Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Solanum lycopersicum; Chrysanthemum morifolium
Organ / tissue: rootAssociated disease: bacterial pith necrosis of the leaves;
wilting of plants in bloom;
necrosis and rot of the roots and rootlets
The structure was elucidated in this paperNCBI PubMed ID: 28601025Publication DOI: 10.1016/j.carres.2017.05.019Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evidente
unina.it
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Dipartimento di Scienze delle Produzioni Agroalimentari e dell'Ambiente, Università degli Studi, 50144 Firenze, Italy, Dipartimento di Scienze della Natura e del Territorio, Università degli Studi, 07100 Sassari, Italy, Dipartimento di Scienze Chimiche, Università di Napoli Federico II, I-80126 Naples, Italy
An O-specific polysaccharide (OPS) was isolated from the lipopolysaccharide of Pseudomonas mediterranea strain C5P1rad1, the causal agents of tomato pith necrosis and Chrysanthemum stem rot, and studied by one- and two-dimensional 1H and 13C NMR spectroscopy. The following structure of the trisaccharide repeating unit of the OPS was established, which, to our knowledge, is unique among the known bacterial polysaccharide structures: →4)-β-d-ManpNAc3NAcA-(1→4)-β-d-ManpNAc3NAcA-(1→3)-α-d-QuipNAc4NAc-(1→ where QuiNAc4NAc and ManNAc3NAcA indicate 2,4-diacetamido-2,4,6-trideoxyglucose and 2,3-diacetamido-2,3-dideoxymannuronic acid, respectively. Pre-treatment of leaves with LPS or OPS preparations at 250 and 50 μg mL-1 did not inhibit development of a hypersensitivity reaction induced by P. mediterranea C5P1rad1 on tobacco, tomato and chrysanthemum plants. The same preparations at 250 μg mL-1 partially prevented elicitation of the hypersensitivity reaction by Pseudomonas syringae KVPT7RC on chrysanthemum but not tobacco and tomato.
Lipopolysaccharide, Pseudomonas aeruginosa, NMR spectroscopy, O-specific polysaccharide, Pith necrosis, Pseudomonas mediterranea
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.49, table 1
Compound class: O-polysaccharide
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, mild acid hydrolysis, GPC
Biological activity: hypersensitivity tests with the LPS and OPS on host and non-host plant leaves; Pre-treatment of leaves with LPS or OPS preparations at 250 and 50 mg mL(-1), did not inhibit the hypersensitive reaction (HR) development against P. mediterranea C5P1rad1.
NCBI Taxonomy refs (TaxIDs): 183795Reference(s) to other database(s): GTC:G76107FS
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac 173.6-176.0 23.2-23.6
3,4,3 Ac 173.6-176.0 23.2-23.6
3,4 bDManpN3NA 100.8 52.8 54.2 71.8 77.4 ?
3,2 Ac 173.6-176.0 23.2-23.6
3,3 Ac 173.6-176.0 23.2-23.6
3 bDManpN3NA 101.8 52.7 53.4 77.1 78.6 ?
2 Ac 173.6-176.0 23.2-23.6
4 Ac 173.6-176.0 23.2-23.6
aDQuipN4N 98.6 54.6 79.8 56.7 69.0 17.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 1.86-2.03
3,4,3 Ac - 1.86-2.03
3,4 bDManpN3NA 4.80 4.26 4.29 3.86 4.03 -
3,2 Ac - 1.86-2.03
3,3 Ac - 1.86-2.03
3 bDManpN3NA 4.75 4.24 4.05 3.77 3.83 -
2 Ac - 1.86-2.03
4 Ac - 1.86-2.03
aDQuipN4N 5.01 3.98 3.74 3.56 3.76 1.12
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.2-23.6/1.86-2.03
3,4,3 Ac 23.2-23.6/1.86-2.03
3,4 bDManpN3NA 100.8/4.80 52.8/4.26 54.2/4.29 71.8/3.86 77.4/4.03
3,2 Ac 23.2-23.6/1.86-2.03
3,3 Ac 23.2-23.6/1.86-2.03
3 bDManpN3NA 101.8/4.75 52.7/4.24 53.4/4.05 77.1/3.77 78.6/3.83
2 Ac 23.2-23.6/1.86-2.03
4 Ac 23.2-23.6/1.86-2.03
aDQuipN4N 98.6/5.01 54.6/3.98 79.8/3.74 56.7/3.56 69.0/3.76 17.8/1.12
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 1.86
2.03 | |
| 3,4,3 | Ac |
| 1.86
2.03 | |
| 3,4 | bDManpN3NA | 4.80 | 4.26 | 4.29 | 3.86 | 4.03 |
|
| 3,2 | Ac |
| 1.86
2.03 | |
| 3,3 | Ac |
| 1.86
2.03 | |
| 3 | bDManpN3NA | 4.75 | 4.24 | 4.05 | 3.77 | 3.83 |
|
| 2 | Ac |
| 1.86
2.03 | |
| 4 | Ac |
| 1.86
2.03 | |
| | aDQuipN4N | 5.01 | 3.98 | 3.74 | 3.56 | 3.76 | 1.12 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | 173.6
176.0 | 23.2
23.6 | |
| 3,4,3 | Ac | 173.6
176.0 | 23.2
23.6 | |
| 3,4 | bDManpN3NA | 100.8 | 52.8 | 54.2 | 71.8 | 77.4 | ? |
| 3,2 | Ac | 173.6
176.0 | 23.2
23.6 | |
| 3,3 | Ac | 173.6
176.0 | 23.2
23.6 | |
| 3 | bDManpN3NA | 101.8 | 52.7 | 53.4 | 77.1 | 78.6 | ? |
| 2 | Ac | 173.6
176.0 | 23.2
23.6 | |
| 4 | Ac | 173.6
176.0 | 23.2
23.6 | |
| | aDQuipN4N | 98.6 | 54.6 | 79.8 | 56.7 | 69.0 | 17.8 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":100.8,"l":"1","c":[0,0,225]},{"s":52.8,"l":"2","c":[0,0,225]},{"s":54.2,"l":"3","c":[0,0,225]},{"s":71.8,"l":"4","c":[0,0,225]},{"s":77.4,"l":"5","c":[0,0,225]},{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":101.8,"l":"1","c":[230,0,30]},{"s":52.7,"l":"2","c":[230,0,30]},{"s":53.4,"l":"3","c":[230,0,30]},{"s":77.1,"l":"4","c":[230,0,30]},{"s":78.6,"l":"5","c":[230,0,30]},{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":174.8,"l":"1","c":[0,0,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":98.6,"l":"1","c":[0,165,0]},{"s":54.6,"l":"2","c":[0,165,0]},{"s":79.8,"l":"3","c":[0,165,0]},{"s":56.7,"l":"4","c":[0,165,0]},{"s":69,"l":"5","c":[0,165,0]},{"s":17.8,"l":"6","c":[0,165,0]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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