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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: thallus

The structure was elucidated in this paper
NCBI PubMed ID: 31078591
Publication DOI: 10.1016/j.ijbiomac.2019.05.056
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: ahensel

uni-muenster.de
Institutions: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Münster, Germany, University of Münster, Institute for Hygiene, Münster, Germany

Hot-water soluble polysaccharides H-1-3 and H-2-1 were isolated from the thalli of the lichen Xanthoria parietina (L.) Th. Fr. and purified by ion exchange and gel permeation chromatography. Structure elucidation was mainly based on 2D-NMR and nano-ESI-Q-TOF MS/MS experiments. H-1-3 (13.7 kDa) was shown to be linear α-glucan with α-D-Glcp-(1 → [→[4)-α-D-Glcp-(1]2 → [6)-α-D-Glcp-(1]3 → 4)]n core backbone. The (1,4)- and (1,6)-α-D-Glcp linkages were in a 2:3 M ratio. H-2-1 (525 kDa) was characterized as a complex branched β-galacto-α-mannan with →[6)-α-D-Manp-(1 → [2,6)-α-D-Manp-(1]2 → [2)-α-D-Manp-(1]2→]n core units and main side chains of (1,3)-β-D-Galf linked at O-6 to →2)-α-D-Manp-(1→, together with minor terminal units of 1,4/1,6-α-D-Glcp units attached to the core chain at O-6 position and α-L-Rhap linked to Galf side chain at O-2 position (Manp: Galf: Glcp: Rhap linkage ratio = 9:3:2:1). H-2-1 exerted strong immunoactivity in vitro and activated murine RAW macrophages 264.7 towards significantly increased phagocytosis, TNF-α and IL-1β secretion. These effects are due to an interaction of the galactomannan with the transmembrane pattern-recognition protein Dectin-2 of the macrophages.

polysaccharides, phagocytosis, Galactomannan, glucan, lichen, mass spectroscopy, Dectin-2, silver adducts, Xanthoria parietina

Structure type: structural motif or average structure ; 13700
Location inside paper: p. 928, Fig. 4, p. 927, Table 3
Compound class: glucan, polysaccharide
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_420419,IEDB_420421,IEDB_857742,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, TLC, acid hydrolysis, GPC, HPSEC, HPAEC-PAD, extraction, acetylation, methylation analysis, ESI-QTOF-MS/MS, reduction, ESI-QTOF-MS, precipitation, macrophage activity assay, ion exchange chromatography, resorcinol-sulfuric acid assay

Related record ID(s): 50069
NCBI Taxonomy refs (TaxIDs): 107463
Reference(s) to other database(s): GTC:G51129ZT
Show glycosyltransferases

NMR conditions: in D2O at 299 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,4	aDGlcp	100.5	72.1	73.4	78.3	69.8	60.9
6,6,6	aDGlcp	100.5	72.1	73.4	78.3	69.8	60.9
6,6	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8
6	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8
	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,4	aDGlcp	5.25	3.50	3.58	3.52	3.37	3.65-3.81
6,6,6	aDGlcp	5.25	3.50	3.58	3.52	3.37	3.65-3.81
6,6	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62-3.87
6	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62-3.87
	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62-3.87


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,6,4	aDGlcp	100.5/5.25	72.1/3.50	73.4/3.58	78.3/3.52	69.8/3.37	60.9/3.65-3.81
6,6,6	aDGlcp	100.5/5.25	72.1/3.50	73.4/3.58	78.3/3.52	69.8/3.37	60.9/3.65-3.81
6,6	aDGlcp	98.3/4.82	71.8/3.50	73.7/3.90	71.5/3.78	70.8/3.72	66.8/3.62-3.87
6	aDGlcp	98.3/4.82	71.8/3.50	73.7/3.90	71.5/3.78	70.8/3.72	66.8/3.62-3.87
	aDGlcp	98.3/4.82	71.8/3.50	73.7/3.90	71.5/3.78	70.8/3.72	66.8/3.62-3.87

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,4	aDGlcp	5.25	3.50	3.58	3.52	3.37	3.65 3.81
6,6,6	aDGlcp	5.25	3.50	3.58	3.52	3.37	3.65 3.81
6,6	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62 3.87
6	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62 3.87
	aDGlcp	4.82	3.50	3.90	3.78	3.72	3.62 3.87

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,4	aDGlcp	100.5	72.1	73.4	78.3	69.8	60.9
6,6,6	aDGlcp	100.5	72.1	73.4	78.3	69.8	60.9
6,6	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8
6	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8
	aDGlcp	98.3	71.8	73.7	71.5	70.8	66.8

There is only one chemically distinct structure:

