75.53/3.45	68.85/4.15
6,3,3	bDGlcp
6,3	bDGlcp	103.00/4.68	73.32/3.28	84.23/3.69	69.62/3.34	76.00/3.46	60.72/3.67
6	bDGlcp	103.00/4.48	73.06/3.46	84.23/3.69	69.62/3.34	75.53/3.45	68.85/4.15
6,6,6	bDGlcp	103.00/4.48	72.84/3.47	75.66/3.68	69.57/3.34	75.43/3.44	60.70/3.84
	bDGlcp	103.00/4.46	73.05/3.26	75.58/3.44	69.48/3.41	74.90/3.57	68.85/3.80

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

Warning = sub-repeat ending at bDGlcp: unknown unit count was assumed to be 3
Warning = sub-repeat ending at bDGlcp: unknown unit count was assumed to be 3
OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3[C@@H](O)[C@H](O[C@@H]4[C@@H](O)[C@H](O[C@H]5[C@H](O)[C@@H](CO[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO[C@@H]8O[C@H](CO[C@@H]9O[C@H](CO[C@@H]%10O[C@H](CO[C@@H]%11O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%11O)[C@@H](O)[C@H](O[C@@H]%11O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%11O)[C@H]%10O)[C@@H](O)[C@H](O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O[C@@H]%11O[C@H](CO)[C@@H](O)[C@H](O[C@@H]%12O[C@H](CO)[C@@H](O)[C@H](O[C@@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%13O)[C@H]%12O)[C@H]%11O)[C@H]%10O)[C@H]9O)[C@@H](O)[C@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O)[C@@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O[C@@H]%11O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%11O)[C@H]%10O)[C@H]9O)[C@H]8O)[C@H]7O)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)O[C@@H](OC[C@H]6O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]6O)[C@@H]5O)O[C@H](CO)[C@H]4O)O[C@H](CO)[C@H]3O)O[C@H](CO)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

3747.258 g/mol (C₁₃₈H₂₃₂O₁₁₆)

Recent studies have found that many marine microbial polysaccharides exhibit distinct immune activity. However, there is a relative scarcity of research on the immunomodulatory activity of marine fungal exopolysaccharides. A novel water-soluble fungal exopolysaccharide ASP-1 was isolated from the fermentation broths of marine coral-associated fungus Aspergillus pseudoglaucus SCAU265, and purified by Diethylaminoethyl-Sepharose-52 (DEAE-52) Fast Flow and Sephadex G-75. Structural analysis revealed that ASP-1 had an average molecular weight of 36.07 kDa and was mainly composed of (1→4)-linked α-D-glucopyranosyl residues, along with highly branched heteropolysaccharide regions containing 1,4,6-glucopyranosyl, 1,3,4-glucopyranosyl, 1,4,6-galactopyranosyl, T(terminal)-glucopyranosyl, T-mannopyranosyl, and T-galactopyranosyl residues. ASP-1 demonstrated significant effects on the proliferation, nitric oxide levels, and the secretion of cytokines TNF-α and IL-6 in macrophage RAW264.7 cells. Metabolomic analysis provided insights into the potential mechanisms of the immune regulation of ASP-1, suggesting its involvement in regulating immune function by modulating amino acid anabolism, particularly arginine synthesis and metabolism. These findings provide fundamental scientific data for further research on its accurate molecular mechanism of immunomodulatory activity.

exopolysaccharide, immunomodulatory activity, amino acid metabolism, coral-associated Aspergillus pseudoglaucus SCAU265

1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4,4,6,4,4,3,4,2,4,6,4,3,4	bDManp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,4	aDGalp	5.29	3.58	3.83	4.19	3.93	3.72
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,4,6,4	bDManp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,4,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,4,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,4,4	aDGalp	5.29	3.58	3.83	4.19	3.93	3.72
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,4	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,4,3	aDGalp
4,4,4,6,4,4,3,4,2,4,6,4	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,4	bDManp
4,4,4,6,4,4,3,4,2,4,6,3,6,4	aDGalp	5.29	3.58	3.83	4.19	3.93	3.72
4,4,4,6,4,4,3,4,2,4,6,3,6,6,4,6,4	bDManp
4,4,4,6,4,4,3,4,2,4,6,3,6,6,4,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,6,6,4,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,6,6,4,4	aDGalp	5.29	3.58	3.83	4.19	3.93	3.72
4,4,4,6,4,4,3,4,2,4,6,3,6,6,4	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,6,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,6,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3,6	aDGlcp
4,4,4,6,4,4,3,4,2,4,6,3	aDGalp
4,4,4,6,4,4,3,4,2,4,6	aDGlcp	4.91	3.51	3.87	3.51	3.83	3.88
4,4,4,6,4,4,3,4,2,4	bDGlcp	4.81	3.50	4.61	3.51	3.94	3.60
4,4,4,6,4,4,3,4,2,6	bDManp	5.27	3.55	3.64	3.87	4.08	3.46
4,4,4,6,4,4,3,4,2	aDGalp	5.28	3.54	3.81	3.57	3.74	3.60
4,4,4,6,4,4,3,4	aDManp	5.27	3.56	3.92	3.79	3.64	3.75
4,4,4,6,4,4,3,6	bDManp	5.27	3.55	3.64	3.87	4.08	3.46
4,4,4,6,4,4,3	aDGalp	5.28	3.54	3.81	3.57	3.74	3.60
4,4,4,6,4,4	aDGlcp	5.27	3.55	3.89	3.87	3.57	3.66-3.84
4,4,4,6,4	aDGlcp	5.33	3.55	3.73	3.58	3.93	3.69
4,4,4,6,4,4,3,4,2,4,6,4,4	aDGlcp	4.89	3.52	3.58	3.34	3.58	3.69
4,4,4,6	aDGlcp
4,4,4	aDGlcp	4.89	3.57	3.65	3.75	3.85	3.75
4,4,6	aDGlcp	4.89	3.52	3.58	3.34	3.58	3.69
4,4	aDGlcp	4.89	3.57	3.65	3.75	3.85	3.75
4,6	aDGlcp	4.89	3.52	3.58	3.34	3.58	3.69
4	aDGlcp	4.89	3.57	3.65	3.75	3.85	3.75
6	aDGlcp	4.89	3.52	3.58	3.34	3.58	3.69
	aDGlcp

SMILES errors: -4)[aDGlcp(1-4)/[bDManp(1-4)[aDGalp(1-4)[bDManp(1-4)/[aDGlcp(1-6)]aDGlcp(1-6)[aDGalp(1-4)]aDGlcp(1-4)/n=2/[aDGlcp(1-6)]aDGlcp(1-6)]aDGlcp(1-6)]aDGalp(1-3)]aDGlcp(1-4)[bDManp(1-4)[aDGalp(1-4)[bDManp(1-4)/[aDGlcp(1-6)]aDGlcp(1-6)[aDGalp(1-4)]aDGlcp(1-4)/n=2/[aDGlcp(1-6)]aDGlcp(1-6)]aDGlcp(1-6)]aDGalp(1-3)]aDGlcp(1-6)bDGlcp(1-4)[bDManp(1-6)]aDGalp(1-2)aDManp(1-4)[bDManp(1-6)]aDGalp(1-3)aDGlcp(1-4)/n=2//aDGlcp(1-4)/n=163/aDGlcp(1-6)]aDGlcp(1-4)[aDGlcp(1-6)]aDGlcp(1-4)[aDGlcp(1-6)]aDGlcp(1-4)[aDGlcp(1-6)]aDGlcp(1-:
SMILES error: number of atoms (~1012) exceeds a structural formula limit (500)

The water-soluble Morchella esculenta polysaccharide 2 (MEP2) was purified and isolated from an aqueous extract of the Morchella esculenta fruiting bodies. MEP2, having a molecular weight of 959 kDa, has a →4)-α-D-Glcp-(1→ glucan backbone, and this branch was substituted at the H-6 position by an α-D-Glcp-(1 → 4)-α-D-Glcp-(1→ residue and an α-D-Glcp-(1→ residue. The hepatoprotective activity and potential mechanism of action of MEP2 were also investigated. MEP2 ameliorated severe liver damage and regulated the liver function indicators and the alcohol-related enzyme levels in chronic alcohol-induced mice. Combined with biochemical detection, the gut microbiota, metabolites, and proteomics results revealed that MEP2 regulates the levels of hepatic cytokines related to inflammatory response and oxidative stress, as well as those of intestinal Bacteroides, Oscillospira, Parabacteroides, Alistipes, and Prevotella, through the ubiquitin-specific peptidase 10 (Usp10)/nuclear factor κB (NF-κB)/nuclear factor erythroid-2 related factor 2 (Nrf2) signaling pathway in the liver of mice induced by long-term alcohol intake. These data provide experimental evidence for the application of MEP2 in chronic alcohol-induced liver injury.

inflammation, oxidative stress, gut microbiota, alcohol liver disease, MEP2, Usp10/NF-kB/Nrf2

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,4,6,4	aDGlcp	98.61	71.66	72.86	72.75	73.03	60.52
4,4,6	%aDGlcp
4,4	aDGlcp	100.08	71.89	73.49	77.24	71.21	69.40
4	aDGlcp	99.87	71.57	73.37	77.04	71.04	60.61
	aDGlcp


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4,6,4	aDGlcp	4.89	3.52	3.58	3.34	3.58	3.62-3.69
4,4,6	%aDGlcp
4,4	aDGlcp	5.29	3.56	3.90	3.58	3.76	3.79-3.92
4	aDGlcp	5.31	3.56	3.88	3.58	3.76	3.76-3.81
	aDGlcp


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4,4,6,4	aDGlcp	98.61/4.89	71.66/3.52	72.86/3.58	72.75/3.34	73.03/3.58	60.52/3.62-3.69
4,4,6	%aDGlcp
4,4	aDGlcp	100.08/5.29	71.89/3.56	73.49/3.90	77.24/3.58	71.21/3.76	69.40/3.79-3.92
4	aDGlcp	99.87/5.31	71.57/3.56	73.37/3.88	77.04/3.58	71.04/3.76	60.61/3.76-3.81
	aDGlcp

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]O[C@@H]1[C@@H](CO[C@H]2O[C@H](CO)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H]([*])[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

810.705 g/mol (C₃₀H₅₀R₂O₂₅, R = next and previous repeats, not counted in mol weight)

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

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

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