[*]O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@@H](CO)O[C@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](OC[C@H]5O[C@H]([*])[C@H](O)[C@@H](O)[C@@H]5O)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

uni-muenster.de
Institutions: University of Münster, Institute of Pharmaceutical Biology and Phytochemistry, Münster, Germany, University of Münster, Institute for Hygiene, Münster, Germany

polysaccharides, phagocytosis, Galactomannan, glucan, lichen, mass spectroscopy, Dectin-2, silver adducts, Xanthoria parietina

Structure type: structural motif or average structure ; 525000
Location inside paper: p. 931, Fig. 8, p. 932, Table 5
Compound class: polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_136105,IEDB_137472,IEDB_140116,IEDB_140629,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_164480,IEDB_190606,IEDB_225177,IEDB_76933,IEDB_885823,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, TLC, acid hydrolysis, GPC, HPSEC, HPAEC-PAD, extraction, acetylation, methylation analysis, ESI-QTOF-MS/MS, reduction, ESI-QTOF-MS, precipitation, macrophage activity assay, ion exchange chromatography, resorcinol-sulfuric acid assay

Related record ID(s): 50068
NCBI Taxonomy refs (TaxIDs): 107463
Show glycosyltransferases

NMR conditions: in D2O at 299 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2	aDManp	101.1	79.4	72.5	70.4	71.6	66.4
2,2,2,2,6,6	aDManp	100.1	71.5	74.3	70.4	71.7	69.7
2,2,2,2,6	aDManp	100.1	71.5	74.3	70.4	71.7	69.7
2,2,2,2,2,2	aLRhap	94.5	71.1	?	?	?	?
2,2,2,2,2	aDManp	101.3-102.2	71.3-76.8	73.3	70.3	71.6	66.4
2,2,2,2	aDManp	100.1	78.2	75.1	70.4	71.1	66.9
2,2,2,6,3,3	bDGalf	106.5	79.7	81.8	81.9	70.8	66.7
2,2,2,6,3	bDGalf	106.5	79.7	81.8	81.9	70.8	66.7
2,2,2,6,6,4	aDGlcp	100.1	72.6	68.4	71.0	72.9	60.7
2,2,2,6,6	aDGlcp	97.9	71.2	78.7	73.7	70.5	62.7-63.1
2,2,2,6	bDGalf	107.9	81.3	83.0	82.9	70.8	66.7
2,2,2	aDManp	100.1	78.2	75.1	70.4	71.1	66.9
2,2	aDManp	101.3-102.2	71.3-76.8	73.3	70.3	71.6	66.4
	aDManp	95.6	74.5	74.3	70.2	71.1	66.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2	aDManp	5.22	4.11	3.76	3.68	3.80	3.86
2,2,2,2,6,6	aDManp	5.18	4.02	3.76	3.60	3.84	3.78
2,2,2,2,6	aDManp	5.18	4.02	3.76	3.60	3.84	3.78
2,2,2,2,2,2	aLRhap	4.76	3.84	?	?	?	?
2,2,2,2,2	aDManp	5.11-5.15	3.89-3.93	3.90	3.60	3.80	3.86
2,2,2,2	aDManp	5.18	4.13	3.76	3.68	3.79	3.98
2,2,2,6,3,3	bDGalf	5.08	4.14	4.05	3.91	3.70	3.68
2,2,2,6,3	bDGalf	5.08	4.14	4.05	3.91	3.70	3.68
2,2,2,6,6,4	aDGlcp	5.25	3.50	3.44	3.39	3.39	3.84
2,2,2,6,6	aDGlcp	4.84	3.53	3.49	3.51	3.70	3.55-3.71
2,2,2,6	bDGalf	4.98	4.02	3.86	3.87	3.74	3.68
2,2,2	aDManp	5.18	4.13	3.76	3.68	3.79	3.98
2,2	aDManp	5.11-5.15	3.89-3.93	3.90	3.60	3.80	3.86
	aDManp	5.03	3.75	3.76	3.67	3.68	3.86


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2	aDManp	101.1/5.22	79.4/4.11	72.5/3.76	70.4/3.68	71.6/3.80	66.4/3.86
2,2,2,2,6,6	aDManp	100.1/5.18	71.5/4.02	74.3/3.76	70.4/3.60	71.7/3.84	69.7/3.78
2,2,2,2,6	aDManp	100.1/5.18	71.5/4.02	74.3/3.76	70.4/3.60	71.7/3.84	69.7/3.78
2,2,2,2,2,2	aLRhap	94.5/4.76	71.1/3.84	?/?	?/?	?/?	?/?
2,2,2,2,2	aDManp	101.3-102.2/5.11-5.15	71.3-76.8/3.89-3.93	73.3/3.90	70.3/3.60	71.6/3.80	66.4/3.86
2,2,2,2	aDManp	100.1/5.18	78.2/4.13	75.1/3.76	70.4/3.68	71.1/3.79	66.9/3.98
2,2,2,6,3,3	bDGalf	106.5/5.08	79.7/4.14	81.8/4.05	81.9/3.91	70.8/3.70	66.7/3.68
2,2,2,6,3	bDGalf	106.5/5.08	79.7/4.14	81.8/4.05	81.9/3.91	70.8/3.70	66.7/3.68
2,2,2,6,6,4	aDGlcp	100.1/5.25	72.6/3.50	68.4/3.44	71.0/3.39	72.9/3.39	60.7/3.84
2,2,2,6,6	aDGlcp	97.9/4.84	71.2/3.53	78.7/3.49	73.7/3.51	70.5/3.70	62.7-63.1/3.55-3.71
2,2,2,6	bDGalf	107.9/4.98	81.3/4.02	83.0/3.86	82.9/3.87	70.8/3.74	66.7/3.68
2,2,2	aDManp	100.1/5.18	78.2/4.13	75.1/3.76	70.4/3.68	71.1/3.79	66.9/3.98
2,2	aDManp	101.3-102.2/5.11-5.15	71.3-76.8/3.89-3.93	73.3/3.90	70.3/3.60	71.6/3.80	66.4/3.86
	aDManp	95.6/5.03	74.5/3.75	74.3/3.76	70.2/3.67	71.1/3.68	66.4/3.86

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2	aDManp	5.22	4.11	3.76	3.68	3.80	3.86
2,2,2,2,6,6	aDManp	5.18	4.02	3.76	3.60	3.84	3.78
2,2,2,2,6	aDManp	5.18	4.02	3.76	3.60	3.84	3.78
2,2,2,2,2,2	aLRhap	4.76	3.84	?	?	?	?
2,2,2,2,2	aDManp	5.11 5.15	3.89 3.93	3.90	3.60	3.80	3.86
2,2,2,2	aDManp	5.18	4.13	3.76	3.68	3.79	3.98
2,2,2,6,3,3	bDGalf	5.08	4.14	4.05	3.91	3.70	3.68
2,2,2,6,3	bDGalf	5.08	4.14	4.05	3.91	3.70	3.68
2,2,2,6,6,4	aDGlcp	5.25	3.50	3.44	3.39	3.39	3.84
2,2,2,6,6	aDGlcp	4.84	3.53	3.49	3.51	3.70	3.55 3.71
2,2,2,6	bDGalf	4.98	4.02	3.86	3.87	3.74	3.68
2,2,2	aDManp	5.18	4.13	3.76	3.68	3.79	3.98
2,2	aDManp	5.11 5.15	3.89 3.93	3.90	3.60	3.80	3.86
	aDManp	5.03	3.75	3.76	3.67	3.68	3.86

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2	aDManp	101.1	79.4	72.5	70.4	71.6	66.4
2,2,2,2,6,6	aDManp	100.1	71.5	74.3	70.4	71.7	69.7
2,2,2,2,6	aDManp	100.1	71.5	74.3	70.4	71.7	69.7
2,2,2,2,2,2	aLRhap	94.5	71.1	?	?	?	?
2,2,2,2,2	aDManp	101.3 102.2	71.3 76.8	73.3	70.3	71.6	66.4
2,2,2,2	aDManp	100.1	78.2	75.1	70.4	71.1	66.9
2,2,2,6,3,3	bDGalf	106.5	79.7	81.8	81.9	70.8	66.7
2,2,2,6,3	bDGalf	106.5	79.7	81.8	81.9	70.8	66.7
2,2,2,6,6,4	aDGlcp	100.1	72.6	68.4	71.0	72.9	60.7
2,2,2,6,6	aDGlcp	97.9	71.2	78.7	73.7	70.5	62.7 63.1
2,2,2,6	bDGalf	107.9	81.3	83.0	82.9	70.8	66.7
2,2,2	aDManp	100.1	78.2	75.1	70.4	71.1	66.9
2,2	aDManp	101.3 102.2	71.3 76.8	73.3	70.3	71.6	66.4
	aDManp	95.6	74.5	74.3	70.2	71.1	66.4

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H](O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO[C@@H]5O[C@@H]([C@H](O)CO[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O[C@@H]6O[C@@H]([C@H](O)CO)[C@H](O[C@@H]7O[C@@H]([C@H](O)CO)[C@H](O)[C@H]7O)[C@H]6O)[C@H]5O)O[C@@H]4O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4O[C@H]4[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]4[*])[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize